Zinc and Copper Complexes of Prodigiosin:  Implications for Copper-Mediated Double-Strand DNA Cleavage

Zinc(II) and copper(II) complexes of prodigiosin (1) have been characterized. All N-atoms of 1 bind Cu(II) to generate 5:  the complex exhibits regiospecific oxidation of the C-pyrrole. In contrast, coordination by Zn(II) to 1 produces Zn(1)2 (8), a 4-coordinate tetrahedral complex. The influence of...

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Bibliographic Details
Published in:Organic letters 2003-01, Vol.5 (2), p.113-116
Main Authors: Park, Gyungse, Tomlinson, John T, Melvin, Matt S, Wright, Marcus W, Day, Cynthia S, Manderville, Richard A
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Binding Sites
Copper - chemistry
DNA - drug effects
DNA - metabolism
Hydrolysis - drug effects
Molecular Structure
Prodigiosin - chemistry
Prodigiosin - pharmacology
Structure-Activity Relationship
Zinc - chemistry
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Summary:Zinc(II) and copper(II) complexes of prodigiosin (1) have been characterized. All N-atoms of 1 bind Cu(II) to generate 5:  the complex exhibits regiospecific oxidation of the C-pyrrole. In contrast, coordination by Zn(II) to 1 produces Zn(1)2 (8), a 4-coordinate tetrahedral complex. The influence of these binding geometries on Cu-mediated double-strand (ds) DNA cleavage by 1 is discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027165s