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Zayka P, Parr B, Robichaud H, Hickey S, Topping A, Holt E, Watts DBE, Soto N, Stein DC, DeShong P, Hurley M. Evaluating methods to create protein functionalized catanionic vesicles. SOFT MATTER 2023; 19:1429-1439. [PMID: 36723251 PMCID: PMC10103230 DOI: 10.1039/d2sm01205g] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Grants] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/18/2023]
Abstract
Catanionic surfactant vesicles (SVs) composed of sodium dodecylbenzenesulfonate (SDBS) and cetyltrimethylammonium tosylate (CTAT) have potential applications as targeted drug delivery systems, vaccine platforms, and diagnostic tools. To facilitate these applications, we evaluated various methods to attach proteins to the surface of SDBS/CTAT vesicles. Acid phosphatase from wheat germ was used as a model protein. Acid phosphatase was successfully conjugated to vesicles enriched with a Triton-X 100 derivative containing an unsaturated ester. Enzymatic activity of acid phosphatase attached to vesicles was assessed using an acid phosphatase assay. Results from the acid phosphatase assay indicated that 15 ± 3% of the attached protein remained functional but the presence of vesicles interferes with the assay. DLS and zeta potential results correlated with the protein functionalization studies. Acid phosphatase functionalized vesicles had an average diameter of 175 ± 85 nm and an average zeta potential of -61 ± 5 mV in PBS. As a control, vesicles enriched with Triton-X 100 were prepared and analyzed by DLS and zeta potential measurements. Triton X-100 enriched vesicles had an average diameter of 140 ± 67 nm and an average zeta potential of -49 ± 2 mV in PBS. Functionalizing the surface of SVs with proteins may be a key step in developing vesicle-based technologies. For drug delivery, antibodies could be used as targeting molecules; for vaccine formulation, functionalizing the surface with spike proteins may produce novel vaccine platforms.
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Affiliation(s)
- Paul Zayka
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
| | - Brendan Parr
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
| | - Hannah Robichaud
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
| | - Skyler Hickey
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
| | - Amber Topping
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
| | - Elizabeth Holt
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
| | - David B E Watts
- Department of Chemistry & Biochemistry, University of Maryland, College Park, MD 20742, USA
| | - Nicholas Soto
- Department of Chemistry & Biochemistry, University of Maryland, College Park, MD 20742, USA
| | - Daniel C Stein
- Department of Cell Biology and Molecular Genetics, University of Maryland, College Park, MD 20742, USA
| | - Philip DeShong
- Department of Chemistry & Biochemistry, University of Maryland, College Park, MD 20742, USA
| | - Matthew Hurley
- Chemistry Department, Saint Anselm College, Manchester, NH 03102, USA.
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2
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Donahue TC, Zong G, Ou C, DeShong P, Wang LX. Catanionic Vesicles as a Facile Scaffold to Display Natural N-Glycan Ligands for Probing Multivalent Carbohydrate-Lectin Interactions. Bioconjug Chem 2023; 34:392-404. [PMID: 36642983 PMCID: PMC10349922 DOI: 10.1021/acs.bioconjchem.2c00560] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/17/2023]
Abstract
Multivalent interactions are a key characteristic of protein-carbohydrate recognition. Phospholipid-based liposomes have been explored as a popular platform for multivalent presentation of glycans, but this platform has been plagued by the instability of typical liposomal formulations in biological media. We report here the exploitation of catanionic vesicles as a stable lipid-based nanoparticle scaffold for displaying large natural N-glycans as multivalent ligands. Hydrophobic insertion of lipidated N-glycans into the catanionic vesicle bilayer was optimized to allow for high-density display of structurally diverse N-glycans on the outer membrane leaflet. In an enzyme-linked competitive lectin-binding assay, the N-glycan-coated vesicles demonstrated a clear clustering glycoside effect, with significantly enhanced affinity for the corresponding lectins including Sambucus nigra agglutinin (SNA), concanavalin A (ConA), and human galectin-3, in comparison with their respective natural N-glycan ligands. Our results showed that relatively low density of high-mannose and sialylated complex type N-glycans gave the maximal clustering effect for binding to ConA and SNA, respectively, while relatively high-density display of the asialylated complex type N-glycan provided maximal clustering effects for binding to human galectin 3. Moreover, we also observed a macromolecular crowding effect on the binding of ConA to high-mannose N-glycans when catanionic vesicles bearing mixed high-mannose and complex-type N-glycans were used. The N-glycan-coated catanionic vesicles are stable and easy to formulate with varied density of ligands, which could serve as a feasible vehicle for drug delivery and as potent inhibitors for intervening protein-carbohydrate interactions implicated in disease.
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Affiliation(s)
- Thomas C Donahue
- Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland20742, United States
| | - Guanghui Zong
- Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland20742, United States
| | - Chong Ou
- Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland20742, United States
| | - Philip DeShong
- Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland20742, United States
| | - Lai-Xi Wang
- Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland20742, United States
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3
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Morzy D, Bastings M. Significance of Receptor Mobility in Multivalent Binding on Lipid Membranes. Angew Chem Int Ed Engl 2022; 61:e202114167. [PMID: 34982497 PMCID: PMC9303963 DOI: 10.1002/anie.202114167] [Citation(s) in RCA: 16] [Impact Index Per Article: 5.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/19/2021] [Revised: 12/07/2021] [Indexed: 01/16/2023]
Abstract
Numerous key biological processes rely on the concept of multivalency, where ligands achieve stable binding only upon engaging multiple receptors. These processes, like viral entry or immune synapse formation, occur on the diffusive cellular membrane. One crucial, yet underexplored aspect of multivalent binding is the mobility of coupled receptors. Here, we discuss the consequences of mobility in multivalent processes from four perspectives: (I) The facilitation of receptor recruitment by the multivalent ligand due to their diffusivity prior to binding. (II) The effects of receptor preassembly, which allows their local accumulation. (III) The consequences of changes in mobility upon the formation of receptor/ligand complex. (IV) The changes in the diffusivity of lipid environment surrounding engaged receptors. We demonstrate how understanding mobility is essential for fully unravelling the principles of multivalent membrane processes, leading to further development in studies on receptor interactions, and guide the design of new generations of multivalent ligands.
