Literature DB >> 20457521

Scaffold rearrangement of dihydroxypyrimidine inhibitors of HIV integrase: Docking model revisited.

Jing Tang1, Kasthuraiah Maddali, Yves Pommier, Yuk Y Sham, Zhengqiang Wang.   

Abstract

A series of dihydroxypyrimidine (DHP) derivatives were designed as inhibitors of HIV integrase (IN) based on known homology models. Through chemical synthesis and biochemical assays it was found that the activity profile of these compounds largely deviates from predictions with existing models. With the recently disclosed IN crystal structure of prototype foamy virus (PFV), a new HIV IN homology model was constructed featuring a critical IN/DNA interface previously lacking. With this new model, docking results completely corroborated observed biological activities. This new model should provide a more accurate and improved platform for the design of new inhibitors of HIV IN. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20457521      PMCID： PMC7323870          DOI： 10.1016/j.bmcl.2010.04.048

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  36 in total

1.  Identification of conserved amino acid residues critical for human immunodeficiency virus type 1 integrase function in vitro.

Authors:  A Engelman; R Craigie
Journal:  J Virol       Date:  1992-11       Impact factor: 5.103

2.  Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy.

Authors:  Richard A Friesner; Jay L Banks; Robert B Murphy; Thomas A Halgren; Jasna J Klicic; Daniel T Mainz; Matthew P Repasky; Eric H Knoll; Mee Shelley; Jason K Perry; David E Shaw; Perry Francis; Peter S Shenkin
Journal:  J Med Chem       Date:  2004-03-25       Impact factor: 7.446

3.  HIV-1 integrase pharmacophore model derived from diverse classes of inhibitors.

Authors:  Gabriela Iurcu Mustata; Alessandro Brigo; James M Briggs
Journal:  Bioorg Med Chem Lett       Date:  2004-03-22       Impact factor: 2.823

4.  Pharmacophore-based design of HIV-1 integrase strand-transfer inhibitors.

Authors:  Maria Letizia Barreca; Stefania Ferro; Angela Rao; Laura De Luca; Maria Zappalà; Anna-Maria Monforte; Zeger Debyser; Myriam Witvrouw; Alba Chimirri
Journal:  J Med Chem       Date:  2005-11-03       Impact factor: 7.446

Review 5.  HIV-1 integration: an interplay between HIV-1 integrase, cellular and viral proteins.

Authors:  Bénédicte Van Maele; Zeger Debyser
Journal:  AIDS Rev       Date:  2005 Jan-Mar       Impact factor: 2.500

6.  Docking studies on a new human immunodeficiency virus integrase-Mg-DNA complex: phenyl ring exploration and synthesis of 1H-benzylindole derivatives through fluorine substitutions.

Authors:  Stefania Ferro; Laura De Luca; Maria Letizia Barreca; Nunzio Iraci; Sara De Grazia; Frauke Christ; Myriam Witvrouw; Zeger Debyser; Alba Chimirri
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446

7.  Inhibitors of strand transfer that prevent integration and inhibit HIV-1 replication in cells.

Authors:  D J Hazuda; P Felock; M Witmer; A Wolfe; K Stillmock; J A Grobler; A Espeseth; L Gabryelski; W Schleif; C Blau; M D Miller
Journal:  Science       Date:  2000-01-28       Impact factor: 47.728

8.  Diketo acid pharmacophore. 2. Discovery of structurally diverse inhibitors of HIV-1 integrase.

Authors:  Raveendra Dayam; Tino Sanchez; Nouri Neamati
Journal:  J Med Chem       Date:  2005-12-15       Impact factor: 7.446

9.  A naphthyridine carboxamide provides evidence for discordant resistance between mechanistically identical inhibitors of HIV-1 integrase.

Authors:  Daria J Hazuda; Neville J Anthony; Robert P Gomez; Samson M Jolly; John S Wai; Linghang Zhuang; Thorsten E Fisher; Mark Embrey; James P Guare; Melissa S Egbertson; Joseph P Vacca; Joel R Huff; Peter J Felock; Marc V Witmer; Kara A Stillmock; Robert Danovich; Jay Grobler; Michael D Miller; Amy S Espeseth; Lixia Jin; I-Wu Chen; Jiunn H Lin; Kelem Kassahun; Joan D Ellis; Bradley K Wong; Wei Xu; Paul G Pearson; William A Schleif; Riccardo Cortese; Emilio Emini; Vincenzo Summa; M Katharine Holloway; Steven D Young
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-26       Impact factor: 11.205

10.  A refined pharmacophore model for HIV-1 integrase inhibitors: Optimization of potency in the 1H-benzylindole series.

