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Synthesis, Characterization and Antitumor Studies of Two Copper(II) Schiff Base Complexes Derived from Glutathione and o-Vanillin
Corresponding Author(s) : Caifeng Bi
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
Two new copper Schiff base complexes (Cu2C19H31N3O11S (1), Cu2(C18H23N3O8S) (C12H8N2)2) (2) [C18H23N3O8S = HL (Schiff base derived from glutathione and o-vanillin), C12H8N2 = 1,10-phenanthroline] were synthesized and characterizated by elemental analysis, IR spectroscopy, 1H NMR and thermogravimetric analysis. The test of cell proliferation observed that complex 2 binding with 1,10-phenanthroline are more potent apoptosis inducers in MDA MB 231 cells than complex 1. Furthermore, our study suggests that complex 2 is capable of inhibiting tumor cellular proteasome activity and induce cancer cell-specific apoptotic death.
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- H. Sies, Free Radic. Biol. Med., 27, 916 (1999); doi:10.1016/S0891-5849(99)00177-X.
- S. Singh, A.R. Khan and A.K. Gupta, J. Exp. Therap. Oncol., 9, 303 (2012).
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- M. Linder, Biochemistry of Copper, Plenum Press, New York (1991).
- L. Finney, S. Vogt, T. Fukai and D. Glesne, Clin. Exp. Pharmacol. Physiol., 36, 88 (2009); doi:10.1111/j.1440-1681.2008.04969.x.
- M.M. Eatock, A. Schatzlein and S.B. Kaye, Cancer Treat. Rev., 26, 191 (2000); doi:10.1053/ctrv.1999.0158.
- J.P. Dutcher, Curr. Oncol. Rep., 3, 353 (2001); doi:10.1007/s11912-001-0089-1.
- S.B. Fox, G. Gasparini and A.L. Harris, Lancet Oncol., 2, 278 (2001); doi:10.1016/S1470-2045(00)00323-5.
- M. Gourley and J.S. Williamson, Curr. Pharm. Des., 6, 417 (2000); doi:10.2174/1381612003400867.
- M.R. Ciriolo, A. Desideri, M. Paci and G. Rotilio, J. Biol. Chem., 265, 11030 (1990).
- D. Chen, Q.C. Cui, H.J. Yang and Q.P. Dou, Cancer Res., 66, 10425 (2006); doi:10.1158/0008-5472.CAN-06-2126.
- X. Zhang, C. Bi, Y. Fan, Q. Cui, D. Chen, Y. Xiao and Q.P. Dou, Int. J. Mol. Med., 22, 677 (2008); doi:10.3892/ijmm_00000072.
- K.G. Daniel, P. Gupta, R.H. Harbach, W.C. Guida and Q.P. Dou, Biochem. Pharmacol., 67, 1139 (2004); doi:10.1016/j.bcp.2003.10.031.
- Y. Xiao, C. Bi, Y. Fan, C. Cui, X. Zhang and Q.P. Dou, Intl. Oncol., 33, 1073 (2008); doi:10.3892/ijo_00000096.
- M. Hochstrasser, Curr. Opin. Cell Biol., 7, 215 (1995); doi:10.1016/0955-0674(95)80031-X.
- R.Z. Orlowski and E.C. Dees, Breast Cancer Res., 5, 1 (2002); doi:10.1186/bcr460.
- M. Hochstrasser, Curr. Opin. Cell Biol., 7, 215 (1995); doi:10.1016/0955-0674(95)80031-X.
- J. Adams, V.J. Palombella, E.A. Sausville, J. Johnson, A. Destree, D.D. Lazarus, J. Maas, C.S. Pien, S. Prakash and P.J. Elliott, Cancer Res., 59, 2615 (1999).
- S. Imajoh-Ohmi, T. Kawaguchi, S. Sugiyama, K. Tanaka, S. Omura and H. Kikuchi, Biochem. Biophys. Res. Commun., 217, 1070 (1995); doi:10.1006/bbrc.1995.2878.
- K. Shinohara, M. Tomioka, H. Nakano, S. Tone, H. Ito and S. Kawashima, Biochem. J., 317, 385 (1996).
- H.C. Drexler, Proc. Natl. Acad. Sci. USA, 94, 855 (1997); doi:10.1073/pnas.94.3.855.
- C.L. Fattman, B. An and Q.P. Dou, J. Cell. Biochem., 67, 399 (1997); doi:10.1002/(SICI)1097-4644(19971201)67:3<399::AID-JCB11>3.0.CO;2-8.
- K. Nakamoto, D.R. Huang and Q.R. Wang, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Chemical Industry Press, Beijing (1988).
