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GU Xiaoke, TANG Xiaobo, HUANG Zhangjian, PENG Hui, ZHANG Yihua. Synthesis and antitumor activity of NO-releasing alkoxylbiphenyl derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(6): 657-661. DOI: 10.11665/j.issn.1000-5048.20140606
Citation: GU Xiaoke, TANG Xiaobo, HUANG Zhangjian, PENG Hui, ZHANG Yihua. Synthesis and antitumor activity of NO-releasing alkoxylbiphenyl derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(6): 657-661. DOI: 10.11665/j.issn.1000-5048.20140606
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Synthesis and antitumor activity of NO-releasing alkoxylbiphenyl derivatives

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    • Abstract
  • A series of NO-releasing alkoxylbiphenyl derivatives( 4a - 4g )were designed and synthesized by coupling the carboxyl group of alkoxylbiphenyl with NO donor. Their antitumor activities were evaluated by MTT assay in HepG-2, Bel-7402, SMMC-7721, QGY-7701 and Bel-7404 cell lines. The results indicated that the target compounds exhibited significant inhibitory effects on the proliferation of tumor cells, especially on HepG-2 cells(IC50=1. 15-4. 34 μmol/L). Notably, the inhibitory effect of the target compounds on non-tumor liver LO2 cells was relatively weak(IC50=5. 00-8. 53 μmol/L)except compound 4f , suggesting that these compounds have selective inhibitory effects on tumor cells in vitro. Additionally, compound 4b could significantly inhibit the parental sensitive K562 and drug-resistant K562/A02 cell proliferation, and the IC50s were 1. 28 and 1. 32 μmol/L, respectively. Importantly, treatment with various concentrations of an NO scavanger significantly reduced the antitumor activity of compound 4b , suggesting that NO produced by compound 4b may play a significant role in inhi-biting the proliferation of K562 and K562/A02 cells.
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  • [1]
    Hu W,Li Y,Zhang CZ.Enantioseparation of racemic anti-hepatitis new drug bicyclol with crystallization[J].Chin Chem Lett(中国化学快报),2005, 16(11):1 471-1 473.
    [2]
    Hung HY,Ohkoshi E,Goto M,et al.Antitumor agents.293.Nontoxic dimethyl-4,4′-dimethoxy-5,6,5′,6′-dimethylenedioxybiphenyl-2,2′-dicarboxylate(DDB)analogues chemosensitize multidrug-resistant cancer cells to clinical anticancer drugs[J].J Med Chem,2012, 55(11):5 413-5 424.
    [3]
    Sun H,Liu GT.Chemopreventive effect of bicyclol on malignant transformation of WB-F344 rat liver epithelial cells and its effect on related signal transduction in vitro[J].Cancer Lett,2006, 236(2):239-249.
    [4]
    Jin J,Sun H,Wei H,et al.The anti-hepatitis drug DDB chemosensitizes multidrug resistant cancer cells in vitro and in vivo by inhibiting P-gp and enhancing apoptosis[J].Invest New Drugs,2007, 25(2):95-105.
    [5]
    Cortier M, Leon L, Sassi N, et al. Nitric oxide is a promising enhancer for cancer therapy[J].Nitric Oxide(NO)Cancer,2010:253-263.
    [6]
    Donia M,Maksimovic-Ivanic D,Mijatovic S,et al.In vitro and in vivo anticancer action of saquinavir-NO,a novel nitric oxide-derivative of the protease inhibitor saquinavir,on hormone resistant prostate cancer cells[J].Cell Cycle,2011, 10(3):492-499.
    [7]
    Han C,Huang ZJ,Zheng C,et al.Novel hybrids of(phenylsulfonyl)furoxan and anilinopyrimidine as potent and selective epidermal growth factor receptor inhibitors for intervention of non-small-cell lung cancer[J].J Med Chem,2013, 56(11):4 738-4 748.
    [8]
    Ling Y, Ye XL, Zhang ZZ, et al. Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid:synthesis and evaluation of antihepatocellular carcinoma activity[J].J Med Chem,2011, 54(9):3 251-3 259.
    [9]
    Huang ZJ,Zhang YH,Zhao L,et al.Synthesis and anti-human hepatocellular carcinoma activity of new nitric oxide-releasing glycosyl derivatives of oleanolic acid[J].Org Biomol Chem,2010, 8(3):632-639.
    [10]
    Chen L,Zhang Y,Kong X,et al.Design,synthesis,and antihepatocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid[J].J Med Chem,2008, 51(15):4 834-4 838.
    [11]
    Fu J,Liu L,Huang Z,et al.Hybrid molecule from O2-(2,4-dinitrophenyl)diazeniumdiolate and oleanolic acid:a glutathione S-transferase pi-activated nitric oxide prodrug with selective anti-human hepatocellular carcinoma activity and improved stability[J].J Med Chem,2013, 56(11):4 641-4 655.
    [12]
    Hutchens S, Manevich Y, He L, et al. Cellular resistance to a nitric oxide releasing glutathione S-transferase P-activated prodrug,PABA/NO[J].Invest New Drug,2011, 29(5):719-729.
    [13]
    Huang Z,Fu J,Liu L,et al.Glycosylated diazeniumdiolate-based oleanolic acid derivatives:synthesis,in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents[J].Org Biomol Chem,2012, 10(19):3 882-3 891.
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