Comparative DNA Binding of Iron and Manganese Complexes by Spectroscopic and ITC Techniques and Antibacterial Activity
Interaction of Schiff base complexes of Iron and
Manganese: Iron [N, N’ Bis (5- (triphenyl phosphonium methyl)
salicylidene) -1, 2 ethanediamine) chloride, [Fe Salen]Cl; Manganese
[N, N’ Bis (5- (triphenyl phosphonium methyl) salicylidene) -1, 2
ethanediamine) acetate, were investigated by spectroscopic and
isothermal titration calorimetry techniques (ITC).
The absorbance spectra of complexes have shown hyper and
hypochromism in the presence of DNA that is indication of
interaction of complexes with DNA. The linear dichroism (LD)
measurements confirmed the bending of DNA in the presence of
complexes.
Furthermore, Isothermal titration calorimetry experiments
approved that complexes bound to DNA on the base of both
electrostatic and hydrophobic interactions. More, ITC profile exhibits
the existence of two binding phases for the complexes. Antibacterial
activity of ligand and complexes were tested in vitro to evaluate their
activity against the gram positive and negative bacteria.
[1] A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi, M. Zarei,
Synthesis of Novel Azo Schiff Bases and Their Antibacterial and
Antifungal Activities”, Molecules, vol. 9, 2004, pp. 815-824.
[2] T. Gupta, S. Dhar, M. Nethaji, A.R. Chakravarty, “Bis
(dipyridophenazine) copper(II) complex as major groove directing
synthetic hydrolase”, Dalton Trans., 2004, pp. 1896–1900.
[3] B.M. Zeglis, V.C. Pierre, J.K. Barton, “Metallo-intercalators and
metallo-insertors”, Chem. Comm., 2007, pp. 4565–4579.
[4] K.E. Erkkila, D.T. Odom, J.K. Barton, “Recognition and Reaction of
Metallointercalators with DNA”, Chem. Rev., vol. 99, 1999, pp. 2777–
2796.
[5] K. Singh, M.S. Barwa, P. Tyagi,” Synthesis and characterization of
cobalt(II), nickel(II), copper(II) and zinc(II) complexes with Schiff base
derived from 4-amino-3-mercapto-6-methyl-5-oxo1,2,4-triazine”, Eur. J.
Med. Chem., vol. 42, 2007, pp. 394-402.
[6] P.G. Cozzi,” Metal–Salen Schiff base complexes in catalysis: practical
aspects”, Chem. Soc. Rev., vol. 33, 2004, pp. 410-421.
[7] S. Chandra, J. Sangeetika, “EPR and electronic spectral studies on
copper(III) complexes of some NO donor ligands”, J. Indian Chem.
Soc., vol. 81, 2004, pp. 203-206.
[8] E. Canpolat, M. Kaya, “Studies on mononuclear chelates derived from
substituted Schiff-base ligands (part 2): synthesis and characterization of
a new 5-bromosalicyliden-p-aminoacetophenone oxime and its
complexes with Co(II), Ni(II),Cu(II) and Zn(II)”, J. Coord. Chem., vol.
57, 2004, pp. 1217-1223.
[9] M. Yildiz, B. Dulger, S.Y. Koyuncu, B.M. Yapici, “Synthesis and
antimicrobial activity of bis(imido) Schiff bases derived from
thiosemicarbazide with some 2-hydroxyaldehydes and metal
complexes”, J. Indian Chem. Soc., vol. 81, 2004, pp. 7-12.
[10] G. w. Yang, X. P. xia, H. Tu, C. X. Zhao, Chinese J. App. Chem., vol.
12, 1995, pp. 13. [11] G. w. Yang, X. P. xia, H. Tu, C. X. Zhao, Chem. Res. App., vol.7, 1995,
pp. 41.
[12] A. Alonso, M.J. Almendral, Y. Curto, J.J. Criado, E. Rodriguez, J.L.
Manzano, “Determination of the DNA-binding characteristics of
ethidium bromide, proflavine, and cisplatin by flow injection analysis:
usefulness in studies on antitumor drugs Anal. Biochem., vol. 355, 2006,
pp. 157–164.
[13] A. Trotta, A. Barbieri Paulsen, A. Silvestri, G. Ruisi, M.A. Girasolo, R.
Barbieri, J. Inorg. Biochem., vol. 88, 2002, pp. 14–18.
