Synthesis, Characterisation and Acetylcholinesterase Inhibition Activity of Nickel(II) and Copper(II) Complexes of 3-Hydroxybenzaldehyde-4-nitrobenzoic Acid Hydrazone
American Journal of Applied Chemistry
Volume 7, Issue 2, April 2019, Pages: 64-71
Received: Feb. 28, 2019;
Accepted: Apr. 29, 2019;
Published: May 26, 2019
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Temitope Adekunle Ajayeoba, Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria
Olawale Folorunso Akinyele, Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria
Ayowole Olaolu Ayeni, Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria
Idowu Julius Olawuni, Department of Biochemistry, Obafemi Awolowo University, Ile-Ife, Nigeria
A new ligand namely 3-hydroxybenzaldehyde-4-nitrobenzoic acid hydrazone, its Nickel(II) and Copper(II) complexes were synthesised and characterised by spectroscopic methods: 1H NMR, Infrared (IR), UV-Vis, magnetic susceptibility measurement and % metal analysis. 1H NMR spectroscopy showed the diagnostic N-H signal at 12.10 ppm indicating the formation of the ligand. Infrared spectra showed that the ligand coordinated to the metal ion in keto form through the carbonyl oxygen (C=O) and the azomethine nitrogen (C=N). The UV-Vis spectrum of the ligand displayed two prominent bands at 47169 cm-1 and 30303 cm-1 which were ascribed to the intraligand transitions of π-π*, and n-π* respectively. These bands had hypsochromic shifts in the metal complexes indicating coordination with the metal ion. The nickel complex had a magnetic moment of 2.92 B.M, suggesting an octahedral geometry, while the copper complex had a value of 1.65 B.M. which is close to the expected value for a d9 copper(II) complex with possibility antiferromagnetic interactions. The % metal calculated had a good agreement with the observed values. The acetylcholinesterase inhibition activity of the ligand measured was 190 ± 20 μg/mL compared to the standard Eserin that had 68 ± 1.13 μg/mL. The copper(II) complex had a value of 220 ± 20 μg/mL, while the Nickel(II) complex had the least inhibitory value at 390 ± 80 μg/mL. The compounds could serve as primary target in the study of acetylcholinesterase inhibitors
Temitope Adekunle Ajayeoba,
Olawale Folorunso Akinyele,
Ayowole Olaolu Ayeni,
Idowu Julius Olawuni,
Synthesis, Characterisation and Acetylcholinesterase Inhibition Activity of Nickel(II) and Copper(II) Complexes of 3-Hydroxybenzaldehyde-4-nitrobenzoic Acid Hydrazone, American Journal of Applied Chemistry.
Vol. 7, No. 2,
2019, pp. 64-71.
Gwaram, N. S., Ali, H. M., Abdulla, M. A., Buckle, M. J. C., Sukumaran, S, D., Chung, L. Y., Othman, R., Alhadi, A. A., Yehye, W. A., Hadi, H. A., Hassandarvish, P., Khaledi, H. and Abdelwahab, S. I. (2012). Synthesis, characterisation, X-ray crystallography, acetylcholinesterase inhibition and antioxidant activities of some novel ketone derivatives of gallic hydrazides-derived Schiff bases. Molecules, 17.3: 2408-2427.
Kaya, B., Ozkay, Y., Temel, H. E and Kaplancikli, Z. A (2016). Synthesis and biological Evaluation of novel Piperazine containing Hydrazone derivatives. Journal of Chemistry. Article ID 5878410, 7 pages.
Taiwo, F. O., Obuotor, E. M., Olawuni, I. J., Ikechukwu, D. A and Iyiola, T. O. (2017). Design, Synthesis and Biological Evaluation of Some Novel 3-methylquinoxaline-2-Hydrazone Derivatives. Organic Chemistry Current Research. 6:2. DOI: 10.4172/21610401.1000181
Perry, E. K., Tomillinson B. E., Blessed G., Bergmann K., Gibson, P. H., Perry R. H. (1978). Correlation of cholinergic abnormalities with senile plaques and mental test scores in senile dementia. British Medical Journal. 6150: 1457-1459.
