Fullerene-based inhibitors of HIV-1 protease

Journal of Peptide Science : an Official Publication of the European Peptide Society
T Amanda StromAndrew R Barron

Abstract

A series of Fmoc-Phe(4-aza-C60)-OH of fullerene amino acid derived peptides have been prepared by solid phase peptide synthesis, in which the terminal amino acid, Phe(4-aza-C60)-OH, is derived from the dipolar addition to C60 of the Fmoc-Nα-protected azido amino acids derived from phenylalanine: Fmoc-Phe(4-aza-C60)-Lys3-OH (1), Fmoc-Phe(4-aza-C60)-Pro-Hyp-Lys-OH (2), and Fmoc-Phe(4-aza-C60)-Hyp-Hyp-Lys-OH (3). The inhibition constant of our fullerene aspartic protease PRIs utilized FRET-based assay to evaluate the enzyme kinetics of HIV-1 PR at various concentrations of inhibitors. Simulation of the docking of the peptide Fmoc-Phe-Pro-Hyp-Lys-OH overestimated the inhibition, while the amino acid PRIs were well estimated. The experimental results show that C60-based amino acids are a good base structure in the design of protease inhibitors and that their inhibition can be improved upon by the addition of designer peptide sequences.

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Citations

May 12, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrew R Barron
Dec 12, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Edison CastroLuis Echegoyen
Oct 19, 2016·Chemistry : a European Journal·Virginie RussoRobert Deschenaux
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Jan 19, 2021·ACS Biomaterials Science & Engineering·Yu Yu AungMochamad Zakki Fahmi

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