In recent times, photoremovable protecting groups (PRPGs) have gained considerable importance particularly in the area of photoresponsive drug delivery systems (DDSs), because of their ability to offer high spatiotemporal control over the release of biologically active molecules on exposure to light. Several PRPGs have been successfully utilized for the construction of photoresponsive DDSs which includes o-nitrobenzyl, coumarinyl-4-ylmethyl, acridin-9-ylmethyl, perylene-3-ylmethyl, perylene-3,4,9,10-tetrayltetramethyl, pyrene-1-ylmethyl and quinolin-2-ylmethyl derivatives. DDSs constructed so far by the means of the aforementioned PRPGs, can deliver only one active molecule at a given time. Recently, dual DDSs have become a promising strategy particularly in cancer treatment. Hence there is a real need to develop single chromophoric photoresponsive dual DDSs which will release two different drugs sequential manner on exposure to light. For this reason, we design and synthesized fluorescent photoremovable protecting group (FPRPG) based on bis-acetyl carbazole for the release of two different functional groups like carboxylic acids, alcohols, thiols and amines in a sequential manner. To demonstrate the application of dual release ability of bis-acetyl carbazole FPRPG, we synthesised drug delivery system (DDS) in which one arm of bis-acetyl carbazole is linked to carboxylic functionality 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 like real-time monitoring, photoregulated dual drug delivery and biocompatibility.

Bis-acetyl carbazole: Photoremovable protecting group for sequential release of two different functional groups and its application for therapeutic release

254th National Meeting (2017)

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