F18, a novel small-molecule nonnucleoside reverse transcriptase inhibitor, inhibits HIV-1 replication using distinct binding motifs as demonstrated by resistance selection and docking analysis

Antimicrobial Agents and Chemotherapy

Volumn 56, Issue 1, 2012, Pages 341-351

  Lu, Xiaofan ^a   Liu, Li ^a   Zhang, Xu ^b   Lau, Terrence Chi Kong ^c   Tsui, Stephen Kwok Wing ^d   Kang, Yuanxi ^a   Zheng, Purong ^b   Zheng, Bojian ^a   Liu, Gang ^b,e   Chen, Zhiwei ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b Tsinghua University   (China)

^c CITY UNIVERSITY OF HONG KONG   (Hong Kong)

^d CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^e INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

'F 18'; AZATHIOPRINE; CALANOLIDE A; CHLOROMETHYL 11 DEMETHYL 12 OXO CALANOLIDE A; EFAVIRENZ; NEVIRAPINE; RALTEGRAVIR; RITONAVIR; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DRUG ANTAGONISM; DRUG RESISTANCE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; MOLECULAR DOCKING; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIORITY JOURNAL; VIRUS REPLICATION;

AMINO ACID MOTIFS; ANTI-HIV AGENTS; BINDING SITES; CELLS, CULTURED; DRUG RESISTANCE, VIRAL; DRUG SYNERGISM; GENOTYPE; HIV INFECTIONS; HIV REVERSE TRANSCRIPTASE; HIV-1; HUMANS; LEUKOCYTES, MONONUCLEAR; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MUTATION; NEVIRAPINE; PYRANOCOUMARINS; REVERSE TRANSCRIPTASE INHIBITORS; VIRUS REPLICATION;

EID: 84455161713     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.05537-11     Document Type: Article

References (47)

