Synthesis and biological evaluation of sulfur-containing cinnamate and salicylate derivatives.
UV irradiation induced formation of reactive oxygen radical species and matrix metalloproteinases (MMPs) are thought to be involved in photo-damage to the skin. MMP-1 is the major collagenolytic enzyme responsible for collagen destruction in skin tissue. To develop new anti-photoaging agents, a series of 2,2'-dithiocinnamate derivatives and 2,2'-dithio or 2-thiobenzoate derivatives were designed and synthesized. The biological activities of the synthesized compounds were assayed for ABTS [2,2'-azinobis-(3-ethyl-benzo-thiazoline-6-sulfonic acid)] radical scavenging activity, MMP-1 inhibitory activity, and cytotoxicity to human dermal fibroblast cells. Compounds with potential of resistance to UV irradiation were identified. These compounds are expected to be useful for preventing photo-damage to the skin.
Chiang
Chih-Chia
CC
Department of Applied Chemistry and Materials Science, Institute of Technology, National Defense University, Ta-shi, Tao-yuan 335, Taiwan, ROC.
Chang
Tsu-Chung
TC
Tsai
Hou-Jen
HJ
Hsu
Ling-Yih
LY
D052160:Benzothiazoles / Q000737:chemistry; D002364:Caseins / Q000737:chemistry; D002470:Cell Survival / Q000187:drug effects; D002934:Cinnamates / Q000737:chemistry* / Q000494:pharmacology*; D003094:Collagen / Q000737:chemistry / Q000528:radiation effects; D005347:Fibroblasts / Q000187:drug effects; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D007202:Indicators and Reagents; D061965:Matrix Metalloproteinase Inhibitors; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D011837:Radiation-Protective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D012459:Salicylates / Q000138:chemical synthesis* / Q000494:pharmacology*; D012867:Skin / Q000737:chemistry / Q000187:drug effects / Q000528:radiation effects; D015595:Skin Aging / Q000187:drug effects*; D013451:Sulfonic Acids / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*; D014466:Ultraviolet Rays
D052160:Benzothiazoles; D002364:Caseins; D002934:Cinnamates; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D061965:Matrix Metalloproteinase Inhibitors; D011480:Protease Inhibitors; D011837:Radiation-Protective Agents; D012459:Salicylates; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D013455:Sulfur; D003094:Collagen