1
652
N.V. Loginova et al. / Polyhedron 29 (2010) 1646–1652
I
demonstrated by means of absorption spectrophotometry. Cu(L )
2
,
[18] A.M. Samuni, E.Y. Chuang, M.C. Krishna, W. Stein, W. DeGraff, A. Russo, J.B.
Mitchell, Proc. Natl Acad. Sci. USA 100 (2003) 5390.
I
II
II
2
HL , Fe(L ) , and HL were found to be characterized by the highest
[
19] E.L. Cavalieri, K.M. Li, N. Balu, M. Saeed, P. Devanesan, S. Higginbotham, J. Zhao,
M.L. Gross, E.G. Rogan, Carcinogenesis 6 (2002) 1071.
rates of Cyt c reduction. It points to the fact that there is no direct
correlation between redox or some other physico-chemical proper-
ties of the compounds under study and their ability to enter into
redox interaction with biological subjects. Hence, the reduction
of Cyt c by the ligands and their Cu(II), Co(II), Fe(II) and Mn(II) com-
plexes may not be related solely to the facility of their oxidation or
ionization. P450R was also shown to increase the rate of Cyt c
[20] A.L. Shen, D.S. Sem, C.B. Kasper, J. Biol. Chem. 274 (1999) 5391.
[
[
2007) 330.
[23] J.J. Müller, A. Lapko, G. Bourenkov, K. Ruckpaul, U. Heinemann, J. Biol. Chem.
76 (2001) 2786.
[
[
21] C.L. Elmore, T.D. Porter, J. Biol. Chem. 277 (2002) 48960.
22] F. Hannemann, A. Bichet, K.M. Ewen, R. Bernhardt, Biochim. Biophys. Acta 1770
(
2
24] F.P. Guengerich, Curr. Drug Metab. 2 (2001) 93.
25] A. Bartoszek, Acta Biochim. Pol. 49 (2002) 323.
I
II
reduction with HL and HL ligands, probably due to providing an
additional route of transferring electrons to Cyt c.
[26] N.R. Bachur, S.L. Gordon, M.V. Gee, H. Kon, Proc. Natl Acad. Sci. USA 76 (1979)
54.
27] N.K. Cˇ enas, I.A. Martsinkyavichene, Iu.Iu. Kulis, S.A. Usanov, Biokhimiya 52
1987) 643 (In Russian).
[28] I. Bertini, G. Cavallaro, A. Rosato, Chem. Rev. 106 (2006) 90.
9
[
The antibacterial activity of these compounds was found to fol-
(
I
I
I
I
I
low the order: (1) Cu(L )
2
> Co(L )
2
> Fe(L )
2
P Mn(L )
2
> HL ; (2)
II
II
II
II
II
[
[
29] K.J. McLean, N.S. Scrutton, A.W. Munro, Biochem. J. 372 (2003) 317.
30] M. Senda, S. Kishigami, S. Kimura, M. Fukuda, T. Ishida, T. Senda, J. Mol. Biol.
Cu(L )
2
> Co(L )
2
> HL > Fe(L )
2
P Mn(L )
2
,
and their reducing
ability (determined electrochemically) followed the same order.
These sequences are not entirely the same as those characterizing
the decrease of the rates of Cyt c reduction with the ligands and
373 (2007) 382.
[31] M. Zeghouf, G. Defaye, M. Fontecave, J. Coves, Biochem. Biophys. Res. Commun.
246 (1998) 602.
[32] W.H. Koppenol, K.J. van Buuren, J. Butler, R. Braams, Biochim. Biophys. Acta
I
I
I
I
2 2 2
their metal complexes: (1) HL > Cu(L ) P Mn(L ) P Co(L ) >
4
49 (1976) 157–168.
33] J. Butler, W.H. Koppenol, E. Margoliash, J. Biol. Chem. 257 (1982) 10747.
ˇenas, Zˇ . Anusevicheus, D. Bironaite, G. Bachmanova, A.I. Archakov, K.
I
II
II
II
II
II
Fe(L )
2
; (2) HL > Fe(L )
2
> Mn(L )
2
ꢃ Co(L )
2 2
> Cu(L ) . Neverthe-
[
less, the results obtained bring out clearly that redox interaction
with oxidoreductases as macromolecular targets can be essential
for realizing their biological effects. It should be noted that when
evaluating the above-mentioned compounds as potential antibac-
terial and antioxidant agents, their ability to reduce Cyt c in mam-
malian mitochondrions should be regarded as either a side or a
pharmacological effect. It is of particular importance in the case
of metal complexes more lipophilic in comparison with parent
ligands.
