Exploring indole-based-thiadiazole derivatives as potent acetylcholinesterase and butyrylcholinesterase enzyme inhibitors

Taha, Muhammad; Uddin, Nizam; Khan, Ihsan Ullah; Iqbal, Naveed; Anouar, El Hassane; Salahuddin, M.; Farooq, Rai Khalid; Gollapalli, Mohammed; Khan, Khalid Mohammed; Zafar, Ameeduzzafar

doi:10.1016/j.ijbiomac.2021.08.065

Cited by 37 publications

(11 citation statements)

References 45 publications

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“…The molecular docking study was validated by re-docking of the original ligand in the binding site of DNA-PK, which yielded an RMSD of 0.99Å and a binding energy of −10.92 kcal-mol −1 . Further steps of the docking of the original ligand and the trial molecules were reported in our previous study [ 54 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, X-ray Crystal Structure, Anticancer, Hirshfeld Surface Analysis, DFT, TD-DFT, ADMET, and Molecular Docking of 3-Phenyl-1,2,4-triazolo[3,4-h]-13,4-thiaza-11-crown-4

et al. 2023

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In this work, we describe the synthesis of new macrocycles derived from 3-phenyl-1,2,4-triazole-5-thione 1 in a heterogeneous medium using liquid–solid phase transfer catalysis (PTC) conditions. The structures of the two compounds (3 and 4) isolated were elucidated based on spectral data (1H-NMR, 13C-NMR) and confirmed in the case of 3-phenyl-1,2,4-triazolo [3,4-h]-13,4--thiaza-11-crown-4 (3) by a single-crystal X-ray diffraction analysis. Furthermore, the experimental spectral and the X-ray geometrical parameters were compared with their corresponding predicted ones obtained at the B3LYP/6-311++G(d,p) level of theory. The intercontacts between crystal units were investigated through Hirshfeld surface analysis. The drug-like macrocycles were predicted using ADMET and drug-likeness properties, which showed that 3 may act as an inhibitor of DNA-dependent protein kinase (DNA-PK). This assumption was confirmed by the well-binding fitting of 3 into the binding site of DNA-PK and the formation of a stable 3-DNA-PK complex with a binding energy of −7 kcal-mol−1. Finally, the anticancer activity of 3 was assessed by an MTT assay against A549 cells, which showed that 3 has moderate anticancer activity compared to that of the doxorubicin reference drug.

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Section: Methodsmentioning

confidence: 99%

Synthesis, X-ray Crystal Structure, Anticancer, Hirshfeld Surface Analysis, DFT, TD-DFT, ADMET, and Molecular Docking of 3-Phenyl-1,2,4-triazolo[3,4-h]-13,4-thiaza-11-crown-4

et al. 2023

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“…Cholinesterase inhibition is one of the most commonly used strategies in the treatment of this disease. [52,53] In this paper, in vitro cholinesterases inhibitory effects of the compounds were examined using spectrophotometer methods. The IC 50 and selective index (SI) values of the compounds on cholinesterases were given in Table 1.…”

Section: Biological Activitiesmentioning

confidence: 99%

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Yalazan

Tüzün

Akkaya

et al. 2022

Applied Organom Chemis

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Quinoline-fused Zn II (ZnPc p /ZnPc np ) and Mg II (MgPc p /MgPc np ) phthalocyanines with four 4-methylquinolin-2-ol (1) at non-peripheral or peripheral positions of the phthalocyanine core have been synthesized via cyclotetramerization of phthalonitrile derivatives (CN p /CN np ) in the presence of zinc (II) and magnesium (II) metal ions in this study. After synthesis and characterization processes, anti-cholinesterase, anti-α-glucosidase, DNA nuclease, antioxidant activities, and in silico calculations of both peripheral and non-peripheral Zn II and Mg II phthalocyanines were investigated. The inhibitory effects of metallated phthalocyanines on acetylcholinesterase, butyrylcholinesterase, and α-glucosidase enzymes were tested by spectrophotometric method. Theoretical methods are used to compare both the chemical and biological activities of the studied phthalonitrile derivatives and metallated phthalocyanine compounds.

