Polymeric dibromomaleimides as extremely efficient disulfide bridging bioconjugation and pegylation agents

Journal of the American Chemical Society

Volumn 134, Issue 3, 2012, Pages 1847-1852

  Jones, Mathew W ^a   Strickland, Rachel A ^a   Schumacher, Felix F ^b   Caddick, Stephen ^b   Baker, James R ^b   Gibson, Matthew I ^a   Haddleton, David M ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIO-CONJUGATION; BUFFERED SOLUTIONS; CLICK REACTION; CLOUD POINTS; COMB POLYMERS; DISULFIDE BONDS; DISULFIDE BRIDGE; DISULFIDE REDUCTION; FUNCTIONALIZED; INDIRECT ROUTES; MALDI-TOF; MALEIMIDES; METHACRYLIC MONOMERS; METHOXY POLY(ETHYLENE GLYCOL); MITSUNOBU REACTIONS; PEGYLATION; PEPTIDE CONFORMATION; POLYMERIZATION INITIATORS; SALMON CALCITONIN; SINGLE PRODUCT; SITE-SPECIFIC; TERTIARY STRUCTURES; TRIS(2-CARBOXYETHYL) PHOSPHINE;

ACETYLENE; BROMINE COMPOUNDS; COVALENT BONDS; ETHYLENE; GLYCOLS; PEPTIDES; PHOSPHORUS COMPOUNDS; POLYETHYLENE GLYCOLS; POLYMERIZATION; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

FUNCTIONAL POLYMERS;

2,3 DIBROMOMALEIMIDE; ALKYNE DERIVATIVE; ANILINE; AZIDE; BROMINE DERIVATIVE; BUFFER; DIBROMOMALEIMIDE DERIVATIVE; DISULFIDE; MACROGOL; MALEIMIDE DERIVATIVE; MONOMER; PEPTIDE DERIVATIVE; POLYMER; POLYMETHACRYLIC ACID DERIVATIVE; SALCATONIN; THIOL DERIVATIVE; TRIS(2 CARBOXYETHYL)PHOSPHINE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CHEMICAL REACTION; CONJUGATION; DISULFIDE BOND; DRUG CONJUGATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MITSUNOBU REACTION; PEGYLATION; PH; POLYMERIZATION; PROTEIN CONFORMATION; PROTEIN STRUCTURE; REACTION TIME; REDUCTION KINETICS; SOLUBILITY; STOICHIOMETRY; SUBSTITUTION REACTION;

ANIMALS; CALCITONIN; DISULFIDES; HALOGENATION; MALEIMIDES; MODELS, MOLECULAR; POLYETHYLENE GLYCOLS; POLYMERS;

EID: 84856278455     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210335f     Document Type: Article

References (56)

