Structure-activity relationships of anti-HIV-1 peptides with disulfide linkage between D- and L-cysteine at positions i and i+3, respectively, derived from HIV-1 gp41 C-peptide

Experimental & Molecular Medicine
Myung Kyu LeeKil Lyong Kim

Abstract

The constrained a-helical structure of a C-peptide is useful for enhancing anti-HIV-1 activity. The i and i+3 positions in an a-helical structure are located close together, therefore D-Cys (dC) and L-Cys (C) were introduced at the positions, respectively, to make a dC-C disulfide bond in 28mer C-peptides. Accordingly, this study tested whether a dC-C disulfide bond would increase the a-helicity and anti-HIV-1 activity of peptides. A C-peptide can be divided into three domains, the N-terminal hydrophobic domain (HPD), middle interface domain (IFD), and C-terminal hydrogen domain (HGD), based on the binding property with an N-peptide. In general, the dC-C modifications in HPD enhanced the anti-HIV-1 activity, while those in IFD and HGD resulted in no or much less activity. The modified peptides with no activity clearly showed much less a-helicity than the native peptides, while those with higher activity showed an almost similar or slightly increased alpha-helicity. Therefore, the present results suggest that the introduction of a dC-C bridge in the N-terminal hydrophobic domain of a C-peptide may be useful for enhancing the anti-HIV-1 activity.

Citations

Jul 28, 2010·Proceedings of the National Academy of Sciences of the United States of America·Gregory H BirdLoren D Walensky
Sep 10, 2008·Experimental & Molecular Medicine·Juneyoung Lee, Dong Gun Lee
Mar 12, 2015·Organic & Biomolecular Chemistry·Conor M Haney, W Seth Horne
Jan 23, 2014·Chemical Reviews·Miriam Góngora-BenítezFernando Albericio
Dec 30, 2014·Organic Letters·Mothukuri Ganesh KumarHosahudya N Gopi
May 3, 2019·Chemical Reviews·Danielle A GuarracinoDesiree Agrinsoni
Oct 5, 2021·Chembiochem : a European Journal of Chemical Biology·Susanne HuhmannBeate Koksch

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