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Isothermal Titration Calorimetry for Characterizing the Zinc2+‐Binding Properties of Photocaged Complexes with Micromolar Affinity

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MorphDeCage (2-(4-methoxy-3-nitrophenyl)-2-morpholinoacetic acid) and PyrDeCage (2-(4-methoxy-3-nitrophenyl)-2-(methyl(pyridin-2-ylmethyl)amino)acetic) are Zn2+ photocages that utilize photodecarboxylation of the methoxy derivative of meta-nitrophenylacetic acid as the release mechanism. Isothermal titration calorimetry (ITC) was used an alternative to usual approaches to measure the Zn2+ binding affinities of these new compounds owing to unsuccessful measurement by competitive titration with 4-(2-pyridylazo)resorcinol (PAR). MorphDeCage forms a 1:1 ligand-metal complex with a 106 μM Kd value. PyrDeCage forms both a 1:1 and 1:2 metal: ligand complexes with 3.2 and 21.7 μM Kd values respectively. To further demonstrate the efficacy of the ITC methodology and provide a comparison to direct UV-vis titrations data, two photocages based on Sanger’s reagent (SRPs) were prepared. The Kd values of the SRPs measured by UV-vis titration and ITC were internally consistent and support the retraction of the original report (J. Am. Chem. Soc.2020, 142, 3806-3813), which was withdrawn due to errors in binding affinity measurements.

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