Vol. 5, 2020
Biochemistry
ANTIMICROBIAL ACTIVITY AND REDOX PROPERTY OF Ni(II) COMPLEXES WITH ORTHO- AND META-DIPHENOL DERIVATIVES
K.A. Nabebina, N.V. Loginova, T.V. Kovalchuk-Rabchinskaya, G.A. Ksendzova, N.P. Osipovich
Pages: 64-67
DOI: 10.37392/RapProc.2020.15
Abstract | References | Full Text (PDF)
The redox-activity of novel bioactive Ni(II) complexes with ortho- and meta-diphenols was investigated. Amorphous water insoluble complexes with general formula NiL2 were synthesized according to the authorial method. It was found that the complexes are highly lipophilic (lgPow= 2.5÷3.5), stable in water-organic media (stability constants logarithm lgβ=15-18) and have a non-electrolyte nature. Voltammetry analysis was used to determine the first oxidation peak (Epa1, V) as a thermodynamic criterion of compounds’ reducing ability. It was found that complexes with ortho-diphenol derivatives possess stronger reducing ability then the complexes with meta-diphenol. Antimicrobial activity of Ni(II) complexes against Mycobacterium smegmatis and Candida albicans were evaluated. Intricate dependence between reducing ability and bactericidal activity was found.
- B. J. Marais, “The global tuberculosis situation and the inexorable rise of drug-resistant disease,” Adv. Drug Deliv. Rev., vol. 102, pp. 3 – 9, Jul. 2016.
DOI: 10.1016/j.addr.2016.01.021
PMid: 26855302 - M. S. Jassal, W. R. Bishal, “Extensively drug-resistant tuberculosis,” Lancet Infect. Dis., vol. 9, no. 1, pp. 19 – 30, Jan. 2009.
DOI: 10.1016/S1473-3099(08)70260-3
PMid: 18990610 - G. McDonnell, A. D. Russell, “Antiseptics and disinfectants: activity, action, and resistance,” Clin. Microbiol. Rev., vol. 12, no. 1, pp. 147 – 179, Jan. 1999.
DOI: 10.1128/CMR.12.1.147
PMid: 9880479
PMCid: PMC88911 - P. J. O’Brien, “Molecular mechanisms of quinone cytotoxicity,” Chem. Biol. Interact., vol. 80, no. 1, pp. 1 – 41, 1991.
DOI: 10.1016/0009-2797(91)90029-7
PMid: 1913977 - J. Cohen, “Approval of novel TB drug celebrated–with restraint,” Science, vol. 339, no. 6116, pp. 130, Jan. 2013.
DOI: 10.1126/science.339.6116.130
PMid: 23307714 - D. T. Hoagland, J. Liu, R. B. Lee, R. E. Lee, “New agents for the treatment of drug-resistant Mycobacterium tuberculosis,” Adv. Drug Deliv. Rev., vol. 102, pp. 55 – 72, Jul. 2016.
DOI: 10.1016/j.addr.2016.04.026
PMid: 27151308
PMCid: PMC4903924 - K. Pethe et al., “Discovery of Q203, a potent clinical candidate for the treatment of tuberculosis,” Nat. Med., vol. 19, no. 9, pp. 1157 – 1160, Sep. 2013.
DOI: 10.1038/nm.3262
PMid: 23913123 - N. V. Loginova et al., “Redox-active antimicrobial metal complexes with sterically hindered o-diphenol and o-aminophenol derivatives,” in Biometals: Molecular Structures, Binding Properties and Applications , G. Blanc, D. Moreau, Eds., 1st ed., New York (NY), USA: Nova Science Publisher’s, 2010, ch. 3, pp. 59 – 90.
- N. V. Loginova et al., “Pharmacologically active of benzene derivatives of synthesis, complexation with biometals and biological evaluation sterically hindered 1,2-dihydroxybenzene and o-aminophenol derivatives,” in Benzene and its derivatives: New Uses and Impacts on Environment and Human Health , G. Tranfo, Eds., 1st ed., New York (NY), USA: Nova Science Publisher’s, 2012, ch. 2, pp. 23 – 68.
- N. V. Loginova et al., “Redox-active silver(I) complexes with sterically hindered 1,2-dihydroxybenzene derivatives: reduction of cytochrome c and antimicrobial activity,” in Cytochromes b and c: Biochemical Properties, Biological Functions and Electrochemical Analysis , R. Thom, Eds., 1st ed., New York (NY), USA: Nova Science Publisher’s, 2014, ch. 5, pp. 121 – 171.
- N. V. Loginova et al., “Redox-active metal complexes with cycloaminomethyl derivatives of diphenols: antibacterial and SOD-like activity, reduction of cytochrome c,” in Antibacterials: Synthesis, Properties and Biological Activities, E. Collins, Eds., 1st ed., New York (NY), USA: Nova Science Publisher’s, 2017, ch. 6, pp. 143 – 180.
- A. B. G. Lansdown, “Silver in health care: antimicrobial effects and safety in use,” in Biofunctional Textiles and the Skin. Curr Probl Dermatol., vol. 33, U. C. Hipler, P. Elsner, Eds., 1st ed., Basel, Switzerland: Karger, 2006, pp. 17 – 34.
