A novel diarylethene-based photoswitchable chelator for reversible release and capture of Ca^sup 2+^ in aqueous media

The synthesis and characterisation of a novel Reversibly Photoswitchable Chelator (RPC) of calcium ions, designed as a stepping stone towards producing pulses of calcium concentration in an aqueous environment, is reported. This RPC is constituted of a photochromic diarylethene core connected on one...

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Published inJournal of photochemistry and photobiology. A, Chemistry. Vol. 360; p. 181
Main Authors Dozova, Nadia, Pousse, Guillaume, Barnych, Bogdan, Mallet, Jean-Maurice, Cossy, Janine, Valeur, Bernard, Plaza, Pascal
Format Journal Article
LanguageEnglish
Published Lausanne Elsevier BV 01.06.2018
Subjects
Affinity
Aqueous solutions
Calcium
Calcium compounds
Calcium ions
Charge transfer
Chelation
Electron transfer
Electrons
Ethane
Ions
Neurobiology
Nitrogen
Polyethylene glycol
Wave division multiplexing
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Summary:The synthesis and characterisation of a novel Reversibly Photoswitchable Chelator (RPC) of calcium ions, designed as a stepping stone towards producing pulses of calcium concentration in an aqueous environment, is reported. This RPC is constituted of a photochromic diarylethene core connected on one side to a BAPTA (1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid) calcium chelator and, on the other side, to an electron-withdrawing group. The operation principle consists in photoswitching on and off an intramolecular charge transfer between one nitrogen atom of the BAPTA moiety and the electron-withdrawing group, thereby modulating the chelating affinity of BAPTA for calcium ions. Solubility of the compound in a partially aqueous solvent was achieved by grafting a short PEG (polyethylene glycol) tail to the electron-withdrawing group. A reduction of the affinity for calcium ions upon photoswitching by a factor of 3–4, in the hundred nM range of dissociation constant, is reported and constitutes a proof of concept of this type of RPC.
ISSN:1010-6030
1873-2666