Saglio, P and Trijasse, S (1998). Behavioral responses to atrazine and diuron in goldfish. Archives of Environmental Contamination and Toxicology. 35: 484-491.
Bretaud, S., Toutant, J. P., Saglio, P. (2000). Effects of carbofuran, diuron and nicosulfuron on acetylcholinesterase activity in goldfish (Carassius auratus). Ecotoxicology and Environmental Safety. 47: 117-124.
Miron, D., Crestani, M., Schetinger, M. R., Morsch, V. M., Baldisserotto, B., Tierno, M. A., Moraes, G., Vieira, V. L. P. (2005). Effects of the herbicides clomazone, quinclorac, and metsulfuric methyl on acetylcholinesterase activity in the silver catfish (Rhamdiaquelen) (Heptapteridae). Ecotoxicology and Environmental Safety 61: 398-403.
Terry, A. V. Jr and Buccafusco, J. J. (2003). The cholinergic hypothesis of age and Alzheimer’s disease related cognitive deficits recent challenges and their implications for novel drug development. Journal of Pharmacology and Experimental Therapeutics. 306.3: 821-827.
Castellani, R. J., Rolston, R. K., and Smith, M. A. R. (2010). Alzheimer disease. Disease-a Month 56.9: 484-546
Alptuzun, V., Prinz, M., Horr, V. (2010). Interaction of (benzylidene-hydrazono)-1, 4 dihydropyridines with 𝛽�-amyloid, acetylcholine and butyrylcholine esterases. Bioorganic and Medicinal Chemistry 18.5: 2049-2059
Ozcelik, A. B., Gokce, M., Orhan, I., Kaynak, F., and Sahin, F. (2010). Synthesis and antimicrobial, acetylcholinesterase and butyrylcholinesterase inhibitory activities of novel ester and hydrazide derivatives of 3(2H)-pyridazinone. Arzneimittel-Forschung 60.7: 452-458.
Utku, S., Gokce, M., Orhan, I., and Sahin, M. F. (2011). Synthesis of novel 6-substituted 3(2H) pyridazinone-2-acetyl-2-(substituted/-nonsubstituted benza)hydrazone derivatives and acetylcholinesterase and butyrylcholinesterase inhibitory activities in-vitro Arzneimittel Forschung 61.1: 1-7.
Duggal, H. K., Agarwal, B. V. (1988). Synthesis and structural studies of chlorobenzoyl and salicyloylhydrazone complexes of tridentate hydrazones. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 18: 871 – 879.
Seleem, H. S. (2011). Transition metal complexes of an Isatinic quinolylhydrazone. Chemistry Central Journal 5: 35.
Ellman, G. L., Courtney, K. D., Andres. V Jr., Feather-Stone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology 7: 88-95.
Ajani, O. A., Obafemi, C. A., Nwinyi, O. C., Akinpelu, D. A. (2010). Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorganic & Medicinal Chemistry 18.1: 214-221.
Babahan, I., Anil, H., Sarikavakli, N. (2011). Synthesis of novel tetraoxime derivative with hydrazone side groups and its metal complexes. Turkish Journal of Chemistry. 35: 613-624.
Bessy-Raj, B. N., Kurupa, M. R. P., Suresh, E. (2008). Synthesis, spectral characterization and crystal structure of N-2-hydroxy-4 methoxybenzaldehyde N-4-nitrobenzoylhydrazone and its square planar Cu(II) complex. Spectrochimica Acta Part A. Molecular and biomolecular Spectroscopy. 71: 1253–1260.
Banerjee, S., Mondal, S., Chakraborty, W., Soma Sen, S., Gachhui, R., Butcher, R. J Slawin, A. M. Z., Mandal, C., Mitra, S. (2009). Synthesis, X-ray crystal structures, DNA binding, oxidative cleavage activities and antimicrobial studies of two Cu(II) hydrazone complexes. Polyhedron 28: 2785-2793.
