Mikrobiol. Z. 2022; 84(2):3-11.
Double Coordination Compounds of Fe(II)/Co(II)/Ni(II)/Cu(II)
1,10-Phenanthroline/2,2ʹ-Bipyridine Cations with Tartratogermanate(IV) Anions as Novel
Nonresistant Antimicrobial Agents
E.V. Afanasenko1, I.I. Seifullina1, O.E. Martsinko1, L.O. Konup2, M.M. Kyryk2
1Mechnikov Odesa National University
2 Dvorianska Str., Odesa, 65000, Ukraine
2NSC Tairov Institute of Viticulture and Winemaking, NAAS of Ukraine
27 40-year Victory Str., Tairove, 65496, Ukraine
Objective. To study the antimicrobial activity of double coordination compounds with 1,10-phenanthroline/2,2ʹ-bipyridine complexes of Fe(II)/Co(II)/Ni(II)/Cu(II) as cations and diff erent tartratogermanate(IV) anions, reveal the main factors of their effi ciency and establish relations between their composition, structure features, and biological properties. Methods. The developed synthesis method allowed us to obtain three diff erent tartratogermanate anions, which exist together in the solution and can be selectively recognized by the certain type of 1,10-phenanthroline/2,2ʹ-bipyridine cation. Th e antimicrobial activity of the compound was investigated by a rapid twofold dilution method in a standard liquid nutrient medium (Hottinger digestion) to determine the minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC). Results. Th e complex nature of studied compounds, synergism of their biologically active structural units, and the presence of diff erent types of intermolecular bonds result in the high antimicrobial activity against a wide range of microorganisms such as gram-positive Planococcus citreus, Microcoсcus luteus, Bacillus cereus, Staphylococcus aureus, Streptococcus lactis, and, in a less degree, gram-negative Escherichia coli and Agrobacterium tumefaciens. Compounds (1)—(8) show a high antimicrobial activity because all of them belong to the type of double coordination compounds and contain similar structural units. Nevertheless, complexes (1) (23.44 μg/mL), (3) (46.9 μg/mL), (4) (23.44 μg/mL), and (8) (46.9 μg/mL) turned out to be the most eff ective, while (6) (>500 μg/mL) and (7) (>500 μg/mL) are less productive. Complexes that have anions [Ge2(OH)(H2Tart)(μ-Tart)2]3- (1), (8) and [Ge2(OH)(HTart)(μ-Tart)2]4- (4) with free hydroxyl and carboxyl groups of the terminal tartaric acid are able to interact with metals in the enzymes of microorganisms and appear to be better antimicrobial drugs because they show lower inhibitory and bactericidal concentrations. Conclusions. Structural features such as the cation-anionic type of compounds, variability of intermolecular interactions, joint of diff erent biologically active units and free chelating groups in tartaric ligands lead to the combination of different action mechanisms and exclude the possibility of strain resistance.
Keywords: antimicrobials, coordination compounds, germanium(IV), 1,10-phenanthroline, 2,2ʹ-bipyridine, d-metal.
- Tegos GP, Hamblin MR. Disruptive innovations: new anti-infectives in the age of resistance, Curr Opin Pharmacol. 2013; 13:673—677. https://doi.org/10.1016/j.coph.2013.08.012
- World Health Organization (WHO). Antimicrobial Resistance. Global Report on Surveillance: Section 1 — Resistance to Antibacterial Drugs. http://apps.who.int/iris/bitstream/10665/112642/1/9789241564748_eng.pdf (Accessed May 12, 2016).
