Binding modes of two novel non-nucleoside reverse transcriptase inhibitors, YM-215389 and YM-228855, to HIV type-1 reverse transcriptase

Antiviral Chemistry and Chemotherapy

Volumn 19, Issue 3, 2008, Pages 133-141

  Kodoma, Eiichi ^a   Orita, Masaya ^b   Masuda, Naoyuki ^b   Yamamoto, Osamu ^b   Fujii, Masahiro ^b   Ohgami, Tetsuro ^b   Kageyama, Shunji ^b   Ohta, Mitsuaki ^b   Hatta, Toshifumi ^b   Inoue, Hiroshi ^b   Suzuki, Hiroshi ^b   Sudo, Kenji ^b   Shimizu, Yasuaki ^b   Matsuoka, Masao ^a  

^a KYOTO UNIVERSITY   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BENZENESULFONAMIDE DERIVATIVE; EFAVIRENZ; NEVIRAPINE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THIAZOLE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; YM 215389; YM 215839; YM 228855; ZIDOVUDINE;

AMINO ACID SUBSTITUTION; ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CLONE; DRUG POTENCY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; PRIORITY JOURNAL; VIRUS RESISTANCE;

ANTI-HIV AGENTS; CELL LINE; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; REVERSE TRANSCRIPTASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; THIAZOLES;

