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Rational design of potent non-nucleoside inhibitors of HIV-1 reverse transcriptase.

Chong P, Sebahar P, Youngman M, Garrido D, Zhang H, Stewart EL, Nolte RT, Wang L, Ferris RG, Edelstein M, Weaver K, Mathis A, Peat A
J Med Chem 55 10601-9 (2012)
Related entries: 2ynf, 2ynh, 2yni

Cited: 22 times
EuropePMC logo PMID: 23137340

Abstract

A new series of non-nucleoside reverse transcriptase inhibitors based on an imidazole-amide biarylether scaffold has been identified and shown to possess potent antiviral activity against HIV-1, including the NNRTI-resistant Y188L mutated virus. X-ray crystallography of inhibitors bound to reverse transcriptase, including a structure of the Y188L RT protein, was used extensively to help identify and optimize the key hydrogen-bonding motif. This led directly to the design of compound 43 that exhibits remarkable antiviral activity (EC50<1 nM) against a wide range of NNRTI-resistant viruses and a favorable pharmacokinetic profile across multiple species.

Reviews - 2yng mentioned but not cited (1)

  1. Molecular Docking Studies of HIV-1 Resistance to Reverse Transcriptase Inhibitors: Mini-Review. Tarasova O, Poroikov V, Veselovsky A. Molecules 23 E1233 (2018)

Articles - 2yng mentioned but not cited (4)

  1. What do docking and QSAR tell us about the design of HIV-1 reverse transcriptase nonnucleoside inhibitors? Paneth A, Płonka W, Paneth P. J Mol Model 23 317 (2017)
  2. Diaryl ethers with carboxymethoxyphenacyl motif as potent HIV-1 reverse transcriptase inhibitors with improved solubility. Frączek T, Kamiński R, Krakowiak A, Naessens E, Verhasselt B, Paneth P. J Enzyme Inhib Med Chem 33 9-16 (2018)
  3. Assessment of Nonnucleoside Inhibitors Binding to HIV-1 Reverse Transcriptase Using HYDE Scoring. Paneth A, Płonka W, Paneth P. Pharmaceuticals (Basel) 12 64 (2019)
  4. NMR structure of the HIV-1 reverse transcriptase thumb subdomain. Sharaf NG, Brereton AE, Byeon IL, Karplus PA, Gronenborn AM. J Biomol NMR 66 273-280 (2016)


Reviews citing this publication (7)

  1. Comprehensive review in current developments of imidazole-based medicinal chemistry. Zhang L, Peng XM, Damu GL, Geng RX, Zhou CH. Med Res Rev 34 340-437 (2014)
  2. HIV-1 reverse transcriptase and antiviral drug resistance. Part 1. Das K, Arnold E. Curr Opin Virol 3 111-118 (2013)
  3. Avoiding Drug Resistance in HIV Reverse Transcriptase. Cilento ME, Kirby KA, Sarafianos SG. Chem Rev 121 3271-3296 (2021)
  4. The Fellowship of Privileged Scaffolds-One Structure to Inhibit Them All. Skoreński M, Sieńczyk M. Pharmaceuticals (Basel) 14 1164 (2021)
  5. Arylsulfone-based HIV-1 non-nucleoside reverse transcriptase inhibitors. Famiglini V, Coluccia A, Brancale A, Pelliccia S, La Regina G, Silvestri R. Future Med Chem 5 2141-2156 (2013)
  6. Structure-enhanced methods in the development of non-nucleoside inhibitors targeting HIV reverse transcriptase variants. Frey KM. Future Microbiol 10 1767-1772 (2015)
  7. Chronic Hepatitis B Treatment Strategies Using Polymerase Inhibitor-Based Combination Therapy. Ohsaki E, Suwanmanee Y, Ueda K. Viruses 13 1691 (2021)

Articles citing this publication (10)

  1. Multiple Machine Learning Comparisons of HIV Cell-based and Reverse Transcriptase Data Sets. Zorn KM, Lane TR, Russo DP, Clark AM, Makarov V, Ekins S. Mol Pharm 16 1620-1632 (2019)
  2. New indolylarylsulfones as highly potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors. Famiglini V, La Regina G, Coluccia A, Pelliccia S, Brancale A, Maga G, Crespan E, Badia R, Clotet B, Esté JA, Cirilli R, Novellino E, Silvestri R. Eur J Med Chem 80 101-111 (2014)
  3. Per-residue energy decomposition pharmacophore model to enhance virtual screening in drug discovery: a study for identification of reverse transcriptase inhibitors as potential anti-HIV agents. Cele FN, Ramesh M, Soliman ME. Drug Des Devel Ther 10 1365-1377 (2016)
  4. Pyridones as NNRTIs against HIV-1 mutants: 3D-QSAR and protein informatics. Debnath U, Verma S, Jain S, Katti SB, Prabhakar YS. J Comput Aided Mol Des 27 637-654 (2013)
  5. Docking-based 3D-QSAR and pharmacophore studies on diarylpyrimidines as non-nucleoside inhibitors of HIV-1 reverse transcriptase. Liu G, Wan Y, Wang W, Fang S, Gu S, Ju X. Mol Divers 23 107-121 (2019)
  6. Design and synthesis of tetrahydrophthalimide derivatives as inhibitors of HIV-1 reverse transcriptase. Penta A, Ganguly S, Murugesan S. Org Med Chem Lett 3 8 (2013)
  7. A cytotoxic survey on 2-amino-1H-imidazol based synthetic marine sponge alkaloid analogues. Gémes N, Makra Z, Neuperger P, Szabó E, Balog JÁ, Flink LB, Kari B, Hackler L, Puskás LG, Kanizsai I, Szebeni GJ. Drug Dev Res 83 1906-1922 (2022)
  8. Catalytic synthesis of α-amino chromone phosphonates and their antimicrobial, toxicity and potential HIV-1 RT inhibitors based on silico screening. Jaiyeola AO, Anand K, Kasumbwe K, Ramesh M, Gengan RM. J Photochem Photobiol B 166 136-147 (2017)
  9. N-Phenyl-1-(phenylsulfonyl)-1H-1,2,4-triazol-3-amine as a New Class of HIV-1 Non-nucleoside Reverse Transcriptase Inhibitor. Lane T, Makarov V, Nelson JAE, Meeker RB, Sanna G, Riabova O, Kazakova E, Monakhova N, Tsedilin A, Urbina F, Jones T, Suchy A, Ekins S. J Med Chem 66 6193-6217 (2023)
  10. Identification of Adjacent NNRTI Binding Pocket in Multi-mutated HIV1- RT Enzyme Model: An in silico Study. Kamil RF, Debnath U, Verma S, Prabhakar YS. Curr HIV Res 16 121-129 (2018)


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