Synthesis, Structural Elucidation and Antimicrobial Activity of Metal (II) Polypyridyl Complexes of 2-Amino-4-(Methylthio) Butanoic Acid

A. O. Rajee; H. F. Babamale; A. A. Aliyu; A. Lawal; S. O. Ayinla; W. A. Osunniran; A. A. Aliyu; I. Musa

doi:10.53704/fujnas.v9i1.322

Authors

A. O. Rajee Department of Chemistry, University of Ilorin, Ilorin, Nigeria.
H. F. Babamale Department of Industrial Chemistry, University of Ilorin, Ilorin, Nigeria
A. A. Aliyu Department of Pure and Industrial Chemistry, Kogi State University, Anyigba, Kogi, Nigeria.
A. Lawal Department of Chemistry, University of Ilorin, Ilorin, Nigeria.
S. O. Ayinla Department of Applied Sciences, Al-Hikmah University, Ilorin, Kwara, Nigeria.
W. A. Osunniran Department of Chemical, Geological and Physical Sciences, Kwara State University, Malete,
A. A. Aliyu Department of Chemistry, faculty of Science, Nigerian Defense Academy, Kaduna, Nigeria
I. Musa Department of Chemistry, faculty of Science, Nigerian Defense Academy, Kaduna, Nigeria

DOI:

https://doi.org/10.53704/fujnas.v9i1.322

Abstract

The interaction of selected biometals with dinitrogen donor ligand, 1,10-phennathroline (phen) and amino acid, 2-amino-4-(methylthio)butanoic acid (methionine; met) resulted in isolation of three mononuclear complexes. The prepared complexes were characterized by diverse techniques including elemental and spectroscopic analysis. From the analytical and spectral data, octahedral geometry was proposed to the synthesized metal (II) complexes. Bonding of the metal ion through N- and O- donor atoms of the ligands is revealed by infrared studies. The compounds showed moderate solubility in distilled water and in some common organic solvents. In vivo evaluation of the antimicrobial activities of the metal complexes showed improved inhibitory activity against some micro-organisms as compared to the ligands, with Co(II) and Cu(II) complexes showing the highest activities against the fungi.

Keywords: antimicrobial; mixed ligands; amino acid; polypyridyl

References

Abdulrahman,F. I., Akan,J.C., Sodipo,O. A. &Onyeyilli,P. A. (2010). Effect of aqueous root bark extract of Vitexdominasweet on hematological paramenters in rats. Journal of American of Science. 6, 8-12.

Alsheikh-Ali,A. A., Kuvin,J. T. &Karas,R. H. (2004). Risk of adverse events with fibrates. American. Journal of Cardiology, 94,935–8.

Anaga,A. O.& Oparah,N. Q. (2009). Investigation of the methanol root extract of Cochlospermum planchonii for pharmacological activities in vitro and in vivo. Pharmaceautical Biology, 47, 1027–1034.

Arranz,S., Chiva-Blanch,G., Valderas-Martínez, P., Medina-Remón, A., Lamuela-Raventós,R. M. &Estruch,R. (2012). Wine, beer, alcohol and polyphenols on cardiovascular disease and cancer. Nutrients 4, 759–781.

Ashafa,A. O. T. & Yakubu,M. T. (2009). Effect of aqueous leaf extract from the leaves of Chrysocoma ciliate Lonsome biochemical parameters of Wistar rats. African Journal of Biotechnology, 8, 1425-1430.

Benoit-Vical,F., Valentin,A., Mallié,M., Bastide,J. M. &Bessière,J. M. (2001). Antiplasmodial activity of Cochlospermum planchonii and C. tinctorium tubercle essential oils. Journal of Essential Oil Research, 13, 65-67.

Blench, R. &Dendo,M. (2007). Hausa names for plants and trees. Draft prepared for comment only 2 (Ed.),United Kingdom, Cambridge.

Bren, U., Mojzer, E.B., Hrncie, M.K., Skerget, M. &Knez, Z. (2016). Polyphenols: Extraction methods, antioxidative actions, bioavailability andanticancinogenic effects. Molecules,21, 901; doi:10.3390/molecules21070901.

Deori,M., Boruah,D. C., Devi,D. &Devi,R. (2014). Antioxidant and antigenotoxic effects of pupae of the muga silk worm Antheraeaassamensis. Food Bioscience, 5, 108 114.doi:10.1016/j.fbio.2013.12.001.

