Synthesis and biological evaluation of furocoumarin derivatives on melanin synthesis in murine B16 cells for the treatment of vitiligo

Chao Niu; Guang Xian Pang; Gen Li; Jun Dou; Li Fei Nie; Helimay Himit; Madina Kabas; Haji Akber Aisa

doi:10.1016/j.bmc.2016.09.056

Synthesis and biological evaluation of furocoumarin derivatives on melanin synthesis in murine B16 cells for the treatment of vitiligo

Bioorg Med Chem. 2016 Nov 15;24(22):5960-5968. doi: 10.1016/j.bmc.2016.09.056. Epub 2016 Sep 23.

Authors

Chao Niu¹, Guang Xian Pang¹, Gen Li¹, Jun Dou¹, Li Fei Nie¹, Helimay Himit¹, Madina Kabas¹, Haji Akber Aisa²

Affiliations

¹ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Chinese Academy of Sciences, Urumqi 830011, China; State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China.
² The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Chinese Academy of Sciences, Urumqi 830011, China; State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China. Electronic address: haji@ms.xjb.ac.cn.

PMID: 27713014
DOI: 10.1016/j.bmc.2016.09.056

Abstract

Furocoumarins, isolated from Psoralen corylifolia L., were found to be the most effective drug in the treatment of vitiligo nowadays. Twenty-five furocoumarin derivatives were thus designed and synthesized in order to improve the melanogenesis in B16 cells for the first time. Among them, twenty-three compounds were more potent than the positive control (8-MOP), the commonly used drug for vitiligo in clinic. Noticeably, compounds 6m (350.5%) and 6p (313.1%) based on the scaffold of 6k (2H-benzofuro[2,3-h]chromen-2-one) were nearly 3-fold stronger than 8-MOP (114.50%). The in vitro melanin synthesis evaluation of these structurally diverse analogues had also led to an outline of structure-activity relationship.

Keywords: Furocoumarin; Melanin; SAR; Synthesis; Vitiligo.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cell Line, Tumor
Dose-Response Relationship, Drug
Ficusin / chemistry
Furocoumarins / chemistry
Furocoumarins / isolation & purification
Furocoumarins / pharmacology*
Melanins / antagonists & inhibitors*
Melanins / biosynthesis
Mice
Molecular Structure
Structure-Activity Relationship
Vitiligo / drug therapy*
Vitiligo / metabolism

Substances

Furocoumarins
Melanins
Ficusin