Vinyl functionalized 5,6‐dimethylbenzimidazolium salts: Synthesis and biological activities

Karaca, Emine Özge; Bingöl, Zeynebe; Gürbüz, Nevin; Özdemır, İsmaıl; Gülçın, İlhami

doi:10.1002/jbt.23255

Cited by 5 publications

(4 citation statements)

References 92 publications

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“…The enzyme BChE catalyzes the breakdown of neurotransmitters into butyrate and choline to act on butyrylcholine and stop its effects in the synaptic cleft. [85][86][87] In the current study, a significant decrease was also observed between the control and HL+bromelain groups in the liver (*p < 0.05; Figure 3). Moreover, a similar situation was observed between the HL-control and HL+bromelain groups in liver (*p < 0.05; Figure 3).…”

Section: Resultssupporting

confidence: 68%

Protective effect of bromelain on some metabolic enzyme activities in tyloxapol‐induced hyperlipidemic rats

Sulumer,

Palabıyık,

Avcı

et al. 2023

Biotech and App Biochem

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Elevation of one or more plasma lipids, such as phospholipids, cholesterol esters, cholesterol, and triglycerides, is known as hyperlipidemia. In humans and experimental animals, bromelain, the primary active ingredient isolated from pineapple stems, has several positive effects, including anti‐tumor growth, anticoagulation, and anti‐inflammation. Hence, the purpose of this study was to determine the possible protective impact of bromelain on some metabolic enzymes (paraoxonase‐1, glutathione S‐transferase, glutathione reductase, sorbitol dehydrogenase [SDH], aldose reductase [AR], butyrylcholinesterase [BChE], and acetylcholinesterase [AChE]), activity in the heart, kidney, and liver of rats with tyloxapol‐induced hyperlipidemia. Rats were divided into three groups: control group, HL‐control group (tyloxapol 400 mg/kg, i.p. administered group), and HL+bromelain (group receiving bromelain 250 mg/kg/o.d. prior to administration of tyloxapol 400 mg/kg, i.p.). BChE, SDH, and AR enzyme activities were significantly increased in all tissues in HL‐control compared to the control, whereas the activity of other studied enzymes was significantly decreased. Bromelain had a regulatory effect on all tissues and enzyme activities. In conclusion, these results prove that bromelain is a new mediator that decreases hyperlipidemia.

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Section: Resultssupporting

confidence: 68%

Protective effect of bromelain on some metabolic enzyme activities in tyloxapol‐induced hyperlipidemic rats

Sulumer,

Palabıyık,

Avcı

et al. 2023

Biotech and App Biochem

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“…In the study on vinyl functionalized 5,6‐dimethylbenzimidazolium salts, the Ki value for hCA I was found to be 484.8‐1389.7 nM, the Ki value for hCA II was 298.9–926.1 nM, and the Ki value for AChE was 27.1–77.6 nM. In our study, trifluoromethoxybenzyl groups exhibited better inhibition effects on hCAI and hCA II enzymes compared to this study, and showed parallelism in the inhibition of AChE enzyme [75] …”

Section: Resultssupporting

confidence: 49%

Benzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesterase

Öner,

Gök,

Demir

et al. 2023

Chemistry & Biodiversity

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This report presents the synthesis and characterization of a range of benzimidazolium salts featuring 3‐cyanopropyl groups on the 1st nitrogen atom and varied alkyl groups on the 3rd nitrogen atom within the benzimidazole structure. Benzimidazolium salts were synthesized by N‐alkylation of 1‐alkyl benzimidazole with 3‐cyanopropyl‐bromide. The new salts were characterized by 1H and 13C‐NMR, FT‐IR spectroscopic and elemental analysis techniques. In this study, the enzyme inhibition abilities of seven nitrile substituted benzimidazolium salts were investigated against acetylcholinesterase (AChE) and carbonic anhydrase isoenzymes I and II (hCA I and hCA II). They showed a highly potent inhibition effect on AChE, hCA I and hCA II (Ki values are in the range of 26.71–119.09 nM for AChE, 19.77 to 133.68 nM for hCA I and 13.09 to 266.38 nM for hCA II). Reflecting the binding mode of the synthesized cyanopropyl series, the importance of the 2,3,5,6‐tetramethylbenzyl, 3‐methylbenzyl and 3‐benzyl groups for optimal interactions with target proteins, evaluated by molecular docking studies. At the same time, the docking findings support the inhibition constants (Ki) values of the related compounds in this study. Potential compounds were also evaluated by their pharmacokinetic properties were predicted.

