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Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives.

ABSTRACT: Schiff-base-bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT-IR, ¹H NMR, ¹³C NMR, and UV-Vis spectroscopic methods and elemental analysis were used to elucidate the identification of the synthesized molecules. The in vitro antioxidant activity of the synthesized compounds was analysed with the 1,1-diphenyl-2-picryl hydrazyl free-radical-trapping process. The synthesized compounds exhibited lower antioxidant activity than the standard ascorbic acid. IC₅₀ values of the synthesized molecules measured from 3.81 ± 0.01 to 29.05 ± 0.11 ?M. Among the synthesized compounds, compound 3 had the best antioxidant activity. Moreover, this study explained the structure-activity relationship of the synthesized molecules with different substituents in radical trapping reactions.

SUBMITTER: Yakan H

PROVIDER: S-EPMC7751920 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives.

Yakan Hasan H

Turkish journal of chemistry 20200818 4

Schiff-base-bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and UV-Vis spectroscopic methods and elemental analysis were used to elucidate the identification of the synthesized molecules. The in vitro antioxidant activity of the synthesized compounds was analysed with the 1,1-diphenyl-2-picryl hydrazyl free-radical-trapping process. The synthesized compounds exhibited lower antioxid ...[more]

PMID: 33488214

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Project description:Isoflavonoids such as genistein (GE) are well known antioxidants. The predictive biological activity of structurally new compounds such as thiogenistein (TGE)-a new analogue of GE-becomes an interesting way to design new drug candidates with promising properties. Two oxidation strategies were used to characterize TGE oxidation products: the first in solution and the second on the 2D surface of the Au electrode as a self-assembling TGE monolayer. The structure elucidation of products generated by different oxidation strategies was performed. The electrospray ionization mass spectrometry (ESI-MS) was used for identifying the product of electrochemical and hydrogen peroxide oxidation in the solution. Fourier transform infrared spectroscopy (FT-IR) with the ATR mode was used to identify a product after hydrogen peroxide treatment of TGE on the 2D surface. The density functional theory was used to support the experimental results for the estimation of antioxidant activity of TGE as well as for the molecular modeling of oxidation products. The biological studies were performed simultaneously to assess the suitability of TGE for antioxidant and antitumor properties. It was found that TGE was characterized by a high cytotoxic activity toward human breast cancer cells. The research was also carried out on mice macrophages, disclosing that TGE neutralized the production of the LPS-induced reactive oxygen species (ROS) and exhibits ABTS (2,2'-azino-bis-3-(ethylbenzothiazoline-6-sulphonic acid) radical scavenging ability. In the presented study, we identified the main oxidation products of TGE generated under different environmental conditions. The electroactive centers of TGE were identified and its oxidation mechanisms were proposed. TGE redox properties can be related to its various pharmacological activities. Our new thiolated analogue of genistein neutralizes the LPS-induced ROS production better than GE. Additionally, TGE shows a high cytotoxic activity against human breast cancer cells. The viability of MCF-7 (estrogen-positive cells) drops two times after a 72-h incubation with 12.5 μM TGE (viability 53.86%) compared to genistein (viability 94.46%).

Dataset Information

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives.

Publications

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives.

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