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1.
Mol Divers ; 2023 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-38123787

RESUMO

Thiosemicarbazide and also 1,3,4-thiadiazole derivatives have been garnering substantial attention from researchers worldwide due to their expansive range of biological activities, encompassing antimicrobial, anti-inflammatory, and anticancer properties. Herein, we embarked on a comprehensive investigation in this study, introducing a novel series of thiosemicarbazides (3a-3i) and their corresponding 1,3,4-thiadiazole (4a-4i) derivatives. The compounds were meticulously designed, synthesized, and subjected to meticulous characterization using various spectroscopic methods such as FT-IR, 1H-NMR, 13C-NMR, and elemental analysis. Afterward, their potential anti-proliferative effectiveness was assessed using MTT assay against two cancer cell lines (U87 and HeLa) and normal fibroblast cells (L929). Among the compounds, 4d showed the highest cytotoxic activity against U87 and 4i against HeLa. Compound 3b exhibited selective cytotoxic activity against both cancer cells. Among the molecules with selective activity against the U87 cell line; 3a, 3b, 4d and 4e were further evaluated by caspase-3 activity levels, Bax and Bcl-2 protein expression, and total oxidant status assay. Besides, carbonic anhydrase IX activity studies were also performed in order to understand the underlying mechanism of action. The results indicated that compound 4e showed higher efficacy than standard acetazolamide (IC50 = 0.58 ± 0.02 µM) with an IC50 value of 0.03 ± 0.01 µM. Furthermore, molecular docking studies were carried out using carbonic anhydrase IX crystals to determine the compound's interactions with the enzyme's active sites. This comprehensive investigation sheds light on the intricate interplay between molecular structure and biological activity, providing valuable insights into the therapeutic potential of these compounds.

2.
Ann Med ; 54(1): 495-506, 2022 01 27.
Artigo em Inglês | MEDLINE | ID: mdl-35112936

RESUMO

Introduction: The genus Euphorbia is known to contain diterpenoids, and several isolated compounds which exhibited biological activities including significant multidrug resistance reversal effects. This work is focused on the isolation, in vitro and in silico studies of two natural bio-active flavonoids (1 & 2) isolated from Euphorbia pulcherrima bark for the very first time.Methods: The phytochemical investigation resulted in the identification of two flavonoids: 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-chromen-4-one (1) and 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-chromen-4-one (2), which were isolated for the first time from Euphorbia pulcherrima.Results: The chemical structures of the two isolated compounds were confirmed by 1H NMR, 13C NMR, and ESI-HRMS spectral data. The Bioactivity activity of these compounds was evaluated; results revealed that compounds 1 & 2 exhibit promising urease inhibitory potential with IC50 values of 15.3 ± 2.13 µM and 19.0 ± 2.43 µM, respectively, whereas the positive control thiourea had an IC50 of 21.0 ± 0.23 µM. Similarly, these compounds were also evaluated against the tyrosinase enzyme; results showed that compound 1 displays significant inhibitory activity with an IC50 value of 48.7 ± 2.19 µM, whereas compound 2 exhibited a moderate effect with an IC50 value of 74.8 ± 1.79 µM, when compared with the standard (alpha-kojic acid, IC50 = 47.6 ± 0.67 µM). Additionally, compounds 1 and 2 also exhibited anti-glycation and phosphodiesterase inhibitory activities.Conclusion: Studies dealing with the drug like properties such as in silico screening (docking study) was also carried out to discover the structural features of both compounds 1 and 2. Results indicated that the docking scores of compounds 1 and 2 are in agreement with their IC50 values. Key messagesIsolation and characterization of two bioactive flavonoids (1 and 2) from Euphorbia pulcherrima.In silico and in vitro enzyme inhibition studies were conducted to identify the therapeutic potential of flavonoids 1 and 2.Drug-like properties were calculated to discover important pharmacophoric features.


