(E)-1-(Furan-2-yl)-(substituted phenyl)prop-2-en-1-one Derivatives as Tyrosinase Inhibitors and Melanogenesis Inhibition: An In Vitro and In Silico Study

Hee Jin Jung; Sang Gyun Noh; Il Young Ryu; Chaeun Park; Ji Young Lee; Pusoon Chun; Hyung Ryong Moon; Hae Young Chung

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(E)-1-(Furan-2-yl)-(substituted phenyl)prop-2-en-1-one Derivatives as Tyrosinase Inhibitors and Melanogenesis Inhibition: An In Vitro and In Silico Study

机译：（e）-1-（呋喃-2-基） - （取代的苯基）prop-2-en-1-一种衍生物作为酪氨酸酶抑制剂和黑素生成抑制作用：体外和硅研究

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A series of (E)-1-(furan-2-yl)prop-2-en-1-one derivatives (compounds 1–8) were synthesized and evaluated for their mushroom tyrosinase inhibitory activity. Among these series, compound 8 (2,4-dihydroxy group bearing benzylidene) showed potent tyrosinase inhibitory activity, with respective IC50 values of 0.0433 μM and 0.28 μM for the monophenolase and diphenolase as substrates in comparison to kojic acid as standard compound 19.97 μM and 33.47 μM. Moreover, the enzyme kinetics of compound 8 were determined to be of the mixed inhibition type and inhibition constant (Ki) values of 0.012 μM and 0.165 μM using the Lineweaver-Burk plot. Molecular docking results indicated that compound 8 can bind to the catalytic and allosteric sites 1 and 2 of tyrosinase to inhibit enzyme activity. The computational molecular dynamics analysis further revealed that compound 8 interacted with two residues in the tyrosinase active site pocket, such as ASN260 and MET280. In addition, compound 8 attenuated melanin synthesis and cellular tyrosinase activity, simulated by α-melanocyte-stimulating hormone and 1-methyl-3-isobutylxanthine. Compound 8 also decreased tyrosinase expressions in B16F10 cells. Based on in vitro and computational studies, we propose that compound 8 might be a worthy candidate for the development of an antipigmentation agent.

机译：合成了一系列（e）-1-（Furan-2-y11-（Furan-2-y1）支撑-2-烯-1-一种衍生物（化合物1-8），并评估其蘑菇酪氨酸酶抑制活性。在这些系列中，化合物8（2,4-二羟基基团亚苄基）显示出有效的酪氨酸酶抑制活性，其相应的IC 50值为0.0433μm和0.28μm，单蛋白酶和二酚酶作为标准化合物的基底作为标准化合物19.97μm和33.47μm。此外，使用Linewer-Burk图，测定化合物8的酶动力学是混合抑制型和0.012μm和0.165μm的抑制常数（ki）值。分子对接结果表明化合物8可以与酪氨酸酶的催化和变构位点1和2结合以抑制酶活性。计算分子动力学分析进一步揭示了化合物8与酪氨酸酶活性位点袋中的两个残基相互作用，例如Asn260和Met280。此外，化合物8减振了黑色素合成和细胞酪氨酸酶活性，通过α-黑色细胞刺激激素和1-甲基-3-异丁基吡喃啶模拟。化合物8也降低了B16F10细胞中的酪氨酸酶表达。基于体外和计算研究，我们提出了化合物8可能是抗抗原剂的有价值的候选者。

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《Molecules》 |2020年第22期|共17页
作者
Hee Jin Jung; Sang Gyun Noh; Il Young Ryu; Chaeun Park; Ji Young Lee; Pusoon Chun; Hyung Ryong Moon; Hae Young Chung;
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furan-chalconemelanogenesismolecular dynamicstyrosinase inhibitor;

机译：Furan-Chalconemelanogesisismolecocularysismetystyrosinase抑制剂;

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(E)-1-(Furan-2-yl)-(substituted phenyl)prop-2-en-1-one Derivatives as Tyrosinase Inhibitors and Melanogenesis Inhibition: An In Vitro and In Silico Study

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