Asian Pacific Journal of Cancer Prevention

  • 제15권15호
  • /
  • Pages.6343-6347
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  • 2014
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  • 1513-7368(pISSN)
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  • 2476-762X(eISSN)
아시아태평양암예방학회 (Asian Pacific Journal of Cancer Prevention)
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Preparation and Antitumor Activity of a Tamibarotene-Furoxan Derivative

  • Wang, Xue-Jian (School of Pharmacy and Biology Science, Weifang Medical University) ;
  • Duan, Yu (School of Pharmacy and Biology Science, Weifang Medical University) ;
  • Li, Zong-Tao (Research and Development Department, Shandong Qidu Pharmaceutical Co. Ltd.) ;
  • Feng, Jin-Hong (Shandong Analysis and Test Center, Shandong Academy of Sciences) ;
  • Pan, Xiang-Po (Clinical Laboratory, Weifang People's Hospital) ;
  • Zhang, Xiu-Rong (School of Pharmacy and Biology Science, Weifang Medical University) ;
  • Shi, Li-Hong (School of Pharmacy and Biology Science, Weifang Medical University) ;
  • Zhang, Tao (Research and Development Department, Shandong Qidu Pharmaceutical Co. Ltd.)
  • 발행 : 2014.08.15
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초록

Multi-target drug design, in which drugs are designed as single molecules to simultaneously modulate multiple physiological targets, is an important strategy in the field of drug discovery. QT-011, a tamibarotene-furoxan derivative, was here prepared and proposed to exert synergistic effects on antileukemia by releasing nitric oxide and tamibarotene. Compared with tamibarotene itself, QT-011 displayed stronger antiproliferative effects on U937 and HL-60 cells and was more effective evaluated in a nude mice U937 xenograft model in vivo. In addition, QT-011 could release nitric oxide which might contribute to the antiproliferative activity. Autodocking assays showed that QT-011 fits well with the hydrophobic pocket of retinoic acid receptors. Taken together, these results suggest that QT-011 might be a highly effective derivative of tamibarotene and a potential candidate compound as antileukemia agent.

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참고문헌

  1. Bellos F, Mahlknecht U (2008). Valproic acid and all-trans retinoic acid: meta-analysis of a palliative treatment regimen in AML and MDS patients. Onkologie, 31, 629-33
  2. Bian HY, Feng JH, Li MY, et al (2011). Novel antileukemic agents derived from tamibarotene and nitric oxide donors. Bioorg Med Chem Lett, 21, 7025-9 https://doi.org/10.1016/j.bmcl.2011.09.103
  3. Boiani M, Cerecetto H, Gonzalez M, et al (2001). 1, 2, 5-Oxadiazole N-oxide derivatives as potential anti-cancer agents: synthesis and biological evaluation. Part IV. Eur J Med Chem, 36, 771-82 https://doi.org/10.1016/S0223-5234(01)01265-X
  4. Cerecetto H, Porcal W (2005). Pharmacological properties of furoxans and benzofuroxans: recent developments. Mini Rev Med Chem, 5, 57-71 https://doi.org/10.2174/1389557053402864
  5. Endo Y, Iijima T, Yaguchi K et al (2001). Structure-Activity study of retinoid agonists bearing substituted dicarba-closododecaborane. Relation between retinoidal activity and conformation of two aromatic nuclei. Bioorg Med Chem Lett, 11, 1307-11 https://doi.org/10.1016/S0960-894X(01)00204-9
  6. Hirst DG, Robson T (2010). Nitrosative stress as a mediator of apoptosis: implications for cancer therapy. Curr Pharm Des, 16, 45-55 https://doi.org/10.2174/138161210789941838
  7. Huang ME, Ye YC, Chen SR, et al (1988). Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood, 72, 567-72
  8. Huerta S, Chilka S, Bonavida B (2008). Nitric oxide donors: novel cancer therapeutics (review). Int J Oncol, 33, 909-27
  9. Konstantin C, Chiara R, Loretta L, et al (2011). Nitric oxide donor doxorubicins accumulate into doxorubicin-resistant human colon cancer cells inducing cytotoxicity. ACS Med Chem Lett, 2, 494-7 https://doi.org/10.1021/ml100302t
  10. Kitamura K, Hoshi S, Koike M, et al (2000). Histone deacetylase inhibitor but not arsenic trioxide differentiates acute promyelocytic leukaemia cells with t (11;17) in combination with all-trans retinoic acid. Br J Haematol, 108, 696-702 https://doi.org/10.1046/j.1365-2141.2000.01933.x
  11. Li XH, Huang ML, Wang SM, et al (2013). Selective inhibition of bicyclic tetrapeptide histone deacetylase inhibitor on HDAC4 and K562 leukemia cell. Asian Pac J Cancer Prev, 14, 7095-100 https://doi.org/10.7314/APJCP.2013.14.12.7095
  12. Lippman SM, Kavanagh JJ, Paredes-Espinoza M, et al (1992). 13-cis-retinoic acid plus interferon alpha-2a: highly active systemic therapy for squamous cell carcinoma of the cervix. J Natl Cancer Inst, 84, 241-5 https://doi.org/10.1093/jnci/84.4.241
  13. Miwako I, Kagechika H (2007). Tamibarotene. Drugs Today, 43, 563-8 https://doi.org/10.1358/dot.2007.43.8.1072615
  14. Savickiene J, Treigyte G, Borutinskaite V, et al (2006). The histone deacetylase inhibitor FK228 distinctly sensitizes the human leukemia cells to retinoic acid-induced differentiation. Ann N Y Acad Sci, 1091, 368-84 https://doi.org/10.1196/annals.1378.081
  15. Wang H, Gui SY, Chen FH, et al (2013). New insights into 4-amino-2-tri-fluoromethyl-phenyl ester inhibition of cell growth and migration in the A549 lung adenocarcinoma cell line. Asian Pac J Cancer Prev, 14, 7265-70 https://doi.org/10.7314/APJCP.2013.14.12.7265
  16. Wang PG, Xian M, Tang X, et al (2002). Nitric oxide donors: chemical activities and biological applications. Chem Rev, 102, 1091-134 https://doi.org/10.1021/cr000040l
  17. Warrell RP, Jr, He LZ, et al (1998). Therapeutic targeting of transcription in acute promyelocytic leukemia by use of an inhibitor of histone deacetylase. J Natl Cancer Inst, 90, 1621-5 https://doi.org/10.1093/jnci/90.21.1621
  18. Wu Q, Dawson MI, Zheng Y, et al (1997). Inhibition of transretinoic acid-resistant human breast cancer cell growth by retinoid X receptor-selective retinoids. Mol Cell Biol, 17, 6598-608
  19. Zou ZH, Lan XB, Qian H, et al (2011). Synthesis and evaluation of furoxan-based nitric oxide-releasing derivatives of tetrahydroisoquinoline as anticancer and multidrug resistance reversal agents. Bioorg Med Chem Lett, 21, 5934-8 https://doi.org/10.1016/j.bmcl.2011.07.077