A p‐Hydroxyphenacyl–Benzothiazole–Chlorambucil Conjugate as a Real‐Time‐Monitoring Drug‐Delivery System Assisted by Excited‐State Intramolecular Proton Transfer |
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| Authors: | Shrabani Barman Sourav K Mukhopadhyay Sandipan Biswas Surajit Nandi Moumita Gangopadhyay Satyahari Dey Anakuthil Anoop N D Pradeep Singh |
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| Affiliation: | 1. Department of Chemistry, Indian Institute of Technology, West Bengal, India;2. Department of Biotechnology, Indian Institute of Technology, West Bengal, India |
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| 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. |
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| Keywords: | drug delivery fluorescence phototriggers real-time monitoring theranostics |
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