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Radical‐Mediated Thiol‐Ene Strategy: Photoactivation of Thiol‐Containing Drugs in Cancer Cells
Author(s) -
Sun Shuang,
Oliveira Bruno L.,
JiménezOsés Gonzalo,
Bernardes Gonçalo J. L.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811338
Subject(s) - thiol , chemistry , ene reaction , cancer cell , combinatorial chemistry , cancer research , biochemistry , biophysics , cancer , stereochemistry , biology , genetics
Photoactivated drugs provide an opportunity to improve efficacy alongside reducing side‐effects in the treatment of severe diseases such as cancer. Described herein is a photoactivation decaging method of isobutylene‐caged thiols through a UV‐initiated thiol‐ene reaction. The method was demonstrated with an isobutylene‐caged cysteine, cyclic disulfide‐peptide, and thiol‐containing drug, all of which were rapidly and efficiently released under mild UV irradiation in the presence of thiol sources and a photoinitiator. Importantly, it is shown that the activity of histone deacetylase inhibitor largazole can be switched off when stapled, but selectively switched on within cancer cells when irradiated with non‐phototoxic light.