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Synthesis of maculalactone A and derivatives for environmental fate tracking studies


Bader, Samuel L; Luescher, Michael U; Gademann, Karl (2015). Synthesis of maculalactone A and derivatives for environmental fate tracking studies. Organic & Biomolecular Chemistry, 13(1):199-206.

Abstract

Maculalactone A (1) constitutes a promising antifouling agent, inhibiting the formation of biofilms in marine and freshwater systems. In this study, we developed a new route, based on a late-stage formation of the butenolide core, leading to the total synthesis of maculalactone A (three steps, overall yield of 45%) and delivering material on a gram scale. In addition, analogues of the title compound were assayed concerning their biological activity, utilizing Artemia franciscana and Thamnocephalus platyurus. The most active analogue was functionalized with a rhodamine B fluorophore and was utilized in an in vivo staining experiment in Artemia salina. Two different tissues were found to accumulate this maculalactone A derivative.

Abstract

Maculalactone A (1) constitutes a promising antifouling agent, inhibiting the formation of biofilms in marine and freshwater systems. In this study, we developed a new route, based on a late-stage formation of the butenolide core, leading to the total synthesis of maculalactone A (three steps, overall yield of 45%) and delivering material on a gram scale. In addition, analogues of the title compound were assayed concerning their biological activity, utilizing Artemia franciscana and Thamnocephalus platyurus. The most active analogue was functionalized with a rhodamine B fluorophore and was utilized in an in vivo staining experiment in Artemia salina. Two different tissues were found to accumulate this maculalactone A derivative.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2015
Deposited On:22 Aug 2017 16:22
Last Modified:19 Aug 2018 09:55
Publisher:Royal Society of Chemistry
ISSN:1477-0520
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1039/c4ob02042a
PubMed ID:25360848
Project Information:
  • : FunderSNSF
  • : Grant ID200020_130475
  • : Project TitleSynthesis and Biological Evaluation of Anticancer Natural Products

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