Azide-reactive liposome for chemoselective and biocompatible liposomal surface functionalization and glyco-liposomal microarray fabrication

Langmuir

Volumn 27, Issue 21, 2011, Pages 13097-13103

  Ma, Yong ^a   Zhang, Hailong ^a   Gruzdys, Valentinas ^a   Sun, Xue Long ^a  

^a CLEVELAND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMEDICAL APPLICATIONS; CARBOHYDRATE-PROTEIN INTERACTIONS; CHEMOSELECTIVE; FLUORESCENCE IMAGING; GLASS SLIDES; LIPOSOMAL SURFACE; PROTEIN BINDING; ROOM TEMPERATURE; STAUDINGER LIGATION; STREPTAVIDIN; TRIPHENYL PHOSPHINES;

BIOCHEMISTRY; CARBOHYDRATES; COENZYMES; GLASS; LIPOSOMES; MEDICAL APPLICATIONS; PHOSPHOLIPIDS; PROTEINS;

FABRICATION;

AZIDE; BIOMATERIAL; BIOMIMETIC MATERIAL; CARBOHYDRATE; GLASS; LIPOSOME; ORGANOPHOSPHORUS COMPOUND; TRIPHENYLPHOSPHINE;

ARTICLE; BIOTINYLATION; CHEMISTRY; ENZYME SPECIFICITY; METHODOLOGY; MICROARRAY ANALYSIS; MICROTECHNOLOGY; PRINTING; SURFACE PROPERTY;

AZIDES; BIOMIMETIC MATERIALS; BIOTINYLATION; CARBOHYDRATES; COATED MATERIALS, BIOCOMPATIBLE; GLASS; LIPOSOMES; MICROARRAY ANALYSIS; MICROTECHNOLOGY; ORGANOPHOSPHORUS COMPOUNDS; PRINTING; SUBSTRATE SPECIFICITY; SURFACE PROPERTIES;

EID: 80054943495     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la2032434     Document Type: Article

References (38)

