Literature DB >> 27568085

Indole-based allosteric inhibitors of HIV-1 integrase.

Pratiq A Patel1, Nina Kvaratskhelia2, Yara Mansour3, Janet Antwi4, Lei Feng2, Pratibha Koneru2, Mathew J Kobe2, Nivedita Jena4, Guqin Shi4, Mosaad S Mohamed5, Chenglong Li4, Jacques J Kessl6, James R Fuchs7.   

Abstract

Employing a scaffold hopping approach, a series of allosteric HIV-1 integrase (IN) inhibitors (ALLINIs) have been synthesized based on an indole scaffold. These compounds incorporate the key elements utilized in quinoline-based ALLINIs for binding to the IN dimer interface at the principal LEDGF/p75 binding pocket. The most potent of these compounds displayed good activity in the LEDGF/p75 dependent integration assay (IC50=4.5μM) and, as predicted based on the geometry of the five- versus six-membered ring, retained activity against the A128T IN mutant that confers resistance to many quinoline-based ALLINIs.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  ALLINI; HIV integrase inhibitor; Scaffold hopping

Mesh：

Substances：

Year:  2016        PMID： 27568085      PMCID： PMC5018460          DOI： 10.1016/j.bmcl.2016.08.037

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


  23 in total

1.  Multimode, cooperative mechanism of action of allosteric HIV-1 integrase inhibitors.

Authors:  Jacques J Kessl; Nivedita Jena; Yasuhiro Koh; Humeyra Taskent-Sezgin; Alison Slaughter; Lei Feng; Suresh de Silva; Li Wu; Stuart F J Le Grice; Alan Engelman; James R Fuchs; Mamuka Kvaratskhelia
Journal:  J Biol Chem       Date:  2012-03-21       Impact factor: 5.157

2.  New class of HIV-1 integrase (IN) inhibitors with a dual mode of action.

Authors:  Manuel Tsiang; Gregg S Jones; Anita Niedziela-Majka; Elaine Kan; Eric B Lansdon; Wayne Huang; Magdeleine Hung; Dharmaraj Samuel; Nikolai Novikov; Yili Xu; Michael Mitchell; Hongyan Guo; Kerim Babaoglu; Xiaohong Liu; Romas Geleziunas; Roman Sakowicz
Journal:  J Biol Chem       Date:  2012-04-25       Impact factor: 5.157

3.  Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor.

Authors:  Keith R Fandrick; Wenjie Li; Yongda Zhang; Wenjun Tang; Joe Gao; Sonia Rodriguez; Nitinchandra D Patel; Diana C Reeves; Jiang-Ping Wu; Sanjit Sanyal; Nina Gonnella; Bo Qu; Nizar Haddad; Jon C Lorenz; Kanwar Sidhu; June Wang; Shengli Ma; Nelu Grinberg; Heewon Lee; Youla Tsantrizos; Marc-André Poupart; Carl A Busacca; Nathan K Yee; Bruce Z Lu; Chris H Senanayake
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-04       Impact factor: 15.336

4.  The A128T resistance mutation reveals aberrant protein multimerization as the primary mechanism of action of allosteric HIV-1 integrase inhibitors.

Authors:  Lei Feng; Amit Sharma; Alison Slaughter; Nivedita Jena; Yasuhiro Koh; Nikolozi Shkriabai; Ross C Larue; Pratiq A Patel; Hiroaki Mitsuya; Jacques J Kessl; Alan Engelman; James R Fuchs; Mamuka Kvaratskhelia
Journal:  J Biol Chem       Date:  2013-04-24       Impact factor: 5.157

5.  Discovery of BI 224436, a Noncatalytic Site Integrase Inhibitor (NCINI) of HIV-1.

Authors:  Lee D Fader; Eric Malenfant; Mathieu Parisien; Rebekah Carson; François Bilodeau; Serge Landry; Marc Pesant; Christian Brochu; Sébastien Morin; Catherine Chabot; Ted Halmos; Yves Bousquet; Murray D Bailey; Stephen H Kawai; René Coulombe; Steven LaPlante; Araz Jakalian; Punit K Bhardwaj; Dominik Wernic; Patricia Schroeder; Ma'an Amad; Paul Edwards; Michel Garneau; Jianmin Duan; Michael Cordingley; Richard Bethell; Stephen W Mason; Michael Bös; Pierre Bonneau; Marc-André Poupart; Anne-Marie Faucher; Bruno Simoneau; Craig Fenwick; Christiane Yoakim; Youla Tsantrizos
Journal:  ACS Med Chem Lett       Date:  2014-01-22       Impact factor: 4.345

6.  An Efficient, Microwave-Assisted, One-Pot Synthesis of Indoles Under Sonogashira Conditions.

Authors:  Yu Chen; Nataliya A Markina; Richard C Larock
Journal:  Tetrahedron       Date:  2009-10-31       Impact factor: 2.457

