SYNTHESIS, PHYSICOCHEMICAL ELUCIDATION AND BIOLOGICAL SCREENING STUDY OF NEW LIGAND DERIVED FROM 5,6-O-ISO PROPYLIDENE-L-ASCORBIC ACID AND ITS METAL(II) COMPLEXES
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Abstract
A simple chemistry method approach was used to synthesise new ligand derivate from L-ascorbic acid and its complexes. All of them were water-soluble and are used quite extensively in the medical and pharmaceutical fields. This study synthesised the new ligand derivative from L-ascorbic acid-base using the following steps: A 5,6-O-isopropylidene-L-ascorbic acid was prepared by reacting dry acetone with L-ascorbic acid followed by reacting it with trichloroacetic acid to yield [chloro(carboxylic)methylidene]-5,6-O-isopropylidene-L-ascorbic acid in the second stage. In the third stage, the derivative was reacted with (methyl(6-methyl-2-pyridylmethyl)amine to create a new ligand (ONMILA). This novel ligand was identified using a number of techniques, namely mass spectroscopy, 1H, 13C-Nuclear magnetic resonance, Fourier Transform Infrared (FT-IR), and Ultraviolet–visible (UV-Vis) spectra. It was observed that several complexes formed between the ligand and divalent metal ions (Co, Ni, Cu, Zn, Cd). Based on Micro Elemental Analysis, the mole ratio was (1:1) (M:L). Magnetic susceptibility, elemental analysis (C.H.N.O) procedures, molar conductivity tests, and proportion of metal ions calculations were used to describe the complexes. The findings showed the novel ligand had a mono, negative charge and behaved like a tridentate ligand type (N.N.O.). Therefore, the octahedral formula is suggested for all compounds. Only one spot was observed on thin layer chromatography (T.L.C.) for ligand (L) and complexes, indicating that the reaction completed and delivered only a single product. These chemicals have been connected to both Gram-negative and Gram-positive bacteria. The results suggested that antibacterial activity in metal complexes is higher than in the free ligand.
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Licensee MJS, Universiti Malaya, Malaysia. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
References
Abdel-Rahman L H., Abu-Dief A M., Ismael M., Mohamed M A., Hashem N A. (2016). Synthesis, structure elucidation, biological screening, molecular modeling and DNA binding of some Cu (II) chelates incorporating imines derived from amino acids, Journal of Molecular Structure, 1103: 232-244.
Abu Dief A M, Abdel Rahman L H., Abdel Mawgoud A H. (2020). A robust in vitro anticancer, antioxidant and antimicrobial agents based on new metal-azomethine chelates incorporating Ag (I), Pd (II) and VO (II) cations: Probing the aspects of DNA interaction, Applied Organometallic Chemistry, 34, no. 2, e5373: 1-20.
Ahmed A. H., Hassan A. H., Gumaa A. B., Mohamed H., Eraky A M. (2016). Nickel (II)-oxaloyldihydrazone complexes: Characterization, indirect band gap energy and antimicrobial evaluation, Cogent Chemistry, 2, no. 1: 1142820: 1-14.
Ahmed N., Riaz M., Ahmed A., Bhagat M. (2015). Synthesis, characterisation, and biological evaluation of Zn (II) complex with tridentate (NNO Donor) schiff base ligand, International Journal of Inorganic Chemistry, 2015: 1-5.
Al-Farhan B S., Basha M T., Abdel Rahman L H., El-Saghier A M., El-Ezz D A., Marzouk A., Shehata M R., Abdalla E. M. (2021). Synthesis, DFT Calculations, Antiproliferative, Bactericidal Activity and Molecular Docking of Novel Mixed-Ligand Salen/8-Hydroxyquinoline Metal Complexes, Molecules, 26, no. 16: 4725.
Al-Khafagy A. (2016). Synthesis, characterization and biological study of some new metal-azo chelate complexes, Journal of Chemical and Pharmaceutical Research, 8, no. 8: 296-302.
Al-Noor T H., Mohapatra R K., Azam M., AbdulKarem L K., Mohapatra P K., Ibrahim A A., Parhi P K., Dash G C., El-ajaily M., Al-Resayes S I., Raval M K., Pintilie L. (2021). Mixed-ligand complexes of ampicillin derived Schiff base ligand and Nicotinamide: Synthesis, physico-chemical studies, DFT calculation, antibacterial study and molecular docking analysis, Journal of Molecular Structure, 1229: 129832.
