1. Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations
- Author
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Georgios Rotas, Ira Daskalaki, Miguel A. Miranda, Georgios C. Vougioukalakis, M. Consuelo Cuquerella, Anna Pantelia, and European Commission
- Subjects
Chemiluminescence ,Science ,Proton Magnetic Resonance Spectroscopy ,Pharmaceutical Science ,phthalhydrazide ,peroxide ,010402 general chemistry ,01 natural sciences ,Peroxide ,Redox ,Article ,Analytical Chemistry ,Luminol ,law.invention ,Acylation ,lcsh:QD241-441 ,chemistry.chemical_compound ,QUIMICA ORGANICA ,Organophosphorus Compounds ,lcsh:Organic chemistry ,law ,Cations ,Drug Discovery ,luminol ,Aminoacylation ,Phosphonium ,Physical and Theoretical Chemistry ,Phthalimides ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Cationic polymerization ,phosphonium ,Combinatorial chemistry ,chemiluminescence ,0104 chemical sciences ,mitochondria ,Hydrazines ,Spectrometry, Fluorescence ,Chemistry (miscellaneous) ,Θετικές Επιστήμες ,Luminescent Measurements ,Molecular Medicine - Abstract
[EN] 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., 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.
- Published
- 2019