Espín, J. C., García-Conesa,M. T. &Tomás-Barberán,F. A. (2007). Nutraceuticals: facts and fiction. Phytochemistry, 68, 2986–3008.

Ezeja,M. I. & Anaga,A. O. (2010). Anti-diarrhoeal activities of the methanolic root bark extract of Cochlospermum planchonii (Hook f). International Journal of Toxicology and Pharmacology Research, 2, 40-45.

Friedwald,W. T., Levy,R. J. & Fredrickson,D. S. (1972). Estimation of concentration of the preparative ultracentrifuge, Clinical Chemistry, 18, 499-509.

Geetha,G., Kalavalarasariel,G. P. &Sankar,V. (2011). Antidiabetic effect of Achyranthes rubrofusca leaf extracts on alloxan induced diabetic rats. Pakistan Journal of Pharmaceutical Sciences, 24(2), 193-199.

Grassi,D., Aggio,A., Onori,L., Croce,G., Tiberti,S., Ferri, C., Ferri, L. &Desideri,G. (2008).Tea, flavonoids and NO-mediated vascular reactivity, Journal of Nutrition, 138, 1554S-1560S.

Grassi,D., Desideri,G., Tiberti,S. &Ferri,C.(2009a). Oxidative stress, endothelial dysfunction and prevention of cardiovascular diseases, AgroFOOD Industry Ii-tech, 20, 76-79.

Grassi,D., Desideri,G., Croce,G., Tiberti,S., Aggio,A. &Ferri,C. (2009b). Flavonoids, vascular function and cardiovascular protection. Curr. Pharm. Des, 15, 1072-1084.

Grundy,S. M., Cleeman, J. I., Merz, B. C. N., Brewer,H. B., Clark,L. T., Hunninghake, D. B., Pasternak,R. C., Smith,S. C.&Stone,N. J. (2004). Implications of recent clinical trials for the National Cholesterol Education Program Adult Treatment Panel III guidelines.Circulations110(2), 227-239.DOI:10.1161/01.CIR.0000133317.49796.0E

Huang,P. L. (2009). A comprehensive definition for metabolic syndrome. Disease Models and Mechanisms,2:231-237; DOI:10.1242/dmm.001180.

Isah,Y., Ndukwe,I. G. &Ayo,R. G. (2013). Phytochemical and antimicrobial analyses of stem-leaf of Cochlospermum planchonii. Journal of Medicinal Plant and Herbal Theraphy Research,1, 13-17.

Jamuna,D. &Rajkumar, J. (2014). Effect of Ambrex(A Herbal Formulation) on Hematological variables inhyperlipidemic Rats. Pakistan Journal of Biological Sciences, 17, 740-743.

Jung, U. J., Lee,M. K., Park,Y. B., Kang,M. A. & Choi,M. S. (2006). Effect of citrus flavonoids on lipidmetabolism and glucose-regulating enzyme mRNA levels in type-2 diabetic mice. International Journal of Biochemistryand Cell Biology, 38, 1134–1145.

Kaur, G. &Meena,C. (2013). Evaluation of anti-hyperlipidemic potential of combinatorial extract of Curcumin, Piperine, and Quercetin in triton-induced hyperlipidemia in rats. Science. International 1 (3), 57-63. Kwaan,H. C. (1992). Changes in blood coagulation, platelet function and plasminogen plasmin system in diabetes,Diabetics41(2), 32-35.

Keshetty, V., Pabba, S., Gudipati, R., Kandukuri,J. M.&Allenki,V. (2009). Antihyperlipidemic Activity of methanolic extract of Garlic (Allium sativum L.) in Triton X-100 induced hyperlipidemic rats. Journal Pharmacy Researcgh, 2(5), 777–80.

Kumar,V., Khan,M. M., Khanna,A. K., Khanna,A. K., Singh,R., Singh,S., Chander,R., Mahdi, F, Sexana,J.K.&Singh,R. K. (2010). Lipid lowering activity of Anthocephalus indicus root in hyperlipidemic rats. Evidence Based Complementary Alternative Medicine, 7(3):317–322, DOI:10.1093/ecam/nen001.

Lee,C. Y., Kim,K. C., Park,H. W., Song,J. H. &Lee,C. H. (2004). Rheological properties of erythrocytes from male hypercholesterolemia. Microvascular Research, 67: 133-138.

