Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones.

Abstract:

:The calothrixins are quinone-based natural products isolated from Calothrix cyanobacteria which show potent antiproliferative properties against several cancer cell lines. Preliminary mechanistic studies suggest that the biological mode of action of the calothrixins may be linked to their ability to undergo redox cycling. In this study we compare the bioactivities of the calothrixins with those of structurally related quinones in order to identify the structural features in the calothrixins essential for biological activity. In particular, the reduction potentials of the calothrixins and some related quinones were measured electrochemically. Our studies indicate that while there is no direct correlation between the reduction potentials and biological activities of the studied compounds, in all cases quinones with EC(50) values <1.6 microM undergo reduction to their respective semiquinones readily, with their E(1/2) values being more positive than -0.5 V versus the standard hydrogen electrode (SHE).

journal_name

J Med Chem

authors

Bernardo PH,Chai CL,Heath GA,Mahon PJ,Smith GD,Waring P,Wilkes BA

doi

10.1021/jm049625o

keywords:

subject

Has Abstract

pub_date

2004-09-23 00:00:00

pages

4958-63

issue

20

eissn

0022-2623

issn

1520-4804

journal_volume

47

pub_type

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