Authors:  Laura De Luca; Maria Letizia Barreca; Stefania Ferro; Nunzio Iraci; Martine Michiels; Frauke Christ; Zeger Debyser; Myriam Witvrouw; Alba Chimirri
Journal:  Bioorg Med Chem Lett       Date:  2008-04-08       Impact factor: 2.823
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  11 in total

1.  Molecular mechanisms of retroviral integrase inhibition and the evolution of viral resistance.

Authors:  Stephen Hare; Ann M Vos; Reginald F Clayton; Jan W Thuring; Maxwell D Cummings; Peter Cherepanov
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-28       Impact factor: 11.205

2.  N-3 Hydroxylation of Pyrimidine-2,4-diones Yields Dual Inhibitors of HIV Reverse Transcriptase and Integrase.

Authors:  Jing Tang; Kasthuraiah Maddali; Christine D Dreis; Yuk Y Sham; Robert Vince; Yves Pommier; Zhengqiang Wang
Journal:  ACS Med Chem Lett       Date:  2011-01       Impact factor: 4.345

3.  Mutations in the amino terminus of herpes simplex virus type 1 gL can reduce cell-cell fusion without affecting gH/gL trafficking.

Authors:  Wenbo Zhou; Feng Chen; Yuri Klyachkin; Yuk Y Sham; Robert J Geraghty
Journal:  J Virol       Date:  2013-10-23       Impact factor: 5.103

4.  Can 5-methylcytosine analogues with extended alkyl side chains guide DNA methylation?

Authors:  D Kotandeniya; C L Seiler; J Fernandez; S S Pujari; L Curwick; K Murphy; S Wickramaratne; S Yan; D Murphy; Yuk Y Sham; N Y Tretyakova
Journal:  Chem Commun (Camb)       Date:  2018-01-25       Impact factor: 6.222

5.  N-Substituted Quinolinonyl Diketo Acid Derivatives as HIV Integrase Strand Transfer Inhibitors and Their Activity against RNase H Function of Reverse Transcriptase.

Authors:  Luca Pescatori; Mathieu Métifiot; Suhman Chung; Takashi Masoaka; Giuliana Cuzzucoli Crucitti; Antonella Messore; Giovanni Pupo; Valentina Noemi Madia; Francesco Saccoliti; Luigi Scipione; Silvano Tortorella; Francesco Saverio Di Leva; Sandro Cosconati; Luciana Marinelli; Ettore Novellino; Stuart F J Le Grice; Yves Pommier; Christophe Marchand; Roberta Costi; Roberto Di Santo
Journal:  J Med Chem       Date:  2015-05-26       Impact factor: 7.446

6.  3-Hydroxypyrimidine-2,4-diones as an inhibitor scaffold of HIV integrase.

Authors:  Jing Tang; Kasthuraiah Maddali; Mathieu Metifiot; Yuk Y Sham; Robert Vince; Yves Pommier; Zhengqiang Wang
Journal:  J Med Chem       Date:  2011-03-07       Impact factor: 7.446

7.  6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase.

Authors:  Jing Tang; Kasthuraiah Maddali; Christine D Dreis; Yuk Y Sham; Robert Vince; Yves Pommier; Zhengqiang Wang
Journal:  Bioorg Med Chem Lett       Date:  2011-02-18       Impact factor: 2.823

8.  4,5-Dihydroxypyrimidine Methyl Carboxylates, Carboxylic Acids, and Carboxamides as Inhibitors of Human Cytomegalovirus pUL89 Endonuclease.

Authors:  Tianyu He; Tiffany C Edwards; Jiashu Xie; Hideki Aihara; Robert J Geraghty; Zhengqiang Wang
Journal:  J Med Chem       Date:  2022-04-04       Impact factor: 8.039

Review 9.  Structural biology of retroviral DNA integration.

Authors:  Xiang Li; Lavanya Krishnan; Peter Cherepanov; Alan Engelman
Journal:  Virology       Date:  2011-01-08       Impact factor: 3.616

10.  Basic quinolinonyl diketo acid derivatives as inhibitors of HIV integrase and their activity against RNase H function of reverse transcriptase.

Authors:  Roberta Costi; Mathieu Métifiot; Suhman Chung; Giuliana Cuzzucoli Crucitti; Kasthuraiah Maddali; Luca Pescatori; Antonella Messore; Valentina Noemi Madia; Giovanni Pupo; Luigi Scipione; Silvano Tortorella; Francesco Saverio Di Leva; Sandro Cosconati; Luciana Marinelli; Ettore Novellino; Stuart F J Le Grice; Angela Corona; Yves Pommier; Christophe Marchand; Roberto Di Santo
Journal:  J Med Chem       Date:  2014-04-11       Impact factor: 7.446
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