In vitro and in silico studies of antioxidant activity of 2-thiazolylhydrazone derivatives

Resende, Marina Ferrara de; Kronenberger, Thales; Lino, Cleudiomar Inácio; Sampaio, Maria Clara Pinheiro Duarte; Pitta, Maíra Galdino da Rocha; Rêgo, Moacyr Jesus Barreto de Melo; Labanca, Renata Adriana; Oliveira, Renata Barbosa de

doi:10.1016/j.jmgm.2018.10.007

Cited by 15 publications

(6 citation statements)

References 35 publications

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“…Tocopherol, p-coumaric acid, ferulic acid, and caffeic acid are the best-known phenolic antioxidant agents. On the other hand, also hydrazone moieties are endowed with potent antioxidant potency [20][21][22][23]. Based on these findings and as a continuation of our works on antioxidant agents [24][25][26], here we report and discuss the antioxidant properties of benzimidazolehydrazones containing a phenolic group and their structure-activity relationships (SAR).…”

Section: Introductionmentioning

confidence: 75%

In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives

et al. 2020

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In the search of multifunctional compounds we designed benzimidazole derivatives endowed with phenolic hydroxy groups and a hydrazone moiety as potential radical-scavenger and the antioxidant agents. The target molecules have been prepared by a simple synthetic procedure and tested for their antioxidant activity by DPPH, FRAP, and ORAC test, for photoprotective activity against UV rays and for antiproliferative activity against Colo-38 melanoma cells. Furthermore, two different dermocosmetic formulations were prepared with the compounds endowed with the best antioxidant and photoprotective profile and their release from formulation evaluated using Franz Cells system. High antioxidant activity is related to the presence of at least two hydroxy groups on arylidene moiety of benzimidazoles. Structure activity analysis revealed that the position of hydroxy groups is crucial for antioxidant activity as well as the presence of a 2-hydroxy-4-(diethylamino)arylidene group. The same correlation pattern was found to be related to photoprotective activity resulting in an UVA Protection Factor better than the commercial solar filter PBSA and antiproliferative activity against melanoma cells without producing cytotoxicity on normal keratinocytes. The release analysis indicated that high antioxidant activities are achieved with limited release at concentration compatible with the use as UV sunscreen filter.

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Section: Introductionmentioning

confidence: 75%

In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives

et al. 2020

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“…This strategy is useful to suggest relationship between molecular properties and biological activities. Therefore, we could infer either a possible mechanism of action of these TPs or an existence of a common molecular target [41–43] …”

Section: Resultsmentioning

confidence: 99%

“…Then, the physicochemical and molecular descriptors of the TPs 2 , 3 , 5 , 7 , 8 , 9 and 10 were calculated with PaDEL descriptor software [52] . At this step, 2187 descriptors were calculated, and then, we carried out the following variable selection strategies based on previously reported works: [41,53–55] (i) Fisher's weight was calculated in order to identify the descriptors with most importance to distinguish the clusters identified on HCA (FW>1); (ii) we calculated Pearson correlation coefficients to identify the highly correlated variables (R>0.80) to both experimental values; (iii) three variables were selected with high correlations with biological activities and least correlations among them. The three descriptors were autoscaled before the PCA studies.…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines

Pereira

Evangelista

Júnior

et al. 2020

Chemistry & Biodiversity

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Cheiloclinium cognatum (Miers) A.C.Sm. is an endemic species of Brazilian Cerrado that belongs to Celastraceae family. The phytochemical study of C. cognatum branches led to the identification of ten triterpenoids (TPs), 3β-acyloxyurs-12-ene (1), friedelin (2), β-friedelinol (3), glut-5-en-3β-ol (4), α-amyrin (5), βamyrin (6), β-sitosterol (7), canophyllol (8), 29-hydroxyfriedelan-3-one (9) and friedelane-3β,29-diol (10). TPs 4, 5 and 6 are described for the first Cheiloclinium genus and TPs 8 and 9 were isolated in expressive amounts. Their cytotoxic activities were evaluated against THP-1 and K562 leukemia cell lines. TPs 3 and 5 were the most active, exhibiting lower or similar IC 50 against both cell lines when compared to the controls. Their mechanisms of action were investigated suggesting an intrinsic mitochondrial pathway of apoptosis evidenced by up-regulation of BAK mRNA expression. Chemometric studies indicated that their activities may be related to their molecular size and shape as well as electronic interactions of C-3 hydroxy group with molecular targets.

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“…Hydrazone and its derivatives have played an integral and important role owing to the azomethine group, characterized by the triatomic structure C=N–N, enabling its use in various fields [ 1 , 2 , 3 ]. The hydrazine derivatives are known to possess a number of biological activities, including anticancer [ 4 , 5 ], antibacterial and anti-fungal [ 6 , 7 ], anticonvulsant [ 8 ], and antioxidant [ 9 , 10 , 11 , 12 , 13 ]. Not only hydrazones but also polyphenolic compounds are known for their excellent antioxidant activity [ 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

et al. 2022

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The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C‒H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental 1H and 13C NMR studies on the key compound 2 are reported. The results of theoretical and experimental 1H and 13C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS•+) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC50 = 4.30 ± 0.21 µM) and DPPH assay (IC50 = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM.

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In vitro and in silico studies of antioxidant activity of 2-thiazolylhydrazone derivatives

Cited by 15 publications

References 35 publications

In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives

In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives

Cytotoxic Activity of Triterpenoids from Cheiloclinium cognatum Branches against Chronic and Acute Leukemia Cell Lines

Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

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