1. Christensen, S. M.; Stamou, D. Surface-based lipid vesicle reactor systems: fabrication and applications Soft Matter 2007, 3, 828-836 (Pubitemid 46946205)
2. Torchilin, P. V. Recent advances with liposomes as pharmaceutical carriers Nat. Rev. Drug Discovery 2005, 4, 145-160
3. Zhang, Y. X.; Aimoto, S.; Lu, L.; Yang, Q.; Lundahl, P. Immobilized liposome chromatography for analysis of interactions between lipid bilayers and peptides Anal. Biochem. 1995, 229, 291-298
4. Ngo, A. T.; Karam, P.; Fuller, E.; Burger, M.; Cosa, G. Liposome encapsulation of conjugated polyelectrolytes: toward a liposome beacon J. Am. Chem. Soc. 2008, 130, 457-459 (Pubitemid 351455556)
5. Jung, S. L.; Shumaker-Parry, S. J.; Campbell, T. C.; Yee, S. S.; Gelb, H. M. Quantification of tight binding to surface-immobilized phospholipid vesicles using surface plasmon resonance: binding constant of phospholipase A2 J. Am. Chem. Soc. 2000, 122, 4177-4184 (Pubitemid 30304852)
6. Brochu, H.; Polidori, A.; Pucci, B.; Vermette, P. Drug delivery systems using immobilized intact liposomes: a comparative and critical review Curr. Drug Delivery 2004, 1, 299-312
7. Stamou, D.; Duschl, C.; Delamarche, E.; Vogel, H. Single vesicle positioning through template-guided self-assembly Angew. Chem., Int. Ed. 2003, 42, 5580-5583
8. Segota, S.; Tezak, D. Spontaneous formation of vesicles Adv. Colloid Interface Sci. 2006, 121, 51-75 (Pubitemid 44403910)
9. Nobs, L.; Buchegger, F.; Gurny, R.; Allemann, E. Current methods for attaching targeting ligands to liposomes and nanoparticles J. Pharm. Sci. 2004, 93, 1980-1992 (Pubitemid 39045480)
10. Kung, V. T.; Redemann, C. T. Synthesis of carboxyacyl derivatives of phosphatidylethanolamine and use as an efficient method for conjugation of protein to liposomes Biochim. Biophys. Acta 1986, 862, 435-439
11. Schelte, P.; Boeckler, C.; Frisch, B.; Schuber, F. Differential reactivity of maleimide and bromoacetyl functions with thiols: application to the preparation of liposomal piepitope constructs Bioconjugate Chem. 2000, 11, 118-123 (Pubitemid 30063352)
12. Nakano, Y.; Mori, M.; Nishinohara, S.; Takita, Y.; Naito, S.; Kato, H.; Taneichi, M.; Komuro, K.; Uchoda, T. Surface-linked liposomal antigen induces IgE-selective unresponsiveness regardless of the lipid components of liposomes Bioconjugate Chem. 2001, 12, 391-402
13. Bourel-Bonnet, L.; Pecheur, E. I.; Grandjean, C.; Blanpain, A.; Baust, T.; Melnyk, O.; Hoflack, B.; Gras-Masse, H. Anchorage of synthetic peptides onto liposomes via hydrazone and α-oxo hydrazone bonds. Preliminary functional investigations Bioconjugate Chem. 2005, 16, 450-457 (Pubitemid 40388221)
14. Saxon, E.; Bertozzi, C. R. Cell surface engineering by a modified staudinger reaction Science 2000, 287, 2007-2010 (Pubitemid 30158675)
15. Kiick, K. L.; Saxon, E.; Tirrell, D. A.; Bertozzi, C. R. Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 19-24 (Pubitemid 34060308)
16. Sun, X. L.; Stabler, C. L.; Cazalis, C. S.; Chaikof, E. L. Carbohydrate and protein immobilization onto solid surfaces by sequential Diels-Alder and azide-alkyne cycloadditions Bioconjugate Chem. 2006, 17, 52-57 (Pubitemid 43157584)
17. Link, A. J.; Tirrell, D. A. Cell surface labeling of Escherichia coli via copper (I)-catalyzed [3 + 2] cycloaddition J. Am. Chem. Soc. 2003, 125, 11164-11165 (Pubitemid 37108030)
18. Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Berozzi, C. R. Second-generation difluorinated cyclooctynes for copper-free click chemistry J. Am. Chem. Soc. 2008, 130, 11486-11493
19. Dieterich, D. C.; Link, A. J.; Graumann, J.; Tirrell, D. A.; Schuman, E. M. Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT) Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 9482-9487 (Pubitemid 43955851)
20. Strable, E.; Prasuhn, D. E.; Udit, A. K.; Brown, S.; Link, A. J.; Ngo, J. T.; Lander, G.; Quispe, J.; Potter, C. S.; Carragher, B.; Tirrell, D. A.; Finn, M. G. Unnatural amino acid incorporation into virus-like particles Bioconjugate Chem. 2008, 19, 866-875 (Pubitemid 351614542)
21. Dube, D. H.; Bertozzi, C. R. Metabolic oligosaccharide engineering as a tool for glycobiology Curr. Opin. Chem. Biol. 2003, 7, 616-625 (Pubitemid 37315799)
22. Chin, J. W.; Cropp, T. A.; Anderson, J. C.; Mukherji, M.; Zhang, Z.; Schultz, P. G. An expanded eukaryotic genetic code Science 2003, 301, 964-967 (Pubitemid 36994808)
23. Kho, Y.; Kim, S. C.; Jiang, C.; Barma, D.; Kwon, S. W.; Cheng, J.; Jaunbergs, J.; Weinbaum, C.; Tamanoi, F.; Falck, J.; Zhao, Y. A tagging-via-substrate technology for detection and proteomics of farnesylated proteins Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12479-12484 (Pubitemid 39122049)
24. Weller, R. L.; Rajski, S. R. DNA methyltransferase-moderated click chemistry Org. Lett. 2005, 7, 2141-2144 (Pubitemid 40826069)
25. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition J. Am. Chem. Soc. 2003, 125, 3192-3193 (Pubitemid 36512443)
26. Hassane, S. F.; Frisch, B.; Schuber, F. Targeted liposomes: convenient coupling of ligands to preformed vesicles using "click chemistry Bioconjugate Chem. 2006, 17, 849-854 (Pubitemid 43794397)
27. Link, A. J.; Vink, M. K. S.; Agard, N. J.; Prescher, J. A.; Bertozzi, C. R.; Tirrell, D. A. Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10180-10185 (Pubitemid 44051140)
28. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. A Strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems J. Am. Chem. Soc. 2004, 126, 15046-15047 (Pubitemid 39557262)
29. Ornelas, C.; Broichhagen, J.; Weck, M. Strain-promoted alkyne azide cycloaddition for the functionalization of poly(amide)-based dendrons and dendrimers J. Am. Chem. Soc. 2010, 132, 3923-3931
30. Prescher, J. A.; Dube, D. H.; Bertozzi, C. R. Chemical remodelling of cell surfaces in living animals Nature 2004, 430, 873-877 (Pubitemid 39119211)
31. Lin, F. L.; Hoyt, H. M.; Van Halbeek, H.; Bergman, R. G.; Bertozzi, C. R. Mechanistic investigation of the Staudinger ligation J. Am. Chem. Soc. 2005, 127, 2686-2695 (Pubitemid 40327832)
32. Zhang, H. L.; Ma, Y.; Sun, X.-L. Chemically-selective surface glyco-functionalization of liposomes through Staudinger ligation Chem. Commun. 2009, 3032-3034
33. Losey, E. A.; Smith, M. D.; Mengm, M.; Best, M. D. Microplate-based analysis of protein membrane binding interactions via immobilization of whole liposomes containing a biotinylated anchor Bioconjugate Chem 2009, 20, 376-383
34. Vermette, P.; Griesser, J. H.; Kambouris, P.; Meagher, L. Characterization of surface-immobilized layers of intact liposomes Biomacromolecules 2004, 5, 1496-1502 (Pubitemid 39089755)
35. Städler, B.; Falconnet, D.; Pfeiffer, I.; Höök, F.; Vörös, J. Micropatterning of DNA-tagged vesicles Langmuir 2004, 20, 11348-11354 (Pubitemid 40049604)
36. Städler, B.; Bally, M.; Grieshaber, D.; Vörös, J. Creation of a functional heterogeneous vesicle array via DNA controlled surface sorting onto a spotted microarray Biointerphases 2006, 142-145
37. Pfeiffer, I.; Höök, F. Bivalent cholesterol-based coupling of oligonucletides to lipid membrane assemblies J. Am. Chem. Soc. 2004, 126, 10224-10225 (Pubitemid 39100758)
38. Sun, X.-L.; Grande, D.; Baskaran, S.; Chaikof, E. L. Glycosaminoglycan- mimetic biomaterials 4: synthesis of sulfated lactose-based glycopolymers that exhibit anticoagulant activity Biomacromolecules 2002, 3, 1065-1070