Synthesis, Structure, and Antioxidant Activity of Tri and Di-organotin Carboxylate Complexes of Tryptophan

Document Type : Research Article

Authors

1 Medical Laboratory, Techniques Departement, Al-Maarif university college, Anbar, IRAQ

2 Department of Medical Instrumentation Technologies Engineering, Hilla university college , Babylon , IRAQ

3 Medical Laboratories Techniques Department, Al‐Mustaqbal University College, Babylon, IRAQ

4 Department of Chemistry, College of Science, University of Babylon, Babylon, IRAQ

Abstract

Three organotin carboxylate complexes were synthesized by condensation of the reaction of methanolic tryptophan solution with Tri, and Diorganotin chloride for 3-4 hours to obtain the corresponding complexes (1-3) with good yields. These complexes were also diagnosed with several techniques, including infrared spectroscopy, Sn119,  and proton NMR, in addition to elemental analysis of the elements. These complexes were applied to find out the antioxidative activity of tryptophan and the prepared complexes by using DDPH and CUPRAC techniques. The results of the antioxidant activity in both ways showed that the prepared complexes are more effective than tryptophan from which they are derived. Also, complex 1 showed more anti-oxidant activity than other complexes.

Keywords

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[1] Bärtsch P., Swenson E.R., Acute High-Altitude Illnesses. New England Journal of Medicine, 368(24): 2294-2302‏ (2013).
[2] Bjelakovic G., Nikolova D., Gluud L.L., Simonetti R.G., Gluud C., Systematic Review and Meta-Analysis Supplements for Primary and Secondary Prevention: Mortality in Randomized Trials of Antioxidant, JAMA, 297(8): 842-857‏ (2007).
[3] Bandyopadhyay U., Das D., Banerjee R.K., Reactive Oxygen Species: Oxidative Damage and Pathogenesis, Current Science, 658-666.‏ (1999).
[4] Vajragupta O., Boonchoong P., Berliner L.J., Manganese Complexes of Curcumin Analogues: Evaluation of Hydroxyl Radical Scavenging Ability, Superoxide Dismutase Activity and Stability Towards Hydrolysis, Free Radical Research, 38(3): 303-314‏ (2004).
[6] Chughtai M.D., Effect of Milk Solids-Not-Fat and Sucrose on the Behavior of Certain Amino Acid Antioxidants in Milk Fat Emulsions (Doctoral dissertation, Oklahoma State University).‏ (1966). 
[7] Becker E.M., Nissen L.R., Skibsted L.H., Antioxidant Evaluation Protocols: Food Quality or Health Effects, European Food Research and Technology, 219(6): 561-571‏ (2004).
[8] Tortora, G., Derrickson, B., Antioxidants Beyond the Hype Medline Plus: Antioxidants "Introduction to the Human Body” (2010).
[9]  Devi T., Lee Y.M.m Nam W., Fukuzumi S.A., Mononuclear Non-Heme Manganese(III)–Aqua Complex in Oxygen Atom Transfer Reactions via Electron Transfer, Coord. Chem. Rev., 143: 1521–1528. (2020).
[10] Devi J., Pachwania S., Syntheses, Molecular Structures, Electrochemical Behavior, Theoretical Study, and Antitumor Activities of Organotin(IV) Complexes Containing 1-(4-Chlorophenyl)-1-cyclopentanecarboxylato Ligands, Inorg. Chem., 91: 44-62 (2018).
[11] Kovala-Demertzi D., Recent Advances on Non-Steroidal Anti-Inflammatory Drugs, NSAIDs: Organotin Complexes of NSAIDs, Journal of Organometallic Chemistry, 691(8): 1767-1774‏ (2006).
[12] Pellerito L., Nagy L., Organotin (IV) n+ Complexes Formed with Biologically Active Ligands: Equilibrium and Structural Studies, and Some Biological Aspects, Coordination Chemistry Reviews, 224(1-2): 111-150‏ (2002).
[13] HADI, Angham G., Jawad, K., Ahmed, D. S., Yousif, Synthesis and Biological Activities of Organotin (IV) Carboxylates: A Review, Systematic Reviews in Pharmacy, 10(1): 26-31 (2019).
[14] HADI, Angham G.; Jawad, Khudheir; Yousif, Emad., Medicinal Applications of Organotin (IV) Complexes and Its Important Place as Effective Antitumor Agents, Indian Journal of Public Health Research & Development, 10(6): (2019).
[15] HADI, Angham G., Yousif, E., El-Hiti, G. A., Ahmed D.S., Jawad K., Alotaibi M.H., Hashim H., Long-Term Effect of Ultraviolet Irradiation on Poly (vinyl chloride) Films Containing Naproxen Diorganotin (IV) Complexes, Molecules, 24(13): 2396 (2019).
[16] HADI, Angham G., Jawad, K., El-Hiti, G. A., Alotaibi M.H., Ahmed, A.A., Ahmed D.S., Yousif E., Photostabilization of Poly (vinyl chloride) by Organotin (IV) Compounds Against Photodegradation, Molecules, 24(19): 3557 (2019).
[17] HADI, Angham G., Baqir, S. J., Ahmed, D. S., El-Hiti G.A., Hashim H., Ahmed A., Yousif E., Substituted Organotin Complexes of 4-Methoxybenzoic Acid for Reduction of Poly (vinyl Chloride) Photodegradation, Polymers, 13(22): 3946 (2021).
