Direct peptide bioconjugation/PEGylation at tyrosine with linear and branched polymeric diazonium salts

Journal of the American Chemical Society

Volumn 134, Issue 17, 2012, Pages 7406-7413

  Jones, Mathew W ^a   Mantovani, Giuseppe ^b   Blindauer, Claudia A ^a   Ryan, Sinead M ^c   Wang, Xuexuan ^c   Brayden, David J ^c   Haddleton, David M ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^c UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ATOM TRANSFER RADICAL POLYMERIZATION; FREE RADICAL REACTIONS; MOTION PICTURE EXPERTS GROUP STANDARDS; PEPTIDES; POLYETHYLENE GLYCOLS;

DIAZONIUM SALTS; HUMAN BREAST CANCER CELLS; INTRACELLULAR CAMP; MONOMETHOXY POLY(ETHYLENE GLYCOL); REACTION CONDITIONS; SALMON CALCITONIN; SITE-SPECIFICITY; TYROSINE RESIDUES;

AMINO ACIDS;

AMINE; CALCITONIN RECEPTOR; CALCIUM; CYCLIC AMP; DIAZONIUM COMPOUND; HISTIDINE; LEUCINE ENKEPHALIN; LYSINE; MACROGOL; MACROGOL 2000; METHACRYLIC ACID DERIVATIVE; PEPTIDE; POLYMER; SALCATONIN; TYROSINE;

AMINO TERMINAL SEQUENCE; ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; BLOOD LEVEL; BREAST CANCER; CHEMICAL STRUCTURE; CONJUGATE; CONJUGATION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PH; RAT; REACTION ANALYSIS; STOICHIOMETRY;

EID: 84860827170     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211855q     Document Type: Article

References (58)

