Literature DB >> 26985324

Small-Molecule CD4-Mimics: Structure-Based Optimization of HIV-1 Entry Inhibition.

Bruno Melillo1, Shuaiyi Liang2, Jongwoo Park1, Arne Schön3, Joel R Courter1, Judith M LaLonde4, Daniel J Wendler1, Amy M Princiotto5, Michael S Seaman5, Ernesto Freire3, Joseph Sodroski6, Navid Madani5, Wayne A Hendrickson7, Amos B Smith1.   

Abstract

The optimization, based on computational, thermodynamic, and crystallographic data, of a series of small-molecule ligands of the Phe43 cavity of the envelope glycoprotein gp120 of human immunodeficiency virus (HIV) has been achieved. Importantly, biological evaluation revealed that the small-molecule CD4 mimics (4-7) inhibit HIV-1 entry into target cells with both significantly higher potency and neutralization breadth than previous congeners, while maintaining high selectivity for the target virus. Their binding mode was characterized via thermodynamic and crystallographic studies.

Entities:  

Keywords:  CD4; HIV; X-ray crystallography; entry inhibitor; gp120; protein−protein interactions; structure-based drug design; thermodynamics; viral inhibition

Year:  2016        PMID： 26985324      PMCID： PMC4789667          DOI： 10.1021/acsmedchemlett.5b00471

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  16 in total

1.  Effectiveness and safety of tenofovir gel, an antiretroviral microbicide, for the prevention of HIV infection in women.

Authors:  Quarraisha Abdool Karim; Salim S Abdool Karim; Janet A Frohlich; Anneke C Grobler; Cheryl Baxter; Leila E Mansoor; Ayesha B M Kharsany; Sengeziwe Sibeko; Koleka P Mlisana; Zaheen Omar; Tanuja N Gengiah; Silvia Maarschalk; Natasha Arulappan; Mukelisiwe Mlotshwa; Lynn Morris; Douglas Taylor
Journal:  Science       Date:  2010-07-19       Impact factor: 47.728

2.  Identification of N-phenyl-N'-(2,2,6,6-tetramethyl-piperidin-4-yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4.

Authors:  Qian Zhao; Liying Ma; Shibo Jiang; Hong Lu; Shuwen Liu; Yuxian He; Nathan Strick; Nouri Neamati; Asim Kumar Debnath
Journal:  Virology       Date:  2005-09-01       Impact factor: 3.616

3.  Synthesis of 2'-O-modified adenosine building blocks and application for RNA interference.

Authors:  Dalibor Odadzic; Jesper B Bramsen; Romualdas Smicius; Claus Bus; Jørgen Kjems; Joachim W Engels
Journal:  Bioorg Med Chem       Date:  2007-09-15       Impact factor: 3.641

4.  Development and validation of a genetic algorithm for flexible docking.

Authors:  G Jones; P Willett; R C Glen; A R Leach; R Taylor
Journal:  J Mol Biol       Date:  1997-04-04       Impact factor: 5.469

5.  CD4 mimetics sensitize HIV-1-infected cells to ADCC.

Authors:  Jonathan Richard; Maxime Veillette; Nathalie Brassard; Shilpa S Iyer; Michel Roger; Loïc Martin; Marzena Pazgier; Arne Schön; Ernesto Freire; Jean-Pierre Routy; Amos B Smith; Jongwoo Park; David M Jones; Joel R Courter; Bruno N Melillo; Daniel E Kaufmann; Beatrice H Hahn; Sallie R Permar; Barton F Haynes; Navid Madani; Joseph G Sodroski; Andrés Finzi
Journal:  Proc Natl Acad Sci U S A       Date:  2015-05-04       Impact factor: 11.205

Review 6.  Tenofovir-based pre-exposure prophylaxis for HIV prevention: evolving evidence.

Authors:  Connie Celum; Jared M Baeten
Journal:  Curr Opin Infect Dis       Date:  2012-02       Impact factor: 4.915

7.  Optimization of CD4/gp120 inhibitors by thermodynamic-guided alanine-scanning mutagenesis.

Authors:  Yingyun Liu; Arne Schön; Ernesto Freire
Journal:  Chem Biol Drug Des       Date:  2013-01       Impact factor: 2.817

8.  Structure-Based Design of a Small Molecule CD4-Antagonist with Broad Spectrum Anti-HIV-1 Activity.

Authors:  Francesca Curreli; Young Do Kwon; Hongtao Zhang; Daniel Scacalossi; Dmitry S Belov; Artur A Tikhonov; Ivan A Andreev; Andrea Altieri; Alexander V Kurkin; Peter D Kwong; Asim K Debnath
Journal:  J Med Chem       Date:  2015-08-28       Impact factor: 7.446

9.  A minimally cytotoxic CD4 mimic as an HIV entry inhibitor.

Authors:  Takaaki Mizuguchi; Shigeyoshi Harada; Tomoyuki Miura; Nami Ohashi; Tetsuo Narumi; Hiromi Mori; Yu Irahara; Yuko Yamada; Wataru Nomura; Shuzo Matsushita; Kazuhisa Yoshimura; Hirokazu Tamamura
Journal:  Bioorg Med Chem Lett       Date:  2015-11-30       Impact factor: 2.823

Review 10.  Structure-based design, synthesis and validation of CD4-mimetic small molecule inhibitors of HIV-1 entry: conversion of a viral entry agonist to an antagonist.

