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Synthesis, antioxidant and anti-tyrosinase activity of 1,2,4-triazole hydrazones as antibrowning agents. 2021

Zhiyun Peng, and Guangcheng Wang, and Qiao-Hui Zeng, and Yufeng Li, and Yi Wu, and Haiquan Liu, and Jing Jing Wang, and Yong Zhao
College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China.

A series of 1,2,4-triazole hydrazones (1-16) were synthesized, and their inhibitory activities and mechanisms on tyrosinase were investigated by ultraviolet spectrophotometry, fluorescence quenching, molecular docking study, etc. Most of compounds possessed potent tyrosinase inhibitory activity. Thereinto, compound 9 presented the superior activity with IC50 of 0.9 μM, which was markedly lower than the standard kojic acid (IC50 = 64.1 μM). Compound 9 not only interacted with copper ions in the active center of the enzyme but also bound to the enzyme-substrate complex, indicating that it was a competitive-noncompetitive mixed inhibitor. Additionally, it also displayed potent DPPH scavenging activity. Antibrowning test showed that compound 9 effectively reduced the enzymatic browning of fresh-cut potatoes. Furthermore, compound 9 exhibited low cytotoxic activity against human normal cell line with IC50 of 49.9 µM. Overall, the present study suggests that these compounds may serve as lead molecules for developing novel antibrowning agents in food industry.

UI MeSH Term Description Entries
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D002470 Cell Survival The span of viability of a cell characterized by the capacity to perform certain functions such as metabolism, growth, reproduction, some form of responsiveness, and adaptability. Cell Viability,Cell Viabilities,Survival, Cell,Viabilities, Cell,Viability, Cell
D002614 Chelating Agents Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. Chelating Agent,Chelator,Complexons,Metal Antagonists,Chelators,Metal Chelating Agents,Agent, Chelating,Agents, Chelating,Agents, Metal Chelating,Antagonists, Metal,Chelating Agents, Metal
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D006835 Hydrazones Compounds of the general formula R:N.NR2, as resulting from the action of hydrazines with aldehydes or ketones. (Grant & Hackh's Chemical Dictionary, 5th ed) Hydrazone
D000363 Agaricales An extensive order of basidiomycetous fungi whose fruiting bodies are commonly called mushrooms. Agaricaceae,Mushrooms,Agaricale,Mushroom
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole

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