Synthesis, characterization and antioxidant activity of organoselenium and organotellurium compound derivatives of chrysin

Fonseca, Sergio F.; Lima, David B.; Alves, Diego; Jacob, Raquel G.; Perin, Gelson; Savegnago, Lucielli

doi:10.1039/c4nj02329c

Cited by 51 publications

(13 citation statements)

References 45 publications

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“…Current literature reports, that the incorporation of methyl substituents at the C-5 and the C-7 positions of chrysin enhanced its anticancer activity against human gastric (SGC-7901) and human colon (HT-29) cell lines [ 22 ]. Furthermore, selenium and tellurium-derivatives of chrysin exhibited high antioxidant [ 23 ] and anticancer activity against lung adenocarcinoma (A-549) cells [ 24 ], comparing to inactive, unmodified 5,7-dihydroxyflavone.…”

Section: Introductionmentioning

confidence: 99%

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

et al. 2019

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In our investigation, we concentrated on naringenin (NG)—a widely studied flavanone that occurs in citrus fruits. As a result of a reaction with a range of alkyl iodides, 7 novel O-alkyl derivatives of naringenin (7a–11a, 13a, 17a) were obtained. Another chemical modification led to 9 oximes of O-alkyl naringenin derivatives (7b–13b, 16b–17b) that were never described before. The obtained compounds were evaluated for their potential antibacterial activity against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The results were reported as the standard minimal inhibitory concentration (MIC) values and compared with naringenin and its known O-alkyl derivatives. Compounds 4a, 10a, 12a, 14a, 4b, 10b, 11b, and 14b were described with MIC of 25 µg/mL or lower. The strongest bacteriostatic activity was observed for 7-O-butylnaringenin (12a) against S. aureus (MIC = 6.25 µg/mL). Moreover, the antitumor effect of flavonoids was examined on human colon cancer cell line HT-29. Twenty-six compounds were characterized as possessing an antiproliferative activity stronger than that of naringenin. The replacement of the carbonyl group with an oxime moiety significantly increased the anticancer properties. The IC50 values below 5 µg/mL were demonstrated for four oxime derivatives (8b, 11b, 13b and 16b).

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Section: Introductionmentioning

confidence: 99%

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

et al. 2019

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“…most important mammalian selenoenzymes, is involved in the detoxification of aerobic living cells from reactive oxygen species (ROS), catalyzing the reduction of hydroperoxides at the expenses of two molecules of glutathione (GSH), which are, in turn, oxidized to GSSG. 1,2 The lack of antioxidant defenses results in an increased ROS concentration, which has been related to the occurrence of a number of diseases, such as cancer, atherosclerosis, diabetes, neurodegenerative diseases, and immune disorder. 3 The two homologous series of selenides and tellurides reported in Figure 1 were studied.…”

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confidence: 99%

Synthesis and catalytic antioxidant activity of functionalized chalcogen-containing GPx mimics

Tanini

Lupori

Nostro

et al. 2019

Phosphorus, Sulfur, and Silicon and the Related Elements

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The synthesis and the evaluation of the thiol peroxidase like antioxidant properties of -functionalized symmetric and non-symmetric organochalcogenides have been explored. The tested catalysts were synthesized exploiting the reactivity of strained heterocycles with silyl chalcogenides. Oxygen-, nitrogen-, and sulfur-containing selenides and tellurides were efficiently achieved from the corresponding epoxides, aziridines, and thiiranes through mild and regioselective ring opening reactions. The thiol peroxidase catalytic activity was investigated by using the dithiothreitol (DTT) oxidation model. The results showed that the nature of the -substituent plays a crucial role in modulating the catalytic properties of the studied GPx mimics. This effect can be reasonably ascribed to the presence of chalcogen bonding interactions involving the selenium or the tellurium atom and the heteroatom (O, S) placed on the moiety at C-2. GRAPHICAL ABSTRACT

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“…Evidence has been provided indicating that organoselenium compounds could be considered as potential antioxidant and neuroprotector compounds, besides their ability to prevent disease, which turns them a target for pharmacological studies [3,4,5,6,7,8]. 4 Selenium is an essential trace element nutritionally important to mammals, with physiological roles as a structural component of antioxidant enzymes involved in the peroxide decomposition [9,10].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Se-phenyl-thiazolidine-4-carboselenoate protective activity against oxidative and behavioral stress in the maniac model induced by ouabain in male rats

Sousa

Seus

Alves

et al. 2017

Neuroscience Letters

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Synthesis, characterization and antioxidant activity of organoselenium and organotellurium compound derivatives of chrysin

Abstract: New selenium and tellurium containing chrysin derivatives were synthesized and their antioxidant activities were evaluated. Butyltelluro-chrysin presented better antioxidant activities.

Cited by 51 publications

References 45 publications

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

Synthesis and catalytic antioxidant activity of functionalized chalcogen-containing GPx mimics

Evaluation of Se-phenyl-thiazolidine-4-carboselenoate protective activity against oxidative and behavioral stress in the maniac model induced by ouabain in male rats

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