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

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

1.
a Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China;
2.
b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding 071002, China;
3.
c Department of Immunology, School of Basic Medical Science, Hebei University, Baoding 071002, China

Corresponding author: Xiao-Liu Li,
Received Date: 31 March 2014
Available Online: 14 May 2014
Fund Project: the Hebei Natural Science Foundation (No. B2012201041) (No. 12966417D)the Foundation of Hebei Education Department (No. YQ2013006). (No. B2012201041)

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).
- Anthraquinone,
- Azasugar,
- Cytotoxic activity
1. [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.
2. [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.
3. [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.
4. [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.
5. [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.
6. [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.
7. [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.
8. [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.
9. [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.
10. [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.
11. [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.
12. [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.
13. [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.
14. [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.
15. [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.
16. [16]
  [16] P. Compain, O.R. Martin, Iminosugars: From Synthesis to Therapeutic Applications, John Wiley and Sons, Ltd, Chichester, 2007, pp. 87-130.
17. [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.
18. [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.
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