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Affiliation(s)
- Diana Morzy
- Programmable Biomaterials Laboratory, Institute of Materials, School of Engineering, École Polytechnique Fédérale de Lausanne, Route Cantonale, 1015, Lausanne, Switzerland
| | - Maartje Bastings
- Programmable Biomaterials Laboratory, Institute of Materials, School of Engineering, École Polytechnique Fédérale de Lausanne, Route Cantonale, 1015, Lausanne, Switzerland
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4
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Morzy D, Bastings M. Significance of Receptor Mobility in Multivalent Binding on Lipid Membranes. Angew Chem Int Ed Engl 2022. [DOI: 10.1002/ange.202114167] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
Affiliation(s)
- Diana Morzy
- Programmable Biomaterials Laboratory Institute of Materials School of Engineering École Polytechnique Fédérale de Lausanne Route Cantonale 1015 Lausanne Switzerland
| | - Maartje Bastings
- Programmable Biomaterials Laboratory Institute of Materials School of Engineering École Polytechnique Fédérale de Lausanne Route Cantonale 1015 Lausanne Switzerland
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5
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Yadav S, Naresh K, Jayaraman N. "Surface Density of Ligands Controls In-Plane and Aggregative Modes of Multivalent Glycovesicle-Lectin Recognitions". Chembiochem 2021; 22:3075-3081. [PMID: 34375491 DOI: 10.1002/cbic.202100321] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Abstract] [Key Words] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/01/2021] [Revised: 08/09/2021] [Indexed: 11/09/2022]
Abstract
Glycovesicles are ideal tools to delineate finer mechanisms of the interactions at the biological cell membranes. Multivalency forms the basis which, in turn, should surpass more than one mechanism in order to maintain multiple roles that the ligand-lectin interactions encounter. Ligand densities hold a prime control to attenuate the interactions. In the present study, mannose trisaccharide interacting with a cognate receptor, namely, Con A, is assessed at the vesicle surfaces. A synthetic (1→3)(1→6)-branched mannose trisaccharide is tethered with a diacetylene monomer and glycovesicles of varying sugar densities are prepared. The polydiacetylene vesicles are prepared by maintaining uniform lipid concentrations. The interactions of the glycovesicles with the lectin are probed through dynamic light scattering and UV-Vis spectroscopy techniques. Binding efficacies are assessed by surface plasmon resonance technique. Aggregative and in-plane modes of interactions follow a ligand density-dependant manner at the vesicle surface. Vesicles with sparsely populated ligands engage lectin in an aggregative mode (trans-), leading to a cross-linked complex formation. Whereas glycovesicles imbedded with dense ligands engage lectin interaction in an in-plane mode intramolecularly (cis-). Sub-nanomolar dissociation constants govern the intramolecular interaction occurring within the plane of the vesicle, relatively more efficacious than the aggregative intermolecular interactions.
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Affiliation(s)
- Shivender Yadav
- Indian Institute of Science, Department of Organic Chemistry, INDIA
| | - Kottari Naresh
- Indian Institute of Science, Department of Organic Chemistry, INDIA
| | - Narayanaswamy Jayaraman
- Indian Institute of Science, Department of Organic Chemistry, Sir C.V. Raman Avenue, 560 012, Bangalore, INDIA
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Extraction of Membrane Components from Neisseria gonorrhoeae Using Catanionic Surfactant Vesicles: A New Approach for the Study of Bacterial Surface Molecules. Pharmaceutics 2020; 12:pharmaceutics12090787. [PMID: 32825235 PMCID: PMC7559012 DOI: 10.3390/pharmaceutics12090787] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/21/2020] [Revised: 08/13/2020] [Accepted: 08/16/2020] [Indexed: 01/11/2023] Open
Abstract
Identification of antigens is important for vaccine production. We tested extraction protocols using cetyltrimethylammonium tosylate (CTAT) and sodium dodecylbenzenesulfonate (SDBS) to formulate surfactant vesicles (SVs) containing components from Neisseria gonorrhoeae. Carbohydrate and protein assays demonstrated that protein and carbohydrates were incorporated into the vesicle leaflet. Depending on the extraction protocol utilized, 100–400 µg of protein/mL of SVs solution was obtained. Gel electrophoresis followed by silver staining demonstrated that SV extracts contained lipooligosaccharide and a subset of bacterial proteins and lipoproteins. Western blotting and mass spectral analysis indicated that the majority of the proteins were derived from the outer membrane. Mass spectrometric and bioinformatics analysis of SVs identified 29 membrane proteins, including porin and opacity-associated protein. Proteins embedded in the SVs leaflet could be degraded by the addition of trypsin or proteinase K. Our data showed that the incorporation of CTAT and SDBS into vesicles eliminated their toxicity as measured by a THP-1 killing assay. Incorporation of gonococcal cell surface components into SVs reduced toxicity as compared to the whole cell extracts, as measured by cytokine induction, while retaining the immunogenicity. This process constitutes a general method for extracting bacterial surface components and identification of antigens that might be included in vaccines.
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Arévalo-Ruiz M, Amrane S, Rosu F, Belmonte-Reche E, Peñalver P, Mergny JL, Morales JC. Symmetric and dissymmetric carbohydrate-phenyl ditriazole derivatives as DNA G-quadruplex ligands: Synthesis, biophysical studies and antiproliferative activity. Bioorg Chem 2020; 99:103786. [DOI: 10.1016/j.bioorg.2020.103786] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/11/2019] [Revised: 02/27/2020] [Accepted: 03/20/2020] [Indexed: 02/04/2023]
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Molejon MI, Weiz G, Breccia JD, Vaccaro MI. Glycoconjugation: An approach to cancer therapeutics. World J Clin Oncol 2020; 11:110-120. [PMID: 32257842 PMCID: PMC7103525 DOI: 10.5306/wjco.v11.i3.110] [Citation(s) in RCA: 16] [Impact Index Per Article: 3.2] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 10/22/2019] [Revised: 01/31/2020] [Accepted: 02/08/2020] [Indexed: 02/06/2023] Open
Abstract
Cancer constitutes the second leading cause of death globally and is considered to have been responsible for an estimated 9.6 million fatalities in 2018. Although treatments against gastrointestinal tumors have recently advanced, those interventions can only be applied to a minority of patients at the time of diagnosis. Therefore, new therapeutic options are necessary for advanced stages of the disease. Glycosylation of antitumor agents, has been found to improve pharmacokinetic parameters, reduce side effects, and expand drug half-life in comparison with the parent compounds. In addition, glycosylation of therapeutic agents has been proven to be an effective strategy for their targeting tumor tissue, thereby reducing the doses of the glycodrugs administered to patients. This review focusses on the effect of the targeting properties of glycosylated antitumor agents on gastrointestinal tumors.
