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Structures and cytotoxic properties of sponge-derived bisannulated acridines.

Authors :
Thale Z
Johnson T
Tenney K
Wenzel PJ
Lobkovsky E
Clardy J
Media J
Pietraszkiewicz H
Valeriote FA
Crews P
Source :
The Journal of organic chemistry [J Org Chem] 2002 Dec 27; Vol. 67 (26), pp. 9384-91.
Publication Year :
2002

Abstract

A reinvestigation of sponge natural products from additional Indo-Pacific collections of Xestospongiacf. carbonaria and X. cf. exigua has provided further insights on the structures, biological activities, and biosynthetic origin of bisannulated acridines. These alkaloids include one known pyridoacridine, neoamphimedine (2), and three new analogues, 5-methoxyneoamphimedine (4), neoamphimedine Y (5), and neoamphimedine Z (6). A completely new acridine, alpkinidine (7), was also isolated. A disk diffusion soft agar assay, using a panel of five cancer cell lines (solid tumors and leukemias) and two normal cells, was used to evaluate the differential cytotoxicity (solid tumor selectivity) of the sponge semipure extracts and selected compounds including amphimedine (1), 2, 4, and 7. While all four compounds were solid tumor selective, 1 and 2 were the most potent and 4 was the most selective. The rationale used to characterize the new structures is outlined along with the related biosynthetic pathways envisioned to generate 2 and 7.

Details

Language :
English
ISSN :
0022-3263
Volume :
67
Issue :
26
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
12492342
Full Text :
https://doi.org/10.1021/jo026459o