Citation: Ming-Dong Lu, Xiao Zhou, Yao-Jun Yu, Pi-Hong Li, Wei-Jian Sun, Cheng-Guang Zhao, Zhi-Qiang Zheng, Tao You, Fei-Hai Wang. Synthesis and in vitro biological evaluation of nitric oxide-releasing derivatives of hydroxylcinnamic acids as anti-tumor agents[J]. Chinese Chemical Letters, ;2013, 24(05): 415-418. shu

Synthesis and in vitro biological evaluation of nitric oxide-releasing derivatives of hydroxylcinnamic acids as anti-tumor agents

  • Corresponding author: Zhi-Qiang Zheng, 
  • Received Date: 25 December 2012
    Available Online: 26 January 2013

  • Novel furoxan-based nitric oxide-releasing derivatives 6a-p of hydroxylcinnamic acids were synthesized by coupling the carboxyl group of hydroxylcinnamic acids with furoxan through various alkylol amines. Compounds 6a, e-i and m-p displayed more potent anti-tumor activities superior to control 5-fluorouracil (5-FU) in most cancer cells tested. Furthermore, 6f could selectively inhibit tumor cells, but not non-tumor cell proliferation. This inhibition was attributed to high levels of NO released in cancer cells and potentially synergistic effect of NO donor moieties and the bioactivity of hydroxylcinnamic acids.

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      [3] A. Murakami, Y. Nakamura, K. Koshimizu, et al., FA 15, a hydrophobic derivative of ferulic acid, suppresses inflammatory responses and skin tumor promotion: comparison with ferulic acid, Cancer Lett. 180 (2002) 121-129.

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      [4] P. Fresco, F. Borges, M.P. Marques, et al., The anticancer properties of dietary polyphenols and its relation with apoptosis, Curr. Pharm. Des. 16 (2010) 114-134.

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      [5] W.Y. Huang, Y.Z. Cai, Y. Zhang, Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention, Nutr. Cancer 62 (2010) 1-20.

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      [6] S. Balakrishnan, V.P. Menon, S. Manoharan, Ferulic acid inhibits 7, 12-dimethylbenz[a]anthracene-induced hamster buccal pouch carcinogenesis, J. Med. Food 11 (2008) 693-700.

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      [10] Q. Jia, A.J. Janczuk, T. Cai, et al., NO donors with anticancer activity, Expert Opin. Ther. Pat. 12 (2002) 819-826.

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      [12] L. Chen, Y. Zhang, X. Kong, et al., Design, Synthesis and anti-hepatocellular carcinoma activity of nitric oxide-releasing derivatives of oleanolic acid, J. Med. Chem. 51 (2008) 4834-4838.

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      [13] Y. Ling, X. Ye, Z. Zhang, et al., Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid: synthesis and evaluation of antihepatocellular carcinoma activity, J. Med. Chem. 54 (2011) 3251-3259.

    14. [14]

      [14] Z. Huang, Y. Zhang, L. Zhao, et al., Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid, Org. Biomol. Chem. 8 (2010) 632-639.

    15. [15]

      [15] Z. Zou, X. Lan, H. Qian, et al., Synthesis and evaluation of furoxan-based nitric oxide-releasing derivatives of tetrahydroisoquinoline as anticancer and multidrug resistance reversal agents, Bioorg. Med. Chem. Lett. 21 (2011) 5934-5938.

    16. [16]

      [16] Y. Lai, L. Shen, Z. Zhang, et al., Synthesis and biological evaluation of furoxanbased nitric oxide-releasing derivatives of glycyrrhetinic acid as anti-hepatocellular carcinoma agents, Bioorg. Med. Chem. Lett. 20 (2010) 6416-6420.

    17. [17]

      [17] X. Kong, Y. Zhang, L. Dai, et al., Synthesis and biological evaluation of nitric oxidereleasing sixalkoxyl biphenyl derivatives as anticancer agents, Chin. Chem. Lett. 19 (2009) 149-152.

    18. [18]

      [18] L. Chen, Q. Wen, J. Tang, et al., Synthesis and bioactivity of novel nitric oxidereleasing ursolic acid derivatives, Chin. Chem. Lett. 22 (2011) 413-416.

    19. [19]

      [19] R. Li, Y. Zhang, H. Ji, et al., Synthesis and anti-inflammatory activity of benzenesulfonylfuroxan-coupled diclofenac, Acta Pharmacol. Sin. 36 (2001) 821-826.

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