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Affiliation(s)
- Maria I Molejon
- Institute of Earth and Environmental Sciences from La Pampa (INCITAP), National University of La Pampa, School of Natural Sciences (CONICET-UNLPam), Santa Rosa 6300, La Pampa, Argentina
- Institute of Biochemistry and Molecular Medicine (UBA-CONICET), Department of Pathophysiology, School of Pharmacy and Biochemistry, University of Buenos Aires, Buenos Aires C1113AAD, Argentina
| | - Gisela Weiz
- Institute of Earth and Environmental Sciences from La Pampa (INCITAP), National University of La Pampa, School of Natural Sciences (CONICET-UNLPam), Santa Rosa 6300, La Pampa, Argentina
| | - Javier D Breccia
- Institute of Earth and Environmental Sciences from La Pampa (INCITAP), National University of La Pampa, School of Natural Sciences (CONICET-UNLPam), Santa Rosa 6300, La Pampa, Argentina
| | - Maria Ines Vaccaro
- Institute of Biochemistry and Molecular Medicine (UBA-CONICET), Department of Pathophysiology, School of Pharmacy and Biochemistry, University of Buenos Aires, Buenos Aires C1113AAD, Argentina
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9
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di Gregorio MC, Severoni E, Travaglini L, Gubitosi M, Sennato S, Mura F, Redondo-Gómez C, Jover A, Pavel NV, Galantini L. Bile acid derivative-based catanionic mixtures: versatile tools for superficial charge modulation of supramolecular lamellae and nanotubes. Phys Chem Chem Phys 2018; 20:18957-18968. [PMID: 29972162 DOI: 10.1039/c8cp02745e] [Citation(s) in RCA: 11] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/11/2022]
Abstract
Self-assembled structures formed by mixtures of cationic and anionic surfactants are interesting tools for applications requiring interactions with charged particles and molecules. Nevertheless, they present instability close to the equimolar composition and poor morphological versatility, which is generally restricted to vesicles and micelles. Against this general trend, we report on bile salt derivative based catanionic mixtures assembling in tubules and lamellae depending on the mixture composition. Electrophoretic mobility measurements prove that the composition also dictates their superficial charge, which can be tuned from negative to positive by increasing the positively charged surfactant fraction in the mixtures. The study of the catanionic aggregates was conducted by means of microscopy and spectroscopy techniques and compared to the self-assembly behaviors of the individual building blocks. This study broadens the so far small array of bile salt derivative catanionic systems, confirming their distinctive behavior in the spectrum of catanionic mixtures.
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10
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Xavier NM, Porcheron A, Batista D, Jorda R, Řezníčková E, Kryštof V, Oliveira MC. Exploitation of new structurally diverse d-glucuronamide-containing N-glycosyl compounds: synthesis and anticancer potential. Org Biomol Chem 2018; 15:4667-4680. [PMID: 28517004 DOI: 10.1039/c7ob00472a] [Citation(s) in RCA: 10] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Abstract] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
Abstract
The synthesis and anticancer evaluation of novel N-glycosyl derivatives containing N-substituted glucuronamide moieties, as nucleoside analogs or as prospective mimetics of glycosyl phosphates or of nucleotides, is reported. These compounds comprise N-anomerically-linked nucleobases or motifs that are surrogates of a phosphate group, such as sulfonamide or phosphoramidate moieties. 1-Sulfonamido glucuronamides containing N-benzyl, N-propargyl or N-dodecyl carboxamide units were synthesized through glycosylation of methanesulfonamide with tetra-O-acetyl glucuronamides. 1-Azido glucuronamides were accessed by microwave-assisted reactions of tetra-O-acetyl glucuronamides with TMSN3 and were further converted into N-glycosylphosphoramidates by treatment with trimethyl phosphite. Potential glucuronamide-based nucleotide mimetics comprising both an anomeric sulfonamide/phosphoramidate group and a benzyltriazolylmethyl amide system at C-5, as nucleobase mimetics, were synthesized via 'click' cycloaddition of N-propargyl glucuronamide derivatives with benzyl azide. N-Dodecyl tetra-O-acetyl glucuronamides were converted into uracil and purine nucleosides via N-glycosylation of the corresponding silylated nucleobases. Biological screening revealed significant antiproliferative activities of the N-dodecyl glucuronamide-containing sulfonamide, phosphoramidate and nucleosides in K562 and MCF-7 cells. The highest effect was exhibited by the N9-linked purine nucleoside in the breast cancer cell MCF-7 with a GI50 value similar to that of clinically used 5-fluorouracil. Immunoblotting and cell cycle analysis of K562 cells treated with the most active compound as well as evaluation of the effect of this nucleoside on the activities of caspases 3 and 7 showed induction of apoptosis as the mechanism of cell death.
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Affiliation(s)
- Nuno M Xavier
- Centro de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Ed. C8, 5° Piso, Campo Grande, 1749-016 Lisboa, Portugal.
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Mahle A, Dashaputre N, DeShong P, Stein DC. Catanionic Surfactant Vesicles as a New Platform for probing Glycan-Protein Interactions. ADVANCED FUNCTIONAL MATERIALS 2018; 28:1706215. [PMID: 31118878 PMCID: PMC6527319 DOI: 10.1002/adfm.201706215] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/09/2023]
Abstract
Glycomics lags substantially behind proteomics and genomics in its ability to decipher and synthesize complex glycans. The slow progress in deciphering glycan interactions at a molecular level is in large part due to the absence of a functional system to express, on a large scale, carbohydrates of known structure, in the context of a biologically relevant assay system. Here we describe the characterization of a glycan-functionalized catanionic surfactant vesicles (CVs) as a platform for glycan synthesis, and to demonstrate that the resulting glycan-functionalized CVs can serve as a scaffold for the interrogation of protein-glycan interactions. We demonstrate that N. gonorrhoeae lipooligosaccharide (LOS) glycosyltransferase LgtE, an enzyme that catalyzes the addition of galactose onto a terminal glucose found on LOS can be used to biochemically modify LOS or glucose functionalized CVs. CVs were characterized by differential lectin binding using flow cytometry. LgtE activity was measured on whole cells and LOS functionalized vesicles and found to have approximately the same biochemical properties. We further demonstrate that CVs can be ink-jet printed. This paper presents proof-of-concept that glycan-functionalized catanionic vesicles can be used to create a high-specificity and high-throughput glycan array that will allow for the investigation of a variety of protein-glycan interactions.