1. Kiick, K. L. Science 2007, 317, 1182
2. Liu, S.; Maheshwari, R.; Kiick, K. L. Macromolecules 2009, 42, 3
3. Wirth, P.; Souppe, J.; Tritsch, D.; Biellmann, J. F. Bioorg. Chem. 1991, 19, 133
4. Kinstler, O. B.; Brems, D. N.; Lauren, S. L.; Paige, A. G.; Hamburger, J. B.; Treuheit, M. J. Pharm. Res. 1996, 13, 996
5. Caliceti, P.; Veronese, F. M. Adv. Drug Delivery Rev. 2003, 55, 1261
6. Ryan, S. M.; Mantovani, G.; Wang, X. X.; Haddleton, D. M.; Brayden, D. J. Expert Opin. Drug Del. 2008, 5, 371
7. Alconcel, S. N. S.; Baas, A. S.; Maynard, H. D. Polym. Chem 2011, 2, 1442
8. Bulmus, V. Polym. Chem. 2011, 2, 1463
9. Le Droumaguet, B.; Nicolas, J. Polym. Chem. 2010, 1, 563
10. Velonia, K. Polym. Chem. 2010, 1, 944
11. Magnusson, J. P.; Saeed, A. O.; Fernandez-Trillo, F.; Alexander, C. Polym. Chem. 2011, 2, 48
12. Smith, D.; Holley, A. C.; McCormick, C. L. Polym. Chem 2011, 2, 1428
13. Lutz, J.-F.; Boerner, H. G. Prog. Polym. Sci. 2008, 33, 1
14. Krishna, O. D.; Kiick, K. L. Pept. Sci. 2010, 94, 32
15. Top, A.; Kiick, K. L. Adv. Drug Delivery Rev. 2010, 62, 1530
16. Canalle, L. A.; Lowik, D. W. P. M; van Hest, J. C. M. Chem. Soc. Rev. 2010, 39, 329
17. Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U. S. Angew. Chem., Int. Ed. 2010, 49, 6288
18. Joralemon, M. J.; McRae, S.; Emrick, T. Chem. Commun. 2010, 46, 1377
19. Nicolas, J.; Mantovani, G.; Haddleton, D. M. Macromol. Rapid Commun. 2007, 28, 1083
20. Lecolley, F.; Tao, L.; Mantovani, G.; Durkin, I.; Lautru, S.; Haddleton, D. M. Chem. Commun. 2004, 2026
21. Samanta, D.; McRae, S.; Cooper, B.; Hu, Y. X.; Emrick, T. Biomacromolecules 2008, 9, 2891
22. Zarafshani, Z.; Obata, T.; Lutz, J. F. Biomacromolecules 2010, 11, 2130
23. 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
24. Geng, J.; Mantovani, G.; Tao, L.; Nicolas, J.; Chen, G. J.; Wallis, R.; Mitchell, D. A.; Johnson, B. R. G.; Evans, S. D.; Haddleton, D. M. J. Am. Chem. Soc. 2007, 129, 15156
25. Da Pieve, C.; Williams, P.; Haddleton, D. M.; Palmer, R. M. J.; Missailidis, S. Bioconjugate Chem. 2010, 21, 169
26. Heredia, K. L.; Tao, L.; Grover, G. N.; Maynard, H. D. Polym. Chem. 2010, 1, 168
27. Li, M.; De, P.; Li, H. M.; Sumerlin, B. S. Polym. Chem. 2010, 1, 854
28. Bontempo, D.; Heredia, K. L.; Fish, B. A.; Maynard, H. D. J. Am. Chem. Soc. 2004, 126, 15372
29. Heredia, K. L.; Nguyen, T. H.; Chang, C. W.; Bulmus, V.; Davis, T. P.; Maynard, H. D. Chem. Commun. 2008, 3245
30. Liu, J.; Bulmus, V.; Herlambang, D. L.; Barner-Kowollik, C.; Stenzel, M. H.; Davis, T. P. Angew. Chem., Int. Ed. 2007, 46, 3099
31. Jones, M. W.; Mantovani, G.; Ryan, S. M.; Wang, X. X.; Brayden, D. J.; Haddleton, D. M. Chem. Commun. 2009, 5272
32. Jones, M. W.; Gibson, M. I.; Mantovani, G.; Haddleton, D. M. Polym. Chem. 2011, 2, 572
33. Bourne, T.; Fossati, G.; Nesbitt, A. BioDrugs 2008, 22, 331
34. Lu, Y.; Harding, S. E.; Turner, A.; Smith, B.; Athwal, D. S.; Grossmann, J. G.; Davis, K. G.; Rowe, A. J. J. Pharm. Sci. 2008, 97, 2062
35. Shaunak, S.; Godwin, A.; Choi, J.-W.; Balan, S.; Pedone, E.; Vijayarangam, D.; Heidelberger, S.; Teo, I.; Zloh, M.; Brocchini, S. Nat. Chem. Biol. 2006, 2, 312
36. Balan, S.; Choi, J.-w.; Godwin, A.; Teo, I.; Laborde, C. M.; Heidelberger, S.; Zloh, M.; Shaunak, S.; Brocchini, S. Bioconjugate Chem. 2006, 18, 61
37. Balan, S.; Choi, J.-W.; Godwin, A.; Teo, I.; Laborde, C. M.; Heidelberger, S.; Zloh, M.; Shaunak, S.; Brocchini, S. Bioconjugate Chem. 2007, 18, 61
38. Tedaldi, L. M.; Smith, M. E. B.; Nathani, R. I.; Baker, J. R. Chem. Commun. 2009, 6583
39. Smith, M. E. B.; Schumacher, F. F.; Ryan, C. P.; Tedaldi, L. M.; Papaioannou, D.; Waksman, G.; Caddick, S.; Baker, J. R. J. Am. Chem. Soc. 2010, 132, 1960
40. Schumacher, F. F.; Nobles, M.; Ryan, C. P.; Smith, M. E. B.; Tinker, A.; Caddick, S.; Baker, J. R. Bioconjugate Chem. 2011, 22, 132
41. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721
42. Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614
43. Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559
44. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661
45. Henriksen, K.; Bay-Jensen, A.-C.; Christiansen, C.; Karsdal, M. A. Expert Opin. Biol. Ther. 2010, 10, 1617
46. Walker, M. A. J. Org. Chem. 1995, 60, 5352
47. Deng, G. H.; Chen, Y. M. Macromolecules 2004, 37, 18
48. Lutz, J.-F.; Schmidt, B. V. K. J.; Pfeifer, S. Macromol. Rapid Commun. 2011, 32, 127
49. Tolstyka, Z. P.; Kopping, J. T.; Maynard, H. A. Macromolecules 2008, 41, 599
50. Gauthier, M. A.; Gibson, M. I.; Klok, H.-A. Angew. Chem., Int. Ed. 2009, 48, 48
51. Mantovani, G.; Ladmiral, V.; Tao, L.; Haddleton, D. M. Chem. Commun. 2005, 2089
52. Lutz, J.-F.; Hoth, A. Macromolecules 2006, 39, 893
53. Lutz, J.-F.; Akdemir, O.; Hoth, A. J. Am. Chem. Soc. 2006, 128, 13046
54. Lavigueur, C.; Garcia, J. G.; Hendriks, L.; Hoogenboom, R.; Cornelissen, J. J. L. M.; Nolte, R. J. M. Polym. Chem 2011, 2, 333
55. Roth, P. J.; Jochum, F. D.; Forst, F. R.; Zentel, R.; Theato, P. Macromolecules 2010, 43, 4638
56. Ryan, C. P.; Smith, M. E. B.; Schumacher, F. F.; Grohmann, D.; Papaioannou, D.; Waksman, G.; Werner, F.; Baker, J. R.; Caddick, S. Chem. Commun. 2011, 47, 5452