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Activities, crystal structures, and molecular dynamics of dihydro-1H-isoindole derivatives, inhibitors of HIV-1 integrase.

Métifiot M, Maddali K, Johnson BC, Hare S, Smith SJ, Zhao XZ, Marchand C, Burke TR, Hughes SH, Cherepanov P, Pommier Y
ACS Chem Biol 8 209-17 (2013)
Related entries: 4bdy, 4bdz, 4be1, 4be2

Cited: 28 times
EuropePMC logo PMID: 23075516

Abstract

On the basis of a series of lactam and phthalimide derivatives that inhibit HIV-1 integrase, we developed a new molecule, XZ-259, with biochemical and antiviral activities comparable to raltegravir. We determined the crystal structures of XZ-259 and four other derivatives in complex with the prototype foamy virus intasome. The compounds bind at the integrase-Mg(2+)-DNA interface of the integrase active site. In biochemical and antiviral assays, XZ-259 inhibits raltegravir-resistant HIV-1 integrases harboring the Y143R mutation. Molecular modeling is also presented suggesting that XZ-259 can bind in the HIV-1 intasome with its dimethyl sulfonamide group adopting two opposite orientations. Molecular dynamics analyses of the HIV-1 intasome highlight the importance of the viral DNA in drug potency.

Articles - 4be0 mentioned but not cited (1)

  1. Activities, crystal structures, and molecular dynamics of dihydro-1H-isoindole derivatives, inhibitors of HIV-1 integrase. Métifiot M, Maddali K, Johnson BC, Hare S, Smith SJ, Zhao XZ, Marchand C, Burke TR, Hughes SH, Cherepanov P, Pommier Y. ACS Chem Biol 8 209-217 (2013)


Reviews citing this publication (7)

  1. Targeting Metalloenzymes for Therapeutic Intervention. Chen AY, Adamek RN, Dick BL, Credille CV, Morrison CN, Cohen SM. Chem Rev 119 1323-1455 (2019)
  2. Blind prediction of HIV integrase binding from the SAMPL4 challenge. Mobley DL, Liu S, Lim NM, Wymer KL, Perryman AL, Forli S, Deng N, Su J, Branson K, Olson AJ. J Comput Aided Mol Des 28 327-345 (2014)
  3. HIV integrase inhibitors: 20-year landmark and challenges. Métifiot M, Marchand C, Pommier Y. Adv Pharmacol 67 75-105 (2013)
  4. Dancing with chemical formulae of antivirals: A panoramic view (Part 2). De Clercq E. Biochem Pharmacol 86 1397-1410 (2013)
  5. Progress in HIV-1 Integrase Inhibitors: A Review of their Chemical Structure Diversity. Hajimahdi Z, Zarghi A. Iran J Pharm Res 15 595-628 (2016)
  6. Retroviral integrase protein and intasome nucleoprotein complex structures. Grawenhoff J, Engelman AN. World J Biol Chem 8 32-44 (2017)
  7. 6,7-Dihydroxyisoindolin-1-one and 7,8-Dihydroxy-3,4-Dihydroisoquinolin- 1(2H)-one Based HIV-1 Integrase Inhibitors. Zhao XZ, Metifiot M, Smith SJ, Maddali K, Marchand C, Hughes SH, Pommier Y, Burke TR. Curr Top Med Chem 16 435-440 (2016)

Articles citing this publication (20)

