Synthesis and in vitro biological activity of retinyl retinoate, a novel hybrid retinoid derivative.
A new hybrid, retinyl retinoate 1, was synthesized with a condensing reaction between retinol and retinoic acid to improve the photo-stability, and the in vitro biological activity of the hybrid was analyzed. This retinol derivative had enhanced thermal stability and decreased photosensitivity, and exhibited decreased cell toxicity compared to that of retinol. In addition, RAR activity analysis showed that retinyl retinoate 1 had higher inhibitory activity against c-Jun than retinol and showed superior effects on collagen synthesis compared to retinol. Thus, retinyl retinoate 1 may have the potential to be conveniently used as an additive in cosmetics for prevention and improvement of skin aging and medicines for the treatment of skin troubles due to its excellent stability under severe and accelerated conditions.
Department of Biotechnology, Yonsei University, 134 Shinchon-dong, Seoul 120-749, Republic of Korea.
Hyojung
H
Kim
Bora
B
Kim
Hyuk
H
Kim
Soojong
S
Um
Joodong
J
Lee
Heechang
H
Ryoo
Hyungil
H
Jung
D002478:Cells, Cultured; D003094:Collagen / Q000096:biosynthesis / Q000187:drug effects; D006801:Humans; D008027:Light; D012333:RNA, Messenger / Q000378:metabolism; D018168:Receptors, Retinoic Acid / Q000819:agonists / Q000235:genetics / Q000378:metabolism; D012176:Retinoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000084562:Retinyl Esters; D015595:Skin Aging / Q000187:drug effects*; D018808:Transcription Factor AP-1 / Q000037:antagonists & inhibitors; D014212:Tretinoin / Q000737:chemistry* / Q000494:pharmacology; D014801:Vitamin A / Q000737:chemistry* / Q000494:pharmacology
D012333:RNA, Messenger; D018168:Receptors, Retinoic Acid; D012176:Retinoids; D000084562:Retinyl Esters; D018808:Transcription Factor AP-1; C082928:retinoic acid binding protein II, cellular; D014801:Vitamin A; D014212:Tretinoin; C529924:retinyl retinoate; D003094:Collagen