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A p ‐Hydroxyphenacyl–Benzothiazole–Chlorambucil Conjugate as a Real‐Time‐Monitoring Drug‐Delivery System Assisted by Excited‐State Intramolecular Proton Transfer
Author(s) -
Barman Shrabani,
Mukhopadhyay Sourav K.,
Biswas Sandipan,
Nandi Surajit,
Gangopadhyay Moumita,
Dey Satyahari,
Anoop Anakuthil,
Pradeep Singh N. D.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508901
Subject(s) - benzothiazole , chemistry , conjugate , chlorambucil , intramolecular force , deprotonation , photochemistry , combinatorial chemistry , drug delivery , stereochemistry , organic chemistry , medicine , ion , mathematical analysis , mathematics , surgery , chemotherapy , cyclophosphamide
Among the well‐known phototriggers, the p ‐hydroxyphenacyl (pHP) group has consistently enabled the very fast, efficient, and high‐conversion release of active molecules. Despite this unique behavior, the pHP group has been ignored as a delivery agent, particularly in the area of theranostics, because of two major limitations: Its excitation wavelength is below 400 nm, and it is nonfluorescent. We have overcome these limitations by incorporating a 2‐(2′‐hydroxyphenyl)benzothiazole (HBT) appendage capable of rapid excited‐state intramolecular proton transfer (ESIPT). The ESIPT effect also provided two unique advantages: It assisted the deprotonation of the pHP group for faster release, and it was accompanied by a distinct fluorescence color change upon photorelease. In vitro studies showed that the p ‐hydroxyphenacyl–benzothiazole–chlorambucil conjugate presents excellent properties, such as real‐time monitoring, photoregulated drug delivery, and biocompatibility.