Synthesis and anti-HIV-1 integrase activity of modified dinucleotides

European Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2009, Pages 5029-5044

  Aubert, Yves ^a   Chassignol, Marcel ^a   Roig, Victoria ^a   Mbemba, Gladys ^b   Weiss, Julien ^a   Meudal, Hervé ^a   Mouscadet, Jean François ^b   Asseline, Ulysse ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

HIV 1 integrase inhibitors; Intercalator dinucleotide conjugates; Modified dinucleotides

Indexed keywords

COMPLEMENTARY DNA; DINUCLEOTIDE; HUMAN IMMUNODEFICIENCY VIRUS ANTIBODY; INTEGRASE; INTERCALATING AGENT; NUCLEOTIDE DERIVATIVE; PERYLENE; VIRUS DNA;

3' UNTRANSLATED REGION; ARTICLE; CONTROLLED STUDY; DINUCLEOTIDE REPEAT; DNA FLANKING REGION; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME SYNTHESIS; HOST CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN TISSUE; PEPTIDE MAPPING; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN STRUCTURE; PROVIRUS;

BIOLOGICAL ASSAY; DINUCLEOSIDE PHOSPHATES; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; MOLECULAR STRUCTURE; PERYLENE;

EID: 70449622763     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.09.007     Document Type: Article

References (45)

