Literature DB >> 26331669

Macrocyclic Envelope Glycoprotein Antagonists that Irreversibly Inactivate HIV-1 before Host Cell Encounter.

Adel A Rashad1, Ramalingam Venkat Kalyana Sundaram1,2, Rachna Aneja1, Caitlin Duffy1, Irwin Chaiken1.   

Abstract

We derived macrocyclic HIV-1 antagonists as a new class of peptidomimetic drug leads. Cyclic peptide triazoles (cPTs) retained the gp120 inhibitory and virus-inactivating signature of parent PTs, arguing that cyclization locked an active conformation. The six-residue cPT 9 (AAR029b) exhibited submicromolar antiviral potencies in inhibiting cell infection and triggering gp120 shedding that causes irreversible virion inactivation. Importantly, cPTs were stable to trypsin and chymotrypsin compared to substantial susceptibility of corresponding linear PTs.

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Year:  2015        PMID： 26331669      PMCID： PMC4936186          DOI： 10.1021/acs.jmedchem.5b00935

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  22 in total

1.  Mode of action for linear peptide inhibitors of HIV-1 gp120 interactions.

Authors:  Alyssa C Biorn; Simon Cocklin; Navid Madani; Zhihai Si; Tijana Ivanovic; James Samanen; Donald I Van Ryk; Ralph Pantophlet; Dennis R Burton; Ernesto Freire; Joseph Sodroski; Irwin M Chaiken
Journal:  Biochemistry       Date:  2004-02-24       Impact factor: 3.162

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

Review 3.  Constraining cyclic peptides to mimic protein structure motifs.

Authors:  Timothy A Hill; Nicholas E Shepherd; Frederik Diness; David P Fairlie
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-06       Impact factor: 15.336

4.  Cell-free HIV-1 virucidal action by modified peptide triazole inhibitors of Env gp120.

Authors:  Arangassery R Bastian; Karyn McFadden; Caitlin Duffy; Srivats Rajagopal; Mark R Contarino; Elisabeth Papazoglou; Irwin Chaiken
Journal:  ChemMedChem       Date:  2011-06-28       Impact factor: 3.466

5.  Peptide Triazole Inactivators of HIV-1 Utilize a Conserved Two-Cavity Binding Site at the Junction of the Inner and Outer Domains of Env gp120.

Authors:  Rachna Aneja; Adel A Rashad; Huiyuan Li; Ramalingam Venkat Kalyana Sundaram; Caitlin Duffy; Lauren D Bailey; Irwin Chaiken
Journal:  J Med Chem       Date:  2015-04-28       Impact factor: 7.446

6.  Antiviral breadth and combination potential of peptide triazole HIV-1 entry inhibitors.

Authors:  Karyn McFadden; Patricia Fletcher; Fiorella Rossi; Muddagowda Umashankara; Vanessa Pirrone; Srivats Rajagopal; Hosahudya Gopi; Fred C Krebs; Julio Martin-Garcia; Robin J Shattock; Irwin Chaiken
Journal:  Antimicrob Agents Chemother       Date:  2011-11-14       Impact factor: 5.191

7.  Synthesis, stability, antiviral activity, and protease-bound structures of substrate-mimicking constrained macrocyclic inhibitors of HIV-1 protease.

Authors:  J D Tyndall; R C Reid; D P Tyssen; D K Jardine; B Todd; M Passmore; D R March; L K Pattenden; D A Bergman; D Alewood; S H Hu; P F Alewood; C J Birch; J L Martin; D P Fairlie
Journal:  J Med Chem       Date:  2000-09-21       Impact factor: 7.446

8.  Increasing protein stability by improving beta-turns.

Authors:  Hailong Fu; Gerald R Grimsley; Abbas Razvi; J Martin Scholtz; C Nick Pace
Journal:  Proteins       Date:  2009-11-15

9.  Interactions of peptide triazole thiols with Env gp120 induce irreversible breakdown and inactivation of HIV-1 virions.

