Synthesis of caffeic acid ester morpholines and their activation effects on tyrosinase |
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| Affiliation: | 1. Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystems, School of Life Sciences, Xiamen University, Xiamen 361102, China;2. Biobank, The First Affiliated Hospital of Xiamen University, Xiamen 361003, China;1. Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea;2. Department of Chemistry, Kongju National University, Gongju, Chungnam 32588, Republic of Korea;3. Institute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road, Lahore 54590, Pakistan;4. School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia (UKM), 43600 Bangi, Selangor, Malaysia;1. College of Pharmacy, Pusan National University, Busan 46241, South Korea;2. College of Pharmacy and Inje Institute of Pharmaceutical Sciences and Research, Inje University, Gimhae, Gyeongnam 50834, South Korea;1. Department of Biotechnology, Shivaji University, Kolhapur 416004, India;2. GE Healthcare Life Sciences, John F Welch Technology Centre, EPIP, Phase 2, Whitefield Road, Bangalore 560048, India;3. Department of Biochemistry, Shivaji University, Kolhapur 416004, India |
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| Abstract: | 
Two new caffeic acid ester derivatives, caffeic acid-4-(2-hydroxyethyl) morpholine ester (Z-1) and caffeic acid-4-(3-hydroxypropyl) morpholine ester (Z-2), were synthesized, and their structures were characterized by LC–MS, IR, and 1H NMR. The activation effects of the two compounds on tyrosinase activity were evaluated. Compounds Z-1 and Z-2 showed potent activation effects, and their EC50 values were determined to be 0.075 and 0.0375 mmol/L, respectively. Moreover, the activation mechanism was determined to be of noncompetitive activation type. Interactions of the two compounds with tyrosinase were further analyzed by fluorescence quenching and molecular simulation assays. The results indicated that the effects on the tyrosinase activity were relative to the length of the carbon chain of the compounds. In addition, human M14 melanoma cells showed increased intracellular tyrosinase activity after treatment with the two compounds for 24 h. The expressions of TYR, TRP-1, TRP-2, and α-MSH proteins were upregulated in a dose-dependent manner during a 24-h treatment. These results suggested that compounds Z-1 and Z-2 might represent a novel approach for an effective therapy for diseases associate with tyrosinase dysfunction, such as vitiligo and hair graying. |
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| Keywords: | Caffeic acid-4-(2-hydroxyethyl) morpholine ester Caffeic acid-4-(3-hydroxypropyl) morpholine ester Synthetize Activation Tyrosinase |
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