Copper (II) complexes of sterically hindered o-diphenol derivatives: synthesis, characterization and microbiological studies

• Authors: Natalia Loginova , Tat’yana Koval’chuk , Rimma Zheldakova , Anna Chernyavskaya , Nikolai Osipovich , Gennady Glushonok , Henry Polozov , Victor Sorokin , Oleg Shadyro
• Languages of publication: EN

Abstracts

EN

Cu (II) complexes with the sterically hindered diphenol derivatives 3,5-di(tert-butyl)-1,2-benzenediol (I), 4,6-di(tert-butyl)-1,2,3-benzenetriol (II) and the sulfur-containing 4,6-di(tert-butyl)-3-(2-hydroxyethylsulfanyl)-1,2-benzenediol (III) and 2-[4,6-di(tert-butyl)-2,3-dihydroxyphenylsulfanyl]acetic acid (IV) have been synthesized and characterized by elemental analysis, TG/DTA, FT-IR, ESR, XPS, XPD and conductivity measurements. Compounds I–III can coordinate in their singly deprotonated forms and act as bidentate ligands. These compounds yield Cu (II) complexes of the stoichiometry Cu(L)2, which have square planar geometry (g| > g⊥ > ge). Unlike them, compound IV behaves as a terdentate ligand, and its complex Cu(LIV)2 has distorted octahedral geometry. According to ESR data, only the Cu(LII)2 complex contains a very small amount of phenoxyl radicals. Antimicrobial activities of these ligands and their respective Cu (II) complexes have been determined with respect to Gram-positive and Gram-negative bacteria, as well as on yeasts. Their phytotoxic properties against Chlorella vulgaris 157 were also examined.

Keywords

EN

Copper (II) complexes; sterically hindered o-diphenols; spectroscopic study; antimicrobial activities; phytotoxic properties

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2006
• Volume: 4
• Issue: 3
• Pages: 440-457

Dates

published

1 - 9 - 2006

online

1 - 9 - 2006

Contributors

author

Natalia Loginova

• Faculty of Chemistry, Belarusian State University, Minsk, 220050, Belarus

author

Tat’yana Koval’chuk

• Faculty of Chemistry, Belarusian State University, Minsk, 220050, Belarus

author

Rimma Zheldakova

• Department of Microbiology, Belarusian State University, Minsk, 220064, Belarus

author

Anna Chernyavskaya

• Faculty of Chemistry, Belarusian State University, Minsk, 220050, Belarus

author

Nikolai Osipovich

• Research Institute for Physico-Chemical Problems, Belarusian State University, Minsk, 220050, Belarus

author

Gennady Glushonok

• Research Institute for Physico-Chemical Problems, Belarusian State University, Minsk, 220050, Belarus

