Synthesis, in vitro and in vivo release kinetics, and anti-HIV activity of A sustained-release prodrug (mPEG-AZT) of 3′-azido-3′-deoxythymidine (AZT, Zidovudine)

ChemMedChem

Volumn 5, Issue 11, 2010, Pages 1893-1898

  Li, Wenjun ^a   Chang, Yu ^a   Zhan, Peng ^a   Zhang, Na ^a   Liu, Xinyong ^a   Pannecouque, Christophe ^b   De Clercq, Erik ^b  

^a SHANDONG UNIVERSITY   (China)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

conjugation; HIV; pharmacokinetics; poly(ethylene glycol); prodrugs; zidovudine

Indexed keywords

MACROGOL; PRODRUG; ZIDOVUDINE;

ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG HALF LIFE; DRUG RELEASE; DRUG RETENTION; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; MALE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SUSTAINED DRUG RELEASE;

ADMINISTRATION, ORAL; ANIMALS; ANTI-HIV AGENTS; HIV INFECTIONS; MICE; POLYETHYLENE GLYCOLS; PRODRUGS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; ZIDOVUDINE;

EID: 78349234664     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000352     Document Type: Article

References (41)

1. G. D′Andrea, F. Brisdelli, A. Bozzi, Curr. Clin. Pharmacol. 2008, 3, 20 - 37.
2. E. De Clercq, J. Clin. Virol. 2004, 30, 115 - 133.
3. N. Schlienger, S. Peyrottes, T. Kassem, J. L. Imbach, G. Gosselin, A. M. Aubertin, C. Périgaud, J. Med. Chem. 2000, 43, 4570 - 4574.
4. P. Vlieghe, F. Bihel, T. Clerc, C. Pannecouque, M. Witvrouw, E. De Clercq, J. P. Salles, J. C. Chermann, J. L. Kraus, J. Med. Chem. 2001, 44, 777 - 786.
5. M. D. Lynx, E. E. McKee, Biochem. Pharmacol. 2006, 72, 239 - 243.
6. T. Mavromoustakos, T. Calogeropoulou, M. Koufaki, A. Kolocouris, I. Daliani, C. Demetzos, Z. Meng, A. Makriyannis, J. Balzarini, E. De Clercq, J. Med. Chem. 2001, 44, 1702 '1709.
7. D. Wu, S. Ji, Y. Wu, Y. Ju, Y. Zhao, Bioorg. Med. Chem. Lett. 2007, 17, 2983 - 2986.
8. S. X. Jin, D. Z. Bi, J. Wang, Y. Z. Wang, H. G. Hu, Y. H. Deng, Pharmazie 2005, 60, 840 - 843.
9. V. V. Iyer, G. W. Griesgraber, M. R. Radmer, E. J. McIntee, C. R. Wagner, J. Med. Chem. 2000, 43, 2266 - 2274.
10. J. Nyce, S. Leonard, D. Canupp, S. Schulz, S. Wong, Proc. Natl. Acad. Sci. USA 1993, 90, 2960 - 2964.
11. J. Ren, R. M. Esnouf, A. L. Hopkins, E. Y. Jones, I. Kirby, J. Keeling, C. K. Ross, B. A. Larder, D. I. Stuart, D. K. Stammers, Proc. Natl. Acad. Sci. USA 1998, 95, 9518 - 9523.
12. L. M. Mansky, L. C. Bernard, J. Virol. 2000, 74, 9532 - 9539.
13. S. Wannachaiyasit, P. Chanvorachote, U. Nimmannit, AAPS. PharmSciTech. 2008, 9, 840 - 850.
14. F. Bonina, C. Puglia, M. G. Rimolib, L. Avalloneb, E. Abignenteb, G. Boatto, M. Nieddu, R. Meli, M. Amorena, P. Caprariis, Eur. J. Pharm. Sci. 2002, 16, 167 '174.
15. G. Giammona, G. Cavallaro, G. Fontana, G. Pitarresi, B. Carlisi, J. Controlled Release 1998, 54, 321 '331.