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Affiliation(s)
- Amanda Mahle
- Department of Cell Biology and Molecular Genetics, University of Maryland, College Park, MD 20742
| | - Neeraja Dashaputre
- Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742
| | - Philip DeShong
- Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742
| | - Daniel C. Stein
- Department of Cell Biology and Molecular Genetics, University of Maryland, College Park, MD 20742
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12
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Villalva DG, Giansanti L, Mauceri A, Ceccacci F, Mancini G. Influence of the state of phase of lipid bilayer on the exposure of glucose residues on the surface of liposomes. Colloids Surf B Biointerfaces 2017; 159:557-563. [DOI: 10.1016/j.colsurfb.2017.08.025] [Citation(s) in RCA: 11] [Impact Index Per Article: 1.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/10/2017] [Revised: 07/18/2017] [Accepted: 08/16/2017] [Indexed: 11/27/2022]
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13
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Dhawan VV, Nagarsenker MS. Catanionic systems in nanotherapeutics – Biophysical aspects and novel trends in drug delivery applications. J Control Release 2017; 266:331-345. [DOI: 10.1016/j.jconrel.2017.09.040] [Citation(s) in RCA: 23] [Impact Index Per Article: 2.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/10/2017] [Accepted: 09/28/2017] [Indexed: 01/10/2023]
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14
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Physicochemical characterization of lauryl glycinate-dodecyl sulfate equimolar complex: A base-triggerable catanionic liposomal system. Colloids Surf A Physicochem Eng Asp 2017. [DOI: 10.1016/j.colsurfa.2016.12.012] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/23/2022]
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15
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Richard K, Mann BJ, Qin A, Barry EM, Ernst RK, Vogel SN. Monophosphoryl Lipid A Enhances Efficacy of a Francisella tularensis LVS-Catanionic Nanoparticle Subunit Vaccine against F. tularensis Schu S4 Challenge by Augmenting both Humoral and Cellular Immunity. CLINICAL AND VACCINE IMMUNOLOGY : CVI 2017; 24:e00574-16. [PMID: 28077440 PMCID: PMC5339645 DOI: 10.1128/cvi.00574-16] [Citation(s) in RCA: 10] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Subscribe] [Scholar Register] [Received: 01/03/2017] [Accepted: 01/06/2017] [Indexed: 01/01/2023]
Abstract
Francisella tularensis, a bacterial biothreat agent, has no approved vaccine in the United States. Previously, we showed that incorporating lysates from partially attenuated F. tularensis LVS or fully virulent F. tularensis Schu S4 strains into catanionic surfactant vesicle (V) nanoparticles (LVS-V and Schu S4-V, respectively) protected fully against F. tularensis LVS intraperitoneal (i.p.) challenge in mice. However, we achieved only partial protection against F. tularensis Schu S4 intranasal (i.n.) challenge, even when employing heterologous prime-boost immunization strategies. We now extend these findings to show that both LVS-V and Schu S4-V immunization (i.p./i.p.) elicited similarly high titers of anti-F. tularensis IgG and that the titers could be further increased by adding monophosphoryl lipid A (MPL), a nontoxic Toll-like receptor 4 (TLR4) adjuvant that is included in several U.S. FDA-approved vaccines. LVS-V+MPL immune sera also detected more F. tularensis antigens than LVS-V immune sera and, after passive transfer to naive mice, significantly delayed the time to death against F. tularensis Schu S4 subcutaneous (s.c.) but not i.n. challenge. Active immunization with LVS-V+MPL (i.p./i.p.) also increased the frequency of gamma interferon (IFN-γ)-secreting activated helper T cells, IFN-γ production, and the ability of splenocytes to control intramacrophage F. tularensis LVS replication ex vivo Active LVS-V+MPL immunization via heterologous routes (i.p./i.n.) significantly elevated IgA and IgG levels in bronchoalveolar lavage fluid and significantly enhanced protection against i.n. F. tularensis Schu S4 challenge (to ∼60%). These data represent a significant step in the development of a subunit vaccine against the highly virulent type A strains.
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Affiliation(s)
- Katharina Richard
- Department of Microbiology and Immunology, University of Maryland School of Medicine, Baltimore, Maryland, USA
| | - Barbara J Mann
- Department of Medicine, University of Virginia, Charlottesville, Virginia, USA
| | - Aiping Qin
- Department of Medicine, University of Virginia, Charlottesville, Virginia, USA
| | - Eileen M Barry
- Center for Vaccine Development, University of Maryland School of Medicine, Baltimore, Maryland, USA
| | - Robert K Ernst
- Department of Microbial Pathogenesis, University of Maryland School of Dentistry, Baltimore, Maryland, USA
| | - Stefanie N Vogel
- Department of Microbiology and Immunology, University of Maryland School of Medicine, Baltimore, Maryland, USA
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16
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Na G, He Y, Kim Y, Lee M. Switching of carbohydrate nanofibers for regulating cell proliferation. SOFT MATTER 2016; 12:2846-2850. [PMID: 26907533 DOI: 10.1039/c5sm03073k] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/05/2023]
Abstract
We report switchable, fluorescent carbohydrate nanofibers formed through the self-assembly of aromatic rod amphiphiles with a combination of mannose epitopes and thermoresponsive oligoether dendrons. The carbohydrate nanofibers undergo reversible switching between carbohydrate-exposed and hidden states on their surface in response to a thermal signal, and have the ability to regulate cell proliferation.
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Affiliation(s)
- Guangren Na
- State Key Lab of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China.
| | - Ying He
- State Key Lab of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China.
| | - Yongju Kim
- State Key Lab of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China.
| | - Myongsoo Lee
- State Key Lab of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China.
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17
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Delbianco M, Bharate P, Varela-Aramburu S, Seeberger PH. Carbohydrates in Supramolecular Chemistry. Chem Rev 2015; 116:1693-752. [PMID: 26702928 DOI: 10.1021/acs.chemrev.5b00516] [Citation(s) in RCA: 180] [Impact Index Per Article: 18.0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/03/2023]
Abstract
Carbohydrates are involved in a variety of biological processes. The ability of sugars to form a large number of hydrogen bonds has made them important components for supramolecular chemistry. We discuss recent advances in the use of carbohydrates in supramolecular chemistry and reveal that carbohydrates are useful building blocks for the stabilization of complex architectures. Systems are presented according to the scaffold that supports the glyco-conjugate: organic macrocycles, dendrimers, nanomaterials, and polymers are considered. Glyco-conjugates can form host-guest complexes, and can self-assemble by using carbohydrate-carbohydrate interactions and other weak interactions such as π-π interactions. Finally, complex supramolecular architectures based on carbohydrate-protein interactions are discussed.