Ahmed, A. H., Hassan, A. M., Gumaa, H. A., Mohamed, B. H and Eraky, A. M. Ayman. (2016). Nickel(II)-oxaloyldihydrazone complexes: Characterisation, indirect band gap energy and antimicrobial evaluation. Cogent Chemistry 2: 1142820. doi:10.1080/23312009.2016.1142820
Odunola, O. A., Oladipo, M. A., Woods, J. A. O., and Gelebe, A. C. (2003). Synthesis andstructural studies of some ternary copper(II) complexes containing β-diketones with 1,10 phenanthroline and 2,21-bipyridyl and X-ray structure of [Cu(C6H5COCHCOCH3)(bipy)Cl}. Synthesis and Reactivity in Inorganic and Metal Organic Chemistry, 33.5: 857-871
Quinn, D. M. (1987). Acetylcholinesterase: enzyme structure, reaction dynamics and virtual transition states. Chemical Reviews. 87.5: 955-979.
Recanatini, M., Cavalli, A., Hansch, C. (1997). A comparative QSAR analysis of acetylcholinesterase inhibitors currently studied for the treatment of Alzheimer’s disease. Chemico-Biological Interactions. 105.3: 199- 228.
Yu, Q-S., Holloway, H. W., Flippen-Anderson, J. L., Hoffman, B., Brossi, A. and Greig, N. H. (2001). Methyl Analogues of the experimental Alzheimer Drug Phenserine: Synthesis and structure/Activity Relationships for Acetyl- and Butyrylcholinesterase inhibitory Action. Journal of Medicinal Chemistry. 44.24: 4062 – 4071.
Ajayeoba, T. A., Akinyele, O. F and Oluwole, A. O. (2017). Synthesis, Characterisation and Antimicrobial Studies of Mixed Nickel(II) and Copper(II) Complexes of Aroylhydrazones with 2, 2-bipyridine and 1, 10-phenanthroline. Ife Journal of Science. 19.1: 119 – 132.
Hegazy, W. H and Al-Motawaa, I. H (2011). Lanthanide complexes of substituted β-diketone hydrazone derivatives: Synthesis, Characterisation and Biological activities. Bioinorganic Chemistry and Applications. Volume 2011, Article ID 531946, 10 pages doi:10.1155/2011/531946
Christie, R. J., Anderson, D. J and Grainger, D. W. (2010). Comparison of Hydrazone Heterobifunctional Crosslinking Agents for Reversible Conjugation of Thiol Containing Chemistry. Bioconjugation Chemistry 21.10: 1779 – 1787.
Saeed, A., Arshad, M. I, Bolte, M., Fantoni A. C., Espinoza, and Z. Y. D., Erben, and M. F. (2016). On the roles of close shell interactions in the structure of acyl-substituted hydrazones: An experimental and theoretical approach. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 157: 138 – 145.
Patel, R. N., Patel, D. K., Shodhiya, V. P., Shukla, K. K., Singh, Y., and Kumar, A. (2013). Synthesis, crystal structure and superoxide dismutase activity of two new bis(μ-acetato/μ-nitrato) bridged copper(II) complexes with N1-[phenyl(pyridine-2-yl)methylidene] benzohydrazone. Inorganica Chimica Acta 405: 209 - 217
Nawar, N., and Hosny, N. M. (1999). Transition Metal Complexes of 2-Acetylpyridine o-Hydroxybenzoylhydrazone (APo-OHBH): Their Preparation, Characterisation and Antimicrobial Activity. Chemical and Pharmaceutical Bulletin. 47.7: 944 – 949
Lakshmi, B., Avaji, P. G., Shivananda, K. N., Nagella, P., Manohar, S. H., Mahendra, K. N. (2011). Synthesis, spectral characterization and in vitro microbiological evaluation of novel glyoxal, biacetyl and benzil bis-hydrazone macrocyclic Schiff bases and their Co(II), Ni(II) and Cu(II) complexes. Polyhedron 30: 1507 – 1515.
Raji, A. A., Ajayi, I. A., Khan, S. U and Iqbal, J (2017). In Silico Screening of Parkia biglobosa Fatty Acids as Inhibitors of A-Glucosidase, Aldehyde Reductase (ALR1) and Aldose Reductase (ALR2) Enzymes. Journal of Physical Chemistry & Biophysics 7.246. doi: 10.4172/2161-0398.1000246