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Quinone Methide Precursors with BODIPY Chromophore: Synthesis, Photochemistry and Biological Activity

Quinone methides (QM) are reactive intermediers that can be generated in photochemical reactions, such as photodeamination.1-4 QMs exhibit biological activity, which is related to their ability to react in Michael addition reactions with various amines and sulfides, including amino acids and nucleotides.5-6 Reaction with nucleotides induce DNA alkylation and cross-linking, and consequently, cytotoxicity.7-9 Photochemical generation of QMs under mild conditions and citotoxic biological activity make QM precursor molecules potential photoactivable anticancer drugs. We incorporated QM precursor units into BODIPY chromophore to obtain molecules with desired photochemical properties which can be excited by visible light.10 BODIPY derivates are commonly used as dyes for biomolecular labeling since they are characterized by good photochemical stability and excellent photophysical and spectral properties.11 Several BODIPY-QM precursor molecules have been synthesized and their photophisical properties and photochemical reactivity were investigated. The experimental observations were backed up by TD-DFT calculations. Non-covalent interactions of BODIPY-QM precursors with biomacromolecules and the ability of photochemically formed QMs to alkylate biomacromolecules were demonstrated by photonduced fluorescent labeling of bovine serum albumin.12 Furthermore, antiproliferative activity of synthesized BODIPY-QM precursors was investigated using MTT assay on several human cancer cell lines with and without irradiation.

photochemistry ; quinone methide ; BODIPY

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