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Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation.

Abstract：

:In our efforts to explore marine cyanobacteria as a source of novel bioactive compounds, we discovered a statine unit-containing linear decadepsipeptide, grassystatin A (1), which we screened against a diverse set of 59 proteases. We describe the structure determination of 1 and two natural analogues, grassystatins B (2) and C (3), using NMR, MS, and chiral HPLC techniques. Compound 1 selectively inhibited cathepsins D and E with IC(50)s of 26.5 nM and 886 pM, respectively. Compound 2 showed similar potency and selectivity against cathepsins D and E (IC(50)s of 7.27 nM and 354 pM, respectively), whereas the truncated peptide analogue grassystatin C (3), which consists of two fewer residues than 1 and 2, was less potent against both but still selective for cathepsin E. The selectivity of compounds 1-3 for cathepsin E over D (20-38-fold) suggests that these natural products may be useful tools to probe cathepsin E function. We investigated the structural basis of this selectivity using molecular docking. We also show that 1 can reduce antigen presentation by dendritic cells, a process thought to rely on cathepsin E.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Kwan JC,Eksioglu EA,Liu C,Paul VJ,Luesch H

doi

10.1021/jm9009394

subject

Has Abstract

pub_date

2009-09-24 00:00:00

pages

5732-47

issue

18

eissn

0022-2623

issn

1520-4804

journal_volume

52

pub_type

杂志文章

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