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Tracking reactions of asymmetric organo-osmium transfer hydrogenation catalysts in cancer cells

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Bolitho, Elizabeth, Coverdale, James P. C., Bridgewater, Hannah E., Clarkson, Guy J., Quinn, Paul D., Sanchez-Cano, Carlos and Sadler, Peter J. (2021) Tracking reactions of asymmetric organo-osmium transfer hydrogenation catalysts in cancer cells. Angewandte Chemie International Edition, 60 (12). pp. 6462-6472. doi:10.1002/anie.202016456

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Official URL: https://doi.org/10.1002/anie.202016456

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Abstract

Most metallodrugs are prodrugs that can undergo ligand exchange and redox reactions in biological media. Here we have investigated the cellular stability of the anticancer complex [OsII[(η6‐p‐cymene)(RR/SS‐MePh‐DPEN)] [1] (MePh‐DPEN=tosyl‐diphenylethylenediamine) which catalyses the enantioselective reduction of pyruvate to lactate in cells. The introduction of a bromide tag at an unreactive site on a phenyl substituent of Ph‐DPEN allowed us to probe the fate of this ligand and Os in human cancer cells by a combination of X‐ray fluorescence (XRF) elemental mapping and inductively coupled plasma‐mass spectrometry (ICP‐MS). The BrPh‐DPEN ligand is readily displaced by reaction with endogenous thiols and translocated to the nucleus, whereas the Os fragment is exported from the cells. These data explain why the efficiency of catalysis is low, and suggests that it could be optimised by developing thiol resistant analogues. Moreover, this work also provides a new way for the delivery of ligands which are inactive when administered on their own.

Item Type: Journal Article
Alternative Title:
Subjects: R Medicine > RM Therapeutics. Pharmacology
R Medicine > RS Pharmacy and materia medica
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Pharmaceutical chemistry, Organometallic chemistry, Prodrugs, Transition metal catalysts, Metal catalysts -- Therapeutic use, Antineoplastic agents -- Research
Journal or Publication Title: Angewandte Chemie International Edition
Publisher: Wiley-Blackwell Publishing Ltd.
ISSN: 1433-7851
Official Date: 15 March 2021
Dates:
DateEvent
15 March 2021Published
15 February 2021Available
25 January 2021Accepted
Volume: 60
Number: 12
Page Range: pp. 6462-6472
DOI: 10.1002/anie.202016456
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
EP/P030572/1 [EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
2019-FELL-000018-01/62/2019Diputación Foral de Gipuzkoahttp://viaf.org/viaf/141389212
MDM-2017-0720María de Maeztu Unit of ExcellenceUNSPECIFIED
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