- Z. Zhang, C. Bi, S.M. Schmitt, Y. Fan, L. Dong, J. Zuo and Q.P. Dou, J. Biol. Inorg. Chem., 17, 1257 (2012); doi:10.1007/s00775-012-0940-x.
References
H. Sies, Free Radic. Biol. Med., 27, 916 (1999); doi:10.1016/S0891-5849(99)00177-X.
S. Singh, A.R. Khan and A.K. Gupta, J. Exp. Therap. Oncol., 9, 303 (2012).
(a) J.H. Ryu, R.T. Chacko, S. Jiwpanich, S. Bickerton, R.P. Babu and S. Thayumanavan, Am. J. Chem. Soc., 132, 17227 (2010); doi:10.1021/ja1069932; (b) A.M. Sauer, A. Schlossbauer, N. Ruthardt, V. Cauda, T. Bein and C. Bräuchle, Nano Lett., 10, 3684 (2010); doi:10.1021/nl102180s.
M. Linder, Biochemistry of Copper, Plenum Press, New York (1991).
L. Finney, S. Vogt, T. Fukai and D. Glesne, Clin. Exp. Pharmacol. Physiol., 36, 88 (2009); doi:10.1111/j.1440-1681.2008.04969.x.
M.M. Eatock, A. Schatzlein and S.B. Kaye, Cancer Treat. Rev., 26, 191 (2000); doi:10.1053/ctrv.1999.0158.
J.P. Dutcher, Curr. Oncol. Rep., 3, 353 (2001); doi:10.1007/s11912-001-0089-1.
S.B. Fox, G. Gasparini and A.L. Harris, Lancet Oncol., 2, 278 (2001); doi:10.1016/S1470-2045(00)00323-5.
M. Gourley and J.S. Williamson, Curr. Pharm. Des., 6, 417 (2000); doi:10.2174/1381612003400867.
M.R. Ciriolo, A. Desideri, M. Paci and G. Rotilio, J. Biol. Chem., 265, 11030 (1990).
D. Chen, Q.C. Cui, H.J. Yang and Q.P. Dou, Cancer Res., 66, 10425 (2006); doi:10.1158/0008-5472.CAN-06-2126.
X. Zhang, C. Bi, Y. Fan, Q. Cui, D. Chen, Y. Xiao and Q.P. Dou, Int. J. Mol. Med., 22, 677 (2008); doi:10.3892/ijmm_00000072.
K.G. Daniel, P. Gupta, R.H. Harbach, W.C. Guida and Q.P. Dou, Biochem. Pharmacol., 67, 1139 (2004); doi:10.1016/j.bcp.2003.10.031.
Y. Xiao, C. Bi, Y. Fan, C. Cui, X. Zhang and Q.P. Dou, Intl. Oncol., 33, 1073 (2008); doi:10.3892/ijo_00000096.
M. Hochstrasser, Curr. Opin. Cell Biol., 7, 215 (1995); doi:10.1016/0955-0674(95)80031-X.
R.Z. Orlowski and E.C. Dees, Breast Cancer Res., 5, 1 (2002); doi:10.1186/bcr460.
M. Hochstrasser, Curr. Opin. Cell Biol., 7, 215 (1995); doi:10.1016/0955-0674(95)80031-X.
J. Adams, V.J. Palombella, E.A. Sausville, J. Johnson, A. Destree, D.D. Lazarus, J. Maas, C.S. Pien, S. Prakash and P.J. Elliott, Cancer Res., 59, 2615 (1999).
S. Imajoh-Ohmi, T. Kawaguchi, S. Sugiyama, K. Tanaka, S. Omura and H. Kikuchi, Biochem. Biophys. Res. Commun., 217, 1070 (1995); doi:10.1006/bbrc.1995.2878.
K. Shinohara, M. Tomioka, H. Nakano, S. Tone, H. Ito and S. Kawashima, Biochem. J., 317, 385 (1996).
H.C. Drexler, Proc. Natl. Acad. Sci. USA, 94, 855 (1997); doi:10.1073/pnas.94.3.855.
C.L. Fattman, B. An and Q.P. Dou, J. Cell. Biochem., 67, 399 (1997); doi:10.1002/(SICI)1097-4644(19971201)67:3<399::AID-JCB11>3.0.CO;2-8.
K. Nakamoto, D.R. Huang and Q.R. Wang, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Chemical Industry Press, Beijing (1988).
Z. Zhang, C. Bi, S.M. Schmitt, Y. Fan, L. Dong, J. Zuo and Q.P. Dou, J. Biol. Inorg. Chem., 17, 1257 (2012); doi:10.1007/s00775-012-0940-x.