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Affiliation(s)
- Martina Delbianco
- Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany
| | - Priya Bharate
- Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.,Institute of Chemistry and Biochemistry, Freie Universität Berlin , Arnimallee 22, 14195 Berlin, Germany
| | - Silvia Varela-Aramburu
- Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.,Institute of Chemistry and Biochemistry, Freie Universität Berlin , Arnimallee 22, 14195 Berlin, Germany
| | - Peter H Seeberger
- Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces , Am Mühlenberg 1, 14476 Potsdam, Germany.,Institute of Chemistry and Biochemistry, Freie Universität Berlin , Arnimallee 22, 14195 Berlin, Germany
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18
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Silva SG, Vale MLCD, Marques EF. Size, Charge, and Stability of Fully Serine-Based Catanionic Vesicles: Towards Versatile Biocompatible Nanocarriers. Chemistry 2015; 21:4092-101. [DOI: 10.1002/chem.201406111] [Citation(s) in RCA: 22] [Impact Index Per Article: 2.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/16/2014] [Indexed: 12/21/2022]
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19
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Sankaran S, Kiren MC, Jonkheijm P. Incorporating Bacteria as a Living Component in Supramolecular Self-Assembled Monolayers through Dynamic Nanoscale Interactions. ACS NANO 2015; 9:3579-86. [PMID: 25738514 DOI: 10.1021/acsnano.5b00694] [Citation(s) in RCA: 32] [Impact Index Per Article: 3.2] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/20/2023]
Abstract
Supramolecular assemblies, formed through noncovalent interactions, has become particularly attractive to develop dynamic and responsive architectures to address living systems at the nanoscale. Cucurbit[8]uril (CB[8]), a pumpkin shaped macrocylic host molecule, has been successfully used to construct various self-assembled architectures for biomedical applications since it can simultaneously bind two aromatic guest molecules within its cavity. Such architectures can also be designed to respond to external stimuli. Integrating living organisms as an active component into such supramolecular architectures would add a new dimension to the capabilities of such systems. To achieve this, we have incorporated supramolecular functionality at the bacterial surface by genetically modifying a transmembrane protein to display a CB[8]-binding motif as part of a cystine-stabilized miniprotein. We were able to confirm that this supramolecular motif on the bacterial surface specifically binds CB[8] and forms multiple intercellular ternary complexes leading to aggregation of the bacterial solution. We performed various aggregation experiments to understand how CB[8] interacts with this bacterial strain and also demonstrate that it can be chemically reversed using a competitor. To confirm that this strain can be incorporated with a CB[8] based architecture, we show that the bacterial cells were able to adhere to CB[8] self-assembled monolayers (SAMs) on gold and still retain considerable motility for several hours, indicating that the system can potentially be used to develop supramolecular bacterial biomotors. The bacterial strain also has the potential to be combined with other CB[8] based architectures like nanoparticles, vesicles and hydrogels.
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Affiliation(s)
- Shrikrishnan Sankaran
- Laboratory group of Bioinspired Molecular Engineering, Molecular Nanofabrication Group, Faculty of Science and Technology and MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, Enschede 7500AE, The Netherlands
| | - Mustafa Can Kiren
- Laboratory group of Bioinspired Molecular Engineering, Molecular Nanofabrication Group, Faculty of Science and Technology and MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, Enschede 7500AE, The Netherlands
| | - Pascal Jonkheijm
- Laboratory group of Bioinspired Molecular Engineering, Molecular Nanofabrication Group, Faculty of Science and Technology and MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, Enschede 7500AE, The Netherlands
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20
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Alliband A, Wang Z, Thacker C, English DS, Burns DH. Developing a targeting system for bacterial membranes: measuring receptor-phosphatidylglycerol interactions with1H NMR, ITC and fluorescence correlation spectroscopy. Org Biomol Chem 2015; 13:502-12. [DOI: 10.1039/c4ob01895h] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
We report the development of a potential targeting system for bacterial membranes containing phosphatidylglycerol.
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Affiliation(s)
| | - Zifan Wang
- Department of Chemistry
- Wichita State University
- Wichita
- USA
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21
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Sun X, Qi Y, Liu H, Peng J, Liu K, Fang Y. "Yin and Yang" tuned fluorescence sensing behavior of branched 1,4-bis(phenylethynyl)benzene. ACS APPLIED MATERIALS & INTERFACES 2014; 6:20016-20024. [PMID: 25313531 DOI: 10.1021/am505588x] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/04/2023]
Abstract
Achieving high sensing performance and good photostability of fluorescent films based on adlayer construction represents a significant challenge in the area of functional fluorescent film research. A solution may be offered by "Yin and Yang", a balance idea from Chinese philosophy, for the design of a fluorophore and the relevant assembly. Accordingly, a 1,4-bis(phenylethynyl)benzene (BPEB) derivative (C2) with two cholesteryl residues in the side chains and two glucono units in the head and tail positions was designed and synthesized. As a control, compound C1 was also prepared. The only difference between C1 and C2 is that the hydroxyl groups in the glucono residues of C1 are fully acetylated. Studies of the fluorescence behaviors of the two compounds in solution revealed that both the profile and the intensity of the fluorescence emission of the compounds, in particular C2, are dependent on their concentration and on the nature of solvents employed. Presence of HCl also alters the emission of the compounds in solution. On the basis of the studies, three fluorescent films were prepared, and their sensing performances to HCl in vapor state were studied. Specifically, Film 1 and Film 3 were fabricated via physical coating, separately, of C2 and C1 on glass plate surfaces. As another comparison, Film 2 was also fabricated with C2 as a fluorophore but at a much lower concentration if compared to that for the preparation of Film 1. As revealed by SEM and fluorescent microscopy studies, Film 1 and Film 2 exhibit well-defined microstructures, which are spherical particles and spherical pores, respectively, while Film 3 is characterized by irregular aggregates of C1. Fluorescence measurements demonstrated that Film 1 and Film 3 both display an aggregation emission, of which the emission from Film 1 is supersensitive to the presence of HCl vapor (detection limit: 0.4 ppb, a lowest value reported in the literatures). For Film 3, however, its emission is insensitive to the presence of the vapor. Similarly, the emission from the nonaggregated state of C2, a characteristic emission of Film 2, is also insensitive to the presence of the vapor. Furthermore, the sensing process of Film 1 to the vapor is highly selective and fully reversible, which lays foundation for its real-life uses. As for C2, the results from solution studies and those from film studies demonstrate clearly that introduction of auxiliary structures with opposite properties onto a typical fluorophore is a good strategy to develop fluorescent supramolecular motifs with rich assembly properties and great potential of applications.