author

Henry Polozov

• Faculty of Chemistry, Belarusian State University, Minsk, 220050, Belarus

author

Victor Sorokin

• Faculty of Chemistry, Belarusian State University, Minsk, 220050, Belarus

author

Oleg Shadyro

• Faculty of Chemistry, Belarusian State University, Minsk, 220050, Belarus

References

• [1] M. Leeb: “A shot in the arm”, Nature, Vol. 431, (2004), pp. 892–893. http://dx.doi.org/10.1038/431892a[Crossref]
• [2] O.I. Shadyro, G.K. Glushonok, T.G. Glushonok, I.P. Edimecheva, A.G. Moroz, A.A. Sosnovskaya, I.L. Yurkova and G.I. Polozov: “Quinones as free-radical fragmentation inhibitors in biologically important molecules”, Free Radical Research, Vol. 36, (2002), pp. 859–867. http://dx.doi.org/10.1080/1071576021000005294[Crossref]
• [3] O.I. Shadyro, I.P. Edimecheva, G.K. Glushonok, N.I. Ostrovskaya, G.I. Polozov, H. Murase and T. Kagiya: “Effects of phenolic compounds on reactions involving various organic radicals”, Free Radical Research, Vol. 37, (2003), pp. 1087–1097. http://dx.doi.org/10.1080/10715760310001600417[Crossref]
• [4] G.N. Shilov, A.I. Balakleevskii, O.I. Shadyro and V.A. Timoshchuk: Patent No 182759 (RF), Official bulletin RF “Inventions, Trademarks and Industrial Designs”, Vol. 26, (1993) (In Russian).
• [5] D.K. Petrikevich, V.A. Timoshchuk, O.I. Shadyro, O.T. Andreeva, V.I. Votyakov and V.E. Zhelobkovich: “Synthesis and antiviral activities of some 3,5-di-tert-butyl-pyrocatechin derivatives”, Khim.-farm. zhurn., Vol. 12, (1995), pp. 32–34 (in Russian).
• [6] T.A. Mikhas’ko, B.V. Dubovik, O.I. Shadyro and G.I. Polozov: “Sterically hindered diphenols derivatives promising for nootropic drug design”, Meditsinskie novosti, Vol. 4, (2002), pp. 81–84 (in Russian).
• [7] O.I. Shadyro, V.A. Timoshchuk, G.I. Polozov, V.N. Povalishev, O.T. Andreeva and V.E. Zhelobkovich: “Synthesis and antiviral activities of sterically hindered phenolic derivatives of 1,3-benzoxathiolan-2-on”, Khim.-farm. zhurn., Vol. 7, (1999), pp. 25–27 (in Russian).
• [8] M.J. Laughton, B. Halliwell, P.J. Evans and J.R.S. Hoult: “Antioxidant and prooxidant action of the plant phenolics, quercetin, gossypol and myricetin”, Biochem. Pharmacol., Vol. 38, (1989), pp. 2859–2865. http://dx.doi.org/10.1016/0006-2952(89)90442-5[Crossref]
• [9] G. Cao, E. Sofic and R. Prior: “Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships”, Free Radical Biol. Med., Vol. 22, (1997), pp. 749–760. http://dx.doi.org/10.1016/S0891-5849(96)00351-6[Crossref]
• [10] D. Metodiewa, A.K. Jaiswal, N. Cenas, E. Dickancaité and J. Segura-Aguilar: “Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product”, Free Radical Biol. Med., Vol. 26, (1999), pp. 107–113. http://dx.doi.org/10.1016/S0891-5849(98)00167-1[Crossref]
• [11] N. Yamashita, H. Tanemura and S. Kawanishi: “Mechanism of oxidative DNA damage induced by quercetin in the presence of Cu(II)”, Mutat. Res., Vol. 425, (1999), pp. 107–115.
• [12] I. Morel, G. Lescoat, O. Cogrel, O. Sergent, N. Pasdeloup, P. Brissot, P. Cillard and J. Cillard: “Antioxidant and iron-chelating activities of the flavonoids cathechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures”, Biochem. Pharmacol., Vol. 45, (1993), pp. 13–19. http://dx.doi.org/10.1016/0006-2952(93)90371-3[Crossref]
