Synthesis, characterization, evaluation of metabolic enzyme inhibitors and in silico studies of thymol based 2-amino thiol and sulfonic acid compounds

Bora, Rıfat Emin; Bilgiçli, Hayriye Genç; Üç, Eda Mehtap; Alagöz, Mehmet Abdullah; Zengin, Mustafa; Gülçın, İlhami

doi:10.1016/j.cbi.2022.110134

Cited by 13 publications

(9 citation statements)

References 75 publications

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“…The liver damage caused by Tacrine prevents it from being used widely and it has been removed from the United States drug market. New AChE inhibitors have been created as a result of Tacrine's success in treating Alzheimer's patients [42,53,54] …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products

Menzek

Bayrak

Taslimi

et al. 2023

Chemistry & Biodiversity

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In addition to the first synthesis of the natural bromophenol butyl 2‐(3,5‐dibromo‐4‐hydroxyphenyl)acetate (1), indene derivatives 34 and 35 were synthesized from 3‐phenylpropenal derivatives in BBr3 medium. Five known natural bromophenols and some derivatives were synthesized by known methods. Cholinesterase (ChEs) inhibitors reduce the breakdown of acetylcholine and are used in the treatment of Alzheimer's disease (AD) and dementia symptoms. The inhibition effects of all obtained compounds were examined towards acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and α‐glycosidase enzymes. All synthesized compounds demonstrated the strong inhibition effects against both cholinergic enzymes. For determination of Ki values of novel bromophenols Lineweaver‐Burk graphs were obtained. Ki values were found in the ranging of 0.13–14.74 nM for AChE, 5.11–23.95 nM for BChE, and 63.96–206.78 nM for α‐glycosidase, respectively. All bromophenols and their derivatives exhibit effective inhibition profile when compared to positive controls.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products

Menzek

Bayrak

Taslimi

et al. 2023

Chemistry & Biodiversity

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“…These inhibitors block the α-glycosidase enzyme in the small intestine, which is responsible for the digestion of complex carbohydrates. This enzymatic process lowers postpartum blood glucose levels by reducing carbohydrate breakdown and glucose absorption [ 79 ]. When the literature was searched, it was observed that Moroccan propolis collected from different regions inhibited the α-glycosidase enzyme with IC 50 values between 0.01–0.07 mg/mL.…”

Section: Discussionmentioning

confidence: 99%

Comprehensive Metabolite Profiling of Berdav Propolis Using LC-MS/MS: Determination of Antioxidant, Anticholinergic, Antiglaucoma, and Antidiabetic Effects

et al. 2023

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Propolis is a complex natural compound that honeybees obtain from plants and contributes to hive safety. It is rich in phenolic and flavonoid compounds, which contain antioxidant, antimicrobial, and anticancer properties. In this study, the chemical composition and antioxidant activities of propolis were investigated; ABTS•+, DPPH• and DMPD•+ were prepared using radical scavenging antioxidant methods. The phenolic and flavonoid contents of propolis were 53 mg of gallic acid equivalent (GAE)/g and 170.164 mg of quercetin equivalent (QE)/g, respectively. The ferric ion (Fe3+) reduction, CUPRAC and FRAP reduction capacities were also studied. The antioxidant and reducing capacities of propolis were compared with those of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol and Trolox reference standards. The half maximal inhibition concentration (IC50) values of propolis for ABTS•+, DPPH• and DMPD•+ scavenging activities were found to be 8.15, 20.55 and 86.64 μg/mL, respectively. Propolis extract demonstrated IC50 values of 3.7, 3.4 and 19.6 μg/mL against α-glycosidase, acetylcholinesterase (AChE) and carbonic anhydrase II (hCA II) enzyme, respectively. These enzymes’ inhibition was associated with diabetes, Alzheimer’s disease (AD) and glaucoma. The reducing power, antioxidant activity and enzyme inhibition capacity of propolis extract were comparable to those demonstrated by the standards. Twenty-eight phenolic compounds, including acacetin, caffeic acid, p-coumaric acid, naringenin, chrysin, quinic acid, quercetin, and ferulic acid, were determined by LC-MS/MS to be major organic compounds in propolis. The polyphenolic antioxidant-rich content of the ethanol extract of propolis appears to be a natural product that can be used in the treatment of diabetes, AD, glaucoma, epilepsy, and cancerous diseases.

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“…Both hCA I and II isoforms were purified using the affinity chromatography technique including Sepharose-4B-L-Tyrosine-sulfanilamide affinity material [ 46 ]. Both isoforms’ activity was spectrophotometrically determined according to the Verpoorte assay [ 47 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Schiff Bases Containing Phenol Rings and Investigation of Their Antioxidant Capacity, Anticholinesterase, Butyrylcholinesterase, and Carbonic Anhydrase Inhibition Properties

et al. 2023

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The widespread usage of Schiff bases in chemistry, industry, medicine, and pharmacy has increased interest in these compounds. Schiff bases and derivative compounds have important bioactive properties. Heterocyclic compounds containing phenol derivative groups in their structure have the potential to capture free radicals that can cause diseases. In this study, we designed and synthesized eight Schiff bases (10–15) and hydrazineylidene derivatives (16–17), which contain phenol moieties and have the potential to be used as synthetic antioxidants, for the first time using microwave energy. Additionally, the antioxidant effects of Schiff bases (10–15) and hydrazineylidene derivatives (16–17) were studied using by the bioanalytical methods of 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical (ABTS•+) and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) scavenging activities, and Fe3+, Cu2+, and Fe3+-TPTZ complex reducing capacities. In the context of studies on antioxidants, Schiff bases (10–15) and hydrazineylidene derivatives (16–17) were found to be as powerful DPPH (IC50: 12.15–99.01 μg/mL) and ABTS•+ (IC50: 4.30–34.65 μg/mL). Additionally, the inhibition abilities of Schiff bases (10–15) and hydrazineylidene derivatives (16–17) were determined towards some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I and II (hCAs I and II), enzymes that are linked to some global disorders including Alzheimer’s disease (AD), epilepsy, and glaucoma. In the context of studies on enzyme inhibition, it was observed that the synthesized Schiff bases (10–15) and hydrazineylidene derivatives (16–17) inhibited AChE, BChE, hCAs I, and hCA II enzymes with IC50 values in ranges of 16.11–57.75 nM, 19.80–53.31 nM, 26.08 ± 8.53 nM, and 85.79 ± 24.80 nM, respectively. In addition, in light of the results obtained, we hope that this study will be useful and guiding for the evaluation of biological activities in the fields of the food, medical, and pharmaceutical industries in the future.

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Synthesis, characterization, evaluation of metabolic enzyme inhibitors and in silico studies of thymol based 2-amino thiol and sulfonic acid compounds

Cited by 13 publications

References 75 publications

Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products

Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products

Comprehensive Metabolite Profiling of Berdav Propolis Using LC-MS/MS: Determination of Antioxidant, Anticholinergic, Antiglaucoma, and Antidiabetic Effects

Synthesis of Schiff Bases Containing Phenol Rings and Investigation of Their Antioxidant Capacity, Anticholinesterase, Butyrylcholinesterase, and Carbonic Anhydrase Inhibition Properties

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