1. Duncan, R. Nat. Rev. Drug Discov. 2003, 2, 347
2. Fishburn, C. S. J. Pharm. Sci. 2008, 97, 4167
3. Jain, R. K.; Stylianopoulos, T. Nat. Rev. Clin. Oncol. 2010, 7, 653
4. Aghemo, A.; Rumi, M. G.; Colombo, M. Nat. Rev. Gastroenterol. Hepatol. 2010, 7, 485
5. Veronese, F. M. Biomaterials 2001, 22, 405
6. Roberts, M. J.; Bentley, M. D.; Harris, J. M. Adv. Drug Delivery Rev. 2002, 54, 459
7. Brocchini, S.; Balan, S.; Godwin, A.; Choi, J.-W.; Zloh, M.; Shaunak, S. Nat. Protocols 2006, 1, 2241
8. Zloh, M.; Shaunak, S.; Balan, S.; Brocchini, S. Nat. Protocols 2007, 2, 1070
9. Espuna, G.; Arsequell, G.; Valencia, G.; Barluenga, J.; Perez, M.; González, J. M. Chem. Commun. 2000, 1307
10. Vilaro, M.; Arsequell, G.; Valencia, G.; Ballesteros, A.; Barluenga, J. Org. Lett. 2008, 10, 3243
11. Ban, H.; Gavrilyuk, J.; Barbas, C. F. J. Am. Chem. Soc. 2010, 132, 1523
12. Tilley, S. D.; Francis, M. B. J. Am. Chem. Soc. 2006, 128, 1080
13. Hooker, J. M.; Kovacs, E. W.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 3718
14. Schlick, T. L.; Ding, Z.; Kovacs, E. W.; Francis, M. B. J. Am. Chem. Soc. 2005, 127, 3718
15. Li, K.; Chen, Y.; Li, S. Q.; Huong, G. N.; Niu, Z. W.; You, S. J.; Mello, C. M.; Lu, X. B.; Wang, Q. A. Bioconjugate Chem. 2010, 21, 1369
16. Joshi, N. S.; Whitaker, L. R.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 15942
17. McFarland, J. M.; Joshi, N. S.; Francis, M. B. J. Am. Chem. Soc. 2008, 130, 7639
18. Romanini, D. W.; Francis, M. B. Bioconjugate Chem. 2008, 19, 153
19. Chemistry of the Diazonium and Diazo Groups, Part 1; Patai, S., Ed.; Wiley-Blackwell: Chichester, 1978; ISBN 0471994928.
20. Chemistry of the Diazonium and Diazo Groups, Part 2; Patai, S., Ed.; Wiley-Blackwell: Chichester, 1978; ISBN 0471994936.
21. Lecolley, F.; Tao, L.; Mantovani, G.; Durkin, I.; Lautru, S.; Haddleton, D. M. Chem. Commun. 2004, 2026
22. Mantovani, G.; Lecolley, F.; Tao, L.; Haddleton, D. M.; Clerx, J.; Cornelissen, J. J. L. M.; Velonia, K. J. Am. Chem. Soc. 2005, 127, 2966
23. Ryan, S. M.; Wang, X.; Mantovani, G.; Sayers, C. T.; Haddleton, D. M.; Brayden, D. J. J. Controlled Release 2009, 135, 51
24. Sayers, C. T.; Mantovani, G.; Ryan, S. M.; Randev, R. K.; Keiper, O.; Leszczyszyn, O. I.; Blindauer, C.; Brayden, D. J.; Haddleton, D. M. Soft Matter 2009, 5, 3038
25. Tao, L.; Mantovani, G.; Lecolley, F.; Haddleton, D. M. J. Am. Chem. Soc. 2004, 126, 13220
26. Lele, B. S.; Murata, H.; Matyjaszewski, K.; Russell, A. J. Biomacromolecules 2005, 6, 3380
27. Gao, W.; Liu, W.; Mackay, J. A.; Zalutsky, M. R.; Toone, E. J.; Chilkoti, A. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 15231
28. Magnusson, J. P.; Bersani, S.; Salmaso, S.; Alexander, C.; Caliceti, P. Bioconjugate Chem. 2010, 21, 671
29. Yasayan, G.; Saeed, A. O.; Fernandez-Trillo, F.; Allen, S.; Davies, M. C.; Jangher, A.; Paul, A.; Thurecht, K. J.; King, S. M.; Schweins, R.; Griffiths, P. C.; Magnusson, J. P.; Alexander, C. Polym. Chem. 2011, 2, 1567
30. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721
31. Wang, J.-S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614
32. Ouchi, M.; Terashima, T.; Sawamoto, M. Chem. Rev. 2009, 109, 4963
33. Pauly, H. Z. Hoppe-Seyl. Z. 1904, 42, 508
34. Howard, A. N.; Wild, F. Biochem. J. 1957, 65, 651
35. Sams, C. F.; Matthews, K. S. Biochim. Biophys. Acta 1984, 787, 61
36. Schalk, I.; Ehret-Sabatier, L.; Le Feuvre, S.; Bon, S.; Massoulie, J.; Goeldner, M. Mol. Pharmacol. 1995, 48, 1063
37. Szurdoki, F.; Szekacs, A.; Le, H. M.; Hammock, B. D. J. Agric. Food Chem. 2002, 50, 29
38. Curreli, N.; Oliva, S.; Rescigno, A.; Rinaldi, A. C.; Sollai, F.; Sanjust, E. J. Appl. Polym. Sci. 1997, 66, 1433
39. DeTraglia, M. C.; Brand, J. S.; Tometsko, A. M. Anal. Biochem. 1979, 99, 464
40. Gorecki, M.; Wilchek, M. Biochim. Biophys. Acta 1978, 532, 81
41. Wong, S. S. Reactive groups of proteins and their modifying agents. Chemistry of Protein Conjugation and Crosslinking; CRC: Boston, MA, 1991; p 8.
42. Edgcomb, S. P.; Murphy, K. P. Proteins 2002, 49, 1
43. Tracey, B. M.; Shuker, D. E. Chem. Res. Toxicol. 1997, 10, 1378
44. Chesnut, C. H.; Azria, M.; Silverman, S.; Engelhardt, M.; Olson, M.; Mindeholm, L. Osteoporosis Int. 2008, 19, 479
45. Epand, R. M.; Epand, R. F.; Stafford, A. R.; Orlowski, R. C. J. Med. Chem. 1988, 31, 1595
46. White, E. H.; Scherrer, H. Tetrahedron Lett. 1961, 2, 758
47. Southam, R. M.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1982, 597
48. Vaughan, K. Chem. Soc. Rev. 1978, 7, 377
49. Lele, B. S.; Murata, H.; Matyjaszewski, K.; Russell, A. J. Biomacromolecules 2005, 6, 3380
50. Sayers, C. T.; Mantovani, G.; Ryan, S. M.; Randev, R. K.; Keiper, O.; Leszczyszyn, O. I.; Blindauer, C.; Brayden, D. J.; Haddleton, D. M. Soft Matter 2009, 5, 3038
51. Aurora, J.; Talwar, N.; Vinayak, P. Eur. Gastroenterol. Rev. 2006, 1
52. Canevari, M.; Castagliuolo, I.; Brun, P.; Cardin, M.; Schiavon, M.; Pasut, G.; Veronese, F. M. Int. J. Pharmaceutics 2009, 368, 171
53. Kopecek, J. J. Controlled Release 1990, 11, 279
54. Kopecek, J.; Kopeckova, P.; Brondsted, H.; Rathi, R.; Rihova, B.; Yeh, P. Y.; Ikesue, K. J. Controlled Release 1992, 19, 121
55. Lee, K. C.; Moon, S. C.; Park, M. O.; Lee, J. T.; Na, D. H.; Yoo, S. D.; Lee, H. S.; DeLuca, P. P. Pharm. Res. 1999, 16, 813
56. Jain, A.; Gupta, Y.; Jain, S. K. Crit. Rev. Ther. Drug. 2006, 23, 349
57. Brown, J. P. Appl. Environ. Microbiol. 1981, 41, 1283
58. Rafii, F.; Franklin, W.; Cerniglia, C. E. Appl. Environ. Microbiol. 1990, 56, 2146