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Chemistry and Industry of Forest Products ›› 2020, Vol. 40 ›› Issue (1): 106-112.doi: 10.3969/j.issn.0253-2417.2020.01.015

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Synthesis and HDAC Inhibitory Activity of Novel Urushiol Hydroxamic Acid Derivatives

Hao ZHOU1,2,Zhiwen QI1,2,Ran TAO1,2,Hongxia CHEN1,2,Chengzhang WANG1,2,*()   

  1. 1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; Key Lab. of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
    2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
  • Received:2019-05-22 Online:2020-02-28 Published:2020-03-06
  • Contact: Chengzhang WANG E-mail:wangczlhs@sina.com
  • Supported by:
    国家自然科学基金资助项目(31600467)

Abstract:

Urushiol was used as raw material, through etherification of o-diphenol hydroxyl group, introducing isoxamic acid group into the tail of side chain, and functional groups of nitro, hydroxyl group into benzene ring or aliphatic chain. Three novel methylene ether urushiol hydroxamic acid derivatives were synthesized. The structure of the synthesized compounds was characterized by means of 1H NMR, 13 C NMR and MS analysis. The interaction mode between the compounds and HDAC 2 was studied by molecular docking. The results showed that three compounds could bind to the active pocket of HDAC 2 and interact with the residues of His145, Tyr 308, Glu103 and Asp104 to form hydrogen bonds. It could form stable chelation with Zn2+ at the bottom of active pocket. The inhibitory activity of compounds on HDAC 2 was detected by kit AK-501. The results showed that the inhibitory effects of compound 2 and 3 on HDAC 2 were better than that of compound 1, and the IC50 values of compound 2 and 3 were similar to that of SAHA(IC50=0.20 mg/L), the half inhibitory concentrations (IC50) of compounds 1, 2 and 3 on HDAC2 were 0.33, 0.29 and 0.24 mg/L, respectively.

Key words: urushiol, hydroxamic acid derivatives, HDAC inhibitor

CLC Number: