New cyclic peptides with cytotoxic activity from the ascidian Lissoclinum patella

The isolation and structures of a new patellamide (patellamide D) and two new lissoclinamides (lissoclinamides 4 and 5) from the aplousobranch ascidian Lissoclinum patella are described. Structures were determined largely by using two-dimensional NMR techniques and mass spectrometry. These peptides...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1989-06, Vol.32 (6), p.1349-1354
Main Authors: Degnan, Bernard M, Hawkins, Clifford J, Lavin, Martin F, McCaffrey, Elizabeth J, Parry, David L, Van den Brenk, Anna L, Watters, Diane J
Format: Article
Language:English
Subjects:
Animals
Antineoplastic agents
Biological and medical sciences
Cell Line, Transformed
Cell Survival - drug effects
Chromatography, High Pressure Liquid
cytology
DNA - biosynthesis
Fibroblasts - cytology
Fibroblasts - drug effects
Fibroblasts - metabolism
General aspects
Humans
lissoclinanamide 4
lissoclinanamide 5
Lissoclinum patella
Magnetic Resonance Spectroscopy
Marine
Mass Spectrometry
mass spectroscopy
Medical sciences
Molecular Conformation
Molecular Structure
N.M.R
patellamide D
peptides
Peptides, Cyclic - isolation & purification
Peptides, Cyclic - pharmacology
Pharmacology. Drug treatments
spectroscopic techniques
Structure-Activity Relationship
tumor cell lines
Tumor Cells, Cultured
Urinary Bladder Neoplasms - metabolism
Urinary Bladder Neoplasms - pathology
Urochordata - analysis
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Summary:The isolation and structures of a new patellamide (patellamide D) and two new lissoclinamides (lissoclinamides 4 and 5) from the aplousobranch ascidian Lissoclinum patella are described. Structures were determined largely by using two-dimensional NMR techniques and mass spectrometry. These peptides and other members of the patellamide and lissoclinamide families that have been reported previously are found within the obligate algal symbiont of the genus Prochloron. The cytotoxicities of the compounds toward fibroblast and tumor cell lines are reported. One of these compounds, lissoclinamide 4, is markedly more toxic than other members of the family. Structure-activity relationships are discussed.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00126a034