Design and synthesis of BODIPY-clickate based Hg²⁺ sensors: the effect of triazole binding mode with Hg²⁺ on signal transduction

Abstract

BODIPY-clickates, F1 and F2, for the detection of Hg(2+) have been designed, synthesized and characterized. Both F1 and F2 showed hyperchromic shifts in the UV-visible spectra in response to increasing Hg(2+) concentrations. Hg(2+) ion binding caused perturbation of the emission quenching process and chelation induced enhanced bathochromic emission of F1 and F2 to 620 nm and 660 nm, respectively. Job's plot clearly indicated that the binding ratio of F1 and F2 with Hg(2+) was 1 : 1. The NMR titration of BODIPY-clickates with Hg(2+) confirmed that aromatic amines and triazoles were involved in the binding event. Furthermore, HRMS data of F1-Hg(2+) and F2-Hg(2+) supported the formation of mercury complexes of BODIPY-clickates. The dissociation constant for the interaction between fluorescent probes F1 and F2 with Hg(2+) was found to be 24.4 ± 5.1 μM and 22.0 ± 3.9 μM, respectively. The Hg(2+) ion induced fluorescence enhancement was almost stable in a pH range of 5 to 8. Having less toxicity to live cells, both the probes were successfully used to map the Hg(2+) ions in live A549 cells.

A dual‐function chemosensor based on coumarin for fluorescent turn‐on recognition of Hg2+ and colorimetric detection of Cu2+ in aqueous media

“…Mercury ion (Hg 2+ ) is the most toxic and dangerous contamination, which exists in the form of inorganic salt or organic mercury compound in the food chain. It has high capability of coordination with sulfhydryl groups in biological systems, and has harmful effects on biological systems, which can result in many diseases and even death . Considering that the potential impact of Cu 2+ and Hg 2+ ions can threaten human health and the environment, the development of highly sensitive and selective chemosensors, which can detect and estimate trace levels of Cu 2+ and Hg 2+ ions, is very essential.…”

Design and synthesis of the BODIPY–BSA complex for biological applications

“…Ojida et al developed the BODIPY metal complex for imaging neurofibrillary tangles . We recently reported a BODIPY‐based Hg 2+ sensor that operates on a TICT mechanism with a large Stokes shift . Furthermore, we optimized the method for the synthesis of styryl–BODIPY derivative microwave‐assisted Knoevenegal condensation .…”

“…[9] We recently reported a BODIPY-based Hg 2+ sensor that operates on a TICT mechanism with a large Stokes shift. [10] Furthermore, we optimized the method for the synthesis of styryl-BODIPY derivative microwave-assisted Knoevenegal condensation. [11] Here, we report the preparation and characterization of the quinoxaline and anisyl appended BODIPYbovine serum albumin (BSA) complex, which has the potential to be used to identify kinase enzymes qualitatively.…”

Mercury Sensing Probes

“…5 Vedamalai et al reported on a BODIPY-clickate based fluorescence probe. 6 These developed compounds were applied to determine Hg 2+ not only in aqueous water but also for imaging of living cells. 5,6 A specific T-Hg-T mismatch on DNA was also applied to the fluorometric detection of Hg.…”

“…6 These developed compounds were applied to determine Hg 2+ not only in aqueous water but also for imaging of living cells. 5,6 A specific T-Hg-T mismatch on DNA was also applied to the fluorometric detection of Hg. Zhang et al used N-methyl mesoporphylin IX (NMM)/G-quadruplex DNA system as reporter.…”