EID: 56249140069     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. Tantillo C, Ding J, Jacobo-Molina A, et al. Locations of anti-AIDS drug binding sites and resistance mutations in the three-dimensional structure of HIV-1 reverse transcriptase. Implications for mechanisms of drug inhibition and resistance. J Mol Biol 1994; 243:369-387.
2. Mitchla Z, Sharland M. Current treatment options to prevent perinatal transmission of HIV. Expert Opin Pharmacother 2000; 1:239-248.
3. Lallemant M, Jourdain G, Le Coeur S, et al. Single-dose perinatal nevirapine plus standard zidovudine to prevent mother-to-child transmission of HIV-1 in Thailand. N Engl J Med 2004; 351:217-228.
4. Adkins JC, Noble S. Efavirenz. Drugs 1998; 56:1055-1064.
5. Staszewski S, Morales-Ramirez J, Tashima KT, et al. Efavirenz plus zidovudine and lamivudine, efavirenz plus indinavir, and indinavir plus zidovudine and lamivudine in the treatment of HIV-1 infection in adults. Study 006 Team. N Engl J Med 1999; 341:1865-1873.
6. Lucas GM, Chaisson RE, Moore RD. Comparison of initial combination antiretroviral therapy with a single protease inhibitor, ritonavir and saquinavir, or efavirenz. AIDS 2001; 15:1679-1686.
7. Robbins GK, De Gruttola V, Shafer RW, et al. Comparison of sequential three-drug regimens as initial therapy for HIV-1 infection. N Engl J Med 2003; 349:2293-2303.
8. Gulick RM, Ribaudo HJ, Shikuma CM, et al. Triple-nucleoside regimens versus efavirenz-containing regimens for the initial treatment of HIV-1 infection. N Engl J Med 2004; 350:1850-1861.
9. Hsiou Y, Ding J, Das K, et al. The Lys103Asn mutation of HIV-1 RT: a novel mechanism of drug resistance. J Mol Biol 2001; 309:437-445.
10. Richman DD, ACTG 164/168 Study Team. Loss of nevirapine activity associated with emergence of resistance in clinical trials. VIII International Conference on AIDS/III STD World Congress. 19-24 July 1992, Amsterdam, the Netherlands. Abstract PoB 3576.
11. Richman DD, Shih C-K, Lowy I, et al. Human immunodeficiency virus type 1 mutants resistant to nonnucleoside inhibitors of reverse transcriptase arise in tissue culture. Proc Natl Acad Sci U S A 1991; 88:11241-11245.
12. Bacheler L, Jeffrey S, Hanna G, et al. Genotypic correlates of phenotypic resistance to efavirenz in virus isolates from patients failing nonnucleoside reverse transcriptase inhibitor therapy. J Virol 2001; 75:4999-5008.
13. Bacheler LT, Anton ED, Kudish P, et al. Human immunodeficiency virus type 1 mutations selected in patients failing efavirenz combination therapy. Antimicrob Agents Chemother 2000; 44:2475-2484.
14. Masuda N, Yamamoto O, Fujii M, et al. Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives. Bioorg Med Chem 2005; 13:949-961.
15. Fujiwara M, Ijichi K, Hanasaki Y, et al. Thiadiazole derivatives: highly potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) replications in vitro. Microbiol Immunol 1997; 41:301-308.
16. Fujiwara M, Kodama EN, Okamoto M, et al. Characterization of human immunodeficiency virus type 1 strains resistant to the non-nucleoside reverse transcriptase inhibitor RD4-2217. Antivir Chem Chemother 1999; 10:315-320.
17. Masuda N, Yamamoto O, Fujii M, et al. Studies of nonnucleoside HIV-1 reverse transcriptase inhibitors. Part 1: design and synthesis of thiazolidenebenzenesulfonamides. Bioorg Med Chem 2004; 12:6171-6182.
18. Kimpton J, Emerman M. Detection of replication-competent and pseudotyped human immunodeficiency virus with a sensitive cell line on the basis of activation of an integrated beta-galactosidase gene. J Virol 1992; 66:2232-2239.
19. Kodama EI, Kohgo S, Kitano K, et al. 4′-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro. Antimicrob Agents Chemother 2001; 45:1539-1546.
20. Nameki D, Kodama E, Ikeuchi M, et al. Mutations conferring resistance to human immunodeficiency virus type 1 fusion inhibitors are restricted by gp41 and Rev-responsive element functions. J Virol 2005; 79:764-770.
21. Shimura K, Kodama F, Sakagami Y, et al. Broad antiretroviral activity and resistance profile of the novel human immunodeficiency virus integrase inhibitor elvitegravir (JTK-303/GS-9137). J Virol 2008; 82:764-774.
22. Jones G, Willett P, Glen RC. Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J Mol Biol 1995; 245:43-53.
23. Berman HM, Westbrook J, Feng Z, et al. The Protein Data Bank. Nucleic Acids Res 2000; 28:235-242.
24. Protein data base, NCBI Structure. (Accessed 27 May 2008.) Available from http://www.ncbi.nlm.nih.gov/Structure/
25. Ren J, Milton J, Weaver KL, Short SA, Stuart DI, Stammers DK. Structural basis for the resilience of efavirenz (DMP-266) to drug resistance mutations in HIV-1 reverse transcriptase. Structure Fold Des 2000; 8:1089-1094.
26. Allen FH. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr B 2002; 58:380-388.
27. Kantor R, Machekano R, Gonzales MJ, Dupnik K, Schapiro JM, Shafer RW. Human Immunodeficiency Virus Reverse Transcriptase and Protease Sequence Database: an expanded data model integrating natural language text and sequence analysis programs. Nucleic Acids Res 2001; 29:296-299.
28. Shafer RW. Stanford HIV Drug Resistance Database, NNRTI Resistance notes. (Accessed 27 May 2008.) Available from http://hivdb.stanford.edu/ cgi-bin/NNRTIResiNote.cgi 2008
29. Clark SA, Calef C, Mellors JW. Mutations in retroviral genes associated with drug resistance. In HIV Sequence Compendium 2005. Edited by T Leitner, B Hahn, P Marx, F McCutchan, J Mellors, S Wolinsky & B Korber. New Mexico: Los Alamos National Laboratory 2005; pp. 80-174.
30. Parikh U, Calef C, Clark SA, Mellors JW. Mutations in retroviral genes associated with drug resistance. In HIV Sequence Compendium 2003. Edited by T Leitner, B Hahn, P Marx, F McCutchan, J Mellors, S Wolinsky & B Korber. New Mexico: Los Alamos National Laboratory 2003; pp. 38-122.
31. Balzarini J, Kleim JP, Riess G, Camarasa MJ, De Clercq E, Karlsson A. Sensitivity of (138 Glu->Lys) mutated human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) to HIV-1-specific RT inhibitors. Biochem Biophys Res Commun 1994; 201:1305-1312.
32. Schinazi RF, Larder BA, Mellon JW. Mutations in retroviral genes associated with drug resistance: 1999-2000 update. Int Antiviral News 1999; 7:46-69.
33. Ding J, Das K, Moereels H, et al. Structure of HIV-1 RT/TIBO R 86183 complex reveals similarity in the binding of diverse nonnucleoside inhibitors. Nat Struct Biol 1995; 2:407-415.
34. Ren J, Esnouf R, Garman E, et al. High resolution structures of HIV-1 RT from four RT-inhibitor complexes. Nat Struct Biol 1995; 2:293-302.
35. Smerdon SJ, Jager J, Wang J, et al. Structure of the binding site for nonnucleoside inhibitors of the reverse transcriptase of human immunodeficiency virus type 1. Proc Natl Acad Sci U S A 1994; 91:3911-3915.
36. Kohlstaedt LA, Wang J, Friedman JM, Rice PA, Steitz TA. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science 1992; 256:1783-1790.
37. Esnouf R, Ren J, Ross C, Jones Y, Stammers D, Stuart D. Mechanism of inhibition of HIV-1 reverse transcriptase by non-nucleoside inhibitors. Nat Struct Biol 1995; 2:303-308.
38. Spence RA, Kati WM, Anderson KS, Johnson KA. Mechanism of inhibition of HIV-1 reverse transcriptase by nonnucleoside inhibitors. Science 1995; 267:988-993.
39. Das K, Lewi PJ, Hughes SH, Arnold E. Crystallography and the design of anti-AIDS drugs: conformational flexibility and positional adaptability are important in the design of non-nucleoside HIV-1 reverse transcriptase inhibitors. Prog Biophys Mol Biol 2005; 88:209-231.
40. Das K, Clark AD, Jr, Lewi PJ, et al. Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants. J Med Chem 2004; 47:2550-2560.
41. Palmer S, Margot N, Gilbert H, Shaw N, Buckheit R, Jr, Miller M. Tenofovir, adefovir, and zidovudine susceptibilities of primary human immunodeficiency virus type 1 isolates with non-B-subtypes or nucleoside resistance. AIDS Res Hum Retroviruses 2001; 17:1167-1173.
42. Srinivas RV, Fridland A. Antiviral activities of 9-R-2-phosphonomethoxypropyl adenine (PMPA) and bis(isopropyloxymethylcarbonyl)PMPA against various drug-resistant human immunodeficiency virus strains. Antimicrob Agents Chemother 1998; 42:1484-1487.
43. Tuske S, Sarafianos SG, Clark AD, Jr, et al. Structures of HIV-1 RT-DNA complexes before and after incorporation of the anti-AIDS drug tenofovir. Nat Struct Mol Biol 2004; 11:469-474.
44. Yoshimura K, Kato R, Yusa K, et al. JE-2147: a dipeptide protease inhibitor (PI) that potently inhibits multi-PI-resistant HIV-1. Proc Natl Acad Sci U S A 1999; 96:8675-8680.