PEPPSI type Pd(II)NHC complexes bearing chloro-/fluorobenzyl group: Synthesis, characterization, crystal structures, α-glycosidase and acetylcholinesterase inhibitory properties

Bal, Selma; Demirci, Özlem; Şen, Betül; Taslimi, Parham; Aktaş, Aydın; Gök, Yetkın; Aygün, Muhıttın; Gülçın, İlhami

doi:10.1016/j.poly.2021.115060

Cited by 35 publications

(22 citation statements)

References 69 publications

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“…These changes in substrate specificity and transglycosylation activity result from structural changes in the catalytic and substrate binding sites of enzymes. [ 43–45 ]…”

Section: Introductionmentioning

confidence: 99%

“…These changes in substrate specificity and transglycosylation activity result from structural changes in the catalytic and substrate binding sites of enzymes. [43][44][45] Alzheimer's disease (AD) is a progressive degenerative disease that first begins with memory loss and eventually affects all cognition and behavior with a prevalence of over 40 million people worldwide is one of the most common age-related diseases. [46][47][48] This disease is characterized by progressive memory loss, various cognitive impairments, and a decline in language skills.…”

Section: Introductionmentioning

confidence: 99%

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Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Tezcan

Gök

Sevinçek

et al. 2022

J Biochem & Molecular Tox

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Here, we report the synthesis, characterization, and biological activities of a series of benzimidazolium salts bearing the trifluoromethylbenzyl group. All benzimidazolium salts were characterized by using nuclear magnetic resonance (NMR) ( 1 H NMR and 13 C NMR), Fourier transform-infrared spectroscopy, and elemental analysis techniques. The crystal structures of some of these compounds were obtained by the single-crystal X-ray diffraction method. Furthermore, the acetylcholinesterase (AChE) and α-glycosidase (α-Gly) enzyme inhibition activities of these compounds were investigated. The obtained results revealed that 2e, with K i value of 1.36 ± 0.34 µM against AChE and 3d with K i value of 91.37 ± 10.38 µM against α-Gly, were the most potent compounds against both assigned enzymes. It should be noted that most of the synthesized compounds were more potent than standard inhibitor tacrine (TAC) against AChE. In silico studies, we focused on compound 2e, 3d, 3e, and 3f as potent inhibitors of AChE and α-Gly, the compound 2e showed good binding energy (−10.23 kcal/mol), among the three selected compounds and positive control (−10.18, −10.08, and −7.37 kcal/mol for 3d, 3f, and TAC, respectively). Likewise, as a result of the same compounds against the α-Gly enzyme, the compound 3d had the highest binding affinity (−8.39 kcal/mol) between the four selected compounds and the positive control (−8.27, −8.10, −8.06, and −7.53 kcal/mol for 3f, 3e, 2e, and acarbose, respectively). From the absorption, distribution, metabolism, excretion, and toxicity analyses, it can be concluded that the compounds under consideration exhibited more drug-likeness properties in the prediction studies compared to positive controls.

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“…These changes in substrate specificity and transglycosylation activity result from structural changes in the catalytic and substrate binding sites of enzymes. [ 43–45 ]…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Tezcan

Gök

Sevinçek

et al. 2022

J Biochem & Molecular Tox

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“…[3] Hence, inhibition of these enzymes will ultimately reduce this elevated blood-sugar level. [4] Several drug molecules such as Acarbose, Voglibose, some novel molecules [5] and natural products [6] are found to be useful in the treatment of hyperglycemia caused during diabetes. The adverse effects entailing to these drugs have led to further research in identification of potent lead molecules to inhibit the metabolism of dietary sugars via α-glucosidase and α-amylase.…”

Section: Introductionmentioning

confidence: 99%

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

Kumar

Ramu

Shirahatti³

et al. 2021

ChemistrySelect

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In our effort to identify potent fluorinated small molecules as antidiabetic compounds, a novel fluorinated series of 2-chloro-6-(trifluoromethyl)benzyloxy arylidene derived Rhodanine and Rhodanine-acetic acid derivatives were synthesized and screened for α-glucosidase and α-amylase inhibitory activity. Newly synthesized compounds were characterized by 1 HNMR, 13 C NMR, and LCMS spectral data. Among the tested compounds, (Z)-5-(4-(2-chloro-6-(trifluoromethyl)benzyloxy) benzylidene)-2-thioxothiazolidin-4-one(5 a) and 2-((Z)-5-(4-(2chloro-6-(trifluoromethyl)benzyloxy)benzylidene)-4-oxo-2-thioxothiazoli-din-3-yl)acetic acid(6 a) emerged as most promising α-glucosidase inhibitors with IC 50 values 4.76 � 0.64 μM and 4.91 � 0.45 μM, respectively. Further, the kinetic inhibition experiments against yeast α-glucosidase for compounds 5 a and 6 a indicated that these are competitive inhibitors with inhibitory constant (Ki) 0.54 μg and 1.15 μg respectively.Molecular docking studies on α-glucosidase was performed by homology modelingfor the most potent compounds 5 a and 6 a to understand the putative binding mode. The study revealed substantial binding of the compounds to the active site of α-glucosidase, indicating that the position of the substituent plays a key role in its inhibitory potential.

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“…With all this, it is well established that polyphenols also have anti-AD properties and α-glycosidase inhibition profiles. Therefore, one of the most important therapy approaches for neurodegenerative diseases and DM is natural compounds and products including phenolic compounds [28,29,30,31]. However, current evidence demonstrates that patients with DM have an increased risk of developing AD.…”

Section: Introductionmentioning

confidence: 99%

Antidiabetic, anticholinergic and antioxidant activities of aerial parts of shaggy bindweed (Convulvulus betonicifolia Miller subsp.) – profiling of phenolic compounds by LC-HRMS

Bingöl

Kızıltaş

Gören

et al. 2021

Heliyon

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In order to evaluate the antioxidant activity of evaporated ethanolic extract (EESB) and lyophilized water extract (WESB) of Shaggy bindweed (Convulvulus betonicifolia Mill. Subs), some putative antioxidant methods such as DPPH⋅ scavenging activity, ABTS þ scavenging effect, ferric ions (Fe 3þ ) reduction method, cupric ions (Cu 2þ ) reducing capacity, and ferrous ions (Fe 2þ ) binding activities were separately performed. Also, ascorbic acid, α-tocopherol and BHT were used as the standard compounds. Additionally, some phenolic compounds that responsible for antioxidant abilities of EESB and WESB were screened by liquid chromatography-high resolution mass spectrometry (LC-HRMS). At the same concentration, EESB and WESB demonstrated effective antioxidant abilities when compared to standards. In addition, EESB demonstrated IC 50 values of 1.946 μg/mL against acetylcholinesterase (AChE), 0.815 μg/mL against α-glycosidase and 0.675 μg/mL against α-amylase enzymes.

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PEPPSI type Pd(II)NHC complexes bearing chloro-/fluorobenzyl group: Synthesis, characterization, crystal structures, α-glycosidase and acetylcholinesterase inhibitory properties

Cited by 35 publications

References 69 publications

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

Antidiabetic, anticholinergic and antioxidant activities of aerial parts of shaggy bindweed (Convulvulus betonicifolia Miller subsp.) – profiling of phenolic compounds by LC-HRMS

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