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Synthesis, antimicrobial and antineoplastic activities for agelasine and agelasimine analogs with a beta-cyclocitral derived substituent.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
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2007 (English)In: Archiv der Pharmazie, ISSN 0365-6233, E-ISSN 1521-4184, Vol. 340, no 12, 625-634 p.Article in journal (Refereed) Published
Abstract [en]

Agelasines and agelasimines are antimicrobial and cytotoxic purine derivatives isolated from marine sponges (Agelas sp.). We have synthesized structurally simplified analogs of these natural products starting from beta-cyclocitral. The novel compounds were found to be strong inhibitors of a wide variety of pathogenic microorganisms (incl. Mycobacterium tuberculosis) as well as cancer cell lines. The biological activities were generally in the same range as those previously found for the structurally more complex agelasines and agelasimines isolated in small amounts from natural sources. We also report for the first time that agelasine and agelasimine analogs inhibit growth of protozoa (Acanthamoeba castellanii and Acanthamoeba polyphaga). Acanthamoeba keratitis is an increasingly common and severe corneal infection, closely associated with contact lens wear.

Place, publisher, year, edition, pages
2007. Vol. 340, no 12, 625-634 p.
Keyword [en]
agelasiminea, agelasine, anti-cancer activity, antimicrobial activity, beta-cyclocitral
National Category
Pharmaceutical Sciences
URN: urn:nbn:se:uu:diva-102015DOI: 10.1002/ardp.200700137ISI: 000251827400001PubMedID: 17994607OAI: oai:DiVA.org:uu-102015DiVA: diva2:213861
Available from: 2009-04-29 Created: 2009-04-29 Last updated: 2010-03-24Bibliographically approved

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