Abstract
The two water-soluble designed palladium(II) complexes, [Pd(bpy)(pip-Ac)]NO3 and [Pd(bpy)(mor-Ac)]NO3, (where bpy is 2,2′-bipyridine, pip-Ac is 1-piperidineacetato and mor-Ac is 4-morpholineacetato) have been synthesized and characterized by elemental analyses, molar conductivity measurements and spectroscopic methods (FT-IR, 1H NMR, UV–Vis). The complexes have been tested for in vitro cytotoxic activity against human breast cancer cell line, T47D. The binding of these complexes with DNA has been investigated by absorption spectroscopy, fluorescence titration spectra, EB displacement and gel chromatography. The results suggest that the complexes can bind to DNA cooperatively through a static mechanism at low concentrations (~0.57 μM). The thermodynamic parameters indicated that the van der Waals and hydrogen binding might play a major role in the interaction of these complexes with DNA.
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B. Spingler, D.A. Whittington, S.J. Lippard, Inorg. Chem. 40, 5596 (2001)
S.E. Sherman, S.J. Lippard, Chem. Rev. 87, 1153 (1987)
M. Galanski, S. Slaby, M.A. Jakupec, B.K. Keppler, J. Med. Chem. 46, 4946 (2003)
N. Summa, W. Schiessl, R. Puchta, N.E. Hommes, R. Eldik, Inorg. Chem. 45, 2948 (2006)
B.E. Lippert, Cisplatin: chemistry and biochemistry of a leading anticancer drug (Wiley-VCH, Zurich, 1999), pp. 111–147
M. Fox, J.J. Roberts, Cancer Metast. Rev. 87, 261 (1987)
A.M. Galea, V. Murray, Biochim. Biophys. Acta 1579, 142 (2002)
J.J. Roberts, A.J. Thomson, Prog. Nucleic Acid Res. Mol. Biol. 22, 71 (1979)
S.L. Bruhn, J.H. Toney, S.J. Lippard, Prog. Inorg. Chem. 38, 478 (1991)
S. Komeda, M. Lutz, A.L. Spek, Y. Yamanaka, T. Sato, M. Chikuma, J. Reedijk, J. Am. Chem. Soc. 124, 4738 (2002)
A.J. Kraker, J.D. Hoeschele, W.L. Elliott, H.D.H. Showalter, D. Sercel, N.P. Farrell, J. Med. Chem. 35, 4526 (1992)
A. Divsalar, A.A. Saboury, H. Mansouri-Torshizi, F. Ahmad, J. Phys. Chem. B 114, 3639 (2010)
A. Divsalar, A.A. Saboury, H. Mansouri-Torshizi, B. Hemmatinejad, Bull. Korean Chem. Soc. 27, 1801 (2006)
R. Mital, T.S. Srivastava, J. Inorg. Biochem. 40, 111 (1990)
H. Wu, X. Huang, J. Yuan, F. Kou, F. Jia, B. Liu, K. Wang, Eur. J. Med. Chem. 45, 5324 (2010)
E. Ramachandran, S.P. Thomas, P. Poornima, P. Kalaivani, R. Prabhakaran, V.V. Padma, K. Natarajan, Eur. J. Med. Chem. 50, 405 (2012)
N.V. Kulkarni, A. Kamath, S. Budagumpi, V.K. Revankar, J. Mol. Struct. 1006, 580 (2011)
F.A. Palocsay, J.V. Rund, Inorg. Chem. 8, 524 (1969)
J. Marmur, J. Mol. Biol. 3, 208 (1961)
M.F. Reichman, S.A. Rice, C.A. Thomas, P. Doty, J. Am. Chem. Soc. 76, 3047 (1954)
P. Barczyñski, Z. Dega-Szafran, E. Dulewicz, M. Petryna, M. Szafran, Polish. J. Chem. 74, 1149 (2000)
H. Mansouri-Torshizi, M. I-Moghaddam, A. Divsalar, A.A. Saboury, Bioorg. Med. Chem. 16, 9616 (2008)
R. Mital, N. Jain, T.S. Srivastava, Inorg. Chim. Acta 166, 135 (1989)
H. Mansouri-Torshizi, M.H. Akhbari Shad, T.S. Srivastava, Iran. J. Sci. Tech. Trans. A 25, 154 (2001)
E. Gao, L. Wang, M. Zhu, L. Liu, W. Zhang, Eur. J. Med. Chem. 45, 311 (2010)
A.I. Matesanz, J.M. Pérez, P. Navarro, J.M. Moreno, E. Colacio, P. Souza, J. Inorg. Biochem. 76, 29 (1999)
E. Gao, M. Zhu, H. Yin, L. Liu, Q. Wu, Y. Sun, J. Inorg. Biochem. 102, 1958 (2008)
A. Divsalar, A.A. Saboury, H. Mansouri-Torshizi, A.A. Moosavi-Movahedi, J. Biomol. Struct. Dyn. 25, 173 (2007)
H. Mansouri-Torshizi, M. Saeidifar, A. Divsalar, A.A. Saboury, Spectrochim. Acta, Part A 77, 312 (2010)
