In vitro Antioxidant Activities of Some Re(I) Metal Carbonyls Synthesized from Isatin Derivatives http://www.doi.org/10.26538/tjnpr/v6i10.28
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Abstract
Isatin is a natural indole found in some plants, brains, and human tissues, which possesses numerous medicinal applications. Rhenium complexes of different Schiff bases have multiple biological applications like anti-tumour, anti-microbial and antioxidant activities. Little information exist in literature on the Re(I) metal carbonyls of isatin derivatives and their biological significance. Therefore, the aim was to determine the antioxidant capacities of Re(I) complexes of the Schiff bases of isatin with aniline (C14H10N2O) and isatin with sulphanilamide (C14H11N3O3S) using three antioxidant assays to facilitate further plausible biological and medicinal applications. 2,2-diphenyl-1picrylhydrazyl (DPPH) and hydrogen peroxide radical scavenging activities of the Re(I) isatin derivative complexes and their reducing power were evaluated. Complex 1 was [Re(C14H10N2O)(CO)3Cl], Complex 2 was [Re(C14H10N2O)(CO)3Br] and complex 3 was [Re(C14H11N3O3S)(CO)3Br]. It was observed that Complexes 2 and 3, which contain bromine in their coordination spheres, had better DPPH scavenging activities than Complex 3, which had chlorine in its coordination sphere. Although [Re(C14H10N2O)(CO)3Br] has better DPPH and hydrogen peroxide radical scavenging abilities than [Re(C14H11N3O3S)(CO)3Br], it was observed that [Re(C14H11N3O3S)(CO)3Br] was a better reducing agent than [Re(C14H10N2O)(CO)3Br]. These results showed good antioxidant properties of the complexes, recommendable for further applications such as anti-tumor or cell imaging known with isatin derivatives and Re(I) compounds. Also, this might arouse the interest to study the structure to function relationships in aniline and sulphanilamide-containing complexes, which could be of great medicinal significance.
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References
Seifriz I, Konzen M, Paula MMS, Norberto S, Goncalves A, Sponganickz B, Tania B, Creczynski-Pasa B, Vilson R, Bonnetti B, Beirith A, Joao B, Calixto C, Franco CV. Synthesis, potentiometric titration, electrochemical investigation and biological properties of trans-[RuCl2(dinic)4](dinic = 3,5-pyridinecarboxylic acid). J Inorg Biochem. 1999; 76:153–163.
Beirith A, Creczynski-Pasa TB, Bonetti VR, Konzen M, Seifriz I, Paula MS, Franco CV, Calixto JB. Antinociceptive properties and nitric oxide synthase inhibitory action of new ruthenium complexes. Eur J Pharmacol. 1999; 369:289-297.
Creczynski-Pasa TB, Bonetti VR, Beirith A, Ckless K, Konzen M, Seifriz I, Paula MS, Franco CV, Filho DW, Calixto JB. Complexes trans-[RuCl2(nic)4] and trans-[RuCl2(i-nic)4] as free radical scavengers, J. Inorg. Biochem. 2001; 86:587-594.
Domenichini A, Casari I, Simpson PV, Desai NM, Chen L, Dustin C, Edmands JS, Vliet AV, Mohammadi M, Massi M, Falasca M. Rhenium N-heterocyclic carbene complexes block growth of aggressive cancers by inhibiting FGFR- and SRC-mediated signalling. J Exp Clin Cancer Res. 2020; 39:276.
Sridhar SK, Pandeya SN, Stables JP, Ramesh A. Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. Eur J Pharm Sci. 2002; 16:129-132.
Ikotun AA, Adelani PO, Egharevba GO. 1-Benzyl-3 [(4methylphenyl)imino]-indolin-2-one. Acta Cryst. 2012; E68:o2098.
Visagaperumal S, Ezekwem JE, Munji H, Chandy V. Isatin Schiff base – an overview. Pharma Tutor. 2018; 6(5):38-47.
Matesic L, Locke JM, Bremner JB, Pyne SG, Skropeta D, Ranson M, Vine KL, N-Phenethyl and N-naphthylmethyl isatins and analoges as in vitro cytotoxic agents. Bioorg Med Chem. 2008; 16(6):3118-3124.
