Photo-cleavable analog of BAPTA for the fast and efficient release of Ca²⁺

Abstract

A new photocleavable analog of BAPTA chelating ligand has a high affinity towards Ca2+ ions (K= 2.5*106 M−1). The use of photolabile 3-(hydroxymethyl)-2-naphthol core in the design of photo-BAPTA allows for the efficient (Φ=0. 63) and very fast (τ <12 μs) release of Ca2+ ions upon 300 or 350 nm irradiation.

Sanger’s Reagent Sensitized Photocleavage of Amide Bond for Constructing Photocages and Regulation of Biological Functions

“…Light promoted bond cleavage reactions of photocaged compounds serve as powerful tools to create materials in a highly spatially and temporally controlled manner. As a result, these substances have found wide applications in tissue engineering, biosensing, counterfeit detection, controlled release of functional molecules, and regulation of gene expression. − Moreover, owing to their use of noninvasive optical triggers, and its high spatial and temporal precision, photocaged substances have been utilized to explore biological processes and elucidate their mechanistic nature. − Arylcarbonylmethyl, nitroaryl ( ortho -nitrobenzyl, ortho -nitroanilides), azobenzene, xanthene, coumarin-4-ylmethyl, − and indoline groups , are the commonly used photoreaction triggers to construct photocages for controlled release of metal ions (Ca 2+ , Zn 2+ , Cu 2+ ), drugs, and other bioactive substances. − Particularly, incorporation of nitrobenzene derivatives along with metal ion-binding ligands has become a prevailing tool to investigate the signaling processes in biological systems that are governed by metal ions. − In addition, photocage containing metal ion complexes along with fluorophores whose optical properties are altered by metal ion binding and release have been employed to elucidate cellular processes and signaling …”

Nitric Oxide Sensing through Azo-Dye Formation on Carbon Dots

“…Similar fluorescence quenching inhibitory action was recorded upon preincubating the cells with BAPTA-AM, a Ca 2+ chelator known to interfere with NOS enzymatic activity (Figures 12 and 13, SI). 56 These results are noteworthy, since they indicate that the new C-dot NO sensor could be employed for screening and assessing the activity of NOS inhibitors.…”

Highly Efficient Visible Light-Induced Ca2+ Chelation

“…44 3 exhibited the highest quantum yield (0.83), attributable to the heightened ring and torsional strain inherent in the three-membered aziridine ring. [51][52][53][54] Ring strain arises when the bond angles in a cyclic structure deviate from the ideal angles, leading to increased energy. 52,54 Higher ring strain can result in more energetic intermediates during photochemical processes, potentially contributing to a higher quantum yield.…”

“…[51][52][53][54] Ring strain arises when the bond angles in a cyclic structure deviate from the ideal angles, leading to increased energy. 52,54 Higher ring strain can result in more energetic intermediates during photochemical processes, potentially contributing to a higher quantum yield. 54 In contrast, the four-membered azetidine ring in 2 experiences lower ring strain, likely accounting for its comparatively lower quantum yield.…”