• [13] M.C. Linder and C.A. Goode (Eds.): Biochemistry of Copper, New York, 1991.
• [14] M. Gielen and E.R.T. Tiekink (Eds.): Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. The Use of Metals in Medicine, Wiley-VCH, Weinheim, 2005.
• [15] M. Navarro, E.J. Cisneros-Fajardo, T. Lehmann, R.A. Sanchez-Delgado, R. Atencio, P. Silva, R. Lira and J.A. Urbina: “Toward a novel metal-based chemotherapy against tropical diseases: synthesis and characterization of new copper(II) and gold(I) clotrimazole and ketoconazole complexes and evaluation of their activity against Trypanosoma cruzi”, Inorg. Chem., Vol. 40, (2001), pp. 6879–6884. http://dx.doi.org/10.1021/ic0103087[Crossref]
• [16] P.R. Bontchev, I.N. Pantcheva, T. Todorov, D.R. Mehandjiev and N.S. Savov: “Complexation of the antihypertensive drug oxprenolol with copper(II)”, J. Inorg. Biochem., Vol. 83, (2001), pp. 25–30. http://dx.doi.org/10.1016/S0162-0134(00)00126-4[Crossref]
• [17] J.E. Weder, C.T. Dillon, T.W. Hambley, B.J. Kennedy, P.A. Lay, J. Ray Biffin, H.L. Regtop and N.M. Davies: “Copper complexes of non-steroidal anti-inflammatory drugs: an opportunity yet to be realized”, Coord. Chem. Rev., Vol. 232, (2002), pp. 95–126. http://dx.doi.org/10.1016/S0010-8545(02)00086-3[Crossref]
• [18] M. Di Vaira, C. Bazzicalupi, P. Orioli, L. Messori, B. Bruni and P. Zatta: “Clioquinol, a drug for Alzheimer’s disease specifically interfering with brain metal metabolism: structural characterization of its zinc(II) and copper(II) complexes”, Inorg. Chem., Vol. 43, (2004), pp. 3795–3797. http://dx.doi.org/10.1021/ic0494051[Crossref]
• [19] W. Szczepanik, P. Kaczmarek and M. Jeżowska-Bojczuk: “Identification of copper(II) binding sites in actinomycin D, a cytostatic drug - correlation of coordination with DNA damage”, J. Inorg. Biochem., Vol. 98, (2004), pp. 2141–2148. http://dx.doi.org/10.1016/j.jinorgbio.2004.09.023[Crossref]
• [20] S.J. Lippard and J.M. Berg (Eds.): Principles of Bioinorganic Chemistry, University Science Books, Mill Valley, CA, 1994.
• [21] N.P. Farrell (Ed.): Uses of Inorganic Chemistry in Medicine, RCS, 1999.
• [22] J.G.L. Baquial and J.R.J. Sorenson: “Down-regulation of NADPH-diaphorase (nitric oxide synthase) may account for the pharmacological activities of Cu(II)2(3,5-disopropylsalicylate)4”, J. Inorg. Biochem., Vol. 60, (1995), pp. 133–148. http://dx.doi.org/10.1016/0162-0134(95)00008-C[Crossref]
• [23] F.T. Greenaway, J.J. Hahn, N. Xi and J.R.J. Sorenson: “Interaction of Cu(II) 3,5-diisopropylsalicylate with human serum albumin - an evaluation of spectroscopic data”, Biometals, Vol. 11, (1998), pp. 21–26. http://dx.doi.org/10.1023/A:1009201206216[Crossref]
• [24] U. Sandbhor, S. Padhye, D. Billington, D. Rathbone, S. Franzblau, C.E. Anson and A.K. Powell: “Metal complexes of carboxamidrazone analogs as antitubercular agents: 1. Synthesis, X-ray crystal-structures, spectroscopic properties and antimycobacterial activity against Mycobacterium tuberculosis H37Rv”, J. Inorg. Biochem., Vol. 90, (2002), pp. 127–136. http://dx.doi.org/10.1016/S0162-0134(02)00406-3[Crossref]