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Affiliation(s)
- Xiaohuan Sun
- Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University , Xi'an 710062, P. R. China
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22
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Harano K, Yamada J, Mizuno S, Nakamura E. High-Density Display of Protein Ligands on Self-Assembled Capsules via Noncovalent Fluorous Interactions. Chem Asian J 2014; 10:172-6. [DOI: 10.1002/asia.201403144] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/04/2014] [Indexed: 11/11/2022]
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Novel catanionic surfactant vesicle vaccines protect against Francisella tularensis LVS and confer significant partial protection against F. tularensis Schu S4 strain. CLINICAL AND VACCINE IMMUNOLOGY : CVI 2013; 21:212-26. [PMID: 24351755 DOI: 10.1128/cvi.00738-13] [Citation(s) in RCA: 19] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Abstract] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 12/19/2022]
Abstract
Francisella tularensis is a Gram-negative immune-evasive coccobacillus that causes tularemia in humans and animals. A safe and efficacious vaccine that is protective against multiple F. tularensis strains has yet to be developed. In this study, we tested a novel vaccine approach using artificial pathogens, synthetic nanoparticles made from catanionic surfactant vesicles that are functionalized by the incorporation of either F. tularensis type B live vaccine strain (F. tularensis LVS [LVS-V]) or F. tularensis type A Schu S4 strain (F. tularensis Schu S4 [Schu S4-V]) components. The immunization of C57BL/6 mice with "bare" vesicles, which did not express F. tularensis components, partially protected against F. tularensis LVS, presumably through activation of the innate immune response, and yet it failed to protect against the F. tularensis Schu S4 strain. In contrast, immunization with LVS-V fully protected mice against intraperitoneal (i.p.) F. tularensis LVS challenge, while immunization of mice with either LVS-V or Schu S4-V partially protected C57BL/6 mice against an intranasal (i.n.) F. tularensis Schu S4 challenge and significantly increased the mean time to death for nonsurvivors, particularly following the i.n. and heterologous (i.e., i.p./i.n.) routes of immunization. LVS-V immunization, but not immunization with empty vesicles, elicited high levels of IgG against nonlipopolysaccharide (non-LPS) epitopes that were increased after F. tularensis LVS challenge and significantly increased early cytokine production. Antisera from LVS-V-immunized mice conferred passive protection against challenge with F. tularensis LVS. Together, these data indicate that functionalized catanionic surfactant vesicles represent an important and novel tool for the development of a safe and effective F. tularensis subunit vaccine and may be applicable for use with other pathogens.
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24
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Grochmal A, Ferrero E, Milanesi L, Tomas S. Modulation of in-membrane receptor clustering upon binding of multivalent ligands. J Am Chem Soc 2013; 135:10172-7. [PMID: 23763669 DOI: 10.1021/ja404428u] [Citation(s) in RCA: 33] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/16/2022]
Abstract
In living cells and biomimetic systems alike, multivalent ligands in solution can induce clustering of membrane receptors. The link between the receptor clustering and the ligand binding remains, however, poorly defined. Using minimalist divalent ligands, we develop a model that allows quantifying the modulation of receptor clustering by binding of ligands with any number of binding sites. The ligands, with weak binding affinity for the receptor and with binding sites held together by flexible linkers, lead to nearly quantitative clustering upon binding in a wide range of experimental conditions, showing that efficient modulation of receptor clustering does not require pre-organization or large binding affinities per binding site. Simulations show that, in the presence of ligands with five or more binding sites, an on/off clustering response follows a very small change in receptor density in the membrane, which is consistent with the highly cooperative behavior of multivalent biomolecular systems.
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Affiliation(s)
- Anna Grochmal
- Institute of Structural and Molecular Biology and Department of Biological Sciences, School of Science, Birkbeck University of London, Malet Street, London WC1E 7HX, UK
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25
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Jayaraman N, Maiti K, Naresh K. Multivalent glycoliposomes and micelles to study carbohydrate-protein and carbohydrate-carbohydrate interactions. Chem Soc Rev 2013; 42:4640-56. [PMID: 23487184 DOI: 10.1039/c3cs00001j] [Citation(s) in RCA: 105] [Impact Index Per Article: 8.8] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
This tutorial review describes multivalent carbohydrate-protein and carbohydrate-carbohydrate interaction studies that utilize self-assembled aggregates of thermodynamically stable liposomes and micelles. Strategies to prepare multivalent glycoliposomes and micelles include: (i) insertion of synthetic glycolipids into matrix lipids; (ii) preparation of glycolipids that aggregate to liposomes and micelles and (iii) modification of the hydrophilic surfaces with desired sugars. Several design strategies have been developed in order to obtain constituent glycolipids, having multivalent sugar moieties and their subsequent interactions with proteins were assessed in relation to the type of linkers that connect the hydrophilic and lipophilic segments. Lipophilic segments other than alkyl chains have also been developed. Polymer based glycoliposomes and micelles form an emphasis. Further, glycoliposomes facilitate studies of carbohydrate-carbohydrate interactions. An overview of the various types of glycoliposomes and micelles used to study carbohydrate-protein and carbohydrate-carbohydrate recognition phenomena is presented.
