Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 12, Pages 3143-3147Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800288
Keywords
bioorthogonal chemistry; flavoproteins; metal-based prodrugs; photocatalysis; photochemotherapy
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Funding
- Spanish MINECO [CTQ2016-80844-R, BIO2016-77367-C2-1-R, BIO2015-69887-R, BES-2013-065642]
- COST action [CM1303]
- European Research Council [ERC-CoG-648071-ProNANO]
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Recent advances in bioorthogonal catalysis promise to deliver new chemical tools for performing chemoselective transformations in complex biological environments. Herein, we report how FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), and four flavoproteins act as unconventional photocatalysts capable of converting Pt-IV and Ru-II complexes into potentially toxic Pt-II or Ru-II-OH2 species. In the presence of electron donors and low doses of visible light, the flavoproteins mini singlet oxygen generator (miniSOG) and NADH oxidase (NOX) catalytically activate Pt-IV prodrugs with bioorthogonal selectivity. In the presence of NADH, NOX catalyzes Pt-IV activation in the dark as well, indicating for the first time that flavoenzymes may contribute to initiating the activity of Pt-IV chemotherapeutic agents.
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