NDLI: 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

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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

Content Provider	Semantic Scholar
Author	Kueh, Jui Thiang Brian Stanley, Nathan J. Hewitt, Russell J. Woods, Laura M. Larsen, Lesley Harrison, Joanne C. Rennison, David Brimble, Margaret A. Sammut, Ivan A. Larsen, David S.
Copyright Year	2017
Abstract	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 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.
Starting Page	5454
Ending Page	5459
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/c7sc01647f
PubMed reference number	28970925
Journal	Medline
Volume Number	8
Alternate Webpage(s)	http://pubs.rsc.org/en/content/articlepdf/2017/sc/c7sc01647f
Alternate Webpage(s)	http://www.rsc.org/suppdata/c7/sc/c7sc01647f/c7sc01647f1.pdf
Alternate Webpage(s)	https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/f9/75/SC-008-C7SC01647F.PMC5609517.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c7sc01647f
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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