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26
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Reduced steric hindrance and optimized spatial arrangement of carbohydrate ligands in imprinted monolayers for enhanced protein binding. BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES 2013; 1828:792-800. [DOI: 10.1016/j.bbamem.2012.11.006] [Citation(s) in RCA: 16] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Received: 07/05/2012] [Revised: 09/26/2012] [Accepted: 11/06/2012] [Indexed: 11/20/2022]
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27
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Kauscher U, Ravoo BJ. Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin-carbohydrate recognition. Beilstein J Org Chem 2012; 8:1543-51. [PMID: 23209484 PMCID: PMC3510984 DOI: 10.3762/bjoc.8.175] [Citation(s) in RCA: 36] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/25/2012] [Accepted: 08/17/2012] [Indexed: 12/03/2022] Open
Abstract
Cyclodextrin vesicles are versatile models for biological cell membranes since they provide a bilayer membrane that can easily be modified by host–guest interactions with functional guest molecules. In this article, we investigate the multivalent interaction of the lectin concanavalin A (ConA) with cyclodextrin vesicles decorated with mannose–adamantane conjugates with one, two or three adamantane units as well as one or two mannose units. The carbohydrate–lectin interaction in this artificial, self-assembled glycocalyx was monitored in an agglutination assay by the increase of optical density at 400 nm. It was found that there is a close relation between the carbohydrate density at the cyclodextrin vesicle surface and the multivalent interaction with ConA, and the most efficient interaction (i.e., fastest agglutination at lowest concentration) was observed for mannose–adamantane conjugates, in which both the cyclodextrin–adamantane and the lectin–mannose interaction is inherently multivalent.
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Affiliation(s)
- Ulrike Kauscher
- Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster, Correnstraße 40, 48149 Münster, Germany
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28
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Wang X, Huang X, Xin Y, Du X. Myoglobin-directed assemblies of binary monolayers functionalized with iminodiacetic acid ligands at the air-water interface through metal coordination for multivalent protein binding. Phys Chem Chem Phys 2012; 14:5470-8. [PMID: 22415292 DOI: 10.1039/c2cp40104e] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
Myoglobin binding to the binary monolayers composed of sodium hexadecylimino diacetate and hexadecanol at the air-water interface by means of metal coordination has been investigated using infrared reflection absorption spectroscopy (IRRAS). In the absence of Cu(2+), no myoglobin binding to the binary monolayers was observed. In the presence of Cu(2+), remarkable myoglobin binding to the binary monolayers resulted from the formation of ternary complexes of iminodiacetate (IDA)-Cu(2+)-surface histidine. Myoglobin-directed assemblies of the binary monolayers facilitated multivalent protein binding through lateral rearrangements of the IDA ligands and reorientations of the alkyl chains for enhanced protein binding. Myoglobin binding to and desorption from the binary monolayers could be readily controlled through metal coordination.
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Affiliation(s)
- Xiaoyu Wang
- Key Laboratory of Mesoscopic Chemistry (Ministry of Education), and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China
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29
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Sánchez-Pomales G, Morris TA, Falabella JB, Tarlov MJ, Zangmeister RA. A lectin-based gold nanoparticle assay for probing glycosylation of glycoproteins. Biotechnol Bioeng 2012; 109:2240-9. [DOI: 10.1002/bit.24513] [Citation(s) in RCA: 24] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/12/2011] [Revised: 03/08/2012] [Accepted: 03/20/2012] [Indexed: 12/15/2022]
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30
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Pond MA, Zangmeister RA. Carbohydrate-functionalized surfactant vesicles for controlling the density of glycan arrays. Talanta 2012; 91:134-9. [DOI: 10.1016/j.talanta.2012.01.036] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/21/2011] [Revised: 01/12/2012] [Accepted: 01/17/2012] [Indexed: 12/15/2022]
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31
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Li X, Wu P, Gao GF, Cheng S. Carbohydrate-Functionalized Chitosan Fiber for Influenza Virus Capture. Biomacromolecules 2011; 12:3962-9. [DOI: 10.1021/bm200970x] [Citation(s) in RCA: 44] [Impact Index Per Article: 3.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/16/2022]
Affiliation(s)
- Xuebing Li
- CAS Key Laboratory of Pathogenic
Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China
| | - Peixing Wu
- Lanzhou Institute of Animal Science
and Veterinary Pharmaceutics, Chinese Academy of Agricultural Science, Lanzhou 730050, China
| | - George F. Gao
- CAS Key Laboratory of Pathogenic
Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China
| | - Shuihong Cheng
- CAS Key Laboratory of Pathogenic
Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China
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32
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Wang Y, Gao J, Gu G, Li G, Cui C, Sun B, Lou H. In situ RBL receptor visualization and its mediated anticancer activity for solasodine rhamnosides. Chembiochem 2011; 12:2418-20. [PMID: 21953983 DOI: 10.1002/cbic.201100551] [Citation(s) in RCA: 25] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/30/2011] [Indexed: 12/11/2022]
Affiliation(s)
- Yanyan Wang
- Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, China
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33
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Zheng H, Du X. Multivalent protein binding in carbohydrate-functionalized monolayers through protein-directed rearrangement and reorientation of glycolipids at the air-water interface. BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES 2011; 1808:2128-35. [PMID: 21640072 DOI: 10.1016/j.bbamem.2011.04.019] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [Track Full Text] [Subscribe] [Scholar Register] [Received: 12/06/2010] [Revised: 04/05/2011] [Accepted: 04/07/2011] [Indexed: 11/29/2022]
Abstract
Multivalent protein binding plays an important role not only in biological recognition but also in biosensor preparation. Infrared reflection absorption spectroscopy and surface plasmon resonance techniques have been used to investigate concanavalin A (Con A) binding to binary monolayers composed of 1,2-di-O-hexadecyl-sn-glycerol and derived glycolipids with the mannose moieties. The glycolipids in the binary monolayers at the air-water interface underwent both lateral rearrangement and molecular reorientation directed by Con A in the subphase favorable to access of the carbohydrate ligands to protein binding pockets for the formation of multivalent binding sites and the minimization of steric crowding of neighboring ligands for enhanced binding. The amounts of specifically bound proteins in the binary monolayers at the air-water interface were accordingly increased in comparison with those in the initially immobilized monolayers at the air-water interface. The directed rearranged binary monolayers with multivalent protein binding were preserved for the preparation of biosensors.
