Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya

Derek C Radisky, Evette S Radisky, Louis R. Barrows, Brent R. Copp, Robert A. Kramer, Chris M. Ireland

Research output: Contribution to journalArticle

198 Citations (Scopus)

Abstract

We present the isolation and characterization of seven novel [natural] pyrroloiminoquinones, the makaluvamines A-F (1-6), makaluvone (7), and the known compounds discorhabdin A (8) and damirone B (9) from the Fijian sponge Zyzzya cf. marsailis. The makaluvamines exhibit potent in vitro cytotoxicity toward the human colon tumor cell-line HCT 116, show differential toxicity toward the topoisomerase II sensitive CHO cell-line xrs-6, and inhibit topoisomerase II in vitro. This activity may be mediated by intercalation into DNA and single-stranded breakage. Makaluvamine A and C exhibited in vivo antitumor activity against the human ovarian carcinoma Ovcar3 implanted in athymic mice. The makaluvamines suggest a plausible interrelationship between the batzelline/isobatzelline and discorhabdin/prianosin classes of compounds.

Original languageEnglish (US)
Pages (from-to)1632-1638
Number of pages7
JournalJournal of the American Chemical Society
Volume115
Issue number5
StatePublished - Mar 10 1993
Externally publishedYes

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Pyrroloiminoquinones
Type II DNA Topoisomerase
Porifera
Cytotoxicity
Intercalation
Toxicity
Tumors
DNA
Cells
CHO Cells
Single-Stranded DNA
Tumor Cell Line
Nude Mice
Human Activities
Colon
Carcinoma
Cell Line
makaluvamine A
In Vitro Techniques

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya. / Radisky, Derek C; Radisky, Evette S; Barrows, Louis R.; Copp, Brent R.; Kramer, Robert A.; Ireland, Chris M.

In: Journal of the American Chemical Society, Vol. 115, No. 5, 10.03.1993, p. 1632-1638.

Research output: Contribution to journalArticle

Radisky, Derek C ; Radisky, Evette S ; Barrows, Louis R. ; Copp, Brent R. ; Kramer, Robert A. ; Ireland, Chris M. / Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya. In: Journal of the American Chemical Society. 1993 ; Vol. 115, No. 5. pp. 1632-1638.
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