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Review

Current structure-based Methods for Designing non-nucleoside Reverse Transcriptase Inhibitors

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Pages 537-544 | Received 20 May 2019, Accepted 18 Jul 2019, Published online: 22 Aug 2019

References

  • AIDSInfo . Clinical guidelines. http://aidsinfo.nih.gov
  • Sebaaly JC , KelleyD. HIV clinical updates: new single-tablet regimens. Ann. Pharmacother., 53(1), 82–94 (2019).
  • Dousson C , AlexandreFR, AmadorAet al. Discovery of the aryl-phospho-indole IDX899, a highly potent anti-HIV non-nucleoside reverse transcriptase inhibitor. J. Med. Chem., 59(5), 1891–1898 (2016).
  • Gray WT , FreyKM, LaskeySBet al. Potent inhibitors active against HIV reverse transcriptase with K101P, a mutation conferring rilpivirine resistance. ACS Med. Chem. Lett., 6(10), 1075–1079 (2015).
  • Yang Y , KangD, NguyenLAet al. Structural basis for potent and broad inhibition of HIV-1 RT by thiophene[3,2-d]pyrimidine non-nucleoside inhibitors. Elife, 7, e36340 (2018).
  • Chan AH , LeeWG, SpasovKAet al. Covalent inhibitors for eradication of drug-resistant HIV-1 reverse transcriptase: from design to protein crystallography. Proc. Natl Acad. Sci USA, 114(36), 9725–9730 (2017).
  • Namasivayam V , VanangamudiM, KramerVGet al. The journey of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) from lab to clinic. J. Med. Chem., 62(10), 4851–4883 (2019).
  • Seckler JM , BarkleyMD, WintrodePL. Allosteric suppression of HIV-1 reverse transcriptase structural dynamics upon inhibitor binding. Biophys. J., 100(1), 144–153 (2011).
  • Spence RA , KatiWM, AndersonKS, JohnsonKA. Mechanism of inhibition of HIV-1 reverse transcriptase by nonnucleoside inhibitors. Science, 267(5200), 988–993 (1995).
  • Johnson M , KumarP, MolinaJMet al. Switching to doravirine/lamivudine/tenofovir disoproxil fumarate (DOR/3TC/TDF) maintains HIV-1 virologic suppression through 48 weeks: results of the DRIVE-SHIFT trial. J. Acquir. Immune Defic. Syndr., 81(4), 463–472 (2019).
  • Orkin C , DejesusE, RamgopalMet al. Switching from tenofovir disoproxil fumarate to tenofovir alafenamide coformulated with rilpivirine and emtricitabine in virally suppressed adults with HIV-1 infection: a randomised, double-blind, multicentre, Phase 3b, non-inferiority study. Lancet HIV, 4(5), e195–e204 (2017).
  • Permpalung N , PutcharoenO, AvihingsanonA, RuxrungthamK. Treatment of HIV infection with once-daily regimens. Expert Opin. Pharmacother., 13(16), 2301–2317 (2012).
  • Desai M , FieldN, GrantR, McCormackS. Recent advances in pre-exposure prophylaxis for HIV. BMJ, 359, j5011 (2017).
  • Smerdon SJ , JagerJ, WangJet al. Structure of the binding site for nonnucleoside inhibitors of the reverse transcriptase of human immunodeficiency virus type 1. Proc. Natl Acad. Sci. USA, 91(9), 3911–3915 (1994).
  • Cote B , BurchJD, Asante-AppiahEet al. Discovery of MK-1439, an orally bioavailable non-nucleoside reverse transcriptase inhibitor potent against a wide range of resistant mutant HIV viruses. Bioorg. Med. Chem. Lett., 24(3), 917–922 (2014).
  • Feng M , WangD, GroblerJA, HazudaDJ, MillerMD, LaiMT. In vitro resistance selection with doravirine (MK-1439), a novel nonnucleoside reverse transcriptase inhibitor with distinct mutation development pathways. Antimicrob. Agents Chemother., 59(1), 590–598 (2015).