Bellavite P., Donzelli A. (2020). Hesperidin and SARS-CoV-2: New Light on the Healthy Function of Citrus Fruits, Antioxidants, 9, 742: 1-18.
Chatterjee I. (1973). "Evolution and the biosynthesis of ascorbic acid, Science, 182, no. 4118: 1271-1272.
El-Sonbati A., El-Bindary A., Mohamed G., Morgan S M., Hassan W., Elkholy A. (2016). Geometrical structures, thermal properties and antimicrobial activity studies of azodye complexes, Journal of Molecular Liquids, 218: 16-34.
Fodor G., Arnold R., Mohacsi T., Karle I., Flippen-Anderson J. (1983). A new role for L-ascorbic acid: Michael donor to α, β-unsaturated carbonyl compounds, Tetrahedron, 39, no. 13: 2137-2145.
Gao K., Mi H. (2021). Application of Membrane-Inlet Mass Spectrometry to Measurements of Photosynthetic Processes, Research Methods of Environmental Physiology in Aquatic Sciences, Springer: 187–192.
Hameed G F., Wadday F Y., Farhan M A A., Hussain S A. (2021). Synthesis, Spectroscopic characterization and bactericidal valuation of some metal (II) complexes with new Tridentate Heterocyclic Azo Ligand Type (NNO) Donor, Egyptian Journal of Chemistry,64, no.3:10-11.
Hanukoglu I. (2006). Antioxidant protective mechanisms against reactive oxygen species (ROS) generated by mitochondrial P450 systems in steroidogenic cells, Drug metabolism reviews,38, no. 1-2: 171-196.
Hariprasath K., Deepthi B., Babu I., Venkatesh S P., Sharfudeen S., Soumya V. (2010). Metal complexes in drug research-a review, Journal of Chemical and Pharmaceutical Research, 2, no. 4: 496-499.
Hollis L S., Amundsen A R., Stern E W. (1985). Synthesis, structure and antitumor properties of platinum complexes of vitamin C, Journal of the American Chemical Society, 107, no. 1: 274-276.
John N., James C. (2009). Scientific opinion of the panel on food additive and nutrient sources added to food on a request from the commission on calcium ascorbate, magnesium ascorbate and zinc ascorbate added for nutritional purposes in food supplements, The European Food Safety Authority Journal, 994: 1-22.
Kareem M J., Al-Hamdani A A., Al Zoubi Y K., Mohammed S G. (2021). Synthesis, characterization, and determination antioxidant activities for new Schiff base complexes derived from 2-(1H-indol-3-yl)-ethylamine and metal ion complexes, Journal of molecular Structure, 1231, 129669: 1-18.
Lawal M., Obaleye J A., Bamigboye M. O., Nnabuike G G., Ayinla S O., Rajee, A O., Babamale H. F., Ajibola A A. (2017). Mixed metal complexes of isoniazid and ascorbic acid: chelation, characterization and antimicrobial activities, Nigerian Journal of Chemical Research, 22, no. 1: 20-28.
Loke W M., Proudfoot J M., McKinley A J., Croft K D. (2006). Augmentation of monocyte intracellular ascorbate in vitro protects cells from oxidative damage and inflammatory responses, Biochemical and biophysical research communications, 345, no. 3: 1039-1043.
Mutlu Gençkal H., Erkisa M., Alper P., Sahin S., Ulukaya E., Ari F. (2020). Mixed ligand complexes of Co (II), Ni (II) and Cu (II) with quercetin and diimine ligands: Synthesis, characterization, anti-cancer and anti-oxidant activity, JBIC Journal of Biological Inorganic Chemistry, 25, no. 1: 161-177.
Naji S H. (2014). Synthesis, Spectroscopic and biological studies of some metal complexes with 2,4–dinitro–2'–amino hydrazo benzene Al- Mustansiriyah Journal of Science, 25, No.2: 73-88.
Nisah K., Ramli M., Idroes R., Safitri E. (2021). Study of linearity and stability of Pb (II)-1, 10-phenanthroline complex with the presence of Fe (II) dan Mg (II) matrix ions using UV-Vis spectrophotometry, in IOP Conference Series: Materials Science and Engineering, 1087, 012052, no. 1: IOP Publishing: 1-7.
