Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 48, Pages 21546-21552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005612
Keywords
controlled release; fluorescent probes; hydroxyl radicals; prodrug activation; radiation-induced cleavage
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Funding
- National Natural Science Foundation of China
- NSFC [U1867209, NSFC 21778003]
- Ministry of Science and Technology of the People's Republic of China [2017YFA0506300]
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Radiation-induced cleavage for controlled release in vivo is yet to be established. We demonstrate the use of 3,5-dihydroxybenzyl carbamate (DHBC) as a masking group that is selectively and efficiently removed by external radiation in vitro and in vivo. DHBC reacts mainly with hydroxyl radicals produced by radiation to afford hydroxylation atpara/orthopositions, followed by 1,4- or 1,6-elimination to rescue the functionality of the client molecule. The reaction is rapid and can liberate functional molecules under physiological conditions. This controlled-release platform is compatible with living systems, as demonstrated by the release of a rhodol fluorophore derivative in cells and tumor xenografts. The combined benefits of the robust caging group, the good release yield, and the independence of penetration depth make DHBC derivatives attractive chemical caging moieties for use in chemical biology and prodrug activation.
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