[14] A. Silvestri, G. Ruisi, M.A. Girasolo,” The dynamics of 57Fe nuclei in
FeII–DNA and [FeII(1-methyl-2-mercaptoimidazole)2]–DNA
condensates ”, J. Inorg. Biochem., vol. 92, 2002, pp. 171–176.
[15] F. Capolongo, M. Giomini, A.M. Giuliani, B.F. Matzanke, U. Russo, A.
Silvestri, A.X. Trautwein, R. Barbieri,” The interactions of Fe3+ ions
with adriamycin studied by 57Fe Mössbauer and electronic
spectroscopies”, J. Inorg. Biochem., vol. 65, 1997, pp. 115–122.
[16] A. Haikarainen, J. Sipila, P.P. Pietikainen, A. Pajunen, I. Mutikainen,
“Synthesis and characterization of bulky salen-type complexes of Co,
Cu, Fe, Mn and Ni with amphiphilic solubility properties”, J. Chem.
Soc., Dalton Trans., 2001, pp. 991–995.
[17] M. N. Dehkordi, A-K Bordbar, P. Lincoln, V. Mirkhani, “Spectroscopic
Study on the interaction of ct-DNA with manganese Salen complex containing
triphenyl phosphonium groups”, Spect. Act. Part A, vol. 90, 2012,) pp.
50– 54.
[18] B. Bahramian, V. Mirkhani, S. Tangestaninejad, M. Moghadam,
“Catalytic epoxidation of olefins and hydroxylation of alkanes with
sodium periodate by water-soluble manganese (III)salen”, J. Mol. Catal.
A, vol. 244, 2006, pp. 139-145.
[19] C.V. Kumar, E.H. Asuncion, “DNA binding studies and site selective
fluorescence sensitization of an anthryl probe”, J. Am. Chem. Soc., vol.
115, 1993, pp. 8547–8553.
[20] T. Meehan, H. Gamper, J.F. Becker, “Characterization of reversible,
physical binding of benzopyrene derivatives to DNA”, J. Biol. Chem.,
vol. 257, 1982, pp. 10479–10485.
[21] O. B. Irobi, M. Moo-Young, W. A. Anderson, “Antimicrobial activity of
Annatto (Bixa orellana extract)”, Int. J. Pharm., vol. 34, 1996, pp.87.
[22] K. Fant, B. Norden, P. Lincoln, “Using ethidium to probe
nonequilibrium states of DNA condensed for gene delivery”, Biochem.,
vol. 50, 2011, pp. 1125-1127.
[23] J. D. McGhee, P. H. Von Hipple, “Theoretical aspects of DNA- protein
interactions: Co-operative and non-co-operative binding of large ligands
to a one-dimensional homogeneous lattice”, J. Mol. Biol., vol. 86, 1974,
pp. 469-489.
[24] R. OBrien, I. Haq, Applications of biocalorimetry: binding, stability and
enzyme kinetics, in: J.E. Ladbury, M. Doyle (Eds.), Biocalorimetry,
John Wiley and Sons Ltd, West Sussex, England, 2004.
[25] J.B. Chaires, “Equilibrium studies on the interaction of daunomycin with
deoxypolynucleotides”, Biochem., vol. 22, 1983, pp. 4204–4211.
[26] K.J. Breslauer, D.P. Remeta, W.Y. Chou, R. Ferrante, J. Curry, D.
Zaunczkowski, J.G. Snyder, L.A. Marky, “Enthalpy-entropy
compensations in drug-DNA binding studies”, Proc. Nat. Acad. Sci.
USA., vol. 84, 1987, pp. 8922–8926.
[27] C. Sanchez-Cano, M. Huxley, C. Ducani, A. E. Hamad, M. J. Browning,
C. Navarro-Ranninger, A. G. Quiroga, A. Rodger, M. J. Hannon,
“Conjugation of testosterone modifies the interaction of mono-functional
cationic platinum(II) complexes with DNA, causing significant
alterations to the DNA helix”, Dalton Trans., vol. 39(47), 2010, pp.
11365-74.
[28] M. V. Angelusiu, S. F. Barbuceanu, C. Draghici, G. L. Almajan, “New
Cu(II), Co(II), Ni(II) complexes with aroyl-hydrazone based ligand.
Synthesis, spectroscopic characterization and in vitro antibacterial
evaluation”, Eur. J. Med. Chem., vol. 45, 2010, pp. 2055–2062.
[1] A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi, M. Zarei,
Synthesis of Novel Azo Schiff Bases and Their Antibacterial and
Antifungal Activities”, Molecules, vol. 9, 2004, pp. 815-824.