Pradeep SD, Sebastian D, Gopalakrishnan AK, Mohan PV. A novel and cost effective isatin based Schiff base fluorophore: a highly efficient ‘turn-off’ fluorescence sensor for the selective detection of cysteine in an aqueous medium. New J Chem. 2021; 45:16306-16312.
Schindler K and Zobi F. Anticancer and Antibiotic Rhenium Triand Dicarbonyl Complexes: Current Research and Future Perspectives. Molecules. 2022; 27(2):539.
Coogan MP, Fernandez-Moreira V, Kariuki BM, Pope SJA, Thorp - Greenwood FL. A rhenium fac-tricarbonyl 4’-oxo-terpy trimer as a luminescent molecular vessel with a removable silver stopper. Angew. Chem Int Ed Engl. 2009; 48:4965-8.
Ikotun AA, Owoseni AA, Egharevba GO. Synthesis, physicochemical and antimicrobial properties of rhenium (I) tricarbonyl complexes of isatin Schiff bases. Afr J Biotec. 2021; 20(5):175-185.
Ikotun AA, Coogan MP, Owoseni AA, Egharevba GO. Design, Synthesis, Physicochemical and Antimicrobial Properties of Rhenium (I) tricarbonyl complexes of 3-(phenylimino)indole-2- one. J Chem Soc Nig. 2019; 44(5):948-958.
Ikotun AA and Omolekan TO. Microwave-assisted Synthesis, Characterization, Indolin-2-One and Its Co(II) Complex. Chem Sc Int J. 2019; 28(1):1-12.
Gyamfi MA, Yonamine M, Aniya Y. Free radical scavenging activity of medicinal herb of Ghana: Thonningia sanguinea on experimentally induced liver injuries. Gen Pharmacol. 1999; 32:661–667.
Yupparach P and Konsue A. Phytochemical Screening and Antioxidant Activities of Cornukaempferia chayanii Extracts and in vitro Inhibitory Effects on Digestive Enzymes. Trop J Nat Prod Res. 2022; 6(5):705-708.
Awote OK, Adeyemo AG, Igbalaye JO, Awosemo RB, Ibrahim AB, Omolaja BE, Abdulrafiu F, Fajobi T. In Vitro Alpha-Amylase Inhibitory Activity, Antioxidant Activity and HPLC Analysis of Eichhornia crassipes (water hyacinth) Methanol Extracts. Trop J Nat Prod Res. 2021; 5(12):2174-2181.
Omolekan TO, Esan AM, Olaiya CO, Anjorin AJ, Aremu KA, Adeyemi HR. Comparative effects of postharvest ultraviolet light treatments on antioxidants properties, nutritional and vitamin D contents of some indigenous green leafy vegetables. ALST. 2021; 88:33-42
Olaleye OO, Sofidiya MO, Ogba JO, Lasore W. Antioxidant activities of Daniellia oliveri (Rolfe) Hutch. & Dalziel and Daniellia ogea (Harms) Rolfe ex Holland (Caesalpiniaceae). Trop J Nat Prod Res. 2020; 4(5):210-215.
Meida NS, Purwanto B, Wasita B, Senyum Indrakila S, Soetrisno, S, Poncorini E, Cilmiaty R, Pratiwi WR, Setyandriana Y, Almahira
S. Effect of Propolis Extract on Oxidative Stress Biomarker in Diabetic Wistar Rat (Rattus novergicus). Trop J Nat Prod Res. 2022; 6(8):1193-1196.
Török B, Sood A, Bag S, Tulsan R, Ghosh S, Borkin D, Kennedy AR, Melanson M, Madden R, Zhou W, Levine H, Torok M. Diaryl hydrazones as multifunctional inhibitors of amyloid self-assembly. Biochem. 2013; 52:1137–1148.
Zain MH, Al-Ismaeel WNH, Al-Jaber GT. Cytotoxic and Antioxidant Activities of Clary Sage (Salvia sclarea L.) Essential Oil against AMJ-13 Cancer Cell Line. Trop J Nat Prod Res. 2022; 6(5):732-735.
Ikotun AA, Egharevba GO, Obafemi CA, Owoseni OO. Ring deactivating effect on antimicrobial activities of metal complexes of the Schiff base of p-nitroaniline and isatin. J Chem Pharm Res. 2012; 4(1):416-422.