  • Basson AE , RheeSY, ParryCMet al. Impact of drug resistance-associated amino acid changes in HIV-1 subtype C on susceptibility to newer nonnucleoside reverse transcriptase inhibitors. Antimicrob. Agents Chemother., 59(2), 960–971 (2015).
  • Das K , ArnoldE. HIV-1 reverse transcriptase and antiviral drug resistance. Part 1. Curr. Opin. Virol., 3(2), 111–118 (2013).
  • Das K , ArnoldE. HIV-1 reverse transcriptase and antiviral drug resistance. Part 2. Curr. Opin. Virol., 3(2), 119–128 (2013).
  • Sluis-Cremer N , WainbergMA, SchinaziRF. Resistance to reverse transcriptase inhibitors used in the treatment and prevention of HIV-1 infection. Future Microbiol., 10(11), 1773–1782 (2015).
  • Ceccherini-Silberstein F , GagoF, SantoroMet al. High sequence conservation of human immunodeficiency virus type 1 reverse transcriptase under drug pressure despite the continuous appearance of mutations. J. Virol., 79(16), 10718–10729 (2005).
  • Usach I , MelisV, PerisJE. Non-nucleoside reverse transcriptase inhibitors: a review on pharmacokinetics, pharmacodynamics, safety and tolerability. J. Int. AIDS Soc., 16, 1–14 (2013).
  • Medrano J , BarreiroP, TumaPet al. Risk for immune-mediated liver reactions by nevirapine revisited. AIDS Rev., 10(2), 110–115 (2008).
  • Apostolova N , FunesHA, Blas-GarciaA, GalindoMJ, AlvarezA, EspluguesJV. Efavirenz and the CNS: what we already know and questions that need to be answered. J. Antimicrob. Chemother., 70(10), 2693–2708 (2015).
  • Decloedt EH , MaartensG. Neuronal toxicity of efavirenz: a systematic review. Expert Opin. Drug Saf., 12(6), 841–846 (2013).
  • Pozniak AL , Morales-RamirezJ, KatabiraEet al. Efficacy and safety of TMC278 in antiretroviral-naive HIV-1 patients: week 96 results of a Phase IIb randomized trial. AIDS, 24(1), 55–65 (2010).
  • Wilkin A , PozniakAL, Morales-RamirezJet al. Long-term efficacy, safety, and tolerability of rilpivirine (RPV, TMC278) in HIV type 1-infected antiretroviral-naive patients: week 192 results from a Phase IIb randomized trial. AIDS Res. Hum. Retroviruses, 28(5), 437–446 (2012).
  • Giguere P , NheanS, TsengAL, HughesCA, AngelJB. Getting to the heart of the matter: a review of drug interactions between HIV antiretrovirals and cardiology medications. Can. J. Cardiol., 35(3), 326–340 (2019).
  • Frey KM . Structure-enhanced methods in the development of non-nucleoside inhibitors targeting HIV reverse transcriptase variants. Future Microbiol., 10(11), 1767–1772 (2015).
  • Das K , BaumanJD, ClarkADJret al. High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: strategic flexibility explains potency against resistance mutations. Proc. Natl Acad. Sci. USA, 105(5), 1466–1471 (2008).
  • Lansdon EB , BrendzaKM, HungMet al. Crystal structures of HIV-1 reverse transcriptase with etravirine (TMC125) and rilpivirine (TMC278): implications for drug design. J. Med. Chem., 53(10), 4295–4299 (2010).
  • Gong Z , XieZ, QiuJ, WangG. Synthesis, biological evaluation and molecular docking study of 2-substituted-4,6-diarylpyrimidines as alpha-glucosidase inhibitors. Molecules, 22(11), 1865 (2017).
  • Huang B , KangD, YangJ, ZhanP, LiuX. Novel diarylpyrimidines and diaryltriazines as potent HIV-1 NNRTIs with dramatically improved solubility: a patent evaluation of US20140378443A1. Expert Opin. Ther. Pat., 26(2), 281–289 (2016).
  • Jin K , YinH, DeClercq E, PannecouqueC, MengG, ChenF. Discovery of biphenyl-substituted diarylpyrimidines as non-nucleoside reverse transcriptase inhibitors with high potency against wild-type and mutant HIV-1. Eur. J. Med. Chem., 145, 726–734 (2018).
