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Molecules 2013, 18(4), 3948-3961; doi:10.3390/molecules18043948

Synthesis and Biological Evaluation of Unsymmetrical Curcumin Analogues as Tyrosinase Inhibitors

1
Institute of Natural Medicine & Green Chemistry, School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
2
Department of Chemistry, Zhejiang Normal University, Jinhua 321004, China
3
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China
*
Authors to whom correspondence should be addressed.
Received: 31 January 2013 / Revised: 14 March 2013 / Accepted: 22 March 2013 / Published: 3 April 2013
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Synthesis and biological evaluation of unsymmetrical curcumin analogues (UCAs) have been achieved. Tyrosinase inhibitory activities were found for most of the prepared synthetic UCAs. Among them, compounds containing 4-hydroxyl-substituted phenolic rings with C-2/C-4- or C-3/C-4-dihydroxyl-substituted diphenolic rings were more active (IC50 = 1.74~16.74 μM) than 4-butylresorcinol and kojic acid, which suggested that the 4-hydroxyl groups in UCAs play a crucial role in tyrosinase inhibitory activities. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed compounds 3c and 3i containing catecholic rings were mixed-competitive inhibitors, whereas compounds 3d and 3j containing resorcinolic rings were competitive inhibitors. The preliminary evaluation results of acute toxicity showed the representative 3d and 3j were non-toxic in mice dosed at 1,200 mg/kg. This research suggests that, with the advantage of being readily prepared small molecules, polyphenolic UCAs have the potential to develop into pharmacological inhibitors of tyrosinase. View Full-Text
Keywords: unsymmetrical curcumin analogues; synthesis; tyrosinase inhibitors; biological evaluation; inhibition kinetics unsymmetrical curcumin analogues; synthesis; tyrosinase inhibitors; biological evaluation; inhibition kinetics
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Jiang, Y.; Du, Z.; Xue, G.; Chen, Q.; Lu, Y.; Zheng, X.; Conney, A.H.; Zhang, K. Synthesis and Biological Evaluation of Unsymmetrical Curcumin Analogues as Tyrosinase Inhibitors. Molecules 2013, 18, 3948-3961.

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