- Viganor L, Howe O, McCarron P, McCann M, Devereux M. The antibacterial activity of metal complexes containing 1,10-phenanthroline: potential as alternative therapeutics in the era of antibiotic resistance. Current Topics in Medicinal Chemistry. 2017; 11:1280—1302. https://doi.org/10.2174/1568026616666161003143333
- Lemire JA, Harrison JJ, Turner RJ. Antimicrobial activity of metals: mechanisms, molecular targets and applications. Nature Reviews Microbiology. 2013. https://doi.org/10.1038/nrmicro3028
- Arif R, Nayab PS, Ansari IA, Shahid M, Irfan M, Alam S, Abid M. Synthesis. Molecular Docking and DNA Binding Studies of Phthalimide-Based Copper(II) Complex: In Vitro Antibacterial, Hemolytic and Antioxidant Assessment. J Mol Struct. 2018; 1160:142—153. https://doi.org/10.1016/j.molstruc.2018.02.008
- Saravanan K, Elancheran R, Divakar S, Anand SAA, Ramanathan M, Kotoky J, Lokanath NK, Kabilan S. Design, Synthesis and Biological Evaluation of 2-(4-Phenylthiazol-2-Yl) Isoindoline-1,3-Dione Derivatives as Anti-Prostate Cancer Agents. Bioorg Med Chem Lett. 2017; 27:1199—1204. https://doi.org/10.1016/j.bmcl.2017.01.065
- Claudel M, Schwarte JV, Fromm KM. New Antimicrobial Strategies Based on Metal Complexes. Chemistry. 2020; 2:849—899. https://doi.org/10.3390/chemistry2040056
- Möhler JS, Kolmar T, Synnatschke K, Hergert M, Wilson LA, Ramu S, Elliott AG, Blaskovich MAT, Sidjabat HE, Paterson DL, et al. Enhancement of antibiotic-activity through complexation with metal ions — Combined ITC, NMR, enzymatic and biological studies. J Int Biochem. 2017; 167:134—141. https://doi.org/10.1016/j.jinorgbio.2016.11.028
- De Clercq E. Inhibition of HIV Infection by Bicyclams, Highly Potent and Specific CXCR4 Antagonists. Mol Pharmacol. 2000; 57:833—839.
- Karcz D, Matwijczuk A, Kaminski D, Creaven B, Ciszkowicz E, Lecka-Szlachta K, Starzak K. Structural Features of 1,3,4-Th iadiazole-Derived Ligands and Their Zn(II) and Cu(II) Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin. Int J Mol. Sci. 2020; 21:5735. https://doi.org/10.3390/ijms21165735
- Tarallo MB, Urquiola C, Monge A, Costa BP, Ribeiro RR, Costa-Filho AJ, Mercader RC, Pavan FR, Leite CQF, Torre MH, et al. Design of novel iron compounds as potential therapeutic agents against tuberculosis. J Inorg Biochem. 2010; 104:1164—1170. https://doi.org/10.1016/j.jinorgbio.2010.07.005
- Seifullina E, Martsinko E, Afanasenko E. [Design and synthesis of new homo- and heterometal coordination compounds of Germanium(IV) for preparation of low toxic drugs with a wide therapeutic action]. Visn Odes Nac Univ, Him. 2015; 4:617. Ukrainian.
- Shemonayeva CF, Matushkina MV, Kresun VI, Seifullina II. [Study of the effect of new (Mg, Li) tartratogermanates (IV) on aggressive-protective and conflict behavior of rats]. Modern approach of experimental and preclinical pharmacology. Kharkiv: 2021. P. 209—210. Ukrainian.
- Seifullina, II, Martsinko EE, Chebanenko EA, Afanasenko EV, Shishkina SV, D’yakonenko VV. Complex Formation Products in the GeO2—Tartaric Acid— CuCl2—1,10-Phenanthroline System: Syntheses and Structures. Rus J of Coord Chem. 2019; 45:496—504. https://doi.org/10.1134/S107032841906006X
- Seifullina I, Martsinko E, Chebanenko E, Afanasenko E, Dyakonenko V, Shishkina S. Supramolecular organization and structure of Cu(II), Ni(II), 2,2'-bipyridine cations and tartratogermanate anions. Polyhedron. 2019; 164:261—265. https://doi.org/10.1016/j.poly.2019.04.061
- Afanasenko E, Seifullina I, Martsinko E, Chebanenko E, Dyakonenko V, Shishkina S. Selective Recognition of Different Tartratogermanate Anions using 1,10-phenantroline Complexes of Fe(II), Co(II), Ni(II). ChemistrySelect. 2020; 5:2164—2167. https://doi.org/10.1002/slct.201904839
- Afanasenko E, Seifullina I, Martsinko E, Chebanenko E, Dyakonenko V, Shishkina S. Supramolecular Salts of Germanium (IV) with Tartaric Acid, Zinc and 1,10-Phenanthroline/2,2‘-Bipirydine: Synthesis, Structural Features and Selective Recognition. ChemistrySelect. 2021; 6:1—6. https://doi.org/10.1002/slct.202100363
- Chebanenko EA, Buchko OV, Afanasenko EV, Seifullina II, Martsinko EE. [Hydrogen bonds in the formation of copper(II) 1,10-phenanthroline hydroxycarboxylatogermanate crystals using hirshfeld surface analysis]. Visn Odes Nac Univ, Him. 2021; 5:85—93. Ukrainian. https://doi.org/10.18524/2304-0947.2021.1(77).226142
- Mertens RT, Parkin S, Awuah SG. Exploring six-coordinate germanium(IV)-diketonate complexes as anticancer agents. Inorg Chim Acta. 2020; 503:119375. https://doi.org/10.1016/j.ica.2019.119375
- Fulton JR. Germanium, Tin and Lead, Reference Module in Chemistry. Molecular Sciences and Chemical Engineering. 2020.