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Affiliation(s)
- Haifu Zheng
- Key Laboratory of Mesoscopic Chemistry (Ministry of Education), State Key Laboratory of Coordination Chemistry, and School of Chemistry and Chemical Engineering, Nanjing University,Nanjing 210093, People's Republic of China
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34
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Vico RV, Voskuhl J, Ravoo BJ. Multivalent interaction of cyclodextrin vesicles, carbohydrate guests, and lectins: a kinetic investigation. LANGMUIR : THE ACS JOURNAL OF SURFACES AND COLLOIDS 2011; 27:1391-1397. [PMID: 21090662 DOI: 10.1021/la1038975] [Citation(s) in RCA: 52] [Impact Index Per Article: 3.7] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/30/2023]
Abstract
An artificial glycocalix self-assembles when unilamellar bilayer vesicles of amphiphilic β-cyclodextrins are decorated with maltose- and lactose-adamantane conjugates by host-guest interactions. The maltose-decorated vesicles aggregate in the presence of lectin concanavalin A whereas the lactose-decorated vesicles aggregate in the presence of lectin peanut agglutinin. The kinetics of the orthogonal multivalent interfacial interactions present in this ternary system of vesicles, carbohydrates, and lectins were studied by time-dependent measurements of the optical density at 400 nm. The average vesicle and vesicle aggregate sizes were monitored by dynamic light scattering. The aggregation process was evaluated as a function of lectin concentration, vesicle concentration, and surface coverage of the vesicles by the carbohydrate-adamantane conjugates. The initial rate of vesicle aggregation scales linearly with the lectin as well as the cyclodextrin vesicle concentration. Furthermore, each lectin requires a characteristic critical density of carbohydrates at the vesicle surface. These observations allow a prediction of the response of the ternary supramolecular system at different concentrations of its components. Also, the effective binding site separation in a multivalent receptor such as a multiple binding site protein can be accurately determined. This methodology can be extended to multivalent noncovalent interactions in other ligand-receptor systems at interfaces.
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Affiliation(s)
- Raquel V Vico
- Instituto de Investigaciones en Fisicoquímica de Córdoba (INFIQC-UNC-CONICET), Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, Argentina
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35
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Leal MP, Assali M, Fernández I, Khiar N. Copper-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Polydiacetylene: “Click Glycoliposome” as Biosensors for the Specific Detection of Lectins. Chemistry 2011; 17:1828-36. [DOI: 10.1002/chem.201002236] [Citation(s) in RCA: 37] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/04/2010] [Indexed: 01/24/2023]
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36
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Mutual modulation between membrane-embedded receptor clustering and ligand binding in lipid membranes. Nat Chem 2010; 2:1077-83. [PMID: 21107373 DOI: 10.1038/nchem.892] [Citation(s) in RCA: 38] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/17/2010] [Accepted: 08/20/2010] [Indexed: 11/09/2022]
Abstract
Thanks largely to a cooperative chelate effect, clustered membrane-embedded proteins favourably bind to multivalent ligands in solution and, conversely, a multivalent receptor can induce the clustering of membrane-embedded proteins. Here, we use a chemical model to show that the binding of a monovalent ligand and the clustering of a membrane-embedded receptor are closely related processes that modulate each other without the contribution of any apparent multivalence effect. Clearly, the confinement of the receptor within the surface reveals cooperative effects between clustering and binding that are too weak to detect in bulk-solution systems. This work shows that for membrane-embedded receptors that undergo some degree of spontaneous clustering, analyses based on multivalence-mediated cooperativity are insufficient to describe fully the molecular recognition events induced by ligands in solution. Instead, a binding-clustering thermodynamic cycle is proposed for the analysis of the interaction of any kind of ligand with membrane-embedded receptors.
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37
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Zhong S, Pochan DJ. Cryogenic Transmission Electron Microscopy for Direct Observation of Polymer and Small-Molecule Materials and Structures in Solution. POLYM REV 2010. [DOI: 10.1080/15583724.2010.493254] [Citation(s) in RCA: 24] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
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38
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Katrlík J, Svitel J, Gemeiner P, Kozár T, Tkac J. Glycan and lectin microarrays for glycomics and medicinal applications. Med Res Rev 2010; 30:394-418. [PMID: 20099267 DOI: 10.1002/med.20195] [Citation(s) in RCA: 77] [Impact Index Per Article: 5.1] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/24/2022]
Abstract
Three different array formats to study a challenging field of glycomics are presented here, based on the use of a panel of immobilized glycan or lectins, and on in silico computational approach. Glycan and lectin arrays are routinely used in combination with other analytical tools to decipher a complex nature of glycan-mediated recognition responsible for signal transduction of a broad range of biological processes. Fundamental aspects of the glycan and lectin array technology are discussed, with the focus on the choice and availability of the biorecognition elements, fabrication protocols, and detection platforms involved. Moreover, practical applications of both technologies especially in the field of clinical diagnostics are provided. The future potential of a complementary in silico array technology to reveal details of the protein-glycan-binding profiles is discussed here.
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Affiliation(s)
- Jaroslav Katrlík
- Department of Glycobiotechnology, Center for Glycomics, Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovakia
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39
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Voskuhl J, Stuart M, Ravoo B. Sugar-Decorated Sugar Vesicles: Lectin-Carbohydrate Recognition at the Surface of Cyclodextrin Vesicles. Chemistry 2010; 16:2790-6. [DOI: 10.1002/chem.200902423] [Citation(s) in RCA: 107] [Impact Index Per Article: 7.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/06/2022]
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40
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41
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Zheng H, Du X. Protein-Directed Spatial Rearrangement of Glycolipids at the Air−Water Interface for Bivalent Protein Binding: In Situ Infrared Reflection Absorption Spectroscopy. J Phys Chem B 2009; 114:577-84. [DOI: 10.1021/jp908559n] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
Affiliation(s)
- Haifu Zheng
- Key Laboratory of Mesoscopic Chemistry (Ministry of Education), State Key Laboratory of Coordination Chemistry, and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People’s Republic of China
| | - Xuezhong Du
- Key Laboratory of Mesoscopic Chemistry (Ministry of Education), State Key Laboratory of Coordination Chemistry, and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People’s Republic of China
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42
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Zheng H, Du X. Enhanced Binding and Biosensing of Carbohydrate-Functionalized Monolayers to Target Proteins by Surface Molecular Imprinting. J Phys Chem B 2009; 113:11330-7. [DOI: 10.1021/jp9060279] [Citation(s) in RCA: 24] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
Affiliation(s)
- Haifu Zheng
- Key Laboratory of Mesoscopic Chemistry (Ministry of Education), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People’s Republic of China
| | - Xuezhong Du
- Key Laboratory of Mesoscopic Chemistry (Ministry of Education), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People’s Republic of China
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Lioi SB, Wang X, Islam MR, Danoff EJ, English DS. Catanionic surfactant vesicles for electrostatic molecular sequestration and separation. Phys Chem Chem Phys 2009; 11:9315-25. [DOI: 10.1039/b908523h] [Citation(s) in RCA: 47] [Impact Index Per Article: 2.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
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