Assuntos
Euphorbia , Euphorbia/química , Flavonoides/farmacologia , Humanos , Extratos Vegetais/farmacologia
3.
Chem Biol Drug Des ; 98(2): 270-282, 2021 08.
Artigo em Inglês | MEDLINE | ID: mdl-34021971

RESUMO

The purpose of this study was to synthesize imidazo[2,1-b]thiazole derivatives, characterize them with spectroscopical techniques and investigate for cytotoxic and apoptotic effects on glioma C6 cancer cell line. The in vitro anticancer activities were also investigated against focal adhesion kinase. Most of the compounds, particularly the derivatives carrying 3-oxo-1-tiya-4-azaspiro[4.5]decane moiety, exhibited higher or comparable activities in comparison with the reference drug, cisplatin. Compounds with methyl, propyl, phenyl moieties at the eighth and second position of the spirothiazolidinone ring showed high FAK inhibitory activities. In addition, molecular docking studies shed light on the binding modes of the synthesized compounds. The critical interactions with amino acid residues located in the active site were revealed. The results obtained from both biological assay data and computational results might provide insight into developing new inhibitors against focal adhesion kinase.


Assuntos
Antineoplásicos/síntese química , Proteína-Tirosina Quinases de Adesão Focal/antagonistas & inibidores , Imidazóis/química , Inibidores de Proteínas Quinases/química , Tiazóis/química , Antineoplásicos/metabolismo , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Sítios de Ligação , Domínio Catalítico , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Proteína-Tirosina Quinases de Adesão Focal/metabolismo , Humanos , Imidazóis/metabolismo , Imidazóis/farmacologia , Simulação de Acoplamento Molecular , Inibidores de Proteínas Quinases/metabolismo , Inibidores de Proteínas Quinases/farmacologia , Eletricidade Estática , Relação Estrutura-Atividade , Tiazóis/metabolismo , Tiazóis/farmacologia
4.
J Oleo Sci ; 69(10): 1281-1285, 2020 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-32908100

RESUMO

In this study two different strategy were followed to obtain a D-fructose-oleic acid ester. One of the strategies has been well established enzymatic synthesis of an ester bond. The other strategy excluded the biocatalyst and only used a mixture of two organic solvents as the reaction media, 2-methyl-2-butanol / dimethyl sulfoxide or tert-butanol / dimethyl sulfoxide for the production of D-fructose-oleic acid ester. Ester products obtained were characterised by using FT-IR, NMR, by MS. Product yield was also assessed by HPLC. Results of structural analyses and yield measurement indicated that two approaches produced almost identical ester products.


Assuntos
Dimetil Sulfóxido/química , Ésteres/síntese química , Frutose/síntese química , Ácido Oleico/síntese química , Pentanóis/química , terc-Butil Álcool/química , Animais , Biocatálise , Células Cultivadas , Cromatografia Líquida de Alta Pressão , Esterificação , Ésteres/química , Ésteres/toxicidade , Frutose/química , Frutose/toxicidade , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Ácido Oleico/química , Ácido Oleico/toxicidade , Espectroscopia de Infravermelho com Transformada de Fourier
5.
J Oleo Sci ; 69(8): 907-912, 2020 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-32641616

RESUMO

D-ribose-oleic acid esters were produced with or without a biocatalyst, using in the same organic media, dimethyl sulfoxide (DMSO): tert-butanol (TBU) or 2-methyl-2-butanol (2M2B). The yield of the ester product was above 90% in both of the reactions. The biocatalyst used was lipase B of Candida antarctica. Molecular characterization was performed by using all the analytical methods available: IR, 1H-NMR and 13C-NMR, HSQC, and ESI-MS.


Assuntos
Biocatálise , Ésteres/síntese química , Proteínas Fúngicas/química , Lipase/química , Ácidos Oleicos/síntese química , Ribose/síntese química , Dimetil Sulfóxido/química , Esterificação , Ésteres/química , Ácidos Oleicos/química , Pentanóis/química , Ribose/química , terc-Butil Álcool/química
6.
J Oleo Sci ; 69(7): 737-742, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32612023

RESUMO

Esterification of D-glucose with oleic- and palmitic acids were carried out in the absence and presence of a biocatalyst, Candida antarctica lipase. The reaction medium was a mixture of dimethyl sulphoxide and tert-butanol (1:4, v/v). The reaction products were analysed by FTIR, 1H-NMR and 13C-NMR, HSQC, and by ESI-MS. Results indicated that the ester products formed were 6-O-glucose oleate and 6-O-glucose palmitate both in the absence and in the presence of the biocatalyst, with yields above 90%.


Assuntos
Biocatálise , Ésteres/síntese química , Glucose/química , Ácido Oleico/síntese química , Ácidos Oleicos/química , Palmitatos/síntese química , Ácidos Palmíticos/química , terc-Butil Álcool/química , Dimetil Sulfóxido/química , Esterificação , Proteínas Fúngicas/química , Lipase/química
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