Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis

被引：20
|
作者：
Jo, Hyeju [1 ,2 ]
Choi, Minho [1 ,2 ]
Sim, Jaeuk [1 ,2 ]
Viji, Mayavan [1 ,2 ]
Li, Siyuan [1 ,2 ]
Lee, Young Hee [1 ,2 ]
Kim, Youngsoo [1 ,2 ]
Seo, Seung-Yong [3 ,4 ]
Zhou, Yuanyuan [5 ]
Lee, Kiho [5 ]
Kim, Wun-Jae [6 ]
Hong, Jin Tae [1 ,2 ]
Lee, Heesoon [1 ,2 ]
Jung, Jae-Kyung [1 ,2 ]
机构：
[1] Chungbuk Natl Univ, Coll Pharm, Cheongju 28160, South Korea
[2] Chungbuk Natl Univ, Med Res Ctr, Cheongju 28160, South Korea
[3] Gachon Univ, Coll Pharm, Incheon 21936, South Korea
[4] Gachon Univ, Gachon Inst Pharmaceut Sci, Incheon 21936, South Korea
[5] Korea Univ, Coll Pharm, Sejong 30019, South Korea
[6] Chungbuk Natl Univ, Coll Med, Cheongju 28644, South Korea
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 15期
基金：
新加坡国家研究基金会;
关键词：
Caffeic acid; Melanogenesis; alpha-MSH; Caffeamide; Skin whitening; B16; MELANOMA-CELLS; TYROSINASE INHIBITORS; DOWN-REGULATION; SIGNALING PATHWAYS; SKIN PIGMENTATION; AGENTS; MELANOCYTES; DISCOVERY; ESTER;
D O I：
10.1016/j.bmcl.2017.06.011
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of alpha-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed that cyclohexyl ester and secondary amide derivatives of caffeic acid showed significant inhibitory activities. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3374 / 3377
页数：4
相关论文
共 50 条
  • [1] Synthesis, biological evaluation, and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of α-MSH-stimulated melanogenesis
    Jo, Hyeju
    Zhou, Yuanyuan
    Viji, Mayavan
    Choi, Minho
    Lim, Jae Young
    Sim, Jaeuk
    Rhee, Jeongtae
    Kim, Youngsoo
    Seo, Seung-Yong
    Kim, Wun-Jae
    Hong, Jin Tae
    Lee, Heesoon
    Lee, Kiho
    Jung, Jae-Kyung
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (21) : 4854 - 4857
  • [2] Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis
    Arepalli, Sateesh Kumar
    Lee, Chaerim
    Jung, Jae-Kyung
    Kim, Youngsoo
    Lee, Kiho
    Lee, Heesoon
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2019, 29 (18) : 2604 - 2608
  • [3] EARLY STAGES OF MELANOGENESIS IN MSH-STIMULATED CELL-CULTURES
    GIESELER, MJ
    FULLER, BB
    FERRIS, WR
    YALE JOURNAL OF BIOLOGY AND MEDICINE, 1977, 50 (05): : 559 - 559
  • [4] Synthesis and Biological Evaluation of Resveratrol Derivatives as Melanogenesis Inhibitors
    Liu, Qing
    Kim, CheongTaek
    Jo, Yang Hee
    Kim, Seon Beom
    Hwang, Bang Yeon
    Lee, Mi Kyeong
    MOLECULES, 2015, 20 (09) : 16933 - 16945
  • [5] ARP101 inhibits α-MSH-stimulated melanogenesis by regulation of autophagy in melanocytes
    Kim, Eun Sung
    Jo, Yoon Kyung
    Park, So Jung
    Chang, Huikyoung
    Shin, Ji Hyun
    Choi, Eun Sun
    Kim, Jun Bum
    Seok, Su Hyeon
    Kim, Jae-Sung
    Oh, Jeong Su
    Kim, Myoung-Hwan
    Lee, Eunjoo H.
    Cho, Dong-Hyung
    FEBS LETTERS, 2013, 587 (24) : 3955 - 3960
  • [6] Synthesis and Biological Evaluation of Water-Soluble Oleanolic Acid Derivatives for use as Melanogenesis Inhibitors
    An, Hyun-Jin
    Yoon, Young-kyung
    Lee, Jae-Duck
    Jeong, Noh-Hee
    APPLIED CHEMISTRY FOR ENGINEERING, 2020, 31 (06): : 653 - 659
  • [7] Synthesis and biological evaluation of caffeic acid phenethyl ester (CAPE) derivatives as xanthine oxidase inhibitors
    Onate, Sandra
    Istre, Hannah
    Heppler, Ben
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [8] Inhibitory Effect of Chlorogenic Acid Analogues Comprising Pyridine and Pyrimidine on α-MSH-Stimulated Melanogenesis and Stability of Acyl Analogues in Methanol
    Sim, Jaeuk
    Lanka, Srinu
    Jo, Jeong-Woong
    Chaudhary, Chhabi Lal
    Vishwanath, Manjunatha
    Jung, Chan-Hyun
    Lee, Young-Hee
    Kim, Eun-Yeong
    Kim, Young-Soo
    Hyun, Soon-Sil
    Lee, Hee-Soon
    Lee, Kiho
    Seo, Seung-Yong
    Viji, Mayavan
    Jung, Jae-Kyung
    PHARMACEUTICALS, 2021, 14 (11)
  • [9] Quercetin Inhibits α-MSH-stimulated Melanogenesis in B16F10 Melanoma Cells
    Yang, Yeon-Mi
    Son, Young-Ok
    Lee, Seung-Ah
    Jeon, Young-Mi
    Lee, Jeong-Chae
    PHYTOTHERAPY RESEARCH, 2011, 25 (08) : 1166 - 1173
  • [10] Synthesis and biological evaluation of geniposide derivatives as potent and selective PTPlB inhibitors
    Lei, Shuwen
    Zhang, Dongdong
    Qi, Yunyue
    Chowdhury, Sharmin Reza
    Sun, Ran
    Wang, Juntao
    Du, Yi
    Fu, Lei
    Jiang, Faqin
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 205
12345