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“…They play a role in regulating the acidity of gastric juice and in the secretion of mucus and bicarbonate from epithelial cells on tissue surfaces in the gastrointestinal tract. In addition, the hCA II isoenzyme is effective in adjusting the intracellular pH and Ca 2+ level to prevent bone resorption [ 82 ]. Most hCA I is found in erythrocytes.…”

Section: Discussionmentioning

confidence: 99%

Screening of Antiglaucoma, Antidiabetic, Anti-Alzheimer, and Antioxidant Activities of Astragalus alopecurus Pall—Analysis of Phenolics Profiles by LC-MS/MS

et al. 2023

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Astragalus species are traditionally used for diabetes, ulcers, leukemia, wounds, stomachaches, sore throats, abdominal pain, and toothaches. Although the preventive effects of Astragalus species against diseases are known, there is no record of the therapeutic effects of Astragalus alopecurus. In this study, we aimed to evaluate the in vitro antiglaucoma, antidiabetic, anti-Alzheimer’s disease, and antioxidant activities of the methanolic (MEAA) and water (WEAA) extracts of the aerial part of A. alopecurus. Additionally, its phenolic compound profiles were analyzed by liquid chromatography–tandem mass spectrometry (LC–MS/MS). MEAA and WEAA were evaluated for their inhibition ability on α-glycosidase, α-amylase, acetylcholinesterase (AChE), and human carbonic anhydrase II (hCA II) enzymes. The phenolic compounds of MEAA were analyzed by LC-MS/MS. Furthermore, total phenolic and flavonoid contents were determined. In this context, the antioxidant activity was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), N,N-dimethyl-p-phenylene diamine (DMPD), ferric reducing antioxidant power (FRAP), cupric ions (Cu2+) reducing antioxidant capacity (CUPRAC), ferric ions (Fe3+) reducing, and ferrous ions (Fe2+) chelating methods. MEAA and WEAA had IC50 values of 9.07 and 2.24 μg/mL for α-glycosidase, 693.15 and 346.58 μg/mL for α-amylase, 1.99 and 2.45 μg/mL for AChE, and 147.7 and 171.7 μg/mL for hCA II. While the total phenolic amounts in MEAA and WEAA were 16.00 and 18.50 μg gallic acid equivalent (GAE)/mg extract, the total flavonoid contents in both extracts were calculated as 66.23 and 33.115 μg quercetin equivalent (QE)/mg, respectively. MEAA and WEAA showed, respectively, variable activities on DPPH radical scavenging (IC50: 99.02 and 115.53 μg/mL), ABTS radical scavenging (IC50: 32.21 and 30.22 µg/mL), DMPD radical scavenging (IC50: 231.05 and 65.22 μg/mL), and Fe2+ chelating (IC50: 46.21 and 33.01 μg/mL). MEAA and WEAA reducing abilities were, respectively, Fe3+ reducing (λ700: 0.308 and 0.284), FRAP (λ593: 0.284 and 0.284), and CUPRAC (λ450: 0.163 and 0.137). A total of 35 phenolics were scanned, and 10 phenolic compounds were determined by LC-MS/MS analysis. LC-MS/MS revealed that MEAA mainly contained isorhamnetin, fumaric acid, and rosmarinic acid derivatives. This is the first report indicating that MEAA and WEAA have α-glycosidase, α-amylase, AChE, hCA II inhibition abilities, and antioxidant activities. These results demonstrate the potential of Astragalus species through antioxidant properties and enzyme inhibitor ability traditionally used in medicine. This work provides the foundation for further research into the establishment of novel therapeutics for diabetes, glaucoma, and Alzheimer’s disease.

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Vinyl functionalized 5,6‐dimethylbenzimidazolium salts: Synthesis and biological activities

Cited by 5 publications

References 92 publications

Protective effect of bromelain on some metabolic enzyme activities in tyloxapol‐induced hyperlipidemic rats

Protective effect of bromelain on some metabolic enzyme activities in tyloxapol‐induced hyperlipidemic rats

Benzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesterase

Screening of Antiglaucoma, Antidiabetic, Anti-Alzheimer, and Antioxidant Activities of Astragalus alopecurus Pall—Analysis of Phenolics Profiles by LC-MS/MS

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