Trachycladindoles A-G: cytotoxic heterocycles from an Australian marine sponge, Trachycladus laevispirulifer

A southern Australian marine sponge, Trachycladus laevispirulifer, yielded the cytotoxic agents trachycladindoles A-G (1-7) as a selection of novel indole-2-carboxylic acids bearing a 2-amino-4,5-dihydroimidazole moiety. The trachycladindoles displayed promising selective cytotoxicity against a pane...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2008-01, Vol.6 (15), p.2765-2771
Main Authors: Capon, Robert J, Peng, Chongsheng, Dooms, Cedric
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Australia
Breast Neoplasms - drug therapy
Cell Line, Tumor
Colorectal Neoplasms - drug therapy
Drug Screening Assays, Antitumor
Heterocyclic Compounds - chemistry
Heterocyclic Compounds - isolation & purification
Heterocyclic Compounds - pharmacology
Humans
Indoles - chemistry
Indoles - isolation & purification
Indoles - pharmacology
Lung Neoplasms - drug therapy
Magnetic Resonance Spectroscopy
Models, Molecular
Porifera - chemistry
Structure-Activity Relationship
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Summary:A southern Australian marine sponge, Trachycladus laevispirulifer, yielded the cytotoxic agents trachycladindoles A-G (1-7) as a selection of novel indole-2-carboxylic acids bearing a 2-amino-4,5-dihydroimidazole moiety. The trachycladindoles displayed promising selective cytotoxicity against a panel of human cancer cell lines and their structures were assigned on the basis of detailed spectroscopic analysis. Preliminary structure activity relationship (SAR) investigations by co-metabolite defined structural features key to the trachycladindole pharmacophore, highlighting an unusual bioactive molecular motif deserving of future investigation.
ISSN:1477-0520
1477-0539
DOI:10.1039/b803455a