A photolabile ligand for light-activated release of caged copper

Journal of the American Chemical Society
Katie L CiesienskiKatherine J Franz

Abstract

A photosensitive caged copper complex has been prepared from a tetradentate ligand (H2cage) composed of two pyridyl-amide arms connected by a photoreactive nitrophenyl group. H2cage binds Cu2+ in aqueous solution with a stability constant (log beta) of 10.8, which corresponds to a KD of 16 pM at pH 7.4. The neutral Cu2+ complex, [Cu(OH2)(cage)], crystallizes as a distorted trigonal bipyramid coordinated by two amide and two pyridyl N atoms, with a water molecule bound in the trigonal plane. Photolysis with 350 nm UV light cleaves the ligand backbone to release photoproducts with significantly diminished affinity for Cu2+, thereby uncaging the metal ion. When coordinated as the caged complex, copper has diminished reactivity to produce hydroxyl radicals from Fenton-like reaction mixtures containing hydrogen peroxide and ascorbic acid. Postphotolysis, uncaged copper promotes hydroxyl radical formation under the same conditions. The strategy of caging copper is promising for applications where light could be used to trigger release of copper as a pro-oxidant to increase oxidative stress or as a tool to release copper intracellularly to study mechanisms of copper trafficking.

Citations

Sep 1, 2009·Chemical Reviews·Kathryn L Haas, Katherine J Franz
Jul 2, 2010·Inorganic Chemistry·Katie L CiesienskiKatherine J Franz
Nov 17, 2010·Journal of the American Chemical Society·Evan W MillerChristopher J Chang
Feb 1, 2011·Journal of the American Chemical Society·Thomas A Shell, David S Lawrence
Nov 12, 2009·Chemical Communications : Chem Comm·Celina GwizdalaShawn C Burdette
Aug 27, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Katie L CiesienskiKatherine J Franz
Jan 12, 2012·Physical Chemistry Chemical Physics : PCCP·Xu Zhang, Yi Chen
Nov 3, 2009·Chemical & Pharmaceutical Bulletin·Yoshiyuki KageyamaShin Aoki
May 9, 2014·Inorganic Chemistry·Chen-Jui LinChien-Hou Wu
Oct 7, 2015·Inorganic Chemistry·Anna LeonidovaGilles Gasser
Apr 24, 2012·Biochimica Et Biophysica Acta·Kevin M DeanAmy E Palmer
Dec 29, 2012·Current Opinion in Chemical Biology·Celina Gwizdala, Shawn C Burdette
Feb 14, 2017·Journal of the American Chemical Society·Mahdi KarimiMichael R Hamblin
Jan 26, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Ana ZamoraEdith C Glazer
Jan 20, 2011·Angewandte Chemie·Katie L Ciesienski, Katherine J Franz
Aug 27, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Philipp AnstaettGilles Gasser
Jun 11, 2009·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Xu Zhang, Yi Chen
Jan 23, 2010·Physical Chemistry Chemical Physics : PCCP·Xu Zhang, Yi Chen
Apr 25, 2012·Chemical Communications : Chem Comm·Hannah W MbatiaShawn C Burdette
Feb 19, 2013·Chemical Communications : Chem Comm·Anupa A KumbharKatherine J Franz
May 1, 2012·Chemical Communications : Chem Comm·Hidehiro ItoEiji Yashima
Jun 12, 2009·Organic Letters·Daniel P KennedyShawn C Burdette
Sep 28, 2010·Organic Letters·Daniel P KennedyShawn C Burdette
Aug 18, 2012·Biochemistry·Hannah W Mbatia, Shawn C Burdette
Oct 31, 2020·Chemical Reviews·Roy WeinstainPetr Klán

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