  • Xue P , LuHH, ZhuYYet al. Design and synthesis of hybrids of diarylpyrimidines and diketo acids as HIV-1 inhibitors. Bioorg. Med. Chem. Lett., 27(8), 1640–1643 (2017).
  • Simon P , BaszczynskiO, SamanDet al. Novel (2,6-difluorophenyl)(2-(phenylamino)pyrimidin-4-yl)methanones with restricted conformation as potent non-nucleoside reverse transcriptase inhibitors against HIV-1. Eur. J. Med. Chem., 122, 185–195 (2016).
  • Bollini M , DomaoalRA, ThakurVVet al. Computationally-guided optimization of a docking hit to yield catechol diethers as potent anti-HIV agents. J. Med. Chem., 54(24), 8582–8591 (2011).
  • Frey KM , BolliniM, MislakACet al. Crystal structures of HIV-1 reverse transcriptase with picomolar inhibitors reveal key interactions for drug design. J. Am. Chem. Soc., 134(48), 19501–19503 (2012).
  • Frey KM , PuleoDE, SpasovKA, BolliniM, JorgensenWL, AndersonKS. Structure-based evaluation of non-nucleoside inhibitors with improved potency and solubility that target HIV reverse transcriptase variants. J. Med. Chem., 58(6), 2737–2745 (2015).
  • Lee WG , Gallardo-MaciasR, FreyKMet al. Picomolar inhibitors of HIV reverse transcriptase featuring bicyclic replacement of a cyanovinylphenyl group. J. Am. Chem. Soc., 135(44), 16705–16713 (2013).
  • Asahchop EL , OliveiraM, WainbergMAet al. Characterization of the E138K resistance mutation in HIV-1 reverse transcriptase conferring susceptibility to etravirine in B and non-B HIV-1 subtypes. Antimicrob. Agents Chemother., 55(2), 600–607 (2011).
  • Singh K , MarchandB, RaiDKet al. Biochemical mechanism of HIV-1 resistance to rilpivirine. J. Biol. Chem., 287(45), 38110–38123 (2012).
  • Kang D , FangZ, LiZet al. Design, synthesis, and evaluation of thiophene[3,2-d]pyrimidine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors with significantly improved drug resistance profiles. J. Med. Chem., 59(17), 7991–8007 (2016).
  • Kang D , FangZ, HuangBet al. Structure-based optimization of thiophene[3,2-d]pyrimidine derivatives as potent HIV-1 non-nucleoside reverse transcriptase inhibitors with improved potency against resistance-associated variants. J. Med. Chem., 60(10), 4424–4443 (2017).
  • Huang B , ChenW, ZhaoTet al. Exploiting the tolerant region I of the non-nucleoside reverse transcriptase inhibitor (NNRTI) binding pocket: discovery of potent diarylpyrimidine-typed HIV-1 NNRTIs against wild-type and E138K mutant virus with significantly improved water solubility and favorable safety profiles. J. Med. Chem., 62(4), 2083–2098 (2019).
  • Kang D , ZhangH, WangZet al. Identification of Dihydrofuro[3,4- d]pyrimidine derivatives as novel HIV-1 non-nucleoside reverse transcriptase inhibitors with promising antiviral activities and desirable physicochemical properties. J. Med. Chem., 62(3), 1484–1501 (2019).
  • Aly YL , PedersenEB, LaColla P, LoddoR. Synthesis and anti-HIV-1 activity of new MKC-442 analogues with an alkynyl-substituted 6-benzyl group. Arch. Pharm. (Weinheim), 340(5), 225–235 (2007).
  • Petersen L , JessenCH, PedersenEB, NielsenC. Synthesis and evaluation of new potential HIV-1 non-nucleoside reverse transcriptase inhibitors. New analogues of MKC-442 containing Michael acceptors in the C-6 position. Org. Biomol. Chem., 1(20), 3541–3545 (2003).
  • Azeem SM , MuwongeAN, ThakkarN, LamKW, FreyKM. Structure-based methods to predict mutational resistance to diarylpyrimidine non-nucleoside reverse transcriptase inhibitors. J. Mol. Graph. Model., 79, 133–139 (2018).

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