Lichtenstein,A. H., Appel,L. J., Brands,M., Carnethon,M., Daniels,S., Franch,H. A., Franklin,B., Kris-Etherton,P., Harris,W. S., Howard,B., Karanja, N., Lefevre,M.,Rudel, L., Sacks,F., Van Horn,L., Winston,M. &Wylie-Rosett,J. (2006). Diet and lifestyle recommendations revision 2006 -a scientific statement from the Am Hrt Association Nutrition Committee. Circulation 114(1), 82-96.

Mehta,L. K., Balaraman,R., Amin,A. H., Bafna,P. A. & Gulati,O. D. (2003). Effect of fruits of Moringa oleiferaon the lipid profile of normal and hypercholesterolaemic rabbits. Journal of Ethnopharmarcy, 86, 191-5.

Miller,M. (2009). Dyslipidemia and cardiovascular risk: the importance of early prevention. QJM, 102(9),657–667.

Nafiu,M. O., Akanji,M. A. &Yakubu,M. T. (2011). Phytochemical and mineral constituents of Cochlospermum planchonii (Hook. Ef. x Planch) Root. Bioresearch Bulletin, 5, 51-56.

Program NCE. (2002). Third report of the National Cholesterol Education Program (NCEP) expert panel on detection, evaluation, and treatment of high blood cholesterol in adults (adult treatment panel III) final report.

Rajput,M. S., Balekar,N. & Jain,D. K. (2014). Lagenaria siceraria ameliorates athero-matous lesions by modulating HMG-CoA reductase and lipoprotein lipaseenzymes activity in hypercholesterolemic rats. Journalof Acute Diseases, 3(1), 14–21.

Talayero, B. G. & Sacks,F. M. (2011). The role of triglycerides in atherosclerosis, Current Cardiology Report, 13(6), 544–552.

Tangney, C. & Rasmussen, H. E.(2013). Polyphenols, inflammation, and cardiovascular disease. CurrentAtherosclerosisReport, 15(5), 324.

Thanga, K., Kumari S, Packia, L. M., Muthukumarasamy, S. & Mohan VR. (2013). Antihyperlipidemic effect of ethanol extract of whole plant of Canscora perfoliata Lam in Triton X-100 induced hyperlipidemic rats. International Journal of Advance Research,1(5), 166–170.

Togola,A, Austerheim,I., Theïs,A., Diallo,D. &Paulsen,B. S. (2008). Ethnorpharmacological uses of Erythrina senegalensis: A comparison of three areas in Mali; and a link between traditional knowledge and modern biological science. Journal of Ethnobiology and Ethnomedicine, 4(6), 1-9.

Tresserra-Rimbau,A., Rimm,E. B., Medina-Remón,A., Martínez-González,M. A., De la Torre,R., Corella,D., Salas-Salvadi,J., Gomez-Gracia,E, Lapetra,J., Aros,F., Fiol,M., Serra-Magem,L., Pinto,X., Saez,G. T., Basora,J., Sorli,J. V., Martinez, J. A., Vinyoles,E., Ruiz-Gutierrez,V., Estrush,R. &Lamuela-Raventos,R. M. (2014). Inverse association between habitual polyphenol intake and incidence of cardiovascular events in the PREDIMED study. Nutrition Metabolism Cardiovascular Diseases, 24(6),639–647.

Tsao,R. (2010). Chemistry and biochemistry of dietary polyphenols. Nutrients 2, 1231–1246.

Venkatesan,N., Devaraj,S. N. and Devaraj,H. (2003). Increased binding of LDL and VLDL to apo B, E receptors of hepatic plasma membrane of rats treated with Fibernat. European Journal of Nutrition, 42(5),262-271.

Villaseñor, J. L. (2016). Checklist of the native vascular plants of Mexico. Revista Mexicana de Biodiversidad, 87(3):559–902.

Vonthron-Sénécheau,C. V, Weniger, B, Ouattara M, Tra, B.F, Kamenan A, Lobstein, A., Brun, R. and Anton R. (2003). In vitroantiplasmodial activity and cytotoxicity of ethnobotanically selected Ivorian plants. Journal of Ethnopharmcy, 87, 221-225.

Yakubu,M. T., Akanji,M. A. & Nafiu,M. O. (2010). Pharmacology Anti-diabetic activity of aqueous extract of Cochlospermum planchoniiroot in alloxan-induced diabetic rats. Cameroon Journal of Experimental Biology, 6(20),91-100.

Yokozawa,T., Cho,E. J.&Sasaki, S. (2006). The protective role of Chinese prescription kangen-karyu extract on diet-induced hypercholesterolemia in rats. Bioland Pharma Bulletin., 29(4), 760-765.