Synthesis, Biological Activity and Molecular Docking Studies of Novel Sulfonate Derivatives Bearing Salicylaldehyde

Abstract

Enzyme activity alterations have been associated with many metabolism disorders and have crucial roles in the pathogenesis of some diseases. Tyrosinase is a key enzyme in melanin biosynthesis, which is responsible for skin pigmentation to protect the skin from solar radiation. Pancreatic lipase has been considered a key enzyme for the treatment of obesity. Herein, we reported the synthesis and enzyme inhibitions of a series of sulfonates as possible tyrosinase and pancreatic lipase inhibitors. According to the calculated IC50 values, compound 3f (74.1±11.1 μM) and compound 3c (86.6±6.9 μM) were determined to be the best inhibitors among the synthesized compounds for the tyrosinase and pancreatic lipase enzymes, respectively. The approach yielded at extremely high level by creating very flexible structural domains for the chemically modified groups. The structural characterization of the target molecules was implemented by 1H‐NMR, 13C‐NMR, and HR‐MS analyses. Also, molecular docking studies of the synthesized compounds with tyrosinase and pancreatic lipase enzymes were conducted using AutoDock Vina software. Additionally, the studies of the absorption distribution, metabolism, and excretion (ADME) were performed to uncover the target compounds′ pharmacokinetics, drug similarities, and medicinal properties of the novel sulfonate derivatives bearing salicylaldehyde.

Biopanning, Heterologous Expression, and Characterization of a Shark-Derived Single-Domain Antibody Fusion Protein against Pancreatic Lipase

“…PL-D2S did not achieve the equivalent inhibitory capacity compared with the positive control orlistat (IC 50 = 0.811 μg/mL) and sulfonate derivatives synthesized by Korkmaz et al (approximately 0.66−0.8 equivalent PL inhibitory activity of orlistat). 17,23 However, compared with the reported pancreatic inhibitors in natural products, the fusion protein PL-D2S still showed a significantly lower IC 50 inhibition rate, such as polyphenols (IC 50 = 460 μg/ mL), 39 saponins (IC 50 = 750 μg/mL), 40 and terpene compounds (IC 50 = 614 μg/mL). 41 Moreover, sdAbs have good physicochemical stability, high yield, and an easier preparation procedure.…”

Synthesis, DFT calculations, α‐glucosidase inhibitor activity, and docking studies on Schiff base metal complexes containing isothiocyanate

“…The RMSD value obtained at 0.446 Å indicates that the selected docking parameters are acceptable. [ 107,108 ] Optimized parameters were used to dock for complexes 1–5 and genistein into the active site of the α‐glucosidase homology model.…”

“…The RMSD value obtained at 0.446 Å indicates that the selected docking parameters are acceptable. [107,108] Optimized parameters were used to dock for complexes 1-5 and genistein into the active site of the α-glucosidase homology model. The docking results were used to explain the binding energies and estimated inhibition constants of the complexes.…”

Acetone O-(4-chlorophenylsulfonyl)Oxime as an Agent Alleviating the Adverse Effects of Drought Stress in Maize

“…Since various organic sulfonate derivatives such as AO show anticancer, antimicrobial, apoptosis inducer, enzyme inhibition, chelating, and anti-inflammatory biological properties, the interest in these compounds is increasing day by day (Kendre et el. 2019;Kanabar et al 2020;Taslimi et al 2021;Su et al 2021;Yetişsin and Kardeş, 2021;Korkmaz and Bursal, 2022;Şenkardeş et al 2022). It can be said that Acetone O-(4-chlorophenylsulfonyl)oxime (AO), a sulfonated derivative of acetone oxime, can provide the attachment of radicals due to the atoms it has and the double bonds in its structure.…”