Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs

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Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs.

A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromo-norborn-2-en-7-one Diels-Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH ...

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Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs† †Electronic supplementary information (ESI) available: Experimental details for the synthesis of compounds, supporting figures and schemes, and NMR spectra. See DOI: 10.1039/c7sc01647f Click here for additional data file.

A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromonorborn-2-en-7-one Diels–Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7....

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Carbon Monoxide Releasing Pharmaceuticals

Carbon monoxide (CO) was ignored by the medical research community for decades, who thought that no biological relevance could emerge from exploring the physiological effects of a gas that had earned itself a reputation over the years as a ‘silent killer’ [2] . The well-known poisoning by carbon monoxide is a result of it binding to Hemoglobin, the oxygen carrier in blood with very high affinit...

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Biological signaling by carbon monoxide and carbon monoxide-releasing molecules.

Carbon monoxide (CO) is continuously produced in mammalian cells during the degradation of heme. It is a stable gaseous molecule that reacts selectively with transition metals in a specific redox state, and these characteristics restrict the interaction of CO with defined biological targets that transduce its signaling activity. Because of the high affinity of CO for ferrous heme, these targets...

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Antimicrobial action of carbon monoxide-releasing compounds.

Carbon monoxide (CO) is endogenously produced in the human body, mainly from the oxidation of heme catalyzed by heme oxygenase (HO) enzymes. The induction of HO and the consequent increase in CO production play important physiological roles in vasorelaxation and neurotransmission and in the immune system. The exogenous administration of CO gas and CO-releasing molecules (CO-RMs) has been shown ...

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ژورنال

عنوان ژورنال: Chemical Science

سال: 2017

ISSN: 2041-6520,2041-6539

DOI: 10.1039/c7sc01647f