Dual effects of caffeoyl-amino acidyl-hydroxamic acid as an antioxidant and depigmenting agent

• Published in: Bioorganic & medicinal chemistry letters 2011-09, Vol.21 (18), p.5155-5158
• Main Authors: Kwak, Seon-Yeong, Lee, Song, Choi, Hye-Ryung, Park, Kyung-Chan, Lee, Yoon-Sik
• Format: Article
• Language: English
• Subjects: Agaricales - enzymology; amino acids; Amino Acids - chemistry; Amino Acids - pharmacology; Antioxidant; antioxidant activity; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; bioassays; Biological and medical sciences; Caffeic acid; Caffeic Acids - chemistry; Caffeic Acids - pharmacology; chelating agents; Depigmenting agent; Dose-Response Relationship, Drug; Dual effector; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; free radical scavengers; General and cellular metabolism. Vitamins; Hydroxamic acid; Hydroxamic Acids - chemistry; Hydroxamic Acids - pharmacology; industry; Lipid Peroxidation - drug effects; Medical sciences; melanogenesis; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - metabolism; Pharmacology. Drug treatments; skin diseases; Skin Pigmentation - drug effects; Skin, nail, hair, dermoskeleton; Structure-Activity Relationship
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2011.07.064

Caffeoyl-amino acidyl-hydroxamic acids were prepared as dual effector molecule for antioxidant and depigmenting activity. Anti-aging and depigmentation have both been an important subject of study for skin disease and the cosmetic industry. Caffeic acid (CA) has shown synergistically enhanced antioxidant activity when conjugated with amino acids. Hydroxamic acid (NHOH) is a well-known metal chelator, potentially having both tyrosinase inhibitory activity and free radical scavenging activity. We prepared caffeoyl-amino acidyl-hydroxamic acid (CA-Xaa-NHOH) and found that caffeoyl-prolyl-hydroxamic acid (CA-Pro-NHOH) contained excellent antioxidant activity and tyrosinase inhibitory activity by various bioassay systems. Also, CA-Pro-NHOH showed mild melanogenesis inhibitory activity in Mel-Ab cells.