Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead

Ippolito, J; Niu, H.; Bertoletti, N.; Carter, Z.; Jin, S.; Spasov, K.; Cisneros, J.; Valhondo, M.; Cutrona, K.; Anderson, K.; Jorgensen, W.

doi:10.1021/acsmedchemlett.0c00612

Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead

Journal Article · 01 January 2022 · ACS Medicinal Chemistry Letters

DOI:https://doi.org/10.1021/acsmedchemlett.0c00612· OSTI ID:1783741

Ippolito, J; Niu, H.; Bertoletti, N.; Carter, Z.; Jin, S.; Spasov, K.; Cisneros, J.; Valhondo, M.; Cutrona, K.; Anderson, K.; Jorgensen, W.

Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Organization:: ~OTHER

DOE Contract Number:: SC0012704

OSTI ID:: 1783741

Report Number(s):: BNL-221423-2021-JACI

Journal Information:: ACS Medicinal Chemistry Letters, Vol. 12, Issue 2

Country of Publication:: United States

Language:: English

References (29)

Global, regional, and national incidence, prevalence, and mortality of HIV, 1980–2017, and forecasts to 2030, for 195 countries and territories: a systematic analysis for the Global Burden of Diseases, Injuries, and Risk Factors Study 2017 Frank, Tahvi D.; Carter, Austin; Jahagirdar, Deepa The Lancet HIV, Vol. 6, Issue 12 https://doi.org/10.1016/S2352-3018(19)30196-1	journal	December 2019
Approved Antiviral Drugs over the Past 50 Years De Clercq, Erik; Li, Guangdi Clinical Microbiology Reviews, Vol. 29, Issue 3 https://doi.org/10.1128/CMR.00102-15	journal	June 2016
Single-Tablet Regimens for the Treatment of HIV-1 Infection Sebaaly, Jamielynn C.; Kelley, Denise Annals of Pharmacotherapy, Vol. 51, Issue 4 https://doi.org/10.1177/1060028016682531	journal	November 2016
Current and emerging non-nucleoside reverse transcriptase inhibitors (NNRTIs) for HIV-1 treatment Wang, Yali; De Clercq, Erik; Li, Guangdi Expert Opinion on Drug Metabolism & Toxicology, Vol. 15, Issue 10 https://doi.org/10.1080/17425255.2019.1673367	journal	October 2019
Two-Drug Regimen for HIV Sancar, Feyza JAMA, Vol. 321, Issue 19 https://doi.org/10.1001/jama.2019.6188	journal	May 2019
Long-Acting HIV Drugs for Treatment and Prevention Gulick, Roy M.; Flexner, Charles Annual Review of Medicine, Vol. 70, Issue 1 https://doi.org/10.1146/annurev-med-041217-013717	journal	January 2019
Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents Bollini, Mariela; Domaoal, Robert A.; Thakur, Vinay V. Journal of Medicinal Chemistry, Vol. 54, Issue 24 https://doi.org/10.1021/jm201134m	journal	December 2011
Picomolar Inhibitors of HIV Reverse Transcriptase Featuring Bicyclic Replacement of a Cyanovinylphenyl Group Lee, Won-Gil; Gallardo-Macias, Ricardo; Frey, Kathleen M. Journal of the American Chemical Society, Vol. 135, Issue 44 https://doi.org/10.1021/ja408917n	journal	October 2013
Picomolar Inhibitors of HIV-1 Reverse Transcriptase: Design and Crystallography of Naphthyl Phenyl Ethers Lee, Won-Gil; Frey, Kathleen M.; Gallardo-Macias, Ricardo ACS Medicinal Chemistry Letters, Vol. 5, Issue 11 https://doi.org/10.1021/ml5003713	journal	September 2014
Design, Conformation, and Crystallography of 2-Naphthyl Phenyl Ethers as Potent Anti-HIV Agents Lee, Won-Gil; Chan, Albert H.; Spasov, Krasimir A. ACS Medicinal Chemistry Letters, Vol. 7, Issue 12 https://doi.org/10.1021/acsmedchemlett.6b00390	journal	September 2016
Computer-aided discovery of anti-HIV agents Jorgensen, William L. Bioorganic & Medicinal Chemistry, Vol. 24, Issue 20 https://doi.org/10.1016/j.bmc.2016.07.039	journal	October 2016
Structural and Preclinical Studies of Computationally Designed Non-Nucleoside Reverse Transcriptase Inhibitors for Treating HIV infection Kudalkar, Shalley N.; Beloor, Jagadish; Chan, Albert H. Molecular Pharmacology, Vol. 91, Issue 4 https://doi.org/10.1124/mol.116.107755	journal	February 2017
From in silico hit to long-acting late-stage preclinical candidate to combat HIV-1 infection Kudalkar, Shalley N.; Beloor, Jagadish; Quijano, Elias Proceedings of the National Academy of Sciences, Vol. 115, Issue 4 https://doi.org/10.1073/pnas.1717932115	journal	December 2017
Structural and pharmacological evaluation of a novel non-nucleoside reverse transcriptase inhibitor as a promising long acting nanoformulation for treating HIV Kudalkar, Shalley N.; Ullah, Irfan; Bertoletti, Nicole Antiviral Research, Vol. 167 https://doi.org/10.1016/j.antiviral.2019.04.010	journal	July 2019
