Synthesis and anti-HIV evaluation of hybrid-type prodrugs conjugating HIV integrase inhibitors with d4t by self-cleavable spacers containing an amino acid residue

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 22, Issue 5, 2007, Pages 608-619

  Fossey, Christine ^a   Huynh, Ngoc Trinh ^a   Vu, Anh Hoang ^a   Vidu, Anamaria ^a   Zarafu, Irina ^a   Laduree, Daniel ^a   Schmidt, Sylvie ^b   Laumond, Geraldine ^b   Aubertin, Anne Marie ^b  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

^b INSERM   (France)

Author keywords

HIV; Integrase; Nucleoside inhibitor; Reverse transcriptase

Indexed keywords

4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXY 4 OXOBUT 2 ENOIC ACID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIRETROVIRUS AGENT; METHYL N [4 (3 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYLATE; METHYL N [4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYLATE; METHYL N [4 (4 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYLATE; N [4 (3 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANINE; N [4 (3 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 2 AMINOBENZYLCARBONATE STAVUDINE; N [4 (3 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 2 AMINOPHENYLMETHANOL; N [4 (3 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 4 AMINOBENZYLCARBONATE STAVUDINE; N [4 (3 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 4 AMINOPHENYLMETHANOL; N [4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANINE; N [4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 2 AMINOBENZYLCARBONATE STAVUDINE; N [4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 2 AMINOPHENYLMETHANOL; N [4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 4 AMINOBENZYLCARBONATE STAVUDINE; N [4 (3,5 DIBENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 4 AMINOPHENYLMETHANOL; N [4 (4 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANINE; N [4 (4 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 2 AMINOBENZYLCARBONATE STAVUDINE; N [4 (4 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 2 AMINOPHENYLMETHANOL; N [4 (4 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 4 AMINOBENZYLCARBONATE STAVUDINE; N [4 (4 BENZYLOXYPHENYL) 2 HYDROXYENOL 4 OXOBUTYRYL]ALANYL 4 AMINOPHENYLMETHANOL; STAVUDINE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; NONHUMAN; PRIORITY JOURNAL; VIRUS INHIBITION;

ALANINE; ANTI-HIV AGENTS; CELLS, CULTURED; DIMERIZATION; HIV; HIV INTEGRASE INHIBITORS; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PRODRUGS; REVERSE TRANSCRIPTASE INHIBITORS; STAVUDINE;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 35348990314     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701425402     Document Type: Article

References (39)

