Synthesis of novel, azasugar-modifi ed anthraquinone derivatives and their cytotoxicity

Ping-Zhu Zhang Hai-Long Yang Cui-Cui Li Zhi-Chao Xia Xiao-Man Wang Hua Wei Rui-Xue Rong Zhi-Ran Cao Ke-Rang Wang Hua Chen Xiao-Liu Li

Citation:  Ping-Zhu Zhang, Hai-Long Yang, Cui-Cui Li, Zhi-Chao Xia, Xiao-Man Wang, Hua Wei, Rui-Xue Rong, Zhi-Ran Cao, Ke-Rang Wang, Hua Chen, Xiao-Liu Li. Synthesis of novel, azasugar-modifi ed anthraquinone derivatives and their cytotoxicity[J]. Chinese Chemical Letters, 2014, 25(7): 1057-1059. doi: 10.1016/j.cclet.2014.05.029 shu

Synthesis of novel, azasugar-modifi ed anthraquinone derivatives and their cytotoxicity

    通讯作者: Xiao-Liu Li,
  • 基金项目:

    the Hebei Key Basic Research (No. 12966417D) (No. 12966417D)

    the Hebei Natural Science Foundation (No. B2012201041)  (No. B2012201041)

    the Foundation of Hebei Education Department (No. YQ2013006). (No. YQ2013006)

摘要: A series of novel, azasugar-modified 2-monosubstituted, 2,6-and 2,7-bissubstituted anthraquinone derivatives have been synthesized by the nucleophilic substitution of N-alkylamino azasugar with mono-, bis(2-chloroacetamido)anthraquinones. Their cytotoxic activities against HeLa and MCF-7 cells were preliminarily evaluated and compound 9a with mono-azasugar pendant at 2-position showed similar activity to the control drug (Cisplatin).

English

  • 
    1. [1] M.L. Bochman, K. Paeschke, V.A. Zakian, DNA secondary structures: stability and function of G-quadruplex structures, Nat. Rev. Genet. 13 (2012) 770-780.[1] M.L. Bochman, K. Paeschke, V.A. Zakian, DNA secondary structures: stability and function of G-quadruplex structures, Nat. Rev. Genet. 13 (2012) 770-780.

    2. [2] N.W. Kim, M.A. Piatyszek, K.R. Prowse, et al., Specific association of human telomerase activity with immortal cells and cancer, Science 266 (1994) 2011-2015.[2] N.W. Kim, M.A. Piatyszek, K.R. Prowse, et al., Specific association of human telomerase activity with immortal cells and cancer, Science 266 (1994) 2011-2015.

    3. [3] S. Müller, S. Kumari, R. Rodriguez, S. Blasubramanian, Small-molecule-mediated G-quadruplex isolation from human cells, Nat. Chem. 2 (2010) 1095-1098.[3] S. Müller, S. Kumari, R. Rodriguez, S. Blasubramanian, Small-molecule-mediated G-quadruplex isolation from human cells, Nat. Chem. 2 (2010) 1095-1098.

    4. [4] D. Koirala, S. Dhakal, B. Ashbridge, et al., A single-molecule platform for investigation of interactions between G-quadruplexes and small-molecule ligands, Nat. Chem. 3 (2011) 782-787.[4] D. Koirala, S. Dhakal, B. Ashbridge, et al., A single-molecule platform for investigation of interactions between G-quadruplexes and small-molecule ligands, Nat. Chem. 3 (2011) 782-787.

    5. [5] S. Lin, M. Xu, G. Yuan, Study of STAT3 G-quadruplex folding patterns by CD spectroscopy and molecular modeling, Chin. Chem. Lett. 23 (2012) 329-331.[5] S. Lin, M. Xu, G. Yuan, Study of STAT3 G-quadruplex folding patterns by CD spectroscopy and molecular modeling, Chin. Chem. Lett. 23 (2012) 329-331.

    6. [6] D. Sun, B. Thompson, B.E. Cathers, et al., Inhibition of human telomerase by a G-quadruplex-interactive compound, J. Med. Chem. 40 (1997) 2113-2116.[6] D. Sun, B. Thompson, B.E. Cathers, et al., Inhibition of human telomerase by a G-quadruplex-interactive compound, J. Med. Chem. 40 (1997) 2113-2116.

    7. [7] M.P. Teulade-Fichou, C. Carrasco, L. Guittat, et al., Selective recognition of G-quadruplex telomeric DNA by a bis(quinacridine) macrocycle, J. Am. Chem. Soc. 125 (2003) 4732-4740.[7] M.P. Teulade-Fichou, C. Carrasco, L. Guittat, et al., Selective recognition of G-quadruplex telomeric DNA by a bis(quinacridine) macrocycle, J. Am. Chem. Soc. 125 (2003) 4732-4740.

