New method for site-specific modification of liposomes with proteins using sortase a-mediated transpeptidation

Bioconjugate Chemistry

Volumn 23, Issue 3, 2012, Pages 650-655

  Guo, Xueqing ^a   Wu, Zhimeng ^a   Guo, Zhongwu ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE; PHOSPHOLIPIDS; PROTEINS;

C-TERMINUS; DIGLYCINE; ENHANCED GREEN FLUORESCENT PROTEIN; ENZYMATIC REACTION; SITE-SPECIFIC MODIFICATIONS; SORTASE; SORTASE A; TRANSPEPTIDATION REACTIONS;

LIPOSOMES;

DIGLYCINE; ENHANCED GREEN FLUORESCENT PROTEIN; LIPOSOME; PHOSPHOLIPID; SORTASE; SORTASE A; UNCLASSIFIED DRUG;

ARTICLE; ENZYME MECHANISM; ENZYME SUBSTRATE; PROTEIN MODIFICATION; PROTEIN MOTIF;

EID: 84858715052     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200694t     Document Type: Article

References (27)

1. Allen, T. M. and Cullis, P. R. (2004) Drug delivery systems: Entering the mainstream Science 303, 1818-1822 (Pubitemid 38374867)
2. Torchilin, V. P. (2005) Recent advances with liposomes as pharmaceutical carriers Nat. Rev. Drug Discovery 4, 145-160 (Pubitemid 40282557)
3. Gurny, R., Nobs, L., Buchegger, F., and Allemann, E. (2004) Current methods for attaching targeting ligands to liposomes and nanoparticles J. Pharm. Sci. 93, 1980-1992 (Pubitemid 39045480)
4. Maruyama, K., Ishida, O., Tanahashi, H., Iwatsuru, M., Sasaki, K., Eriguchi, M., and Yanagie, H. (2001) Liposomes bearing polyethyleneglycol- coupled transferrin with intracellular targeting property to the solid tumors in vivo Pharm. Res. 18, 1042-1048 (Pubitemid 32799953)
5. Martin, F. J., Hubbell, W. L., and Papahadjopoulos, D. (1981) Immunospecific targeting of liposomes to cells: a novel and efficient method for covalent attachment of Fab' fragments via disulfide bonds Biochemistry 20, 4229-4238
6. Hansen, C. B., Kao, G. Y., Moase, E. H., Zalipsky, S., and Allen, T. M. (1995) Attachment of antibodies to sterically stabilized liposomes: evaluation, comparison and optimization of coupling procedures Biochim. Biophys. Acta 1239, 133-144
7. Crosasso, P., Brusa, P., Dosio, F., Arpicco, S., Pacchioni, D., Schuber, F., and Cattel, L. (1997) Antitumoral activity of liposomes and immunoliposomes containing 5-fluorouridine prodrugs J. Pharm. Sci. 86, 832-839 (Pubitemid 27297496)
8. Ansell, S. M., Tardi, P. G., and Buchkowsky, S. S. (1996) 3-(2-Pyridyldithio)propionic acid hydrazide as a cross-linker in the formation of liposome-antibody conjugates Bioconjugate Chem. 7, 490-496 (Pubitemid 26312140)
9. Fleiner, M., Benzinger, P., Fichert, T., and Massing, U. (2001) Studies on protein-liposome coupling using novel thiol-reactive coupling lipids: Influence of spacer length and polarity Bioconjugate Chem. 12, 470-475 (Pubitemid 32696219)
10. Takasaki, J. and Ansell, S. M. (2006) Micelles as intermediates in the preparation of protein-liposome conjugates Bioconjugate Chem. 17, 438-450
11. Torchilin, V. P., Khaw, B. A., Smirnov, V. N., and Haber, E. (1979) Preservation of antimyosin antibody-activity after covalent coupling to liposomes Biochem. Bioph. Res. Commun. 89, 1114-1119
