title: A p-Hydroxyphenacyl-Benzothiazole-Chlorambucil Conjugate as a Real-Time-Monitoring Drug-Delivery System Assisted by Excited-State Intramolecular Proton Transfer.
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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Shrabani
authors.initials: S
authors.lastname: Barman
authors.affiliation: Department of Biotechnology, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Sourav K
authors.initials: SK
authors.lastname: Mukhopadhyay
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Sandipan
authors.initials: S
authors.lastname: Biswas
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Surajit
authors.initials: S
authors.lastname: Nandi
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Moumita
authors.initials: M
authors.lastname: Gangopadhyay
authors.affiliation: Department of Biotechnology, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Satyahari
authors.initials: S
authors.lastname: Dey
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India.
authors.forename: Anakuthil
authors.initials: A
authors.lastname: Anoop
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, West Bengal, India. ndpradeep@chem.iitkgp.ernet.in.
authors.forename: N D
authors.initials: ND
authors.lastname: Pradeep Singh
mesh_terms: D018906:Antineoplastic Agents, Alkylating / Q000008:administration & dosage / Q000737:chemistry*; D052160:Benzothiazoles / Q000737:chemistry*; D045744:Cell Line, Tumor; D002699:Chlorambucil / Q000008:administration & dosage / Q000737:chemistry*; D016503:Drug Delivery Systems; D006801:Humans; D018613:Microscopy, Confocal; D011522:Protons
chemical_list: D018906:Antineoplastic Agents, Alkylating; D052160:Benzothiazoles; D011522:Protons; D002699:Chlorambucil
keywords: drug delivery; fluorescence; phototriggers; real-time monitoring; theranostics