- Lukianchuk VD, Seifullina II, Martsinko OE, Shevchuk OO. Cerebroprotection by germanium coordination compounds in experimental acute global brain ischemia. Intern J Medicine and Medic Res. 2018; 4:60—66. https://doi.org/10.11603/ijmmr.2413-6077.2018.1.9253
- Michalek P, Kociova S, Smerkova K, Kruszynski R, et al. Synthesis and structural characterization of antimicrobial binuclear copper(II) coordination compounds bridged by hydroxy- and/or thiodipropionic acid. J Inorgan Biochem. 2018; 191:8—20. https://doi.org/10.1016/j.jinorgbio.2018.10.011
- Kaushal M, Indoria S, Lobana TS, Sood H, Arora DS, Hundal G, Smolinski VA, Kaur M, Jasinski JP. Synthesis, structures and antimicrobial activity of 5-nitro-salicylaldehy- de- thiosemicarbazonates of Zinc(II) coordinated to substituted bipyridines/phenanthrolines. Polyhedron. 2018; 148:9—21. https://doi.org/10.1016/j.poly.2018.03.027
- Chu H-Y, Fu H, Liu A, Wang P, Cao Y-L, Du A-F, Wang C-C. Two silver-based coordination polymers constructed from organic carboxylate acids and 4,4’-bipyridine-like bidentate ligands: synthesis, structure, and antimicrobial performances. Polyhedron. 2020; 188:114684. https://doi.org/10.1016/j.poly.2020.114684
- Kreofsky NW, Dillenburg MD, Villa EM, Fletcher JT. Ru(II) coordination compounds of N-N bidentate chelators with 1,2,3 triazole and isoquinoline subunits: Synthesis, spectroscopy and antimicrobial properties. Polyhedron. 2019; 177:114259. https://doi.org/10.1016/j.poly.2019.114259
- Hu Q, He M, Mei Y, Feng W, Jing S, Kong J, Zhang X. Sensitive and selective colorimetric assay of alkaline phosphatase activity with Cu(II)-phenanthroline complex. Talanta. 2016; 163:146—152. https://doi.org/10.1016/j.talanta.2016.10.097
- Gudzenko OV, Varbanets LD, Seifullina II, Chebanenko EA, Martsinko EE, Afanasenko EV. The influence of coordinative Tartrate and malatogermanate compounds on the activity of α-l-rhamnosidase preparations from Penicillium tardum, Eupenicillium erubescens and Cryptococcus albidus. Ukr Biochem J. 2020; 4:85—95. https://doi.org/10.15407/ubj92.04.085
- Kang DH, Siragusa GR. A rapid twofold dilution method for microbial enumeration and resuscitation of uninjured and sublethally injured bacteria. Lett Appl Microbiol. 2001; 33:232—236. https://doi.org/10.1046/j.1472-765x.2001.00988.x
- Tagg JR, McGiven AR. Assay system for bacteriocins. Appl Microbiol. 1971; 21:943. https://doi.org/10.1128/am.21.5.943-943.1971
- Ames BN, McCann Y, Yamasaki E. Methods for detection Carcinogens Mutagens with the Salmonella/Mammalian Microsome mutagenicity test. Mut Res. 1975; 31:347—364. https://doi.org/10.1016/0165-1161(75)90046-1
- Konup LO, Konup IP, Kotlyar SA. Antimicrobial activity of perfl uoroalkyl-benzo- and dibenzocrounethers. Odessa Medical Journal. 2002; 5.