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Three‐Arm, Biotin‐Tagged Carbazole–Dicyanovinyl–Chlorambucil Conjugate: Simultaneous Tumor Targeting, Sensing, and Photoresponsive Anticancer Drug Delivery
Author(s) -
Venkatesh Yarra,
Karthik S.,
Rajesh Y.,
Mandal Mahitosh,
Jana Avijit,
Singh N. D. Pradeep
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601264
Subject(s) - conjugate , chlorambucil , drug delivery , carbazole , biotin , drug , chemistry , medicine , cancer research , pharmacology , chemotherapy , biochemistry , photochemistry , organic chemistry , mathematical analysis , mathematics , cyclophosphamide
Abstract 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.