1. De Clercq, E. (2004) J Biochem Cell Biol, 36, pp. 1800-1822.
2. De Clercq, E. (1995) J Med Chem, 38, pp. 2491-2517.
3. De Clercq, E. (2002) Nat Rev Drug Discovery, 1, pp. 13-25.
4. Imamichi, T. (2004) Curr Pharm Des, 10, pp. 4039-4053.
5. Richman, DD (2001) Nature, 410, pp. 995-1001.
6. Dayam, R. and Neamati, N. (2004) Biochemistry of HIV therapeutics. Encyclopedia of molecular cell biology and molecular medicine, pp. 155-178. Wiley-VCH, Weinheim, Germany
7. Barbaro, G., Scozzafava, A., Mastrolorenzo, A. and Supuran, CT (2005) Curr Pharm Des, 11, pp. 1805-1843.
8. Cohen, J. (2002) Science, 296, pp. 2320-2324.
9. Mocroft, A. and Lundgren, JD (2004) Antimicrob Chemother, 54, pp. 10-13.
10. Shehu-Xhilaga, M., Tachedjian, G., Crowe, SM and Kedzierska, K. (2005) Curr Med Chem, 12, pp. 1705-1719.
11. Pommier, Y. and Neamati, N. (1999) Adv Virus Res, 52, pp. 427-458.
12. Asante-Appiah, E. and Skalka, AM (1999) Adv Virus Res, 52, pp. 351-369.
13. Nair, V. (2002) Rev Med Virol, 12, pp. 179-193.
14. Hazuda, DJ and Young, SD (2004) Adv Antiviral Drug Des, 4, pp. 63-77.
15. Pommier, Y., Johnson, AA and Marchand, C. (2005) Nat Rev Drug Disc, 4, pp. 236-248.
16. Goldgur, Y., Craigie, R., Cohen, GH, Fujiwara, T., Yoshinaga, T., Fujishita, T., Sugimoto, H., Endo, T., Murai, H. and Davies, DR (1999) Proc Natl Acad Sci U.S.A, 96, pp. 13040-13043.
17. Hazuda, DJ, Felock, P., Witmer, M., Wolfe, A., Stillmock, K., Grobler, JA, Espeseth, A., Gabryelski, L., Schleif, W., Blau, C. and Miller, MD (2000) Science, 287, pp. 646-650.
18. Espeseth, AS, Felock, P., Wolfe, A., Witmer, M., Grobler, J., Anthony, N., Egbertson, M., Melamed, JY, Young, S., Hamill, T., Cole, JL and Hazuda, DJ (2000) Proc Natl Acad Sci U.S.A, 97, pp. 11244-11249.
19. Fujishita, T. and Yoshinaga, T. (1999) WO 9950245.
20. Wai, JS, Egbertson, MS, Payne, LS, Fisher, TE, Embrey, MW, Tran, LO, Melamed, JY, Langford, HM, Guare Jr, JP, Zhuang, L., Grey, VE, Vacca, JP, Holloway, MK, Naylor-Olsen, AM, Hazuda, DJ, Felock, PJ, Wolfe, AL, Stillmock, KA, Schleif, WA, Gabryelski, LJ and Young, SD (2000) J Med Chem, 43, pp. 4923-4926.
21. Grobler, JA, Stillmock, K., Witmer, M., Felock, P., Espeseth, AS, Wolfe, A., Egbertson, M., Bourgeois, M., Melamed, J., Wai, JS, Young, S., Vacca, J. and Hazuda, DJ (2002) Proc Natl Acad Sci U.S.A, 99, pp. 6661-6666.
22. Pais, GCG, Zhang, X., Marchand, C., Neamati, N., Cowansage, K., Svarovskaia, ES, Pathak, VK, Tang, Y., Nicklaus, M., Pommier, Y. and Burke Jr, TR (2002) J Med Chem, 45, pp. 3184-3194.
23. Zhang, X., Pais, GCG, Svarovskaia, ES, Marchand, C., Johnson, AA, Karki, RG, Nicklaus, MC, Pathak, VK, Pommier, Y. and Burke, TR (2003) Bioorg Med Chem Lett, 13, pp. 1215-1219.
24. Fossey, C., Zarafu, I., Ladurée, D., Schmidt, S., Laumond, G. and Aubertin, AM (2006) J Enz Inhib Med Chem
25. Cass, CE, Young, JD and Baldwin, SA (1998) Biochem Cell Biol, 76, p. 761.
26. Ralevic, V. and Burnstock, G. (1998) Pharmacol Rev, 50, p. 413.
27. Chan, TCK, Shaffer, L., Redmond, R. and Pennington, KL (1993) Biochem Pharmacol, 46, p. 273.
28. Domin, BA, Mahony, WB and Zimmerman, TP (1993) Biochem Pharmacol, 46, p. 725.
29. Mansuri, MM, Starrett, JE, Ghazzouli, I., Hitchcock, MJM, Sterzycki, RZ, Brankovan, V., Lin, T., August, EM, Prusoff, WH, Sommadossi, J. and Martin, JC (1989) J Med Chem, 32, pp. 461-466.
30. Shiragami, H., Uchida, Y. and Izaw, K. (1996) Nucleosides & Nucleotides, 15, pp. 47-58.
31. Lin, T., Schinazi, RF and Prusoff, WH (1987) Biochem Pharmacol, 36, pp. 2713-2718.
32. Balzarini, J., Kang, GJ, Dalal, M., Herdewijn, P., Broder, DeClercqE and Johns, DG (1987) Mol Pharmacol, 32, pp. 162-167.
33. Browne, MJ, Mayer, KH, Chafee, SB, Dudley, MN, Posner, MR, Steinberg, SM, Graham, KK, Geletko, SM, Zinner, SH, Denman, SL, Dunkle, LM, Kaul, S., Laren, C Mc, Skowron, G., Kontlab, NM, Kennedy, TA, Weitberg, AB and Curt, GA (1993) J Infect Dis, 167, pp. 21-29.
34. Moog, C., Wick, A., Ber, P Le, Kirn, A. and Aubertin, AM (1994) Antiviral Res, 24, pp. 275-288.
35. Mosmann, T. (1983) J Immunol Meth, 65, pp. 55-63.
36. Lefebvre, I., Perigaud, C., Pompon, A., Aubertin, AM, Girardet, JL, Kirn, A., Gosselin, G. and Imbach, JL (1995) J Med Chem, 38, pp. 3941-3950.
37. Joshi, BV, Rao, TS and Reese, CB (1992) J Chem Soc Perkin Trans, pp. 2537-2544.
38. Belleau, B. and Malek, GA (1968) J Am Chem Soc, 90, pp. 1651-1652.
39. Hay, MP, Wilson, WR and Denny, WA (2000) Tetrahedron, 56:4, pp. 645-657.