12. Hassane, F. S., Frisch, B., and Schuber, F. (2006) Targeted liposomes: Convenient coupling of ligands to preformed vesicles using "click chemistry" Bioconjugate Chem. 17, 849-854 (Pubitemid 43794397)
13. Sun, X. L., Zhang, H. L., and Ma, Y. (2009) Chemically-selective surface glyco-functionalization of liposomes through Staudinger ligation Chem. Commun. 3032-3034
14. Sun, X. L., Ma, Y., and Zhang, H. L. (2010) Surface-bound cytomimetic assembly based on chemoselective and biocompatible immobilization and further modification of intact liposome Bioconjugate Chem. 21, 1994-1999
15. Reulen, S. W. A., Brusselaars, W. W. T., Langereis, S., Mulder, W. J. M., Breurken, M., and Merkx, M. (2007) Protein-liposome conjugates using cysteine-lipids and native chemical ligation Bioconjugate Chem. 18, 590-596 (Pubitemid 46493534)
16. Reulen, S. W. A. and Merkx, M. (2010) Exchange kinetics of protein-functionalized micelles and liposomes studied by forster resonance energy transfer Bioconjugate Chem. 21, 860-866
17. Chu, N. K., Olschewski, D., Seidel, R., Winklhofer, K. F., Tatzelt, J., Engelhard, M., and Becker, C. F. W. (2010) Protein immobilization on liposomes and lipid-coated nanoparticles by protein trans-splicing J. Pept. Sci. 16, 582-588
18. Mazmanian, S. K., Liu, G., Ton-That, H., and Schneewind, O. (1999) Staphylococcus aureus sortase, an enzyme that anchors surface proteins to the cell wall Science 285, 760-763
19. Mazmanian, S. K., Ton-That, H., and Schneewind, O. (2001) Sortase-catalysed anchoring of surface proteins to the cell wall of Staphylococcus aureus Mol. Microbiol. 40, 1049-1057 (Pubitemid 32574974)
20. Ilangovan, U., Ton-That, H., Iwahara, J., Schneewind, O., and Clubb, R. T. (2001) Structure of sortase, the transpeptidase that anchors proteins to the cell wall of Staphylococcus aureus Proc Natl Acad Sci U S A 98, 6056-6061 (Pubitemid 32488192)
21. Popp, M. W.-L. and Ploegh, H. L. (2011) Making and breaking peptide bonds: protein engineering using sortase Angew. Chem., Int. Ed. 50, 5024-5032
22. Proft, T. (2010) Sortase-mediated protein ligation: an emerging biotechnology tool for protein modification and immobilisation Biotechnol. Lett. 32, 1-10
23. Tsukiji, S. and Nagamune, T. (2009) Sortase-mediated ligation: a gift from Gram-positive bacteria to protein engineering ChemBioChem 10, 787-798
24. Wu, Z. and Guo, Z. (2012) Sortase-mediated transpeptidation for site-specific modification of peptides, glycopeptides, and proteins J. Carbohydr. Chem. 31, 48-66
25. Wu, Z., Guo, X., Wang, Q., Swarts, B. M., and Guo, Z. (2010) Sortase A-catalyzed transpeptidation of glycosylphosphatidylinositol derivatives for chemoenzymatic synthesis of GPI-anchored proteins J. Am. Chem. Soc. 132, 1567-1571
26. Guo, X., Wang, Q., Swarts, B. M., and Guo, Z. (2009) Sortase-catalyzed peptide-glycosylphosphatidylinositol analog ligation J. Am. Chem. Soc. 131, 9878-9879
27. Strijkers, G. J., Mulder, W. J., van Heeswijk, R. B., Frederik, P. M., Bomans, P., Magusin, P. C., and Nicolay, K. (2005) Relaxivity of liposomal paramagnetic MRI contrast agents Magma 18, 186-192 (Pubitemid 41428270)