[34] N. C
Öllinger, Arch. Biochem. Biophys. 315 (1994) 400.
35] S. Ramji, C. Lee, T. Inaba, A.V. Patterson, D.S. Riddick, Cancer Res. 63 (2003)
914.
[36] E. Derouet-Humbert, C.-A. Dr a˘ gan, T. Hakki, M. Bureik, Apoptosis 12 (2007)
135.
[
6
2
[
37] A.V. Aleshukina, Medicinal Microbiology, Phoenix, Rostov-on-Don, 2003 (In
Russian).
[38] A.A. Akhrem, N.V. Lapko, A.G. Lapko, V.M. Shkumatov, V.L. Chashchin, Acta
Biol. Med. Ger 38 (1979) 257.
[
39] S. Tamura, K.R. Korzekwa, S. Kimura, H.V. Gelboin, F.J. Gonzalez, Arch.
Biochem. Biophys. 293 (1992) 219.
[
[
[
[
40] C.C. Winterbourn, Biochem. J. 207 (1982) 609.
41] G.F.Z. da Silva, W.M. Tay, Li-J. Ming, J. Biol. Chem. 280 (2005) 16601.
42] N. Rahman, Y. Ahmad, S.N.H. Azmi, AAPS Pharm Sci. Tech. 6 (2005) 543.
43] W.J. Geary, Coord. Chem. Rev. 7 (1971) 81.
Acknowledgement
This work was supported by International Science and Technol-
ogy Center (ISTC Grant B-1645).
[44] C.N. Verani, Rational synthesis and characterization of paramagnetic
heteropolynuclear systems, Ph.D. thesis, Ruhr-Universität Bochum, Mülheim
an der Ruhr, 2000.
[
45] B. Wunderlich, Macromolecular Physics I, Crystal Structure, Morphology,
Defects, Academic Press, New York, 1973.
References
[
46] K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination
Compounds: Theory and Applications in Inorganic Chemistry, John Wiley &
Sons Inc., New York, 1997.
[
[
1] P. von Sengbusch, Molekular und Zellbiologie, Springer-Verlag, Berlin-
Heidelberg-New York, 1979.
2] B. Coyle, P. Kinsella, M. McCann, M. Devereux, R.O. Connor, M. Clynes, K.
Kavanagh, Toxicol. In Vitro 18 (2004) 63.
[47] S. Belaid, S. Djebbar, O. Benali-Baitich, M. Khan, G. Bouet, J. Inorg. Biochem. 102
(2008) 63.
[
[
3] B. Coyle, K. Kavanagh, M. McCann, M. Devereux, Biometals 16 (2003) 321.
4] B.S. Creaven, D.A. Egan, D. Karcz, K. Kavanagh, M. McCann, M. Mahon, A. Noble,
B. Thati, M. Walsh, J. Inorg. Biochem. 101 (2007) 1108.
[48] A. Carrington, E. MacLachlan, Introduction to Magnetic Resonance with
Applications to Chemistry and Chemical Physics, Harper and Row, New York,
1967.
[
[
[
5] M. McCann, B. Coyle, S. McKay, P. McCormack, K. Kavanagh, M. Devereux, V.
McKee, P. Kinsella, R. O’Connor, M. Clynes, Biometals 17 (2004) 635.
6] A. Eshwika, B. Coyle, M. Devereux, M. McCann, K. Kavanagh, Biometals 17
[49] A.B.P. Lever, E.I. Solomon (Eds.), Inorganic Electronic Structure and
Spectroscopy, John Wiley & Sons, New York, 2006.
[50] A. Pui, J.-P. Mahy, Polyhedron 26 (2007) 3143.
(
2004) 415.
[51] A.M. Shaker, M.Sh. Adam, Synth. React. Inorg. Met.-Org. Chem. 33 (2003) 1081.
[52] M.J. Sever, J.J. Wilker, J. Chem. Soc., Dalton Trans. (2004) 1061.
[53] M.L. Childers, J. Cho, C.A.S. Regino, M.W. Brechbiel, A.G. DiPasquale, A.L.
Rheingold, S.V. Torti, F.M. Torti, R.P. Planalp, J. Inorg. Biochem. 102 (2008) 150.