[2] T. Gupta, S. Dhar, M. Nethaji, A.R. Chakravarty, “Bis
(dipyridophenazine) copper(II) complex as major groove directing
synthetic hydrolase”, Dalton Trans., 2004, pp. 1896–1900.
[3] B.M. Zeglis, V.C. Pierre, J.K. Barton, “Metallo-intercalators and
metallo-insertors”, Chem. Comm., 2007, pp. 4565–4579.
[4] K.E. Erkkila, D.T. Odom, J.K. Barton, “Recognition and Reaction of
Metallointercalators with DNA”, Chem. Rev., vol. 99, 1999, pp. 2777–
2796.
[5] K. Singh, M.S. Barwa, P. Tyagi,” Synthesis and characterization of
cobalt(II), nickel(II), copper(II) and zinc(II) complexes with Schiff base
derived from 4-amino-3-mercapto-6-methyl-5-oxo1,2,4-triazine”, Eur. J.
Med. Chem., vol. 42, 2007, pp. 394-402.
[6] P.G. Cozzi,” Metal–Salen Schiff base complexes in catalysis: practical
aspects”, Chem. Soc. Rev., vol. 33, 2004, pp. 410-421.
[7] S. Chandra, J. Sangeetika, “EPR and electronic spectral studies on
copper(III) complexes of some NO donor ligands”, J. Indian Chem.
Soc., vol. 81, 2004, pp. 203-206.
[8] E. Canpolat, M. Kaya, “Studies on mononuclear chelates derived from
substituted Schiff-base ligands (part 2): synthesis and characterization of
a new 5-bromosalicyliden-p-aminoacetophenone oxime and its
complexes with Co(II), Ni(II),Cu(II) and Zn(II)”, J. Coord. Chem., vol.
57, 2004, pp. 1217-1223.
[9] M. Yildiz, B. Dulger, S.Y. Koyuncu, B.M. Yapici, “Synthesis and
antimicrobial activity of bis(imido) Schiff bases derived from
thiosemicarbazide with some 2-hydroxyaldehydes and metal
complexes”, J. Indian Chem. Soc., vol. 81, 2004, pp. 7-12.
[10] G. w. Yang, X. P. xia, H. Tu, C. X. Zhao, Chinese J. App. Chem., vol.
12, 1995, pp. 13. [11] G. w. Yang, X. P. xia, H. Tu, C. X. Zhao, Chem. Res. App., vol.7, 1995,
pp. 41.
[12] A. Alonso, M.J. Almendral, Y. Curto, J.J. Criado, E. Rodriguez, J.L.
Manzano, “Determination of the DNA-binding characteristics of
ethidium bromide, proflavine, and cisplatin by flow injection analysis:
usefulness in studies on antitumor drugs Anal. Biochem., vol. 355, 2006,
pp. 157–164.
[13] A. Trotta, A. Barbieri Paulsen, A. Silvestri, G. Ruisi, M.A. Girasolo, R.
Barbieri, J. Inorg. Biochem., vol. 88, 2002, pp. 14–18.
[14] A. Silvestri, G. Ruisi, M.A. Girasolo,” The dynamics of 57Fe nuclei in
FeII–DNA and [FeII(1-methyl-2-mercaptoimidazole)2]–DNA
condensates ”, J. Inorg. Biochem., vol. 92, 2002, pp. 171–176.
[15] F. Capolongo, M. Giomini, A.M. Giuliani, B.F. Matzanke, U. Russo, A.
Silvestri, A.X. Trautwein, R. Barbieri,” The interactions of Fe3+ ions
with adriamycin studied by 57Fe Mössbauer and electronic
spectroscopies”, J. Inorg. Biochem., vol. 65, 1997, pp. 115–122.
[16] A. Haikarainen, J. Sipila, P.P. Pietikainen, A. Pajunen, I. Mutikainen,
“Synthesis and characterization of bulky salen-type complexes of Co,
Cu, Fe, Mn and Ni with amphiphilic solubility properties”, J. Chem.
Soc., Dalton Trans., 2001, pp. 991–995.
[17] M. N. Dehkordi, A-K Bordbar, P. Lincoln, V. Mirkhani, “Spectroscopic
Study on the interaction of ct-DNA with manganese Salen complex containing
triphenyl phosphonium groups”, Spect. Act. Part A, vol. 90, 2012,) pp.
50– 54.