Covalent inhibitors for eradication of drug-resistant HIV-1 reverse transcriptase: From design to protein crystallography Chan, Albert H.; Lee, Won-Gil; Spasov, Krasimir A. Proceedings of the National Academy of Sciences, Vol. 114, Issue 36 https://doi.org/10.1073/pnas.1711463114	journal	August 2017
The Design of Covalent Allosteric Drugs Nussinov, Ruth; Tsai, Chung-Jung Annual Review of Pharmacology and Toxicology, Vol. 55, Issue 1 https://doi.org/10.1146/annurev-pharmtox-010814-124401	journal	January 2015
Sticking it to KRAS: Covalent Inhibitors Enter the Clinic McCormick, Frank Cancer Cell, Vol. 37, Issue 1 https://doi.org/10.1016/j.ccell.2019.12.009	journal	January 2020
Lysine-Targeting Covalent Inhibitors Pettinger, Jonathan; Jones, Keith; Cheeseman, Matthew D. Angewandte Chemie International Edition, Vol. 56, Issue 48 https://doi.org/10.1002/anie.201707630	journal	October 2017
Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue Chen, Wentao; Dong, Jiajia; Plate, Lars Journal of the American Chemical Society, Vol. 138, Issue 23 https://doi.org/10.1021/jacs.6b02960	journal	June 2016
Covalent Enzyme Inhibition through Fluorosulfate Modification of a Noncatalytic Serine Residue Fadeyi, Olugbeminiyi O.; Hoth, Lise R.; Choi, Chulho ACS Chemical Biology, Vol. 12, Issue 8 https://doi.org/10.1021/acschembio.7b00403	journal	July 2017
Emerging Utility of Fluorosulfate Chemical Probes Jones, Lyn H. ACS Medicinal Chemistry Letters, Vol. 9, Issue 7 https://doi.org/10.1021/acsmedchemlett.8b00276	journal	June 2018
Crystal Structures of HIV-1 Reverse Transcriptase with Picomolar Inhibitors Reveal Key Interactions for Drug Design Frey, Kathleen M.; Bollini, Mariela; Mislak, Andrea C. Journal of the American Chemical Society, Vol. 134, Issue 48 https://doi.org/10.1021/ja3092642	journal	November 2012
Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry Dong, Jiajia; Krasnova, Larissa; Finn, M. G. Angewandte Chemie International Edition, Vol. 53, Issue 36 https://doi.org/10.1002/anie.201309399	journal	August 2014
One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides Davies, Alyn T.; Curto, John M.; Bagley, Scott W. Chemical Science, Vol. 8, Issue 2 https://doi.org/10.1039/C6SC03924C	journal	January 2017
Covalent inhibitors design and discovery De Cesco, Stephane; Kurian, Jerry; Dufresne, Caroline European Journal of Medicinal Chemistry, Vol. 138 https://doi.org/10.1016/j.ejmech.2017.06.019	journal	September 2017
Matrix-isolation FT-IR spectra and theoretical study of dimethyl sulfate Borba, Ana; Gómez-Zavaglia, Andrea; Simões, Pedro N. N. L. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 61, Issue 7 https://doi.org/10.1016/j.saa.2004.10.050	journal	May 2005
Potential energy functions for atomic-level simulations of water and organic and biomolecular systems Jorgensen, W. L.; Tirado-Rives, J. Proceedings of the National Academy of Sciences, Vol. 102, Issue 19 https://doi.org/10.1073/pnas.0408037102	journal	May 2005
LigParGen web server: an automatic OPLS-AA parameter generator for organic ligands Dodda, Leela S.; Cabeza de Vaca, Israel; Tirado-Rives, Julian Nucleic Acids Research, Vol. 45, Issue W1 https://doi.org/10.1093/nar/gkx312	journal	April 2017
Enzymic and nonenzymic reactions of cyclic sulfonate and sulfate esters Kaiser, Emil Thomas Accounts of Chemical Research, Vol. 3, Issue 5 https://doi.org/10.1021/ar50029a001	journal	May 1970

Similar Records

Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead

Journal Article · 2021 · ACS Med. Chem. Lett. · OSTI ID:1767215

Ippolito, Joseph A.; Niu, Haichan; Bertoletti, Nicole; +8 more

Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead

Journal Article · 2021 · ACS Med. Chem. Lett. · OSTI ID:1770421

Ippolito, Joseph A.; Niu, Haichan; Bertoletti, Nicole; +8 more

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 VARIANT

Journal Article · 2004 · BIOCHEMISTRY · OSTI ID:884348

DAS, K; CLARK, A; LEWI, P; +6 more

Related Subjects

99 GENERAL AND MISCELLANEOUS

Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead

Citation Formats

References (29)

Similar Records

Related Subjects