• [25] M. Navarro, E.J. Cisneros-Fajardo, M. Fernandez-Mestre, D. Arrieche and E. Marchan: “Synthesis, characterization, DNA binding study and biological activity against Leishmania mexicana of [Cu(dppz)2]BF4”, J. Inorg. Biochem., Vol. 97, (2003), pp. 364–369. http://dx.doi.org/10.1016/S0162-0134(03)00290-3[Crossref]
• [26] F. Blasko, L. Perelló, J. Latorre, J. Borrás and S. Garciá-Granda: “Cobalt(II), Nickel(II), and Copper(II) complexes of sulfanilamide derivatives: Synthesis, spectroscopic studies, and antibacterial activity. Crystal structure of [Co(sulfacetamide)2(NCS)2]”, J. Inorg. Biochem., Vol. 61, (1996), pp. 143–154. http://dx.doi.org/10.1016/0162-0134(95)00053-4[Crossref]
• [27] M. Ruiz, L. Perelló, J. Server-Carrió, R. Ortiz, S. Garciá-Granda, M.R. Diaz and E. Cantón: “Cinoxacin complexes with divalent metal ions. Spectroscopic characterization. Crystal structure of a new dinuclear Cd(II) complex having two chelate-bridging carboxylate groups. Antibacterial studies”, J. Inorg. Biochem., Vol. 69, (1998), pp. 231–239. http://dx.doi.org/10.1016/S0162-0134(97)10028-9[Crossref]
• [28] B. Simó, L. Perelló, R. Ortiz, A. Castińeiras, J. Lattore and E. Cantón: “Interactions of metal ions with a 2,4-diaminopyrimidine derivative (trimethoprim): Antibacterial studies”, J. Inorg. Biochem., Vol. 81, (2000), pp. 275–283. http://dx.doi.org/10.1016/S0162-0134(00)00118-5[Crossref]
• [29] P. Deschamps, P.P. Kulkarni, M. Gautam-Basak and B. Sarkara: “The saga of copper(II)-L-histidine”, Coord. Chem. Rev., Vol. 249, (2005), pp. 895–909. http://dx.doi.org/10.1016/j.ccr.2004.09.013[Crossref]
• [30] N.V. Loginova, A.A. Chernyavskaya, G.I. Polozov, T.V. Koval’chuk, E.V. Bondarenko, N.P Osipovich, A.A. Sheryakov and O.I. Shadyro: “Silver (I) interaction and complexation with sterically hindered sulfur-containing diphenol derivatives”, Polyhedron, Vol. 24, (2005), pp. 611–618. http://dx.doi.org/10.1016/j.poly.2005.01.007[Crossref]
• [31] K. Nomiya, A. Yoshizawa, K. Tsukagoshi, N.C. Kasuga, S. Hirakawa and J. Watanabe: “Synthesis and structural characterization of silver(I), aluminium(III) and cobalt(II) complexes with 4-isopropyltropolone (hinokitiol) showing noteworthy biological activities. Action of silver(I)-oxygen bonding complexes on the antimicrobial activities”, J. Inorg. Biochem., Vol. 98, (2004), pp. 46–60. http://dx.doi.org/10.1016/j.jinorgbio.2003.07.002[Crossref]
• [32] A.M. Lee and S.F. Singleton: “Inhibition of the Escherichia coli RecA protein: zinc(II), copper(II) and mercury(II) trap RecA as inactive aggregates”, J. Inorg. Biochem., Vol. 98, (2004), pp. 1981–1986. http://dx.doi.org/10.1016/j.jinorgbio.2004.08.018[Crossref]
• [33] T.V. Kovalchuk and G.A. Ksendzova: “Complexation of Cu(II), Co(II), Ni(II), Zn(II) ions with derivatives of sterically hindered aminophenols”, Proceedings of The National Academy of Sciences of Belarus, Chem. Ser., Vol. 5, (2005), pp. 51–53 (in Russian).
• [34] T.V. Koval’chuk, N.V. Loginova, N.P. Osipovich, G.K. Glushonok, V.L. Sorokin, G.A. Ksendzova and L.S. Ivashkevich: “Complexation of Cu(II), Co(II), Ni(II), Zn(II) with derivatives of sterically hindered diphenols and aminophenols”, Sviridov readings, Vol. 2, (2005), pp. 122–127 (in Russian).
