N-Nitrosamine-{cis--Re[CO]₂}²⁺ cobalamin conjugates as mixed CO/NO-releasing molecules
- Santoro, Giuseppe Department of Chemistry, University of Zürich, Switzerland
- Beltrami, Ruben Department of Chemistry, University of Fribourg, Switzerland
- Kottela, Emmanuel Department of Chemistry, University of Fribourg, Switzerland
- Blacque, Olivier Department of Chemistry, University of Zürich, Switzerland
- Bogdanova, Anna Yu. Institute of Veterinary Physiology, University of Zürich, Switzerland
- Zobi, Fabio Department of Chemistry, University of Fribourg, Switzerland
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19.01.2016
Published in:
- Dalton Transactions. - 2016, vol. 45, no. 4, p. 1504–1513
English
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 (1) and its N-pyrazine nitrosylated derivative (1a). 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.
- Faculty
- Faculté des sciences et de médecine
- Department
- Département de Chimie
- Language
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 258841
- DOI 10.1039/C5DT03402G
- Persistent URL
- https://folia.unifr.ch/unifr/documents/304720
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