[18] Ahmed, Ahmed, El-Hiti G.A., Hadi A.G., Ahmed D.S., Baashen M.A., Hashim, H., Yousif E., Photostabilization of Poly (vinyl chloride) Films Blended with Organotin Complexes of Mefenamic Acid for Outdoor Applications. Applied Sciences, 11(6): 2853 (2021).
[19] JASEM, Hadeer, Hadi, A. G., El-Hiti, G. A., Baashen, M. A., Hashim, H., Ahmed, A. A., ... & Yousif, E. Tin-Naphthalene Sulfonic Acid Complexes as Photostabilizers for Poly (vinyl chloride), Molecules, 26(12): 3629 (2021).
[20] HADI, Angham G., Jawad, K., Yousif, E., El-Hiti, G. A., Alotaibi, M. H., & Ahmed, D. S. Synthesis of Telmisartan Organotin (IV) Complexes and their Use as Carbon Dioxide Capture Media, Molecules, 24(8): 1631 (2019). ‏
[21] Uddin M.N., Ahmed S.S., Alam S.R., Biomedical Applications of Schiff Base Metal Complexes, Journal of Coordination Chemistry, 73(23): 3109-3149‏ (2020).
[22] Hong M., Yin H., Zhang X., Li C., Yue C., Cheng S., Di-and tri-organotin (IV) Complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: Synthesis, Characterization and in Vitro Antitumor Activities, Journal of Organometallic Chemistry, 724: 23-31‏ (2013).
[23] Jr C.E.C., Roner M.R., “Use of Metal-Containing Polymers as Potential Anticancer Agents”‏ (2014).
[24] Abdellah M.A., Hadjikakou S.K., Hadjiliadis N., Kubicki M., Bakas T., Kourkoumelis N., Butler I.S., Synthesis, Characterization, and Biological Studies of Organotin (IV) Derivatives with o-or 
p-Hydroxybenzoic Acids. Bioinorganic Chemistry and Applications, (2009).‏
[25] Nayak BN, Buttar HS. Evaluation of the Antioxidant Properties of Tryptophan and its Metabolites In Vitro Assay, J Complement Integ Med, 13: 129-136. (2016).
[26] Nayak B.N., Buttar H.S., Health Benefits of Tryptophan in Children and Adults, J. Pharm. Sci. Tech. Mgmt., 1: 8-12 (2015).
[27] Tsopmo A, Diehl-Jones BW, Aluko RE, Kitts DD, Elisia I, Friel JK. Tryptophan Released from Mother's Milk Has Antioxidant Properties, Pediatric Res., 66: 614-618 (2009).
[28] Singh R.B., Role of Tryptophan in Health and Disease: Systematic Review of the Anti-Oxidant, Anti-Inflammation, and Nutritional Aspects of Tryptophan and its Metabolites, World Heart Journal, 11(2): 161-178.‏ (2019).
[29] Choi H.J., Kim J.H., Lee C.H., Ahn Y.J., Song J.H., Baek S.H., Kwon D.H., Antiviral Activity of Quercetin 7-Rhamnoside Against Porcine Epidemic Diarrhea Virus, Antiviral Res., 81: 77–81 (2009). 
[31] Liang W., He L., Ning P., Lin J., Li H., Lin Z., Kang K., Zhang Y., (+)-Catechin Inhibition of Transmissible Gastroenteritis Coronavirus in Swine Testicular Cells is Involved its Antioxidation, Res. Vet. Sci. 103: 28–33. (2015). [CrossRef].
[32] Apak R., Güçlü K., Demirata B., Özyürek M., Celik S., Bektaşoğlu B., Berker K.L., Özyurt D., Comparative Evaluation of Various Total Antioxidant Capacity Assays Applied to Phenolic Compounds with the CUPRAC Assay, Molecules, 12(7): 1496-547 (2007).
[33] Kavitha P., Reddy K.L., Synthesis, Spectral Characterisation, Morphology, Biological Activity and DNA Cleavage Studies of Metal Complexes with Chromone Schiff Base, Arab. J. Chem., 9: 596–605 (2016).[CrossRef]
[34] Morozov O.S., Vyshinskii N.N., Rudnevskii N.K., Investigation of Some Organotin Compounds and their Complexes by IR Spectroscopy, J. Appl. Spectrosc., 35: 1019–1023 (1981).
[35] HADI, Sutopo, Fenska, M. D., Wijaya, R. A., Noviany, N., & Suhartati, T. Antimalarial Activity of Some Organotin (IV) Chlorobenzoate Compounds Against Plasmodium Falciparum, Mediterranean Journal of Chemistry, 10(3): 213-219 (2020).
[36] Hadi A.G., Hassen T.F., Mahdi I.J., Synthesis, Characterization, and Antioxidant Material Activities of Organotin (IV) Carboxylates with Tin-Para Methoxy Benzoic Acid, Materials Today: Proceedings, 49(7): 2797-2801 (2021).
[37] Hashim D.J., Falah T.F., Hadi A.G., Enhanced Antioxidant Activity of Di-and Triorganotin Complexes Derived from Mefenamic Acid. Egyptian Journal of Chemistry (2021).
[38] Saddam, N. S., Hadi, A. G., & Mohammed, A. A.  Enhanced Antioxidant Activity of Chitosan Extracted from Fish Shells Materials, Materials Today: Proceedings. 49(7): 2793-2796. (2021).
[39] Hadi A.G., Zaooli R.H., Ahmed D.S., Yousif E., Anti-oxidant Activity of Naproxen and Its Diorganotin Complexes, International Journal of Drug Delivery11(2): 383-385 (2021).
[40] HadeerJasem A.G.H., Enhanced the Antioxidant Activity of 1-Amino-2-naphthol-4-Sulfonic Acid by Complexation with Organotin (IV) Compounds, Annals of the Romanian Society for Cell Biology25(6): 6182-6193 ‏)2021).