1. Katz R.A., and Skalka A.M. Annu. Rev. Biochem. 63 (1994) 133-173
2. Esposito D., and Craigie R. Adv. Virus. Res. 52 (1999) 319-333
3. Asante-Appiah E., and Skalka A.M. Adv. Virus. Res. 12 (1999) 2331-2338
4. Sinha S., and Grandgenett D.P. J. Virol. 79 (2005) 8208-8216
5. Delelis O., Carayon K., Guiot E., Leh H., Tauc P., Brochon J.-C., Mouscadet J.-F., and Deprez E. J. Biol. Chem. 283 (2008) 27838-27849
6. Pommier Y., Johnson A.A., and Marchand C. Nat. Rev. Drug. Discov. 4 (2005) 236-248
7. Gordon C.P., Griffith R., and Keller P.A. Med. Chem. 3 (2007) 199-220
8. Deng J., Dayam R., Al-Mawsawi L.Q., and Neamati N. Curr. Pharm. Des. 13 (2007) 129-141
9. Nair V., and Chi G. Rev. Med. Virol. 17 (2007) 277-295
10. Delelis O., Carayon K., Saïb A., Deprez E., and Mouscadet J.-F. Retrovirology 5 (2008) 114
11. Summa V., Petrocchi A., Bonelli F., Crescenzi B., Donghi M., Ferrara M., Fiore F., Gardelli C., Gonzales Pas O., Hazuda D.J., Jones P., Kinzel O., Laufer R., Monteagudo E., Muraglia E., Nizi E., Orvieto F., Pace P., Pescatore G., Scarpelli R., Stillmock K., Witmer M.V., and Rowley M. J. Med. Chem. 51 (2008) 5843-5855
12. Adamson S., and Freed E.O. Drug Discov. Today 13 (2008) 424-432
13. Marinello J., Marchand C., Mott B.T., Bain A., Thomas C.J., and Pommier Y. Biochemistry 47 (2008) 9345-9354
14. Shafer R.W., and Schapiro J.M. AIDS Rev. 10 (2008) 67-84
15. Lataille M., Chiarella J., and Kozal M.J. Antivir. Ther. 12 (2007) 563-570
16. Charpentier C., Karmochine M., Laureillard D., Tisserand P., Belec L., Weiss L., Si-Mohamed A., and Piketty C. HIV Medicine 9 (2008) 765-770
17. Malet I., Delelis O., Valentin M.A., Montes B., Soulié C., Wirden M., Tchertanov L., Peytavin G., Reynes J., Mouscadet J.F., Katlama C., Calvez V., and Marcelin A.G. Antimicrobial. Agents. Chemother. 52 (2008) 1351-1358
18. Mazumder A., Uchida H., Neamati N., Sunder S., Jaworsta-Maslanka M., Wickstrom E., Zeng F., Jones R.A., Mandes R.F., Chenault H.K., and Pommier Y. Mol. Pharmacol. 51 (1997) 567-575
19. Taktakishvili M., Neamati N., Pommier Y., and Nair V. Bioorg. Med. Chem. Lett. 10 (2000) 249-251
20. Taktakishvili M., Neamati N., Pommier Y., and Nair V. Bioorg. Med. Chem. Lett. 11 (2001) 1433-1435
21. Guenther S., and Nair V. Bioorg. Med. Chem. Lett. 12 (2000) 2233-2236
22. Chi G., Neamati N., and Nair V. Bioorg. Med. Chem. Lett. 14 (2004) 4815-4817
23. Froehler B.C. Tetrahedron Lett. 27 (1986) 5575-5578
24. Schaller H., Weimann G., Lerch B., and Khorana H.G. J. Am. Chem. Soc. 85 (1963) 3821-3827
25. Seela F., and Kretschmer U. J. Org. Chem. 56 (1991) 3861-3869
26. Privat E., and Asseline U. Bioconjug. Chem. 12 (2001) 757-769
27. Asseline U., Chassignol M., Draus J., Durand M., and Maurizot J.-C. Bioorg. Med. Chem. 11 (2003) 3499-3511
28. Marugg J.E., Tromp M., Kuyl-Yeheskiely E., Van der Marel G.A., and Van Boom J.H. Tetrahedron Lett. 2 (1986) 2661-2664
29. Sung W.L. Nucleic Acids Res. 9 (1981) 6139-6151
30. Roig V., and Asseline U. J. Am. Chem. Soc. 15 (2003) 4416-4417
31. Asseline U., Bonfils E., Kurfürst R., Chassignol M., Roig V., and Thuong N.T. Tetrahedron Lett. 48 (1992) 1233-1254
32. O′Sullivan M.C., and Dalrymple D.M. Tetrahedron Lett. 36 (1995) 3451-3452
33. Lerman L.S. J. Mol. Biol. 3 (1961) 18-30
34. Fesen M.R., Kohn K.W., Leteurtre F., and Pommier Y. Proc. Natl. Acad. Sci. U.S.A. 15 (1993) 2399-2403
35. Asseline U., and Thuong N.T. In: Beaucage S., Bergstrom D.E., Glick G.D., and Jones R.A. (Eds). Current protocols in nucleic acid chemistry (2000), John Wiley & Sons 4.3.1.-4.3.16
36. Morgan G.T., and Coulson E.A. J. Chem. Soc. (1929) 2203-2214
37. Asseline U., and Thuong N.T. In: Beaucage S., Bergstrom D.E., Glick G.D., and Jones R.A. (Eds). Current protocols in nucleic acid chemistry (2001), John Wiley & Sons 4.8.1-4.8.15
38. Aubert Y., and Asseline U. Org. Biomol. Chem. 2 (2004) 3496-3503
39. Asseline U., and Cheng E. Tetrahedron Lett. 42 (2001) 9005-9010
40. Aubert Y., Bourgerie S., Meunier L., Mayer R., Roche A.-C., Monsigny M., Thuong N.T., and Asseline U. Nucleic Acids Res. 28 (2000) 818-825
41. Atkinson T., and Smith M. In: Gait M.J. (Ed). Oligonucleotides synthesis: a practical approach (1984), IRL Press, Oxford 35-81
42. Saison-Behmoaras T., Tocqué B., Rey I., Chassignol M., Thuong N.T., and Hélène C. EMBO. J. 10 (1991) 1111-1118
43. Jenny T.F., Schneider K.C., and Benner S.A. Nucleosides Nucleotides 11 (1992) 1257-1261
44. Cantor C.R., Warshaw M.M., and Shapiro H. Biopolymers 9 (1970) 1059-1079
45. Leh H., Brodin P., Bischerour J., Deprez E., Tauc P., Brochon J.C., LeCam E., Coulaud E., Auclair C., and Mouscadet J.F. Biochemistry 39 (2000) 9285-9294