Literature DB >> 27475281

Sulfotyrosine dipeptide: Synthesis and evaluation as HIV-entry inhibitor.

Tong Ju1, Duoyi Hu2, Shi-Hua Xiang3, Jiantao Guo4.   

Abstract

Human immunodeficiency virus type 1 (HIV-1) is responsible for the worldwide AIDS pandemic. Due to the lack of prophylactic HIV-1 vaccine, drug treatment of the infected patients becomes essential to reduce the viral load and to slow down progression of the disease. Because of drug resistance, finding new antiviral agents is necessary for AIDS drug therapies. The interaction of gp120 and co-receptor (CCR5/CXCR4) mediates the entry of HIV-1 into host cells, which has been increasingly exploited in recent years as the target for new antiviral agents. A conserved co-receptor binding site on gp120 that recognizes sulfotyrosine (sTyr) residues represents a structural target to design novel HIV entry inhibitors. In this work, we developed an efficient synthesis of sulfotyrosine dipeptide and evaluated it as an HIV-1 entry inhibitor.
Copyright © 2016 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Antiviral therapy; HIV entry inhibitor; Protein sulfation; Sulfopeptide; Sulfotyrosine; Sulfotyrosine dipeptide; gp120

Mesh:

Substances:

Year:  2016        PMID: 27475281      PMCID: PMC5922769          DOI: 10.1016/j.bioorg.2016.07.012

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  37 in total

1.  A strategy for the synthesis of sulfated peptides.

Authors:  Travis Young; Laura L Kiessling
Journal:  Angew Chem Int Ed Engl       Date:  2002-09-16       Impact factor: 15.336

2.  Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.

Authors:  Valeria M Zakharova; Michaela Serpi; Ivan S Krylov; Larryn W Peterson; Julie M Breitenbach; Katherine Z Borysko; John C Drach; Mindy Collins; John M Hilfinger; Boris A Kashemirov; Charles E McKenna
Journal:  J Med Chem       Date:  2011-08-03       Impact factor: 7.446

3.  HIV-1 membrane fusion mechanism: structural studies of the interactions between biologically-active peptides from gp41.

Authors:  M K Lawless; S Barney; K I Guthrie; T B Bucy; S R Petteway; G Merutka
Journal:  Biochemistry       Date:  1996-10-22       Impact factor: 3.162

4.  Synthesis of cholecystokinin-pancreozymin. I. The C-terminal dodecapeptide.

Authors:  M A Ondetti; J Pluscec; E F Sabo; J T Sheehan; N Williams
Journal:  J Am Chem Soc       Date:  1970-01-14       Impact factor: 15.419

5.  Tyrosine sulfation of the amino terminus of CCR5 facilitates HIV-1 entry.

Authors:  M Farzan; T Mirzabekov; P Kolchinsky; R Wyatt; M Cayabyab; N P Gerard; C Gerard; J Sodroski; H Choe
Journal:  Cell       Date:  1999-03-05       Impact factor: 41.582

6.  Facile solid-phase synthesis of sulfated tyrosine-containing peptides: Part II. Total synthesis of human big gastrin-II and its C-terminal glycine-extended peptide (G34-Gly sulfate) by the solid-phase segment condensation approach.

Authors:  K Kitagawa; C Aida; H Fujiwara; T Yagami; S Futaki
Journal:  Chem Pharm Bull (Tokyo)       Date:  2001-08       Impact factor: 1.645

7.  Molecular recognition of sulfotyrosine and phosphotyrosine by the Src homology 2 domain.

Authors:  Tong Ju; Wei Niu; Ronald Cerny; Joshua Bollman; Anthony Roy; Jiantao Guo
Journal:  Mol Biosyst       Date:  2013-04-09

Review 8.  A Blueprint for HIV Vaccine Discovery.

Authors:  Dennis R Burton; Rafi Ahmed; Dan H Barouch; Salvatore T Butera; Shane Crotty; Adam Godzik; Daniel E Kaufmann; M Juliana McElrath; Michel C Nussenzweig; Bali Pulendran; Chris N Scanlan; William R Schief; Guido Silvestri; Hendrik Streeck; Bruce D Walker; Laura M Walker; Andrew B Ward; Ian A Wilson; Richard Wyatt
Journal:  Cell Host Microbe       Date:  2012-10-18       Impact factor: 21.023

9.  An analysis of FDA-approved drugs for infectious disease: HIV/AIDS drugs.

Authors:  Michael S Kinch; Eric Patridge
Journal:  Drug Discov Today       Date:  2014-05-28       Impact factor: 8.369

10.  AAV-expressed eCD4-Ig provides durable protection from multiple SHIV challenges.

Authors:  Matthew R Gardner; Lisa M Kattenhorn; Hema R Kondur; Markus von Schaewen; Tatyana Dorfman; Jessica J Chiang; Kevin G Haworth; Julie M Decker; Michael D Alpert; Charles C Bailey; Ernest S Neale; Christoph H Fellinger; Vinita R Joshi; Sebastian P Fuchs; Jose M Martinez-Navio; Brian D Quinlan; Annie Y Yao; Hugo Mouquet; Jason Gorman; Baoshan Zhang; Pascal Poignard; Michel C Nussenzweig; Dennis R Burton; Peter D Kwong; Michael Piatak; Jeffrey D Lifson; Guangping Gao; Ronald C Desrosiers; David T Evans; Beatrice H Hahn; Alexander Ploss; Paula M Cannon; Michael S Seaman; Michael Farzan
Journal:  Nature       Date:  2015-02-18       Impact factor: 49.962

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