  1. Structure-activity relationship of pyrrolyl diketo acid derivatives as dual inhibitors of HIV-1 integrase and reverse transcriptase ribonuclease H domain. Cuzzucoli Crucitti G, Métifiot M, Pescatori L, Messore A, Madia VN, Pupo G, Saccoliti F, Scipione L, Tortorella S, Esposito F, Corona A, Cadeddu M, Marchand C, Pommier Y, Tramontano E, Costi R, Di Santo R. J Med Chem 58 1915-1928 (2015)
  2. Basic quinolinonyl diketo acid derivatives as inhibitors of HIV integrase and their activity against RNase H function of reverse transcriptase. Costi R, Métifiot M, Chung S, Cuzzucoli Crucitti G, Maddali K, Pescatori L, Messore A, Madia VN, Pupo G, Scipione L, Tortorella S, Di Leva FS, Cosconati S, Marinelli L, Novellino E, Le Grice SF, Corona A, Pommier Y, Marchand C, Di Santo R. J Med Chem 57 3223-3234 (2014)
  3. Structure-Guided Optimization of HIV Integrase Strand Transfer Inhibitors. Zhao XZ, Smith SJ, Maskell DP, Métifiot M, Pye VE, Fesen K, Marchand C, Pommier Y, Cherepanov P, Hughes SH, Burke TR. J Med Chem 60 7315-7332 (2017)
  4. HIV-1 Integrase Strand Transfer Inhibitors with Reduced Susceptibility to Drug Resistant Mutant Integrases. Zhao XZ, Smith SJ, Maskell DP, Metifiot M, Pye VE, Fesen K, Marchand C, Pommier Y, Cherepanov P, Hughes SH, Burke TR. ACS Chem Biol 11 1074-1081 (2016)
  5. 4-amino-1-hydroxy-2-oxo-1,8-naphthyridine-containing compounds having high potency against raltegravir-resistant integrase mutants of HIV-1. Zhao XZ, Smith SJ, Métifiot M, Marchand C, Boyer PL, Pommier Y, Hughes SH, Burke TR. J Med Chem 57 5190-5202 (2014)
  6. Bicyclic 1-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide-containing HIV-1 integrase inhibitors having high antiviral potency against cells harboring raltegravir-resistant integrase mutants. Zhao XZ, Smith SJ, Métifiot M, Johnson BC, Marchand C, Pommier Y, Hughes SH, Burke TR. J Med Chem 57 1573-1582 (2014)
  7. N-Substituted Quinolinonyl Diketo Acid Derivatives as HIV Integrase Strand Transfer Inhibitors and Their Activity against RNase H Function of Reverse Transcriptase. Pescatori L, Métifiot M, Chung S, Masoaka T, Cuzzucoli Crucitti G, Messore A, Pupo G, Madia VN, Saccoliti F, Scipione L, Tortorella S, Di Leva FS, Cosconati S, Marinelli L, Novellino E, Le Grice SF, Pommier Y, Marchand C, Costi R, Di Santo R. J Med Chem 58 4610-4623 (2015)
  8. Discovery of a new HIV-1 inhibitor scaffold and synthesis of potential prodrugs of indazoles. Kim SH, Markovitz B, Trovato R, Murphy BR, Austin H, Willardsen AJ, Baichwal V, Morham S, Bajji A. Bioorg Med Chem Lett 23 2888-2892 (2013)
  9. Selectivity for strand-transfer over 3'-processing and susceptibility to clinical resistance of HIV-1 integrase inhibitors are driven by key enzyme-DNA interactions in the active site. Métifiot M, Johnson BC, Kiselev E, Marler L, Zhao XZ, Burke TR, Marchand C, Hughes SH, Pommier Y. Nucleic Acids Res 44 6896-6906 (2016)
  10. Exploring the chemical space and the bioactivity profile of lactams: a chemoinformatic study. Saldívar-González FI, Lenci E, Trabocchi A, Medina-Franco JL. RSC Adv 9 27105-27116 (2019)
  11. Structural basis of Mos1 transposase inhibition by the anti-retroviral drug Raltegravir. Wolkowicz UM, Morris ER, Robson M, Trubitsyna M, Richardson JM. ACS Chem Biol 9 743-751 (2014)
  12. HIV-1 Integrase Inhibitors with Modifications That Affect Their Potencies against Drug Resistant Integrase Mutants. Smith SJ, Zhao XZ, Passos DO, Pye VE, Cherepanov P, Lyumkis D, Burke TR, Hughes SH. ACS Infect Dis 7 1469-1482 (2021)
  13. Drug resistant integrase mutants cause aberrant HIV integrations. Varadarajan J, McWilliams MJ, Mott BT, Thomas CJ, Smith SJ, Hughes SH. Retrovirology 13 71 (2016)
  14. Discovery and optimization of 2-pyridinone aminal integrase strand transfer inhibitors for the treatment of HIV. Schreier JD, Embrey MW, Raheem IT, Barbe G, Campeau LC, Dubost D, McCabe Dunn J, Grobler J, Hartingh TJ, Hazuda DJ, Klein D, Miller MD, Moore KP, Nguyen N, Pajkovic N, Powell DA, Rada V, Sanders JM, Sisko J, Steele TG, Wai J, Walji A, Xu M, Coleman PJ. Bioorg Med Chem Lett 27 2038-2046 (2017)
  15. Structural Insights to Human Immunodeficiency Virus (HIV-1) Targets and Their Inhibition. Vanangamudi M, Nair PC, Engels SEM, Palaniappan S, Namasivayam V. Adv Exp Med Biol 1322 63-95 (2021)
  16. A targeted DNA substrate mechanism for the inhibition of HIV-1 integrase by inhibitors with antiretroviral activity. Ammar FF, Hobaika Z, Abdel-Azeim S, Zargarian L, Maroun RG, Fermandjian S. FEBS Open Bio 6 234-250 (2016)
  17. Comparison of Newly Assembled Full Length HIV-1 Integrase With Prototype Foamy Virus Integrase: Structure-Function Prospective. Dayer MR. Jundishapur J Microbiol 9 e29773 (2016)
  18. Influence of Drug Resistance Mutations on the Activity of HIV-1 Subtypes A and B Integrases: a Comparative Study. Shadrina OA, Zatsepin TS, Agapkina YY, Isaguliants MG, Gottikh MB. Acta Naturae 7 78-86 (2015)
  19. Structural basis for the inhibition of HTLV-1 integration inferred from cryo-EM deltaretroviral intasome structures. Barski MS, Vanzo T, Zhao XZ, Smith SJ, Ballandras-Colas A, Cronin NB, Pye VE, Hughes SH, Burke TR, Cherepanov P, Maertens GN. Nat Commun 12 4996 (2021)
  20. Cobalt-Catalyzed Aerobic Aminocyclization of Unsaturated Amides for the Synthesis of Functionalized γ- and δ-Lactams. Freis M, Balkenhohl M, Fischer DM, Georgiev T, Sarott RC, Carreira EM. Org Lett 25 6380-6384 (2023)


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