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Literature DB >> 19497744

Identification of a beta3-peptide HIV fusion inhibitor with improved potency in live cells.

Arjel D Bautista¹, Olen M Stephens, Ligong Wang, Robert A Domaoal, Karen S Anderson, Alanna Schepartz.

Abstract

We recently reported a beta(3)-decapeptide, betaWWI-1, that binds a validated gp41 model in vitro and inhibits gp41-mediated fusion in cell culture. Here we report six analogs of betaWWI-1 containing a variety of non-natural side chains in place of the central tryptophan of the WWI-epitope. These analogs were compared on the basis of both gp41 affinity in vitro and fusion inibition in live, HIV-infected cells. One new beta(3)-peptide, betaWXI-a, offers a significantly improved CC(50)/EC(50) ratio in the live cell assay.

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Year: 2009 PMID： 19497744 PMCID： PMC2737262 DOI： 10.1016/j.bmcl.2009.05.032

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

33 in total

1. De novo design of a monomeric helical beta-peptide stabilized by electrostatic interactions.

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2. Efficient synthesis of a beta-peptide combinatorial library with microwave irradiation.

Authors: Justin K Murray; Bilal Farooqi; Jack D Sadowsky; Mark Scalf; Wesley A Freund; Lloyd M Smith; Jiandong Chen; Samuel H Gellman
Journal: J Am Chem Soc Date: 2005-09-28 Impact factor: 15.419

3. Pharmacokinetic investigation of a 14C-labelled beta 3/alpha tetrapeptide in rats.

Authors: Hansjörg Wiegand; Bernard Wirz; Alain Schweitzer; Gerhard Gross; Maria I Rodriguez Perez; Hendrik Andres; Thierry Kimmerlin; Magnus Rueping; Dieter Seebach
Journal: Chem Biodivers Date: 2004-11 Impact factor: 2.408

4. Small molecules that bind the inner core of gp41 and inhibit HIV envelope-mediated fusion.

Authors: Gary Frey; Sophia Rits-Volloch; X-Q Zhang; Robert T Schooley; Bing Chen; Stephen C Harrison
Journal: Proc Natl Acad Sci U S A Date: 2006-09-08 Impact factor: 11.205

Review 5. Sophistication of foldamer form and function in vitro and in vivo.

Authors: Arjel D Bautista; Cody J Craig; Elizabeth A Harker; Alanna Schepartz
Journal: Curr Opin Chem Biol Date: 2007-11-07 Impact factor: 8.822

6. Potent D-peptide inhibitors of HIV-1 entry.

Authors: Brett D Welch; Andrew P VanDemark; Annie Heroux; Christopher P Hill; Michael S Kay
Journal: Proc Natl Acad Sci U S A Date: 2007-10-17 Impact factor: 11.205

7. Design of helical, oligomeric HIV-1 fusion inhibitor peptides with potent activity against enfuvirtide-resistant virus.

Authors: John J Dwyer; Karen L Wilson; Donna K Davison; Stephanie A Freel; Jennifer E Seedorff; Stephen A Wring; Nicolai A Tvermoes; Thomas J Matthews; Michael L Greenberg; Mary K Delmedico
Journal: Proc Natl Acad Sci U S A Date: 2007-07-19 Impact factor: 11.205

8. Design and evaluation of sifuvirtide, a novel HIV-1 fusion inhibitor.

Authors: Yuxian He; Yonghong Xiao; Haifeng Song; Qing Liang; Dan Ju; Xin Chen; Hong Lu; Weiguo Jing; Shibo Jiang; Linqi Zhang
Journal: J Biol Chem Date: 2008-02-26 Impact factor: 5.157

9. Inhibiting HIV fusion with a beta-peptide foldamer.

Authors: Olen M Stephens; Sunghwan Kim; Brett D Welch; Michael E Hodsdon; Michael S Kay; Alanna Schepartz
Journal: J Am Chem Soc Date: 2005-09-28 Impact factor: 15.419

10. Design of a peptide inhibitor that blocks the cell fusion mediated by glycoprotein 41 of human immunodeficiency virus type 1.

Authors: B S Jin; J R Ryu; K Ahn; Y G Yu
Journal: AIDS Res Hum Retroviruses Date: 2000-11-20 Impact factor: 2.205

12 in total

1. Discovery of HIV fusion inhibitors targeting gp41 using a comprehensive α-helix mimetic library.

Authors: Landon R Whitby; Kristopher E Boyle; Lifeng Cai; Xiaoqian Yu; Miriam Gochin; Dale L Boger
Journal: Bioorg Med Chem Lett Date: 2012-03-03 Impact factor: 2.823

2. Rotamer Libraries for the High-Resolution Design of β-Amino Acid Foldamers.

Authors: Andrew M Watkins; Timothy W Craven; P Douglas Renfrew; Paramjit S Arora; Richard Bonneau
Journal: Structure Date: 2017-10-12 Impact factor: 5.006

3. Bridged beta(3)-peptide inhibitors of p53-hDM2 complexation: correlation between affinity and cell permeability.

Authors: Arjel D Bautista; Jacob S Appelbaum; Cody J Craig; Julien Michel; Alanna Schepartz
Journal: J Am Chem Soc Date: 2010-03-10 Impact factor: 15.419

4. Helix formation in preorganized beta/gamma-peptide foldamers: hydrogen-bond analogy to the alpha-helix without alpha-amino acid residues.

Authors: Li Guo; Aaron M Almeida; Weicheng Zhang; Andrew G Reidenbach; Soo Hyuk Choi; Ilia A Guzei; Samuel H Gellman
Journal: J Am Chem Soc Date: 2010-06-16 Impact factor: 15.419