1. Andries K, et al. 2004. TMC125, a novel next-generation nonnucleoside reverse transcriptase inhibitor active against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 48:4680-4686. (Pubitemid 39577672)
2. Auwerx J, et al. 2005. The role of Thr139 in the human immunodeficiency virus type 1 reverse transcriptase sensitivity to (+)-calanolide A. Mol. Pharmacol. 68:652- 659.
3. Azijn H, et al. 2010. TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTIresistant HIV-1. Antimicrob. Agents Chemother. 54:718-727.
4. Bacheler L, et al. 2001. Genotypic correlates of phenotypic resistance to efavirenz in virus isolates from patients failing nonnucleoside reverse transcriptase inhibitor therapy. J. Virol. 75:4999-5008. (Pubitemid 32448520)
5. Balzarini J, et al. 2005. The amino acid Asn136 in HIV-1 reverse transcriptase (RT) maintains efficient association of both RT subunits and enables the rational design of novel RT inhibitors. Mol. Pharmacol. 68:49-60. (Pubitemid 41007052)
6. Buckheit RW, Jr., et al. 1999. Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrob. Agents Chemother. 43:1827-1834.
7. Cao YZ, Lu HZ. 2005. Care of HIV-infected patients in China. Cell Res. 15:883-890. (Pubitemid 41826255)
8. Chen Z, et al. 2000. Enhanced infectivity of an R5-tropic simian/human immunodeficiency virus carrying human immunodeficiency virus type 1 subtype C envelope after serial passages in pig-tailed macaques (Macaca nemestrina). J. Virol. 74:6501-6510. (Pubitemid 30429818)
9. Currens MJ, et al. 1996. Antiviral activity and mechanism of action of calanolide A against the human immunodeficiency virus type-1. J. Pharmacol. Exp. Ther. 279:645-651. (Pubitemid 27166835)
10. Currens MJ, Mariner JM, McMahon JB, Boyd MR. 1996. Kinetic analysis of inhibition of human immunodeficiency virus type-1 reverse transcriptase by calanolide A. J. Pharmacol. Exp. Ther. 279:652-661. (Pubitemid 27166836)
11. Delaugerre C, et al. 2001. Resistance profile and cross-resistance of HIV-1 among patients failing a non-nucleoside reverse transcriptase inhibitor-containing regimen. J. Med. Virol. 65:445-448. (Pubitemid 32959067)
12. Edmonds A, et al. 2011. The effect of highly active antiretroviral therapy on the survival of HIV-infected children in a resource-deprived setting: a cohort study. PLoS Med. 8:e1001044.
13. El Safadi Y, Vivet-Boudou V, Marquet R. 2007. HIV-1 reverse transcriptase inhibitors. Appl. Microbiol. Biotechnol. 75:723-737. (Pubitemid 47164912)
14. Flavin MT, et al. 1996. Synthesis, chromatographic resolution, and antihuman immunodeficiency virus activity of (±)-calanolide A and its enantiomers. J. Med. Chem. 39:1303-1313. (Pubitemid 26089845)
15. Herschhorn A, Hizi A. 2010. Retroviral reverse transcriptases. Cell. Mol. Life Sci. 67:2717-2747.
16. Ho DD, Bieniasz PD. 2008. HIV-1 at 25. Cell 133:561-565. (Pubitemid 351636315)
17. Hsiou Y, et al. 2001. The Lys103Asn mutation of HIV-1 RT: a novel mechanism of drug resistance. J. Mol. Biol. 309:437- 445.
18. Hsiou Y, et al. 1996. Structure of unliganded HIV-1 reverse transcriptase at 2.7 Å resolution: implications of conformational changes for polymerization and inhibition mechanisms. Structure 4:853-860. (Pubitemid 26312368)
19. Hughes CA, Robinson L, Tseng A, MacArthur RD. 2009. New antiretroviral drugs: a review of the efficacy, safety, pharmacokinetics, and resistance profile of tipranavir, darunavir, etravirine, rilpivirine, maraviroc, and raltegravir. Expert Opin. Pharmacother. 10:2445-2466.
20. Kashman Y, Gustafson KR, Fuller RW, Cardellina JH, II, et al. 1992. The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J. Med. Chem. 35:2735-2743.
21. Katlama C, et al. 2010. Efficacy and safety of etravirine at week 96 in treatment-experienced HIV type-1-infected patients in the DUET-1 and DUET-2 trials. Antivir. Ther. 15:1045-1052.
22. Lai MT, et al. 2009. Antiviral activity of MK-4965, a novel nonnucleoside reverse transcriptase inhibitor. Antimicrob. Agents Chemother. 53:2424-2431.
23. Luo M, et al. 2009. Prevalence of drug-resistant HIV-1 in rural areas of Hubei province in the People's Republic of China. J. Acquir. Immune Defic. Syndr. 50:1-8.
24. Ma T, Gao Q, Chen Z, Wang L, Liu G. 2008. Chemical resolution of (±)-calanolide A, (±)-cordatolide A and their 11-demethyl analogues. Bioorg. Med. Chem. Lett. 18:1079 -1083.
25. Ma T, et al. 2008. Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents. J. Med. Chem. 51:1432-1446. (Pubitemid 351484798)
26. Madruga JV, et al. 2007. Efficacy and safety of TMC125 (etravirine) in treatment-experienced HIV-1-infected patients in DUET-1: 24-week results from a randomised, double-blind, placebo-controlled trial. Lancet 370:29 -38.
27. Menendez-Arias L. 2008. Mechanisms of resistance to nucleoside analogue inhibitors of HIV-1 reverse transcriptase. Virus Res. 134:124-146.
28. Miiro G, et al. 2009. Reduced morbidity and mortality in the first year after initiating highly active anti-retroviral therapy (HAART) among Ugandan adults. Trop. Med. Int. Health 14:556 -563.
29. Milinkovic A, Martinez E. 2004. Nevirapine in the treatment of HIV. Expert Rev. Anti-Infect. Ther. 2:367-373. (Pubitemid 38745097)
30. Morris GM, et al. 1998. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 19:1639 -1662.
31. Morris GM, et al. 2009. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J. Comput. Chem. 30:2785-2791.
32. Nunberg JH, et al. 1991. Viral resistance to human immunodeficiency virus type 1-specific pyridinone reverse transcriptase inhibitors. J. Virol. 65:4887- 4892.
33. Pomerantz RJ, Horn DL. 2003. Twenty years of therapy for HIV-1 infection. Nat. Med. 9:867-873. (Pubitemid 36889928)
34. Prichard MN, Shipman C, Jr. 1990. A three-dimensional model to analyze drug-drug interactions. Antivir. Res. 14:181-205. (Pubitemid 20377558)
35. Richards KH, Clapham PR. 2006. Human immunodeficiency viruses: propagation, quantification, and storage. Curr. Protoc. Microbiol. Chapter 15, Unit 15J.1.
36. Richman DD, et al. 1994. Nevirapine resistance mutations of human immunodeficiency virus type 1 selected during therapy. J. Virol. 68:1660-1666. (Pubitemid 24065732)
37. Sarafianos SG, et al. 2009. Structure and function of HIV-1 reverse transcriptase: molecular mechanisms of polymerization and inhibition. J. Mol. Biol. 385:693-713.
38. Schiller DS, Youssef-Bessler M. 2009. Etravirine: a second-generation nonnucleoside reverse transcriptase inhibitor (NNRTI) active against NNRTI-resistant strains of HIV. Clin. Ther. 31:692-704.
39. Sluis-Cremer N, et al. 2007. Characterization of novel non-nucleoside reverse transcriptase (RT) inhibitor resistance mutations at residues 132 and 135 in the 51 kDa subunit of HIV-1 RT. Biochem. J. 404:151-157. (Pubitemid 46788095)
40. Su B, et al. 2003. HIV-1 subtype B= dictates the AIDS epidemic among paid blood donors in the Henan and Hubei provinces of China. AIDS 17:2515-2520. (Pubitemid 38393325)
41. Tambuyzer L, et al. 2009. Compilation and prevalence of mutations associated with resistance to non-nucleoside reverse transcriptase inhibitors. Antivir. Ther. 14:103-109.
42. Vingerhoets J, et al. 2005. TMC125 displays a high genetic barrier to the development of resistance: evidence from in vitro selection experiments. J. Virol. 79:12773-12782. (Pubitemid 41433197)
43. Xu ZQ, Flavin MT, Jenta TR. 2000. Calanolides, the naturally occurring anti-HIV agents. Curr. Opin. Drug Discov. Dev. 3:155-166. (Pubitemid 30214540)
44. Xue H, et al. 2010. Highly suppressing wild-type HIV-1 and Y181C mutant HIV-1 strains by 10-chloromethyl-11-demethyl-12-oxocalanolide A with druggable profile. J. Med. Chem. 53:1397-1401.
45. Zhang FJ, Pan J, Yu L, Wen Y, Zhao Y. 2005. Current progress of China's free ART program. Cell Res. 15:877- 882.
46. Zhang L, et al. 2004. Molecular characterization of human immunodeficiency virus type 1 and hepatitis C virus in paid blood donors and injection drug users in china. J. Virol. 78:13591-13599. (Pubitemid 39612759)
47. Zhang Y, et al. 2006. Dominance of HIV-1 subtype CRF01-AE in sexually acquired cases leads to a new epidemic in Yunnan province of China. PLoS Med. 3:e443.