• [35] C.N. Verani: Rational synthesis and characterization of paramagnetic heteropolynuclear systems containing [MA-MB-MC], [MA-MB]2 and [M1-2(·R)1-2-3] cores, Thesis (PhD), Ruhr-Universität Bochum, 2000.
• [36] L.A. Maslovskaya, D.K. Petrikevch, V.A. Timoshchuk and O.I. Shadyro: “Synthesis and antioxidant properties of some alkylated pyrocatechin derivatives”, Zhurn. obshchei khimii, Vol. 66, (1996), pp. 1893–1898 (in Russian).
• [37] L.A. Maslovskaya, D.K. Petrikevch, V.A. Timoshchuk and O.I. Shadyro: “Synthesis and antioxidant activity of sulfur-containing 3,5-di-tert-butylpyrocatechin derivatives”, Zhurn. obshchei khimii, Vol. 66, (1996), pp. 1899–1902 (in Russian).
• [38] W. Flaig, T. Ploetz and H. Biergans: “Bildung und Reaktionen einiger Hydroxyl-Chinone”, Lieb. Ann. Chem., Vol. 597, (1955), pp. 196–213.
• [39] I.S. Belostotskaya, N.L. Komissarova, E.V. Dzhuaryan and V.V. Ershov: “Identification of some alkyl-pyrocatechin by thin-layer chromatography on silica”, Izv. AN SSSR, Ser. Chim., (1971), pp. 2816–2818 (in Russian).
• [40] J.S. Thompson and J.C. Calabrese: “Copper-catechol chemistry. Synthesis, spectroscopy, and structure of bis(3,5-di-tert-butyl-o-semiquinato)copper(II)”, J. Am. Chem. Soc., Vol. 108, (1986), pp. 1903–1907. http://dx.doi.org/10.1021/ja00268a031[Crossref]
• [41] G.N. Pershin (Ed.): Metody Experimental’noi Khimioterapii, Meditsina, Moskwa, 1971 (in Russian).
• [42] V.I. Bilai (Ed.): Metody Experimental’noi Mikologii, Nauk. dumka, Kiev, 1982 (in Russian).
• [43] W.J. Geary: “The use of conductivity measurements in organic solvents for the characterization of coordination compounds”, Coord. Chem. Rev., Vol. 7, (1971), pp. 81–122. http://dx.doi.org/10.1016/S0010-8545(00)80009-0[Crossref]
• [44] Y.N. Kukushkin, V.F. Budakova and G.N. Sedova (Eds.): Termicheskie Prevrashcheniya Koordinatsionnykh Soedinenii v Tverdoi Faze, LGU, Leningrad, 1981 (in Russian).
• [45] V.A. Logvinenko (Ed.): Termicheskii Analiz Koordinatsionnykh Soedinenii i Klatratov, Nauka, Novosibirsk, 1982 (in Russian).
• [46] K. Nakamoto (Ed.): Infrared and Raman Spectra of Inorganic and Coordination Compounds, John Wiley & Sons, Inc., New York, 1986.
• [47] A.I. Poddel’sky, V.K. Cherkasov, G.K. Fukin, M.P. Bubnov, L.G. Abakumova and G.A. Abakumov: “New four-and five-coordinated complexes of cobalt with sterically hindered o-iminobenzoquinone ligands: synthesis and structure”, Inorg. Chem. Acta, Vol. 357, (2004), pp. 3632–3640. http://dx.doi.org/10.1016/j.ica.2004.04.013[Crossref]
• [48] A.A. Tak, F. Arjmand and S. Tabassum: “Synthesis, characterization, electrochemistry and kinetics of CTDNA binding of a bis ciprofloxacin borate copper(II) complex”, Transit. Met. Chem., Vol. 27, (2002), pp. 741–747. http://dx.doi.org/10.1023/A:1020365522701[Crossref]
• [49] B.J. Hathaway and D.E. Billing: “The electronic properties and stereochemistry of mono-nuclear complexes of the copper(II) ion”, Coord. Chem. Rev., Vol. 5, (1970), pp. 143–207. http://dx.doi.org/10.1016/S0010-8545(00)80135-6[Crossref]
• [50] M. Ruf, B. Noll, M. Groner, G.T. Yee and C.G. Pierpont: “Pocket semiquinonate complexes of cobalt(II), copper(II), and zinc(II) prepared with the hydrotris(cumenylmethylpyrazolyl)borate ligand”, Inorg. Chem., Vol. 36, (1997), pp. 4860–4865. http://dx.doi.org/10.1021/ic970244t[Crossref]