7.  Indole synthesis: a review and proposed classification.

Authors:  Douglass F Taber; Pavan K Tirunahari
Journal:  Tetrahedron       Date:  2011-09-23       Impact factor: 2.457

8.  Allosteric integrase inhibitor potency is determined through the inhibition of HIV-1 particle maturation.

Authors:  Kellie A Jurado; Hao Wang; Alison Slaughter; Lei Feng; Jacques J Kessl; Yasuhiro Koh; Weifeng Wang; Allison Ballandras-Colas; Pratiq A Patel; James R Fuchs; Mamuka Kvaratskhelia; Alan Engelman
Journal:  Proc Natl Acad Sci U S A       Date:  2013-04-22       Impact factor: 11.205

9.  AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility.

Authors:  Garrett M Morris; Ruth Huey; William Lindstrom; Michel F Sanner; Richard K Belew; David S Goodsell; Arthur J Olson
Journal:  J Comput Chem       Date:  2009-12       Impact factor: 3.376

10.  The allosteric HIV-1 integrase inhibitor BI-D affects virion maturation but does not influence packaging of a functional RNA genome.

Authors:  Nikki van Bel; Yme van der Velden; Damien Bonnard; Erwann Le Rouzic; Atze T Das; Richard Benarous; Ben Berkhout
Journal:  PLoS One       Date:  2014-07-29       Impact factor: 3.240
View more
  8 in total

Review 1.  New targets for HIV drug discovery.

Authors:  Ana C Puhl; Alfredo Garzino Demo; Vadim A Makarov; Sean Ekins
Journal:  Drug Discov Today       Date:  2019-03-15       Impact factor: 7.851

2.  An Isoquinoline Scaffold as a Novel Class of Allosteric HIV-1 Integrase Inhibitors.

Authors:  Tyler A Wilson; Pratibha C Koneru; Stephanie V Rebensburg; Jared J Lindenberger; Matthew J Kobe; Nicholas T Cockroft; Daniel Adu-Ampratwum; Ross C Larue; Mamuka Kvaratskhelia; James R Fuchs
Journal:  ACS Med Chem Lett       Date:  2019-01-30       Impact factor: 4.345

3.  Retroviral integrase: Structure, mechanism, and inhibition.

Authors:  Dario Oliveira Passos; Min Li; Robert Craigie; Dmitry Lyumkis
Journal:  Enzymes       Date:  2021-08-23

4.  HIV-1 integrase tetramers are the antiviral target of pyridine-based allosteric integrase inhibitors.

Authors:  Pratibha C Koneru; Ashwanth C Francis; Nanjie Deng; Stephanie V Rebensburg; Ashley C Hoyte; Jared Lindenberger; Daniel Adu-Ampratwum; Ross C Larue; Michael F Wempe; Alan N Engelman; Dmitry Lyumkis; James R Fuchs; Ronald M Levy; Gregory B Melikyan; Mamuka Kvaratskhelia
Journal:  Elife       Date:  2019-05-23       Impact factor: 8.140

5.  Identification and Optimization of a Novel HIV-1 Integrase Inhibitor.

Authors:  Daniel Adu-Ampratwum; Yuhan Pan; Pratibha C Koneru; Janet Antwi; Ashley C Hoyte; Jacques Kessl; Patrick R Griffin; Mamuka Kvaratskhelia; James R Fuchs; Ross C Larue
Journal:  ACS Omega       Date:  2022-01-24

6.  Multi-Substituted Quinolines as HIV-1 Integrase Allosteric Inhibitors.

Authors:  Long Phi Dinh; Jian Sun; Courtney D Glenn; Krunal Patel; Julie A Pigza; Matthew G Donahue; Larry Yet; Jacques J Kessl
Journal:  Viruses       Date:  2022-07-02       Impact factor: 5.818

7.  A highly potent and safe pyrrolopyridine-based allosteric HIV-1 integrase inhibitor targeting host LEDGF/p75-integrase interaction site.

Authors:  Tatsuya Maehigashi; Seohyun Ahn; Uk-Il Kim; Jared Lindenberger; Adrian Oo; Pratibha C Koneru; Bijan Mahboubi; Alan N Engelman; Mamuka Kvaratskhelia; Kyungjin Kim; Baek Kim
Journal:  PLoS Pathog       Date:  2021-07-22       Impact factor: 6.823

8.  Synthesis and Evaluation of Aryl Quinolines as HIV-1 Integrase Multimerization Inhibitors.

Authors:  Nicholas G Jentsch; Alison P Hart; Jared D Hume; Jian Sun; Kaitlin A McNeely; Chiyang Lama; Julie A Pigza; Matthew G Donahue; Jacques J Kessl
Journal:  ACS Med Chem Lett       Date:  2018-09-14       Impact factor: 4.632
  8 in total

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