Authors:  Arangassery Rosemary Bastian; Mark Contarino; Lauren D Bailey; Rachna Aneja; Diogo Rodrigo Magalhaes Moreira; Kevin Freedman; Karyn McFadden; Caitlin Duffy; Ali Emileh; George Leslie; Jeffrey M Jacobson; James A Hoxie; Irwin Chaiken
Journal:  Retrovirology       Date:  2013-12-13       Impact factor: 4.602

10.  HIV-1 attachment inhibitor prodrug BMS-663068 in antiretroviral-experienced subjects: week 24 sub-group analysis.

Authors:  Cynthia Brinson; Jacob Lalezari; Latiff H Gulam; Melanie Thompson; Juan Echevarria; Sandra Treviño-Pérez; David Stock; Joshi R Samit; Hanna J George; Max Lataillade
Journal:  J Int AIDS Soc       Date:  2014-11-02       Impact factor: 5.396
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  11 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.  Disulfide Sensitivity in the Env Protein Underlies Lytic Inactivation of HIV-1 by Peptide Triazole Thiols.

Authors:  Lauren D Bailey; Ramalingam Venkat Kalyana Sundaram; Huiyuan Li; Caitlin Duffy; Rachna Aneja; Arangassery Rosemary Bastian; Andrew P Holmes; Kantharaju Kamanna; Adel A Rashad; Irwin Chaiken
Journal:  ACS Chem Biol       Date:  2015-10-22       Impact factor: 5.100

3.  Pharmacokinetic stability of macrocyclic peptide triazole HIV-1 inactivators alone and in liposomes.

Authors:  Rachna Aneja; Antonella Grigoletto; Aakansha Nangarlia; Adel A Rashad; Steven Wrenn; Jeffrey M Jacobson; Gianfranco Pasut; Irwin Chaiken
Journal:  J Pept Sci       Date:  2019-02-27       Impact factor: 1.905

4.  Recognition of HIV-inactivating peptide triazoles by the recombinant soluble Env trimer, BG505 SOSIP.664.

Authors:  Kriti Acharya; Adel A Rashad; Francesca Moraca; Per Johan Klasse; John P Moore; Cameron Abrams; Irwin Chaiken
Journal:  Proteins       Date:  2017-03-11

5.  Targeting cell surface HIV-1 Env protein to suppress infectious virus formation.

Authors:  Arangassery Rosemary Bastian; Charles G Ang; Kantharaju Kamanna; Farida Shaheen; Yu-Hung Huang; Karyn McFadden; Caitlin Duffy; Lauren D Bailey; Ramalingam Venkat Kalyana Sundaram; Irwin Chaiken
Journal:  Virus Res       Date:  2017-04-06       Impact factor: 3.303

6.  Peptide triazole inactivators of HIV-1: how do they work and what is their potential?

Authors:  Irwin Chaiken; Adel A Rashad
Journal:  Future Med Chem       Date:  2015-11-24       Impact factor: 3.808

7.  Bifunctional Chimera That Coordinately Targets Human Immunodeficiency Virus 1 Envelope gp120 and the Host-Cell CCR5 Coreceptor at the Virus-Cell Interface.

Authors:  Adel A Rashad; Li-Rui Song; Andrew P Holmes; Kriti Acharya; Shiyu Zhang; Zhi-Long Wang; Ebony Gary; Xin Xie; Vanessa Pirrone; Michele A Kutzler; Ya-Qiu Long; Irwin Chaiken
Journal:  J Med Chem       Date:  2018-06-01       Impact factor: 7.446

8.  The HIV-1 Env gp120 Inner Domain Shapes the Phe43 Cavity and the CD4 Binding Site.

Authors:  Jérémie Prévost; William D Tolbert; Halima Medjahed; Rebekah T Sherburn; Navid Madani; Daria Zoubchenok; Gabrielle Gendron-Lepage; Althea E Gaffney; Melissa C Grenier; Sharon Kirk; Natasha Vergara; Changze Han; Brendan T Mann; Agnès L Chénine; Adel Ahmed; Irwin Chaiken; Frank Kirchhoff; Beatrice H Hahn; Hillel Haim; Cameron F Abrams; Amos B Smith; Joseph Sodroski; Marzena Pazgier; Andrés Finzi
Journal:  mBio       Date:  2020-05-26       Impact factor: 7.867

Review 9.  Recent Advances in Macrocyclic Drugs and Microwave-Assisted and/or Solid-Supported Synthesis of Macrocycles.

Authors:  Dianqing Sun
Journal:  Molecules       Date:  2022-02-02       Impact factor: 4.411

Review 10.  Triazole-Modified Peptidomimetics: An Opportunity for Drug Discovery and Development.

Authors:  Agnieszka Staśkiewicz; Patrycja Ledwoń; Paolo Rovero; Anna Maria Papini; Rafal Latajka
Journal:  Front Chem       Date:  2021-05-20       Impact factor: 5.221
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