Authors:  Joel R Courter; Navid Madani; Joseph Sodroski; Arne Schön; Ernesto Freire; Peter D Kwong; Wayne A Hendrickson; Irwin M Chaiken; Judith M LaLonde; Amos B Smith
Journal:  Acc Chem Res       Date:  2014-02-06       Impact factor: 22.384
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  40 in total

1.  Chemical optimization of macrocyclic HIV-1 inactivators for improving potency and increasing the structural diversity at the triazole ring.

Authors:  Adel A Rashad; Kriti Acharya; Ann Haftl; Rachna Aneja; Alexej Dick; Andrew P Holmes; Irwin Chaiken
Journal:  Org Biomol Chem       Date:  2017-09-26       Impact factor: 3.876

2.  Long-Acting BMS-378806 Analogues Stabilize the State-1 Conformation of the Human Immunodeficiency Virus Type 1 Envelope Glycoproteins.

Authors:  Shitao Zou; Shijian Zhang; Althea Gaffney; Haitao Ding; Maolin Lu; Jonathan R Grover; Mark Farrell; Hanh T Nguyen; Connie Zhao; Saumya Anang; Meiqing Zhao; Mohammadjavad Mohammadi; Scott C Blanchard; Cameron Abrams; Navid Madani; Walther Mothes; John C Kappes; Amos B Smith; Joseph Sodroski
Journal:  J Virol       Date:  2020-05-04       Impact factor: 5.103

3.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

Review 4.  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

5.  Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

Authors:  Kevin P C Minbiole
Journal:  J Antibiot (Tokyo)       Date:  2016-03-02       Impact factor: 2.649

6.  Two Families of Env Antibodies Efficiently Engage Fc-Gamma Receptors and Eliminate HIV-1-Infected Cells.

Authors:  Sai Priya Anand; Jérémie Prévost; Sophie Baril; Jonathan Richard; Halima Medjahed; Jean-Philippe Chapleau; William D Tolbert; Sharon Kirk; Amos B Smith; Bruce D Wines; Stephen J Kent; P Mark Hogarth; Matthew S Parsons; Marzena Pazgier; Andrés Finzi
Journal:  J Virol       Date:  2019-01-17       Impact factor: 5.103

7.  Design, synthesis and evaluation of small molecule CD4-mimics as entry inhibitors possessing broad spectrum anti-HIV-1 activity.

Authors:  Francesca Curreli; Dmitry S Belov; Ranjith R Ramesh; Naisargi Patel; Andrea Altieri; Alexander V Kurkin; Asim K Debnath
Journal:  Bioorg Med Chem       Date:  2016-09-24       Impact factor: 3.641

8.  Preclinical Optimization of gp120 Entry Antagonists as anti-HIV-1 Agents with Improved Cytotoxicity and ADME Properties through Rational Design, Synthesis, and Antiviral Evaluation.

Authors:  Francesca Curreli; Shahad Ahmed; Sofia M Benedict Victor; Ildar R Iusupov; Dmitry S Belov; Pavel O Markov; Alexander V Kurkin; Andrea Altieri; Asim K Debnath
Journal:  J Med Chem       Date:  2020-02-17       Impact factor: 7.446

9.  A New Family of Small-Molecule CD4-Mimetic Compounds Contacts Highly Conserved Aspartic Acid 368 of HIV-1 gp120 and Mediates Antibody-Dependent Cellular Cytotoxicity.

Authors:  Shilei Ding; Melissa C Grenier; William D Tolbert; Dani Vézina; Rebekah Sherburn; Jonathan Richard; Jérémie Prévost; Jean-Philippe Chapleau; Gabrielle Gendron-Lepage; Halima Medjahed; Cameron Abrams; Joseph Sodroski; Marzena Pazgier; Amos B Smith; Andrés Finzi
Journal:  J Virol       Date:  2019-11-26       Impact factor: 5.103

10.  Computational Evaluation of HIV-1 gp120 Conformations of Soluble Trimeric gp140 Structures as Targets for de Novo Docking of First- and Second-Generation Small-Molecule CD4 Mimics.

Authors:  Francesca Moraca; Kriti Acharya; Bruno Melillo; Amos B Smith; Irwin Chaiken; Cameron F Abrams
Journal:  J Chem Inf Model       Date:  2016-09-26       Impact factor: 4.956
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