Phosphatase alkaline inhibition and antithyroid activity of acetylacetone sulfonamide derived Schiff Base. In vitro and in silico studies.

GADDI, GISELA M.; CARO-RAMÍREZ, JANETSI Y.; ANTONENA YAMILA B; CARLOS FRANCA; MARTINEZ HEREDIA LEANDRO; LAVECCHIA MARTIN; WILLIAMS, PATRICIA A. M.; FERRER, EVELINA G.

chemistryselect

chemistryselect

Año: 2024

The sulfonamide-derived compounds have demonstrated various pharmaceutical properties. However, the exploration of certain properties, such as phosphatase inhibition and anti-thyroid activities, has been limited in the existing literature. The present study aimed to investigate these specific activities for the Schiff base (Z)-4-(4-oxopent-2-en-2-ylamino)benzenesulfonamide. The compound underwent thorough physicochemical characterization, including FTIR, Raman, and UV-Vis spectroscopy, along with theoretical DFT calculations. It exhibited inhibitory activity against intestinal alkaline phosphatase, showcasing an IC50 value of 37.0 ± 1.0 μM, with kinetic studies indicating a mixed mode of inhibition. Additional insights into the inhibition process were gained through fluorescence spectroscopy and molecular docking studies. The potential anti-thyroid activity was explored through charge-transfer studies with iodine, revealing a strong interaction (2.16 ± 0.05 x 104 M-1), suggesting a role in reducing the iodination process of triiodothyronine (T3) and thyroxine (T4). Moreover, the compound showed strong, spontaneous, and reversible binding to albumin, indicating potential pharmaceutical relevance. ADME properties were also calculated, confirming favorable drug-likeness. This study provides valuable insights into the multifaceted pharmaceutical properties of the investigated sulfonamide-derived compound, encouraging further exploration of its therapeutic potential