[18] B. Bahramian, V. Mirkhani, S. Tangestaninejad, M. Moghadam,
“Catalytic epoxidation of olefins and hydroxylation of alkanes with
sodium periodate by water-soluble manganese (III)salen”, J. Mol. Catal.
A, vol. 244, 2006, pp. 139-145.
[19] C.V. Kumar, E.H. Asuncion, “DNA binding studies and site selective
fluorescence sensitization of an anthryl probe”, J. Am. Chem. Soc., vol.
115, 1993, pp. 8547–8553.
[20] T. Meehan, H. Gamper, J.F. Becker, “Characterization of reversible,
physical binding of benzopyrene derivatives to DNA”, J. Biol. Chem.,
vol. 257, 1982, pp. 10479–10485.
[21] O. B. Irobi, M. Moo-Young, W. A. Anderson, “Antimicrobial activity of
Annatto (Bixa orellana extract)”, Int. J. Pharm., vol. 34, 1996, pp.87.
[22] K. Fant, B. Norden, P. Lincoln, “Using ethidium to probe
nonequilibrium states of DNA condensed for gene delivery”, Biochem.,
vol. 50, 2011, pp. 1125-1127.
[23] J. D. McGhee, P. H. Von Hipple, “Theoretical aspects of DNA- protein
interactions: Co-operative and non-co-operative binding of large ligands
to a one-dimensional homogeneous lattice”, J. Mol. Biol., vol. 86, 1974,
pp. 469-489.
[24] R. OBrien, I. Haq, Applications of biocalorimetry: binding, stability and
enzyme kinetics, in: J.E. Ladbury, M. Doyle (Eds.), Biocalorimetry,
John Wiley and Sons Ltd, West Sussex, England, 2004.
[25] J.B. Chaires, “Equilibrium studies on the interaction of daunomycin with
deoxypolynucleotides”, Biochem., vol. 22, 1983, pp. 4204–4211.
[26] K.J. Breslauer, D.P. Remeta, W.Y. Chou, R. Ferrante, J. Curry, D.
Zaunczkowski, J.G. Snyder, L.A. Marky, “Enthalpy-entropy
compensations in drug-DNA binding studies”, Proc. Nat. Acad. Sci.
USA., vol. 84, 1987, pp. 8922–8926.
[27] C. Sanchez-Cano, M. Huxley, C. Ducani, A. E. Hamad, M. J. Browning,
C. Navarro-Ranninger, A. G. Quiroga, A. Rodger, M. J. Hannon,
“Conjugation of testosterone modifies the interaction of mono-functional
cationic platinum(II) complexes with DNA, causing significant
alterations to the DNA helix”, Dalton Trans., vol. 39(47), 2010, pp.
11365-74.
[28] M. V. Angelusiu, S. F. Barbuceanu, C. Draghici, G. L. Almajan, “New
Cu(II), Co(II), Ni(II) complexes with aroyl-hydrazone based ligand.
Synthesis, spectroscopic characterization and in vitro antibacterial
evaluation”, Eur. J. Med. Chem., vol. 45, 2010, pp. 2055–2062.
@article{"International Journal of Medical, Medicine and Health Sciences:69569", author = "Maryam Nejat Dehkordi and Per Lincoln and Hassan Momtaz", title = "Comparative DNA Binding of Iron and Manganese Complexes by Spectroscopic and ITC Techniques and Antibacterial Activity", abstract = "Interaction of Schiff base complexes of Iron and
Manganese: Iron [N, N’ Bis (5- (triphenyl phosphonium methyl)
salicylidene) -1, 2 ethanediamine) chloride, [Fe Salen]Cl; Manganese
[N, N’ Bis (5- (triphenyl phosphonium methyl) salicylidene) -1, 2
ethanediamine) acetate, were investigated by spectroscopic and
isothermal titration calorimetry techniques (ITC).
The absorbance spectra of complexes have shown hyper and
hypochromism in the presence of DNA that is indication of
interaction of complexes with DNA. The linear dichroism (LD)
measurements confirmed the bending of DNA in the presence of
complexes.
Furthermore, Isothermal titration calorimetry experiments
approved that complexes bound to DNA on the base of both
electrostatic and hydrophobic interactions. More, ITC profile exhibits
the existence of two binding phases for the complexes. Antibacterial
activity of ligand and complexes were tested in vitro to evaluate their
activity against the gram positive and negative bacteria.
", keywords = "Schiff base complexes, Linear dichroism (LD),
Isothermal titration calorimetry (ITC).", volume = "9", number = "3", pages = "300-5", }
