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Bis‐Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release
Author(s) -
Venkatesh Yarra,
Nandi Surajit,
Shee Maniklal,
Saha Biswajit,
Anoop Anakuthil,
Pradeep Singh N. D.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701253
Subject(s) - chemistry , carbazole , functional group , fluorescence , stereochemistry , combinatorial chemistry , organic chemistry , polymer , physics , quantum mechanics
In this paper, we present fluorescent photoremovable protecting groups (FPRPG) based on bis‐acetyl carbazole for the release of two different functional groups such as carboxylic acids, alcohols, thiols, and amines in a sequential fashion. Dual‐arm caged bis‐acetyl carbazoles with different combinations of two unlike functional groups were synthesized. Photophysical studies showed that caged bis‐acetyl carbazoles are blue fluorescent and their emission properties are sensitive to the environment. Sequential photorelease of two different functional groups by bis‐acetyl carbazole was analyzed by HPLC, UV and emission spectroscopy. The mechanism of the dual release by bis‐acetyl carbazole was investigated and supported by TD‐DFT calculations. To demonstrate the applicability of the dual release ability of bis‐acetyl carbazole FPRPG, we synthesized a drug delivery system (DDS) in which one arm of bis‐acetyl carbazole is linked to the carboxylic functional group of chlorambucil (CBL) and the other arm is attached to the hydroxyl group of ferulic acid ethyl ester (FAEE). In vitro studies showed that our DDS presents excellent properties such as photoregulated dual drug delivery, cellular uptake, and biocompatibility.