Application research of thiosalicylic acid and its derivatives

Introduction

Thiosalicylic acid (Figure 1) molecule provides dual functionality, i.e., thiol (-SH) group and carboxylic (-COOH) group, which can considerably enhance the binding of arsenic species to the adsorbent surface. Secondly, thiosalicylic acid is fairly water insoluble which reduces possibilities of secondary contamination in water bodies as well as no significant toxicological effects of thiosalicylic acid on human and ecology has been reported in the literature.[1]

Thiosalicylic-Acid-Mediated Coordination Structure of Nickel Center

Uniquely functional nanocomplexes with rich coordination environments are critical in energy storage. However, the construction of structurally versatile nanocomplexes remains challenging. In this study, a nickel-based complex with structural variations is designed via thermodynamic modulation using a dual-ligand synthesis strategy. A nickel-based nanomaterial (NiSA-SSA-160) with a large specific surface area is synthesized around the competing coordination of the host and guest molecules that differ in terms of the chemical properties of the O and S elements. Su et al introduced a thiosalicylic acid (SHSA) guest molecule to the system and prepared double-ligand Ni-based complexes using the solvothermal method.As a guest molecule, thiosalicylic acid competes for coordination to form Ni-based dual-ligand complexes. Owing to thermodynamic regulation, O and S atoms competed with each other and the coordination environment changed, thus triggering a thermal response.The thiol functional groups synergistically induced an electron-rich Ni structure, thus increasing the electron density of the central atom. The electrochemical performance of an assembled NiSA-SSA-160//Zn@CC battery is shown to improve significantly, with a maximum energy density of 0.54 mWh cm^-2 and a peak power density of 49.49 mW cm^-2. This study provides a new perspective regarding coordination transformations and offers an idea for the design of functionally rich nanomaterials.[2]

Synthesis and characterization of binuclear copper(II)-complexes with some S-isoalkyl derivatives of thiosalicylic acid 

Isoalkyl (isoalkyl = isopropyl-(L1), isobutyl-(L2) and isoamyl-(L3)) derivatives of thiosalicylic acid (TSA) were prepared by alkylation of TSA with corresponding isoalkyl-chlorides in the alkaline water-ethanol solution. The new free copper(II)-complexes with corresponding S-isoalkyl derivatives of TSA (C1-copper(II)-complex with S-isopropyl derivative of thiosalicylic acid, C2-copper(II)-complex with S-isobutyl derivative of thiosalicylic acid and C3-copper(II)-complex with S-isoamyl derivative of thiosalicylic acid) have been synthesized by direct reaction of copper(II)-nitrate with ligand precursor and then characterized by microanalysis, infrared spectra (IR) and EPR (electron paramagnetic resonance) spectra. The spectroscopically predicted structure of the obtained binuclear copper(II)-complex with S-isopropyl derivative of thiosalicylic acid was confirmed by X-ray analysis. Single crystals suitable for X-ray measurements were obtained by slow crystallization from a water solution. Newly synthesized precursors S-isoalkyl derivatives of thiosalicylic acid and corresponding copper(II)-complexes moderately reduced viability of human and murine lung cancer cells, they showed similar cytotoxic effect on human colorectal cancer cells as cisplatin and lower cytotoxic effect than cisplatin toward normal fibroblasts, evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) colorimetric technique. All new complexes exhibited apoptotic effect toward lung cancer cells, stronger than cisplatin, whereas only C3 induced significant apoptosis of colorectal cancer cells. Complex C1 showed significant antiproliferative effect against murine lung cancer cells, LLC1, while C2 reduced expression of Ki67 in human colorectal cancer cells. All tested complexes induced cell cycle arrest of HCT116 cells in G2/M phase.[3]

Activation of TRPA1 by farnesyl thiosalicylic acid

The nonselective cation channel TRPA1 (ANKTM1, p120) is a potential mediator of pain, and selective pharmacological modulation of this channel may be analgesic. Although several TRPA1 activators exist, these tend to be either reactive or of low potency and/or selectivity. The aim of the present study, therefore, was to identify novel TRPA1 agonists. Using a combination of calcium fluorescent assays and whole-cell electrophysiology, we discovered several compounds that possess potent, selective TRPA1-activating activity, including several lipid compounds (farnesyl thiosalicylic acid, farnesyl thioacetic acid, 15-deoxy-Delta(12,14)-prostaglandin J(2), and 5,8,11,14-eicosatetraynoic acid), and two marketed drugs: disulfiram (Antabuse; a compound used in the treatment of alcohol abuse) and the antifungal agent chlordantoin. Farnesyl thiosalicylic acid activates the channel in excised patches and in the absence of calcium. Furthermore, using a quadruple TRPA1 mutant, we show that the mechanism of action of farnesyl thiosalicylic acid differs from that of the reactive electrophilic reagent allylisothiocyanate. As a TRPA1 agonist with a potentially novel mechanism of action, farnesyl thiosalicylic acid may be useful in the study of TRPA1 channels.[4]

References

[1] Rajput MK, Hazarika R, Sarma D. Removal of As(III)/As(V) from aqueous solution using newly developed thiosalicylic acid coated magnetite [TSA@Fe3O4] nanoparticles. Environ Sci Pollut Res Int. 2023;30(9):23348-23362. doi:10.1007/s11356-022-23852-6

[2] Su Y, Yuan G, Hu J, et al. Thiosalicylic-Acid-Mediated Coordination Structure of Nickel Center via Thermodynamic Modulation for Aqueous Ni-Zn Batteries. Adv Mater. 2024;36(32):e2406094. doi:10.1002/adma.202406094

[3] Dimitrijević J, Arsenijević AN, Milovanović MZ, et al. Synthesis, characterization and cytotoxic activity of binuclear copper(II)-complexes with some S-isoalkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II)-complex with S-isopropyl derivative of thiosalicylic acid. J Inorg Biochem. 2020;208:111078. doi:10.1016/j.jinorgbio.2020.111078

[4] Maher M, Ao H, Banke T, et al. Activation of TRPA1 by farnesyl thiosalicylic acid. Mol Pharmacol. 2008;73(4):1225-1234. doi:10.1124/mol.107.042663

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