Issue 3, 2010
From the journal:

Organic & Biomolecular Chemistry

Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid†

Zhangjian Huang,a   Yihua Zhang,*a   Li Zhao,b   Yongwang Jing,c   Yisheng Lai,a   Luyong Zhang,*c   Qinglong Guo,b   Shengtao Yuan,c   Jianjun Zhang,d   Li Chen,a   Sixun Penga  and  Jide Tiane  

* Corresponding authors

a Center of Drug Discovery, China Pharmaceutical University, Nanjing, P. R. China
E-mail: zyhtgd@hotmail.com
Fax: +86-25-86635503
Tel: +86-25-83271186

b Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing, P. R. China

c New Drug Screening Centre, China Pharmaceutical University, Nanjing, P. R. China
E-mail: lyzhang@cpu.edu.cn
Fax: +86-25-83271500
Tel: +86-25-83591036

d Department of pharmaceutics, China Pharmaceutical University, Nanjing, P. R. China

e Department of Molecular and Medical Pharmacology, University of California Los Angeles, Los Angeles, CA, USA

Abstract

A series of nitric oxide (NO)-releasing glycosyl derivatives (2–14) of oleanolic acid were synthesized to improve the aqueous solubility and cytotoxicity of the parent compound 1. Derivative 3 exhibited better solubility and strong cytotoxicity against human hepatocellular carcinoma (HCC) in vitro. Furthermore, 3 displayed low acute toxicity to mice and significantly inhibited the growth of HCC tumors in vivo, indicating that 3 may be a promising candidate for the treatment of human HCC.

Graphical abstract: Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid

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Article information

DOI
https://doi.org/10.1039/B918846K
Article type
Paper
Submitted
14 Sep 2009
Accepted
31 Oct 2009
First published
08 Dec 2009

Org. Biomol. Chem., 2010,8, 632-639

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Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid

Z. Huang, Y. Zhang, L. Zhao, Y. Jing, Y. Lai, L. Zhang, Q. Guo, S. Yuan, J. Zhang, L. Chen, S. Peng and J. Tian, Org. Biomol. Chem., 2010, 8, 632 DOI: 10.1039/B918846K

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