O'Toole N., Lecourt C., Suffren Y., Hauser A., Khrouz L., Jeanneau E., Brioude A., Luneau D, Desroches C. (2019). Photogeneration of manganese (III) from luminescent manganese (II) complexes with thiacalixarene ligands: Synthesis, structures and photophysical properties, European Journal of Inorganic Chemistry, 2019, no. 1: 73-78.
Omotade E., Oviawe A., Elemike E. (2020). Synthesis, Characterization And Antimicrobial Activity Of Mixed Ligand Complexes of Benzyliminothiosemicarbazide And L-Phenylalanine With Divalent Fe, Co and Ni, Journal of Chemical Society of Nigeria, 45, no. 2: 282 - 289.
Padayatty S J., Katz A., Wang Y., Eck P., Kwon O., Lee J., Chen S., Corpe C., Dutta A., Dutta S K., Levine M. (2003). Vitamin C as an antioxidant: evaluation of its role in disease prevention, Journal of the American college of Nutrition, 22, no. 1: 18-35.
Padmaningrum R. T., Louise I S Y., Yunita I., Sugiyarto K H. (2022). Infrared Spectral And Magnetic Properties Of Basic Copper(Ii) Nitrate Produced By Slow Titration Method, Malaysian Journal Of Science, 41(1): 106-116.
Pang Z., Raudonis R., Glick B R., Lin T J., Cheng Z. (2019). Antibiotic resistance in Pseudomonas aeruginosa: mechanisms and alternative therapeutic strategies, Biotechnology advances, 37, no. 1: 177-192.
Radisavljević S., Petrović B. (2020). Gold (III) complexes: An overview on their kinetics, interactions with DNA/BSA, cytotoxic activity, and computational calculations, Frontiers in chemistry, 8, 379: 1-8.
Raman N., Sobha S. (2010). Synthesis, characterization, DNA interaction and antimicrobial screening of isatin-based polypyridyl mixed ligand Cu (II) and Zn (II) complexes, Journal of the Serbian Chemical Society, 75, no. 6: 773-788.
Sánchez-Lara E., García-García A., González-Vergara E., Cepeda J., Rodríguez-Diéguez A. (2021). Magneto-structural correlations of cyclo-tetravanadates functionalized with mixed-ligand copper (ii) complexes, New Journal of Chemistry, 45, no. 11: 5081-5092.
Shiekhzadeh A., Sohrabi N., Moghadam M E., Oftadeh M. (2020). Kinetic and thermodynamic investigation of human serum albumin interaction with anticancer glycine derivative of platinum complex by using spectroscopic methods and molecular docking, Applied Biochemistry and Biotechnology, 190, no. 2: 506-528.
Tweedy B. (1964). Plant extracts with metal ions as potential antimicrobial agents, Phytopathology, 55: 910-914.
Valarmathy G., Subbalakshmi R., Sumathi R., Renganathan R. (2020). Synthesis of Schiff base ligand from N-substituted benzenesulfonamide and its complexes: Spectral, thermal, electrochemical behavior, fluorescence quenching, in vitro-biological and in-vitro cytotoxic studies, Journal of Molecular Structure, 1199: 127029.
Waddai F Y., Musa F H., Fidhel H A. (2015). Synthesis And Characterization Of Some Metal Complexes With Bis [O, O-2, 3; O, O-5, 6-(N, N-Dicarboxylic Methylidene)-N-2-Methylenepyridyl]-L-Ascorbic Acid, European Chemical Bulletin, 4, no. 2: 74-79.
Wasi N., Singh H., Gajanana A., Raichowdhary A. (1987). Synthesis of metal complexes of antimalarial drugs and in vitro evaluation of their activity against plasmodium falciparum, Inorganica chimica acta, 135, no. 2: 133-137.
Xue L W., Zhang H J., Wang P P. (2020). Synthesis, crystal structures, and antimicrobial activity of copper(II) complexes derived from N′-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide, Inorganic and Nano-Metal Chemistry, 50, no. 8: 637-643.
Yoe J. H., Jones A L. (1944). Colorimetric determination of iron with disodium-1, 2-dihydroxybenzene-3, 5-disulfonate, Industrial and Engineering Chemistry Analytical Edition, 16, no. 2: 111-115.
Zümreoglu-Karan B. (2006). The coordination chemistry of Vitamin C: An overview, Coordination Chemistry Reviews, 250, no. 17-18: 2295-2307.