Biologically useful chelators that release Ca2+ upon illumination

SR Adams, JPY Kao, G Grynkiewicz…

Index: Adams, S. R.; Kao, J. P. Y.; Grynkiewicz, G.; Minta, A.; Tsien, R. Y. Journal of the American Chemical Society, 1988 , vol. 110, # 10 p. 3212 - 3220

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Citation Number: 260

Abstract

Abstract: A series of Ca2+-selective chelators incorporating a photosensitive o- nitrobenzhydryl ether, alcohol, or ester (A,,, 350-360 nm, c 4500 MI cm-l) were synthesized. The key step of the syntheses required the novel and mild trimethylsilyl triflate catalyzed Friedel-Crafts alkylation of a N, N-dialkylaniline by a nitrobenzaldehyde or its acetal. Before photolysis, the chelators show dissociation constants for Ca2+ of about lo-'M, roughly ...