Synthesis and chemiluminescent properties of amino-acylated luminol derivatives bearing phosphonium cations

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Department of Chemistry
Synthesis and chemiluminescent properties of amino-acylated luminol derivatives bearing phosphonium cations
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The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention, due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives’ chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction.
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Anna Pantelia, Ira Daskalaki, M. Consuelo Cuquerella, Georgios Rotas, Miguel A. Miranda, and Georgios C. Vougioukalakis
phthalhydrazide; luminol; chemiluminescence; peroxide; phosphonium; mitochondria.
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This project was financially supported by the European Union's Horizon 2020 framework program for research and innovation under grant agreement No 712921, as well as a Greek State Scholarships Foundation (I.K.Y.) fellowship to A.P.
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