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“…A purificação dos alcaloides testados foi realizada por meio de Cromatografia líquida de alta performance de fase reversa (RP-HPLC) 10,14,15,18,21 , Cromatografia gasosa-espectrometria de massas (GC-MS) 11,12,16,23 , Cromatografia de camada fina (TLC) 22 , Ressonância Magnética Nuclear Unidimensional (RMN-1D) 12 , Ressonância magnética Nuclear Bidimensional (RMN-2D) 13 e Espectrometria de massas de alta resolução com ionização por eletrospray (ESI-HRMS) 12 (tabela 1).…”

Section: Lycorine (+)-9-o-demethylhomolycorine 6-hydroxybuphanisine (...unclassified

Atividade de alcaloides inibidores da acetilcolinesterase no tratamento da doença de Alzheimer: uma revisão sistemática

Mambro

Souza²,

Silva³

2022

J Health Biol Sci.

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Objetivo: descrever a atividade de inibição da enzima acetilcolinesterase (AChE), por meio de ativos extraídos de alcaloides naturais. Metodologia: este estudo se configura como uma revisão sistemática da literatura, no período de janeiro de 2015 a setembro de 2021, nas bases de dados PUBMED, LILACS e SCIENCE DIRECT, com os descritores Acetylcholinesterase; Alzheimer; Alkaloids. As informações obtidas foram tabuladas para avaliação dos alcaloides inibidores da acetilcolinesterase. Resultados: de 563 artigos encontrados, 17 foram utilizados. Dois deles relataram a atividade de alcaloides inibidores da AChE por meio de ensaios clínicos, enquanto os demais a realizaram por testes in vitro. De 160 substâncias estudadas, 48 apresentaram atividade anticolinesterásica, as quais foram avaliadas de acordo com a sua concentração inibitória média (IC50). Discussão: a eficiência dos alcaloides como inibidores da AChE, provavelmente está relacionada com sua carga positiva no pH do organismo e sua boa biodisponibilidade, tendo como consequência uma atividade duradoura in vivo, em comparação com os medicamentos sintéticos. Conclusão: no presente estudo, foi possível observar uma grande diversidade de substâncias alcalóidicas antiAChE. Contudo, torna-se necessária a realização de mais ensaios in vivo e in vitro para a constatação efetiva da atividade dessas moléculas.

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Exploring indole-based-thiadiazole derivatives as potent acetylcholinesterase and butyrylcholinesterase enzyme inhibitors

Cited by 37 publications

References 45 publications

Synthesis, X-ray Crystal Structure, Anticancer, Hirshfeld Surface Analysis, DFT, TD-DFT, ADMET, and Molecular Docking of 3-Phenyl-1,2,4-triazolo[3,4-h]-13,4-thiaza-11-crown-4

Synthesis, X-ray Crystal Structure, Anticancer, Hirshfeld Surface Analysis, DFT, TD-DFT, ADMET, and Molecular Docking of 3-Phenyl-1,2,4-triazolo[3,4-h]-13,4-thiaza-11-crown-4

Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Atividade de alcaloides inibidores da acetilcolinesterase no tratamento da doença de Alzheimer: uma revisão sistemática

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Exploring indole-based-thiadiazole derivatives as potent acetylcholinesterase and butyrylcholinesterase enzyme inhibitors

Cited by 37 publications

References 45 publications

Synthesis, X-ray Crystal Structure, Anticancer, Hirshfeld Surface Analysis, DFT, TD-DFT, ADMET, and Molecular Docking of 3-Phenyl-1,2,4-triazolo[3,4-h]-13,4-thiaza-11-crown-4

Synthesis, X-ray Crystal Structure, Anticancer, Hirshfeld Surface Analysis, DFT, TD-DFT, ADMET, and Molecular Docking of 3-Phenyl-1,2,4-triazolo[3,4-h]-13,4-thiaza-11-crown-4

Quinoline‐fused both non‐peripheral and peripheral ZnIIand MgIIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies

Atividade de alcaloides inibidores da acetilcolinesterase no tratamento da doença de Alzheimer: uma revisão sistemática

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Quinoline‐fused both non‐peripheral and peripheral Zn^IIand Mg^IIphthalocyanines: Anti‐cholinesterase, anti‐α‐glucosidase, DNA nuclease, antioxidant activities, and in silico studies