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Citation
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HERO ID
7548017
Reference Type
Journal Article
Title
Bis-Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release
Author(s)
Venkatesh, Y; Nandi, S; Shee, M; Saha, B; Anoop, A; Singh, NDP; ,
Year
2017
Is Peer Reviewed?
Yes
Journal
European Journal of Organic Chemistry
ISSN:
1434-193X
EISSN:
1099-0690
Publisher
WILEY-V C H VERLAG GMBH
Location
WEINHEIM
Page Numbers
6121-6130
DOI
10.1002/ejoc.201701253
Web of Science Id
WOS:000414849900004
URL
http://doi.wiley.com/10.1002/ejoc.201701253
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Abstract
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.
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