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A Zinc(II) Photocage Based on a Decarboxylation Metal Ion Release Mechanism for Investigating Homeostasis and Biological Signaling
Author(s) -
Basa Prem N.,
Antala Sagar,
Dempski Robert E.,
Burdette Shawn C.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505778
Subject(s) - decarboxylation , xenopus , zinc , metal , chemistry , chelation , metal ions in aqueous solution , photodissociation , combinatorial chemistry , photochemistry , inorganic chemistry , biochemistry , organic chemistry , catalysis , gene
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‐p M 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.