Structure-Activity Relationships of the Lissoclinamides: Cytotoxic Cyclic Peptides from the Ascidian Lissoclinum patella

Watters D.J., Hawkins C.J., van den Brenk A.L., Lavin M.F. and Marshall K.A. (1990) Structure-Activity Relationships of the Lissoclinamides: Cytotoxic Cyclic Peptides from the Ascidian Lissoclinum patella. Journal of Medicinal Chemistry, 33 6: 1634-1638. doi:10.1021/jm00168a016


Author Watters D.J.
Hawkins C.J.
van den Brenk A.L.
Lavin M.F.
Marshall K.A.
Title Structure-Activity Relationships of the Lissoclinamides: Cytotoxic Cyclic Peptides from the Ascidian Lissoclinum patella
Journal name Journal of Medicinal Chemistry   Check publisher's open access policy
ISSN 1520-4804
Publication date 1990-01-01
Sub-type Article (original research)
DOI 10.1021/jm00168a016
Open Access Status Not yet assessed
Volume 33
Issue 6
Start page 1634
End page 1638
Total pages 5
Language eng
Subject 1313 Molecular Medicine
3002 Drug Discovery
Abstract Two new lissoclinamides (lissoclinamides 7 and 8) have been isolated from the aplousobranch ascidian Lissoclinum patella. These lissoclinamides are cyclic heptapeptides with the same structural features as lissoclinamides 4 and 5 reported earlier, containing an oxazoline ring, one proline, one valine, two phenylalanine residues, and thiazole and/or thiazoline rings. All four peptides have the same sequence of amino acids around the ring and differ from one another only in their stereochemistry or the number of thiazole and thiazoline rings. The cytotoxicities of the compounds were tested with human fibroblast and bladder carcinoma cell lines and normal lymphocytes. Slight changes in structure resulted in marked differences in the cytotoxicities of these compounds. The most potent is lissoclinamide 7, containing two thiazoline rings, which rivals didemnin B in cytotoxicity in vitro.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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