    8. [8] T. Lemarteleur, D. Gomez, R. Paterski, et al., Stabilization of the c-myc gene promoter quadruplex by specific ligands' inhibitors of telomerase, Biochem. Biophys. Res. Commun. 323 (2004) 802-808.[8] T. Lemarteleur, D. Gomez, R. Paterski, et al., Stabilization of the c-myc gene promoter quadruplex by specific ligands' inhibitors of telomerase, Biochem. Biophys. Res. Commun. 323 (2004) 802-808.

    9. [9] J.H. Tan, L.Q. Gu, J.Y. Wu, Design of selective G-quadruplex ligands as potential anticancer agents, Mini Rev. Med. Chem. 8 (2008) 1163-1178.[9] J.H. Tan, L.Q. Gu, J.Y. Wu, Design of selective G-quadruplex ligands as potential anticancer agents, Mini Rev. Med. Chem. 8 (2008) 1163-1178.

    10. [10] S.M. Hampel, A. Sidibe, M. Gunaratnam, J.F. Riou, S. Neidle, Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells, Bioorg. Med. Chem. Lett. 20 (2010) 6459-6463.[10] S.M. Hampel, A. Sidibe, M. Gunaratnam, J.F. Riou, S. Neidle, Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells, Bioorg. Med. Chem. Lett. 20 (2010) 6459-6463.

    11. [11] M. Micco, G.W. Collie, A.G. Dale, et al., Structure-based design and evaluation of naphthalene diimide G-quadruplex ligands as telomere targeting agents in pancreatic cancer cells, J. Med. Chem. 56 (2013) 2959-2974.[11] M. Micco, G.W. Collie, A.G. Dale, et al., Structure-based design and evaluation of naphthalene diimide G-quadruplex ligands as telomere targeting agents in pancreatic cancer cells, J. Med. Chem. 56 (2013) 2959-2974.

    12. [12] G. Zagotto, C. Sissi, L. Lucatello, et al., Aminoacyl-anthraquinone conjugates as telomerase inhibitors: synthesis, biophysical and biological evaluation, J. Med. Chem. 51 (2008) 5566-5574.[12] G. Zagotto, C. Sissi, L. Lucatello, et al., Aminoacyl-anthraquinone conjugates as telomerase inhibitors: synthesis, biophysical and biological evaluation, J. Med. Chem. 51 (2008) 5566-5574.

    13. [13] P. Sears, C.H. Wong, Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition, Angew. Chem. Int. Ed. 38 (1999) 2300-2324.[13] P. Sears, C.H. Wong, Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate-mediated biological recognition, Angew. Chem. Int. Ed. 38 (1999) 2300-2324.

    14. [14] I. Manet, F. Manoli, B. Zambelli, et al., Affinity of the anthracycline antitumor drugs doxorubicin and sabarubicin for human telomeric G-quadruplex structures, Phys. Chem. Chem. Phys. 13 (2011) 540-551.[14] I. Manet, F. Manoli, B. Zambelli, et al., Affinity of the anthracycline antitumor drugs doxorubicin and sabarubicin for human telomeric G-quadruplex structures, Phys. Chem. Chem. Phys. 13 (2011) 540-551.

    15. [15] N. Ranjan, K.F. Andreasen, S. Kumar, D. Hyde-Volpe, D.P. Arya, Aminoglycoside binding to oxytricha nova telomeric DNA, Biochemistry 49 (2010) 9891-9903.[15] N. Ranjan, K.F. Andreasen, S. Kumar, D. Hyde-Volpe, D.P. Arya, Aminoglycoside binding to oxytricha nova telomeric DNA, Biochemistry 49 (2010) 9891-9903.

    16. [16] P. Compain, O.R. Martin, Iminosugars: From Synthesis to Therapeutic Applications, John Wiley and Sons, Ltd, Chichester, 2007, pp. 87-130.[16] P. Compain, O.R. Martin, Iminosugars: From Synthesis to Therapeutic Applications, John Wiley and Sons, Ltd, Chichester, 2007, pp. 87-130.

    17. [17] K. Tony, M. Shing, A short and practical synthesis of (2S,5S)-bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine, J. Chem. Soc. Chem. Commun. (1987) 262-263.[17] K. Tony, M. Shing, A short and practical synthesis of (2S,5S)-bishydroxymethyl-(3R,4R)-bishydroxypyrrolidine, J. Chem. Soc. Chem. Commun. (1987) 262-263.

    18. [18] S. Venitt, C. Crofton-Sleigh, M. Agbandje, T.C. Jenkins, S. Neidle, Anthracene-9, 10-diones as potential anticancer agents: bacterial mutation studies of amidosubstituted derivatives reveal an unexpected lack of mutagenicity, J. Med. Chem. 41 (1998) 3748-3752.[18] S. Venitt, C. Crofton-Sleigh, M. Agbandje, T.C. Jenkins, S. Neidle, Anthracene-9, 10-diones as potential anticancer agents: bacterial mutation studies of amidosubstituted derivatives reveal an unexpected lack of mutagenicity, J. Med. Chem. 41 (1998) 3748-3752.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  2008
  • HTML全文浏览量:  47
文章相关
  • 收稿日期:  2014-03-31
  • 网络出版日期:  2014-05-14
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章