[54] N.R. Perron, J.N. Hodges, M. Jenkins, J.L. Brumaghim, Inorg. Chem. 47 (2008)
6153.
[55] M.J. Sabater, A. Corma, J.V. Folgado, H. García, J. Phys. Org. Chem. 13 (2000) 57.
[56] J.J. Alexander, H.B. Gray, J. Am. Chem. Soc. 90 (1968) 4260.
[57] A. Saha, P. Majumdar, S. Goswami, J. Chem. Soc., Dalton Trans. (2000) 1703.
[58] G. Speier, Z. Tyeklar, P. Toth, E. Speier, S. Tisza, A. Rochen-bauer, A.M. Whalen,
N. Alkire, C.G. Pierpont, Inorg. Chem. 40 (2001) 5653.
[59] C.G. Pierpont, Coord. Chem. Rev. 216–217 (2001) 99.
[60] C.G. Pierpont, Coord. Chem. Rev. 219–221 (2001) 415.
[61] F. Scholz (Ed.), Electroanalytical Methods: Guide to Experiments and
Applications, Springer–Verlag, Berlin, 2002.
[62] J. Macyk, R. van Eldik, J. Chem. Soc., Dalton Trans. (2003) 2704.
[63] U. Scholten, A.C. Mercha, K. Bernauer, J.R. Soc. Interface 2 (2005) 109.
[64] J.K. Yandell, Australian J. Chem. 34 (1981) 99.
7] N.V. Loginova, T.V. Koval’chuk, R.A. Zheldakova, A.A. Chernyavskaya, N.P.
Osipovich, G.K. Glushonok, G.I. Polozov, V.L. Sorokin, O.I. Shadyro, Cent. Eur. J.
Chem. 4 (2006) 440.
8] T.V. Koval’chuk, N.V. Loginova, G.I. Polozov, A.A. Chernyavskaya, D.A. Gursky,
O.I. Shadyro, Vestnik BSU. Ser. 2. Khim., Biol. Geogr. (2) (2008) 25 (In Russian).
9] N.V. Loginova, T.V. Koval’chuk, R.A. Zheldakova, A.A. Chernyavskaya, N.P.
Osipovich, G.K. Glushonok, G.I. Polozov, V.N. Povalishev, V.L. Sorokin, O.I.
Shadyro, Polyhedron 25 (2006) 3603.
[
[
[
10] N.V. Loginova, T.V. Koval’chuk, R.A. Zheldakova, N.P. Osipovich, V.L. Sorokin,
G.I. Polozov, G.A. Ksendzova, G.K. Glushonok, A.A. Chernyavskaya, O.I. Shadyro,
Bioorg. Med. Chem. Lett. 16 (2006) 5403.
11] N.V. Loginova, T.V. Koval’chuk, N.P. Osipovich, G.I. Polozov, V.L. Sorokin, A.A.
Chernyavskaya, O.I. Shadyro, Polyhedron 27 (2008) 985.
[
[
12] N.V. Loginova, T.V. Koval’chuk, G.I. Polozov, N.P. Osipovich, P.G. Rytik, I.I.
Kucherov, A.A. Chernyavskaya, V.L. Sorokin, O.I. Shadyro, Eur. J. Med. Chem. 43
(
2008) 1536.
[
13] A. Albert, Selective Toxicity: Physico-Chemical Basis of Therapy, Chapman and
Hall, London, New York, 1985.
[65] A.J. Davison, J. Biol. Chem. 243 (1968) 6064.
[
[
14] F.L. Muller, Y. Liu, H. van Remmen, J. Biol. Chem. 279 (2004) 49064.
15] O. Maneg, F. Malatesta, B. Ludwig, V. Drosou, Biochim. Biophys. Acta 1655
[66] T.V. Koval’chuk, G.A. Ksendzova, Chem. Ser. (5) (2005) 51 (In Russian0029.
[67] D. Lopez-Colón, A.E. Alegría, Ultrason. Sonochem. 11 (2004) 311.
[68] M.J. Picklo, V. Amarnath, D.G. Graham, T.J. Montine, Free Radic. Biol. Med. 3–4
(1999) 271.
(
2004) 274.
[
[
16] H.T. Nagasawa, H.R. Gutmann, M.A. Morgan, J. Biol. Chem. 234 (1958) 1600.
17] M.M.M. Saleem, M.T. Wilson, Biochem. J. 201 (1982) 433.