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- Title
A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer.
- Authors
Barman, Shrabani; Mukhopadhyay, Sourav K.; Biswas, Sandipan; Nandi, Surajit; Gangopadhyay, Moumita; Dey, Satyahari; Anoop, Anakuthil; Pradeep Singh, N. D.
- Abstract
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.
- Subjects
BENZOTHIAZOLE derivatives; CHLORAMBUCIL; DRUG delivery systems; INTRAMOLECULAR proton transfer reactions; ANTIBODY-drug conjugates; PHOTOCHEMISTRY
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 13, p4266
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201508901