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      Synthesis and anti-hepatocellular carcinoma activity of novel O 2-vinyl diazeniumdiolate-based nitric oxide-releasing derivatives of oleanolic acid

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          Abstract

          Considering that high levels of nitric oxide (NO) exert anti-cancer effect and the derivatives of oleanolic acid (OA) have shown potent anti-cancer activity, new O 2-vinyl diazeniumdiolate-based NO releasing derivatives (5a–l, 11a–l) of OA were designed, synthesized, and biologically evaluated in the present study. These derivatives could release different amounts of NO in liver cells. Among them, 5d, 5i, 5j, 11g, 11h, and 11j released more NO in SMMC-7721 cells and displayed stronger proliferative inhibition against SMMC-7721 and HepG2 cells than OA and other tested compounds. The most active compound 5j showed almost 20-fold better solubility than OA in aqueous solution, released larger amounts of NO in liver cancer cells than that in normal ones, and exhibited potent anti-hepatocellular carcinoma activity but little effect on the normal liver cells. The inhibitory activity against the cancer cells was significantly diminished upon addition of an NO scavenger, suggesting that NO may contribute, at least in part, to the activity of 5j.

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          Author and article information

          Journal
          CJNM
          Chinese Journal of Natural Medicines
          Elsevier
          1875-5364
          20 December 2017
          : 15
          : 12
          : 928-937
          Affiliations
          1State Key Laboratory of National Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, China Pharmaceutical University, Nanjing 210009, China
          Author notes
          *Corresponding author: HUANG Zhang-Jian, E-mail: zyhtgd@ 123456163.com , ZHANG Hui-Bin, E-mail: zhanghb80@ 123456163.com , and ZHANG Yi-Hua, E-mail: cpudahuang@ 123456163.com .

          These authors have no conflict of interest to declare.

          Article
          S1875-5364(18)30009-8
          10.1016/S1875-5364(18)30009-8
          Copyright © 2017 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
          Funding
          Funded by: National Natural Science Foundation of China
          Award ID: 81273378
          Award ID: 21372261
          This work was supported by grants from the National Natural Science Foundation of China (Nos. 81273378 and 21372261).

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