Could acetone O-(4-chlorophenylsulfonyl)oxime be a copper chelating and antioxidative molecule on maize seedlings?

Yetişsin, Fuat; Kardeş, İnci

doi:10.1080/15226514.2021.1970101

Cited by 12 publications

(8 citation statements)

References 51 publications

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“…Furthermore, the inhibition properties of carbonic anhydrase IX by benzothiazole‐sulfonamide derivatives have been documented in a recent study [21] . In summary, many studies have been conducted in phytoremediation studies in which sulfonate derivatives have significant potential [22,23] …”

Section: Introductionmentioning

confidence: 98%

“…[21] In summary, many studies have been conducted in phytoremediation studies in which sulfonate derivatives have significant potential. [22,23] Enzymes catalyze various chemical reactions are vital in metabolism. [24] Amylase, pancreatic lipase, and tyrosinase are the three enzymes of this study and have many crucial roles for regular metabolism.…”

Section: Introductionmentioning

confidence: 99%

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In Vitro and In Silico Evaluation of Amylase, Tyrosinase, and Pancreatic Lipase Inhibitions of Novel Benzothiazole‐Sulfonate Derivatives

Korkmaz,

Bursal,

Kurtay

2023

ChemistrySelect

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This paper provides a comprehensive account of the synthesis and assessment of newly developed aryl sulfonate derivatives based on benzothiazole as enzyme inhibitors, specifically focusing on their ability to target tyrosinase, amylase, and pancreatic lipase. The assessments were performed utilizing experimental (in vitro) and computational (in silico) methodologies. For this aim, nine different aryl sulfonate derivatives were synthesized. The synthesized compounds were subjected to structural characterizations by utilizing Nuclear Magnetic Resonance (1H NMR, 13C NMR) and High‐Resolution Mass Spectrometry (HRMS) studies, which provided confirmation of their structural properties. The inhibitory efficiency of the compounds was determined by measuring their 50 % inhibitory concentration (IC50) values and comparing them with the standard inhibitory compounds. According to the in vitro amylase activity, benzo[d]thiazol‐2‐yl 4‐methylbenzenesulfonate showed the best inhibition with the lowest IC50 value (43.31±4.3 μM) which was calculated to be at a close level to the IC50 value of standard acarbose (38.50±3.8 μM). Also, benzo[d]thiazol‐2‐yl 4‐bromobenzenesulfonate (22.73±4.15 μM) and benzo[d]thiazol‐2‐yl 4‐chlorobenzenesulfonate (25.28±1.95 μM) were calculated to have the lowest IC50 values and the most effective inhibition capacities against pancreatic lipase. Benzo[d]thiazol‐2‐yl 4‐fluorobenzenesulfonate and benzo[d]thiazol‐2‐yl 4‐methylbenzenesulfonate significantly exhibited superior tyrosinase inhibition compared to other derivatives and conventional kojic acid. In silico molecular docking affirmed that benzo[d]thiazol‐2‐yl naphthalene‐2‐sulfonate presented the highest binding affinities to the studied enzymes, with values of −7.8 kcal/mol for tyrosinase, −10.7 kcal/mol for pancreatic lipase, and −9.4 kcal/mol for α‐amylase. The pharmacokinetic characteristics and drug‐likeness of the synthesized sulfonate derivatives were also evaluated using absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction. Density Functional Theory (DFT) calculations were employed at the DFT/B3LYP/6‐311 g(d,p) level of theory to investigate the electronic characteristics of the compounds, therefore facilitating the comprehension of the reported enzyme inhibitory actions. In summary, our research highlights the potential of benzothiazole aryl sulfonate derivatives as effective enzyme inhibitors that hold promise for therapeutic applications.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Evaluation of Amylase, Tyrosinase, and Pancreatic Lipase Inhibitions of Novel Benzothiazole‐Sulfonate Derivatives

Korkmaz,

Bursal,

Kurtay

2023

ChemistrySelect

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“…It has been shown that the adverse effects of copper and Cd stress can be alleviated with acetone O-(4chlorophenylsulfonyl)oxime (Yetişsin and Kardeş, 2022;Demiralay, 2022). We think that ANSO, a synthetic sulfonate derivative oxime, may have effects on the phytoremediation of Cd in Cdcontaminated environments and attenuating the adverse effects of Cd stress by affecting different metabolic pathways in plants under Cd stress.…”

Section: Introductionmentioning

confidence: 98%

Acetone O-(2-naphthylsulfonyl)oxime Alleviates the Toxic Effects of Cadmium Stress in Maize Seedlings by Increasing the Phenolic Substance Content and Antioxidant System Activity

Yetişsin

AHNEAK

2023

Preprint

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Cadmium (Cd) is a heavy metal that can have toxic effects on plants even in trace amounts in the soil. In this study, we aimed to elucidate the role of exogenous O-(2-naphthylsulfonyl)oxime (ANSO) in maize plants under Cd stress. For this purpose, the following experimental groups were formed: The control group will be kept in distilled water for 18 hours, the second group will be kept in ANSO (0.3 mM) for 6 hours and then in distilled water for 12 hours, the third group will be in distilled water for 6 hours and then in Cd solution (100 μM) for 12 hours, fourth group ANSO (0.3 mM) for 6 hours, followed by 12 hours of Cd solution (100 µM). When ANSO+Cd application is compared to Cd, the Cd content increased 7.8 times, while the ABA content decreased. RWC content, which was reduced by Cd stress, was not changed by ANSO pre-treatment. Chlorophyll content, which decreased with Cd treatment, increased with ANSO+Cd treatment. While the carotenoid content increased with Cd application, it increased much with ANSO+Cd application. The H2O2 content and lipid peroxidation increased in the plant with Cd stress and decreased with ANSO pre-treatment. With ANSO+Cd treatment, GPX activity decreased compared to Cd treatment, but CAT and APX values increased. ANSO pre-treatment did not significantly change SOD activity. Cd application increased proline content compared to control, but proline content decreased compared to Cd with ANSO pre-treatment. In ANSO+CD application, ascorbic acid, cinnamic acid and catechol values increased compared to the values in plants treated with Cd alone, but the trans-coumaric acid value decreased. As a result, it can be said that ANSO pre-application to maize seedlings under Cd stress provides the preservation of the ion balance of the cells by chelating Cd+2 ions in the cell wall and vacuoles.

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“…(Scheme 1). Furthermore, the biological properties of the organosulfonate derivatives were interesting to many researchers [15–20] …”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, the biological properties of the organosulfonate derivatives were interesting to many researchers. [15][16][17][18][19][20] It is very important to the development of more reliable drugs to be more effective in the treatment of diseases caused by obesity. In our study, firstly, benzothiazole-sulfonate hybrid structures containing azomethine group were synthesized.…”

Section: Introductionmentioning

confidence: 99%

In Silico and in Vitro Biological Evaluation of Novel Serial Sulfonate Derivatives on Pancreatic Lipase Activity

Yetişsin,

Korkmaz,

Kaya

2023

Chemistry & Biodiversity

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The novel benzothiazole sulfonate hybrid derivatives containing azomethine group were synthesized and characterized using 1H NMR, 13C NMR, and HRMS analysis. The potential enzyme inhibition activities against pancreatic lipase of the novel benzothiazole sulfonate hybrid derivatives containing azomethine group were screened with in vitro and in silico methods. IC50 values of compounds 5b (23.89 µM), 5i (28.87 µM), and 5f (30.13±4.32) were found to be more effective pancreatic lipase inhibitors than orlistat (57.75 µM) in vitro studies. Also, the binding affinities of compounds 5b (‐8.7 kcal/mol), 5i (‐8.6 kcal/mol), and 5f (‐8.9 kcal/mol) were found potential inhibitors for pancreatic lipase in silico studies. In addition, the absorption distribution, metabolism, and excretion properties (ADME), molecular properties, toxicity estimation, and bioactivity scores of the synthesized compounds were scanned. It was found to have the ability to cross the brain‐blood barrier for compounds 5a, 5b, 5c, and 5d. All compounds were calculated to be taken orally as drugs, suitable for absorption in the intestinal tract and not carcinogenic, as well as very strongly bound to plasma proteins. Finally, compound 5f was observed to be the best inhibitor for pancreatic lipase according to in vitro and in silico studies.

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Could acetone O-(4-chlorophenylsulfonyl)oxime be a copper chelating and antioxidative molecule on maize seedlings?

Cited by 12 publications

References 51 publications

In Vitro and In Silico Evaluation of Amylase, Tyrosinase, and Pancreatic Lipase Inhibitions of Novel Benzothiazole‐Sulfonate Derivatives

In Vitro and In Silico Evaluation of Amylase, Tyrosinase, and Pancreatic Lipase Inhibitions of Novel Benzothiazole‐Sulfonate Derivatives

Acetone O-(2-naphthylsulfonyl)oxime Alleviates the Toxic Effects of Cadmium Stress in Maize Seedlings by Increasing the Phenolic Substance Content and Antioxidant System Activity

In Silico and in Vitro Biological Evaluation of Novel Serial Sulfonate Derivatives on Pancreatic Lipase Activity

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