Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 24, Pages 3482-3486Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201601264
Keywords
antitumor agents; cancer; drug delivery; glutathione sensing; photochemistry
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Funding
- DST (SERB)
- IIT KGP
- DST, India at CSIR-IICT, Hyderabad [GAP 0546]
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The design, synthesis, and in vitro biological studies of a biotin-carbazole-dicyanovinyl-chlorambucil conjugate (Bio-CBZ-DCV-CBL; 6) are reported. This conjugate (6) is a multifunctional single-molecule appliance composed of a thiol-sensor DCV functionality, a CBZ-derived phototrigger as well as fluorescent reporter, and CBL as the anticancer drug, and Bio as the cancer-targeting ligand. In conjugate 6, the DCV bond undergoes a thiol-ene click reaction at pH<7 with intracellular thiols, thereby shutting down internal charge transfer between the donor CBZ and acceptor DCV units, resulting in a change of the fluorescence color from green to blue, and thereby, sensing the tumor microenvironment. Subsequent photoirradiation results in release of the anticancer drug CBL in a controlled manner.
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