DOI: 10.1159/000093928 - J. C. Fontecilla-Camps, “Biological Nickel,” in Bioinorganic Chemistry: Trace Element Evolution from Anaerobes to Aerobes , R. J. P. Williams, Eds., 1st ed., Berlin Heidelberg, Germany: Springer-Verlag, 1998, ch. 1, pp. 1 – 30.
Retrieved from: http://library.lol/main/C23907F553832C6853F83F576EC92BA5
Retrieved on: Jan. 11, 2020 - H. I. Harbatsevich et al., “Nickel(II) complexes with ‘non innocent’ ligands – cycloaminomethyl derivatives of 1,2-dihydroxybenzene: sod-like and antimicrobial activity,” Radiat. Appl., vol. 2, no. 2, pp. 129 – 133, Jan. 2017.
DOI: 10.21175/RadJ.2017.02.027 - В. А. Климова, Основные микрометоды анализа органических соединений, 2-й изд., Москва, Россия: Химия, 1975, c. 224. (V. A. Klimova, The basis of micro methods of organic compounds analysis, 2nd ed., Moscow, Russia: Chemistry, 1975, p. 224.)
Retrieved from: http://libgen.rs/book/index.php?md5=2DCEF5ED5CEE7BD9F0987A29254DA260
Retrieved on: Nov. 29, 2019 - N. V. Loginova et al., “Redox-active metal(II) complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c,” Polyhedron, vol. 29, no. 6, pp. 1646 – 1652, Apr. 2010.
DOI: 10.1016/j.poly.2010.02.007 - N. V. Loginova et al., “Redox-active metal(II) complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part II. Metal(II) complexes of o-diphenol derivatives of thioglycolic acid,” Polyhedron, vol. 30, no. 15, pp. 2581 – 2591, Sep. 2011.
DOI: 10.1016/j.poly.2011.07.008 - N. V. Loginova et al., “Redox-active metal(II) complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part III. Copper(II) complexes of cycloaminomethyl derivatives of o-diphenols,” Polyhedron, vol. 57, pp. 39 – 46, Jul. 2013.
DOI: 10.1016/j.poly.2013.04.015 - N. V. Loginova et al., “Redox-active metal complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part IV. Silver(I) complexes with hydrazone and thiosemicarbazone derivatives of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde,” Polyhedron, vol. 88, pp. 125 – 137, Mar. 2015.
DOI: 10.1016/j.poly.2014.12.014 - A. Leo, C. Hancsh, D. Elkins, “Partition coefficients and their uses,” Chem. Rev., vol. 71, no. 6. pp. 525 – 616, Dec. 1971.
DOI: 10.1021/cr60274a001 - N. V. Loginova et al., “Interaction of cytochrome c with redox-active dihydroxybenzene-containing antimicrobials: application to antioxidant characterization,” in Cytochrome C: Roles and Therapeutic Implications, N. Arias, Eds., New York (NY), USA: Nova Science Publisher’s, 2019, ch. 2, pp. 51 – 87.
- К. А. Набебина, Н. В. Логинова, Т. В. Ковальчук-Рабчинская, Г. А. Ксендзова, Н. П. Осипович, “Синтез и свойства редокс-активных комплексов Ni(II) с производными дигидроксибензола,” Свиридовские чтения : сборник статей, нo. 15, cтр. 184 – 193, 2019. (K. A. Nabebina, N. V. Loginova, T. V. Koval’chuk-Rabchinskaya, G. A. Ksendzova, N. P. Osipovich, “Synthes and properties of redox active Ni(II) complexes with dihydroxybenzene derivatives” Sviridov Readings: a collection of paper, no. 15, pp. 184 – 193, 2019.)
Retrieved from: https://elib.bsu.by/handle/123456789/237518
Retrieved on: Sep. 20, 2019 - D. Amsterdam, Antibiotics in Laboratory Medicine, 6th ed., Philadelphia (PA), USA: Lippincott Williams Wilkins, 2014.
Retrieved from: http://library.lol/main/C93B8401A35AE671BFE016F06AE8C51F
Retrieved on: Sep. 13, 2019 - W. J. Geary, “The use of conductivity measurements in organic solvents for the characterisation of coordination compounds,” Coord. Chem. Rev ., vol. 7, no. 1, pp. 81 – 122, Oct. 1971.
DOI: 10.1016/S0010-8545(00)80009-0 - M. J. Waring, “Lipophilicity in drug discovery,” Expert Opin. Drug Discov., vol. 5, no. 3, pp. 235 – 248, Mar. 2010.
DOI: 10.1517/17460441003605098
PMid: 22823020 - F. Scholz, Electroanalytical Methods: Guide to Experiments and Applications, vol. 1, 2nd ed., Berlin, Germany: Springer-Verlag, 2010.
Retrieved from: http://library.lol/main/9D15B8E76FB88030D73BBEE0C7649607
Retrieved on: Feb. 10, 2020 - G. Lancini, F. Parenti, Antibiotics: An Integrated View, 1st ed., New York (NY), USA: Springer-Verlag, 1982.
Retrieved from: http://library.lol/main/28AB26730E73E50010156D3FC04B3BB7
Retrieved on: Dec. 25, 2019