Organotin(IV) derivatives of 4-chloro-2-methylphenoxyacetic acid: synthesis, spectral characterization, X-ray structures, anticancer, enzyme inhibition, antileishmanial, antimicrobial and antioxidant activities

Résumé fourni par la source

Four organotin(IV) carboxylate complexes; (C4H9)3SnL (1), CH3SnL (2), (C4H9)2SnL2 (3) and (CH3)2SnL2 (4) are synthesized by the condensation reaction of organotin(IV) chlorides with sodium-4-chloro-2-methylphenoxyacetate (NaL). The FT-IR spectra suggested bridging/chelating bidentate coordination of the ligand to the tin atom. Single-crystal XRD analysis authenticated the FT-IR findings for 1 and 2. The NMR study has shown no significant differences in the signals of the free and coordinated ligand except for absence of a proton and up-filed/down-field shift of the C signal of the carboxyl group in the spectra. Complexes 1–4 have shown better enzyme inhibition, antioxidant, antimicrobial, and anticancer activities compared to the free ligand acid. Complex 3 was the most active inhibitor of AChE, BChE, α-glucosidase and α-amylase with IC50 values of 43.76, 102.39, 232.71 and 91.84 µg/mL, respectively. Additionally, 3 with IC50 values of 7.52 and 8.77 µg/mL in the DPPH and ABTS assays, respectively was better antioxidant than the standard. Complex 4 was the most efficient inhibitor of MAO-B and COX-2 enzymes with IC50 values of 106.99 and 12.98 µg/mL, respectively, while 1 (IC50 = 38.97 µg/mL) has shown the highest 5-LOX inhibition potential. Complexes 1–4 with IC50 values in the range 237.51–168.35 µg/mL have shown better antileishmanial activity than HL (IC50 = 277.57 µg/mL). The compounds showed good to potent antiproliferative activity in malignant glioma U87 cells with IC50 values in the range 12.54 ± 0.05 to 37.65 ± 0.04 µg/mL. Antimicrobial activities have shown promising results for the compounds compared to the standards in some cases.

Ce résumé expose les affirmations des auteurs. BNTIC ne l’interprète pas comme une validation indépendante des résultats.