16. P. Vlieghe, T. Clerc, C. Pannecouque, M. Witvrouw, E. De Clercq, J. P. Salles, J. L. Kraus, J. Med. Chem. 2002, 45, 1275 - 1283.
17. H. Tamamura, A. Omagari, K. Hiramatsu, T. Kanamoto, K. Gotoh, K. Kanbara, N. Yamamoto, H. Nakashima, A. Otaka, N. Fujii, Bioorg. Med. Chem. 2001, 9, 2179 '2187.
18. Y. Chung, H. Cho, Arch. Pharmacal Res. 2004, 27, 878 - 883.
19. F. M. Veronese, G. Pasut, Drug Discovery Today 2005, 10, 1451 - 1458.
20. T. Zhu, J. Gu, K. Yu, J. Lucas, P. Cai, R. Tsao, Y. Gong, F. Li, I. Chaudhary, P. Desai, M. Ruppen, M. Fawzi, J. Gibbons, S. Ayral-Kaloustian, J. Skotnicki, T. Mansour, A. Zask, J. Med. Chem. 2006, 49, 1373 - 1378.
21. C. S. Fishburn, J. Pharm. Sci. 2008, 97, 4167 - 4183.
22. C. Monfardini, F. M. Veronese, Bioconjug. Chem. 1998, 9, 418 - 450.
23. S. Y. Chae, C. H. Jin, H. J. Shin, Y. S. Youn, S. Lee, K. C. Lee, Bioconjugate Chem. 2008, 19, 334 - 341.
24. Y. Chang, X. Y. Liu, CN101066459, 2007.
25. F. K. Hurtado, D. R. Nogueira, F. Bortolini, L. M. Da Silva, E. Zimmermann, N. J. E. Souza, J. De Melo, C. M. Bueno Rolim, J. Liq. Chromatogr. 2007, 30, 1981 - 1989.
26. Z. You, H. Y. Lee, Nucleosides, Nucleotides Nucleic Acids 2006, 25, 37 - 54.
27. I. Chung, C.-K. Lee, C.-S. Ha, W.-J. Cho, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 295 - 303.
28. S. Zalipsky, C. Gilon, A. Zilkha, Eur. Polym. J. 1983, 19, 1177 - 1183.
29. N. D. Eddington, P. Marroum, R. Uppoor, A. Hussain, L. Augsburger, Pharm. Res. 1998, 15, 466 - 473.
30. T. Imai, C. Kawasaki, T. Nishiyama, M. Otagiri, Pharmazie 2000, 55, 218 - 222.
31. H. L. Lin, S. Y. Lin, Y. K. Lin, H. O. Ho, Y. W. Lo, M. T. Sheu, Eur. J. Pharm. Biopharm. 2008, 70, 289 - 301.
32. H. K. Choi, M. K. Chun, S. H. Lee, M. H. Jang, H. D. Kim, C. S. Jung, S. Y. Oh, Int. J. Pharm. 2007, 341, 50 - 57.
33. C. Manoharan, J. Singh, J. Pharm. Sci. 2009, 98, 4237 - 4250.
34. Y. J. Zhao, W. Wei, Z. G. Su, G. H. Ma, Int. J. Pharm. 2009, 379, 90 - 99.
35. A. L. Villard, G. Coussot, I. Lefebvre, P. Augustijns, A. M. Aubertin, G. Gosselin, S. Peyrottes, C. Perigaud, Bioorg. Med. Chem. 2008, 16, 7321 - 7329.
36. S. Penugonda, A. Kumar, H. K. Agarwal, K. Parang, R. Mehvar, J. Pharm. Sci. 2008, 97, 2649 - 2664.
37. H. Z. Liu, Y. G. Wang, F. Han, H. Yao, S. M. Li, J. Pharm. Sci. 2007, 96, 3000 - 3009.
38. R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, E. De Clercq, J. Virol. Methods 1988, 20, 309 - 321.
39. C. Pannecouque, D. Daelemans, E. De Clercq, Nat. Protoc. 2008, 3, 427 - 434.
40. Y. Lin, X. Liu, R. Yan, J. Li, C. Pannecouque, M. Witvrouw, E. De Clercq, Bioorg. Med. Chem. 2008, 16, 157 - 163.
41. A. Dahan, R. Duvdevani, E. Dvir, A. Elmann, A. Hoffman, J. Controlled Release 2007, 119, 86 - 93.