Journal
MOLECULES
Volume 18, Issue 4, Pages 3948-3961Publisher
MDPI
DOI: 10.3390/molecules18043948
Keywords
unsymmetrical curcumin analogues; synthesis; tyrosinase inhibitors; biological evaluation; inhibition kinetics
Funding
- National Natural Science Foundation of China [21272043, 81272452]
- Science and Technology Planning Project of Guangdong Province [2011B090400573, 2012B091000170]
- Guangdong Natural Science Foundation [S2011010004967]
- State Key Laboratory of Natural and Biomimetic Drugs [K20120204]
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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 similar to 16.74 mu M) 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.
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