• [51] G. Speier, J. Csihony, A.M. Whalen and C.G. Pierpont: “Studies on aerobic reactions of ammonia/3,5-di-tert-butylcatechol Schiff-base condensation products with copper, copper(I), and copper(II). Strong copper(II)-radical ferromagnetic exchange and observations on a unique N-N coupling reaction”, Inorg. Chem., Vol. 35, (1996), pp. 3519–3524. http://dx.doi.org/10.1021/ic950805l[Crossref]
• [52] S. Katawa, S. Kitagawa, H. Kumagai, Ch. Kudo and M. Katada: “Rational design of a novel intercalation system. Layer-gap control of crystalline coordination polymers, {[Cu(CA)(H2O)m](G)}n (m = 2, G = 2,5-dimethylpyrazine and phenazine; m = 1, G = 1,2,3,4,6,7,8,9-octahydrophenazine)”, Inorg. Chem., Vol. 35, (1996), pp. 4449–4461. http://dx.doi.org/10.1021/ic9603520[Crossref]
• [53] D. Kivelson and R. Neiman: “ESR studies on the bonding in copper complexes”, J. Chem. Phys., Vol. 35, (1961), pp. 149–155. http://dx.doi.org/10.1063/1.1731880[Crossref]
• [54] S. Mandal, G. Das, R. Singh, R. Shukla and P.K. Bharadwaj: “Synthesis and studies of Cu (II)-thiolato complexes: bioinorganic perspectives”, Coord. Chem. Rev., Vol. 160, (1997), pp. 191–235. http://dx.doi.org/10.1016/S0010-8545(96)01342-2[Crossref]
• [55] A.A. Chernyavskaya and V.N. Povalishev: “Complexation and redox interaction of silver(I) with sterically hindered diphenols and aminophenols”, Proceedings of The National Academy of Sciences of Belarus, Chem. Ser., Vol. 5, (2005), pp. 132–134 (in Russian).
• [56] P. Chaudhuri, C.N. Verani, E. Bill, E. Bothe, T. Weyhermuller and K. Wieghardt: “Electronic structure of [Bis(o-iminobenzosemiquinonato)metal complexes (Cu, Ni, Pd). The art of establishing physical oxidation states in transition metal complexes”, J. Am. Chem. Soc., Vol. 123, (2001), pp. 2213–2223. http://dx.doi.org/10.1021/ja003831d[Crossref]
• [57] V.I. Nefedov (Ed.): Rentgenoelektronnaya Spektroskopiya Khimicheskikh Soedinenii, Khimiya, Moskwa, 1984 (in Russian).
• [58] T.J. Beveridge: “Ultrastructure, chemistry, and function of the bacterial wall”, Int. Rev. Cytol., Vol. 72, (1981), pp. 229–317. http://dx.doi.org/10.1016/S0074-7696(08)61198-5[Crossref]
• [59] J.J. Perry, J.T. Staley and S. Lory et al.: Microbial Life, Sinauer Associates, Inc.: Sunderland, MA, 2002, pp. 61–100.
• [60] W. Jiang, A. Saxena, B. Song, B.B. Ward, T.J. Beveridge and S.C.B. Myneni: “Elucidation of functional groups on Gram-positive and Gram-negative bacterial surfaces using infrared spectroscopy”, Langmuir, Vol. 20, (2004), pp. 11433–11442. http://dx.doi.org/10.1021/la049043+[Crossref]
• [61] N.P. Elinov (Ed.): Khimicheskaya Microbiologiya, Vyssh. Shk., Moskwa, 1989 (in Russian).
• [62] R.P. John, A. Sreekanth, V. Rajakannan, T.A. Ajith and M.R. Prathapachandra Kurup: “New copper(II) complexes of 2-hydroxyacetophenone N(4)-substituted thiosemicarbazones and polypyridyl co-ligands: structural, electrochemical and antimicrobial studies”, Polyhedron, Vol. 23, (2004), pp. 2549–2559. http://dx.doi.org/10.1016/j.poly.2004.09.004

Identifiers

DOI

10.2478/s11532-006-0025-1