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N-Nitrosamine-{cis-Re[CO]2}(2+) cobalamin conjugates as mixed CO/NO-releasing molecules


Santoro, Giuseppe; Beltrami, Ruben; Kottelat, Emmanuel; Blacque, Olivier; Bogdanova, Anna Yu; Zobi, Fabio (2016). N-Nitrosamine-{cis-Re[CO]2}(2+) cobalamin conjugates as mixed CO/NO-releasing molecules. Dalton Transactions, 45(4):1504-1513.

Abstract

Mixed CO/NO-releasing molecules were prepared by conjugation of the 17-electron rhenium dicarbonyl cis-[Re(CO)2Br4](2-) complex to N-nitrosamine modified cyanocobalamin (B12) bio-vectors. The species were fully characterized by standard analytical techniques, including X-ray crystallography for cyanocobalamin-5'-O-pyrazine and () and its N-pyrazine nitrosylated derivative (). The N-nitrosamine B12 derivatives are able to liberate low NO doses in buffer solutions and appear to be "activated" towards NO release if in contact with cultured cells. Coordination of the cis-[Re(CO)2Br4](2-) complex on the axial cyanide of B12 allows for the combined loss of CO and NO from the conjugates. The mixed CO/NO-releasing molecules show cytoprotection in an ischemia-reperfusion model but no significant enhanced synergistic effects over the relative NORMs and CORMs building constituents.

Abstract

Mixed CO/NO-releasing molecules were prepared by conjugation of the 17-electron rhenium dicarbonyl cis-[Re(CO)2Br4](2-) complex to N-nitrosamine modified cyanocobalamin (B12) bio-vectors. The species were fully characterized by standard analytical techniques, including X-ray crystallography for cyanocobalamin-5'-O-pyrazine and () and its N-pyrazine nitrosylated derivative (). The N-nitrosamine B12 derivatives are able to liberate low NO doses in buffer solutions and appear to be "activated" towards NO release if in contact with cultured cells. Coordination of the cis-[Re(CO)2Br4](2-) complex on the axial cyanide of B12 allows for the combined loss of CO and NO from the conjugates. The mixed CO/NO-releasing molecules show cytoprotection in an ischemia-reperfusion model but no significant enhanced synergistic effects over the relative NORMs and CORMs building constituents.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:05 Vetsuisse Faculty > Institute of Veterinary Physiology
07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:570 Life sciences; biology
Language:English
Date:28 January 2016
Deposited On:24 Nov 2016 09:38
Last Modified:08 Dec 2017 20:57
Publisher:Royal Society of Chemistry
ISSN:1477-9226
Publisher DOI:https://doi.org/10.1039/c5dt03402g
PubMed ID:26681365

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