H. Mansouri-Torshizi, M. Saeidifar, A. Divsalar, A.A. Saboury, S. Shahraki, Bull. Korean Chem. Soc. 31, 441 (2010)
A.A. Saboury, A.A. Moosavi-Movahedi, Biochem. Educ. 22, 48 (1994)
Q. Wang, Zh Yang, G. Qi, D. Qin, Eur. J. Med. Chem. 44, 2425 (2009)
H. Mansouri-Torshizi, M. I-Moghaddam, A. Divsalar, A.A. Saboury, J. Biomol. Struct. Dyn. 26, 575 (2009)
A. Arabzadeh, S.Z. Bathaie, H. Farsam, M. Amanlou, A.A. Saboury, A. Shockravi, A.A. Moosavi-Movahedi, Int. J. Pharm. 237, 47 (2002)
Z.H. Xu, F.J. Chen, P.X. Xi, X.H. Liu, Z.Z. Zeng, J. Photochem. Photobiol., A 196, 77 (2008)
L. Peres-Flores, A.J. Ruiz-Chica, J.G. Delcros, F.M. Sanches, F.J. Ramirez, Spectrochim. Acta, Part A 69, 1089 (2008)
P.X. Xi, Z.H. Xu, X.H. Liu, F.J. Cheng, Z.Z. Zeng, Spectrochim. Acta, Part A 71, 523 (2008)
H. Mansouri-Torshizi, M. Saeidifar, F. Khosravi, A. Divsalar, A.A. Saboury, F. Hassani, Bioinorg. Chem. Appl. 2011, 1 (2011)
S.Z. Bathaie, A. Bolhasani, R. Hoshyar, B. Ranjbar, F. Sabouni, A.A. Moosavi-Movahedi, DNA Cell Biol. 26, 533 (2007)
A.M.Q. King, B.H. Nicholson, Biochem. J. 114, 679 (1969)
G.M. Barrow, in Physical Chemistry, 5nd edn. (MC Graw-Hill, New York, 1988) pp. 201–211
F.V. Rocha, C.V. Barra, A.V.G. Netto, A.E. Mauro, I.Z. Carlos, R.C.G. Frem, S.R. Ananias, M.B. Quilles, A. Stevanato, M.C. da Rocha, Eur. J. Med. Chem. 45, 1698 (2010)
G. Scatchard, Ann. N.Y. Acad. Sci. 51, 660 (1949)
A.V. Hill, J. Physiol. 40, 389 (1910)
D. Whitford, Proteins: structure and function (John Wiley, West Sussex, 2005), pp. 66–74
J. Toneatto, R.A. Boero, G. Lorenzatti, A.M. Cabanillas, G.A. Argüello, J. Inorg. Biochem. 104, 697 (2010)
N. Shahabadi, A. Fatahi, J. Mol. Struct. 970, 90 (2010)
H. Mansouri-Torshizi, M. I-Moghaddam, A.A. Saboury, Acta Biochim. Biophys. Sin. 35, 886 (2003)
H. Mansouri-Torshizi, M. Saeidifar, A. Divsalar, A.A. Saboury, J. Biomol. Struct. Dyn. 28, 805 (2011)
A.M. Bond, G.G. Wallace, Anal. Chem. 54, 1706 (1982)
K.E. Erkkila, T.D. Odom, J.K. Barton, Chem. Rev. 99, 2777 (1999)
X.M. He, D.C. Carter, Nature 358, 209 (1992)
A. Divsalar, A.A. Saboury, L. Ahadi, E. Zemanatiyar, H. Mansouri-Torshizi, BMB reports 43, 766 (2010)
M. Khorasani-Motlagh, M. Noroozifar, S. Mirkazehi-Rigi, Spectrochim. Acta, Part A 75, 598 (2010)
C. Qiao, S. Bi, Y. Sun, D. Song, H. Zhang, W. Zhou, Spectrochim. Acta, Part A 70, 136 (2008)
Y.B. Zeng, N.W. Yang, S. Liu, N. Tang, J. Inorg. Biochem. 97, 258 (2003)
C.V. Kumar, J.K. Barton, N.J. Turro, J. Am. Chem. Soc. 107, 5518 (1985)
F. Wu, Y. Xiang, Y. Wu, F. Xi, J. Lumin. 129, 1286 (2009)
H. Mansouri-Torshizi, T.S. Srivastava, S.J. Chavan, M.P. Chitnis, J. Inorg. Biochem. 48, 63 (1992)
H. Mansouri-Torshizi, T.S. Srivastava, H.K. Parekh, M.P. Chitnis, J. Inorg. Biochem. 45, 135 (1992)
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We are grateful for the financial support of the Materials and Energy Research Center, the University of Sistan and Baluchestan and of the University of Tehran.
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Saeidifar, M., Mansouri-Torshizi, H., Divsalar, A. et al. Novel 2,2′-bipyridine palladium(II) complexes with glycine derivatives: synthesis, characterization, cytotoxic assays and DNA-binding studies. J IRAN CHEM SOC 10, 1001–1011 (2013). https://doi.org/10.1007/s13738-013-0237-1
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DOI: https://doi.org/10.1007/s13738-013-0237-1