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Controlled oxygen release from pyridone endoperoxides promotes cell survival under anoxic conditions


Benz, Sebastian; Noetzli, Sarah; Siegel, Jay; Eberli, Daniel; Jessen, Henning Jacob (2013). Controlled oxygen release from pyridone endoperoxides promotes cell survival under anoxic conditions. Journal of Medicinal Chemistry, 56(24):10171-10182.

Abstract

In tissue engineering, survival of larger constructs remains challenging due to limited supply with oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 hours. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.

Abstract

In tissue engineering, survival of larger constructs remains challenging due to limited supply with oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 hours. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.

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Additional indexing

Contributors:Institute of Organic Chemistry, Department of Urology, Center for Inegrative Human Physiology
Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > University Hospital Zurich > Urological Clinic
04 Faculty of Medicine > Center for Integrative Human Physiology
07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:570 Life sciences; biology
610 Medicine & health
540 Chemistry
Language:English
Date:2013
Deposited On:09 Dec 2013 08:23
Last Modified:05 Apr 2016 17:13
Publisher:American Chemical Society
ISSN:0022-2623
Additional Information:This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Medicinal Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see DOI.
Publisher DOI:https://doi.org/10.1021/jm4016137
PubMed ID:24299550

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