Sponge-derived fijianolide polyketide class: Further evaluation of their structural and cytotoxicity properties

Tyler A. Johnson, Karen Tenney, Robert H. Cichewicz, Brandon I. Morinaka, Kimberly N. White, Taro Amagata, Balanehru Subramanian, Joseph Media, Susan L Mooberry, Frederick A. Valeriote, Phillip Crews

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

The sponge-derived polyketide macrolides frjianolides A (1) and B (2), isolaulimalide and laulimalide, have taxol-like microtubule-stabilizing activity, and the latter exhibits potent cytotoxicity. Insight on the biogeographical and phenotypic variations of Cacospongia mycofijiensis is presented that will enable a future study of the biosynthetic pathway that produces the frjianolides. In addition to frjianolides A and B, six new fijianolides, D-I (7-12), were isolated, each with modifications to the C-20 side chain of the macrolide ring. Compounds 7-12 exhibited a range of in vitro activities against HCT-116 and MDA-MB-435 cell lines. Fijianolides 8 and 10 were shown to disrupt interphase and mitotic division, but were less potent than 2. An in vivo evaluation of 2 using tumor-bearing severe combined immuno-deficiency mice demonstrated significant inhibition of growth in HCT-116 tumors over 28 days.

Original languageEnglish (US)
Pages (from-to)3795-3803
Number of pages9
JournalJournal of Medicinal Chemistry
Volume50
Issue number16
DOIs
StatePublished - Aug 9 2007
Externally publishedYes

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Polyketides
Macrolides
Porifera
Cytotoxicity
Tumors
Bearings (structural)
Biosynthetic Pathways
Interphase
Paclitaxel
Microtubules
Neoplasms
Cells
Cell Line
Growth
laulimalide
isolaulimalide
In Vitro Techniques

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Johnson, T. A., Tenney, K., Cichewicz, R. H., Morinaka, B. I., White, K. N., Amagata, T., ... Crews, P. (2007). Sponge-derived fijianolide polyketide class: Further evaluation of their structural and cytotoxicity properties. Journal of Medicinal Chemistry, 50(16), 3795-3803. https://doi.org/10.1021/jm070410z

Sponge-derived fijianolide polyketide class : Further evaluation of their structural and cytotoxicity properties. / Johnson, Tyler A.; Tenney, Karen; Cichewicz, Robert H.; Morinaka, Brandon I.; White, Kimberly N.; Amagata, Taro; Subramanian, Balanehru; Media, Joseph; Mooberry, Susan L; Valeriote, Frederick A.; Crews, Phillip.

In: Journal of Medicinal Chemistry, Vol. 50, No. 16, 09.08.2007, p. 3795-3803.

Research output: Contribution to journalArticle

Johnson, TA, Tenney, K, Cichewicz, RH, Morinaka, BI, White, KN, Amagata, T, Subramanian, B, Media, J, Mooberry, SL, Valeriote, FA & Crews, P 2007, 'Sponge-derived fijianolide polyketide class: Further evaluation of their structural and cytotoxicity properties', Journal of Medicinal Chemistry, vol. 50, no. 16, pp. 3795-3803. https://doi.org/10.1021/jm070410z
Johnson, Tyler A. ; Tenney, Karen ; Cichewicz, Robert H. ; Morinaka, Brandon I. ; White, Kimberly N. ; Amagata, Taro ; Subramanian, Balanehru ; Media, Joseph ; Mooberry, Susan L ; Valeriote, Frederick A. ; Crews, Phillip. / Sponge-derived fijianolide polyketide class : Further evaluation of their structural and cytotoxicity properties. In: Journal of Medicinal Chemistry. 2007 ; Vol. 50, No. 16. pp. 3795-3803.
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