A Zinc(II) Photocage Based on a Decarboxylation Metal Ion Release Mechanism for Investigating Homeostasis and Biological Signaling

Angewandte Chemie
Prem N BasaShawn C Burdette

Abstract

Metal ion signaling in biology has been studied extensively with ortho-nitrobenzyl photocages; however, the low quantum yields and other optical properties are not ideal for these applications. We describe the synthesis and characterization of NTAdeCage, the first member in a new class of Zn(2+) photocages that utilizes a light-driven decarboxylation reaction in the metal ion release mechanism. NTAdeCage binds Zn(2+) with sub-pM affinity using a modified nitrilotriacetate chelator and exhibits an almost 6 order of magnitude decrease in metal binding affinity upon uncaging. In contrast to other metal ion photocages, NTAdeCage and the corresponding Zn(2+) complex undergo efficient photolysis with quantum yields approaching 30 %. The ability of NTAdeCage to mediate the uptake of (65) Zn(2+) by Xenopus laevis oocytes expressing hZIP4 demonstrates the viability of this photocaging strategy to execute biological assays.

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Citations

Mar 15, 2016·Journal of the American Chemical Society·Hitesh K AgarwalGraham C R Ellis-Davies
May 19, 2017·Angewandte Chemie·Nicholas AnkenbruckAlexander Deiters
Apr 2, 2019·Chemistry : a European Journal·Jingjing YanShawn C Burdette
Nov 16, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jingjing YanShawn C Burdette
May 11, 2017·Essays in Biochemistry·Chelsea A Barr, Shawn C Burdette
Oct 31, 2020·Chemical Reviews·Roy WeinstainPetr Klán
Oct 5, 2021·Acta Crystallographica. Section D, Structural Biology·Diana C F MonteiroArwen R Pearson

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