Yeni rutenyum-azol komplekslerinin sentezi ve antioksidan özellikleri

Yıl 2017, , 1121 - 1126, 01.12.2017

Neslihan Şahin , Serap Şahin Bölükbaşı

https://doi.org/10.16984/saufenbilder.338219

Cited By: 1

Öz

Bu çalışmada,
iki yeni dikloro-(1-alkilimidazolin)-(p-simen)rutenyum(II),
3 ve dikloro-(1-alkilbenzimidazol)-(p-simen)rutenyum(II), 4 kompleksi sentezlendi ve yapıları spektroskopik
tekniklerle karakterize edildi. Bu yeni metal komplekslerin in vitro antioksidan aktiviteleri; 2,2-difenil-1-pikrilhidrazil
(DPPH), hidroksil (^•OH) ve süperoksit  (O₂^-.) radikallerini inhibe etme özellikleri ile araştırıldı. Ayrıca
her bir metal kompleksinin toplam antioksidan aktivitesi de saptandı. 3
Numaralı kompleksin DPPH, hidroksil ve süperoksit radikallerini süpürme aktivitelerinin
ve toplam antioksidan aktivitesinin 4 numaralı kompleksten daha etkili olduğu bulundu.

Anahtar Kelimeler

İmidazolin; Benzimidazol; Rutenyum; DPPH; Hidroksil radikali; Süperoksit radikali; Antioksidan Aktivite

Synthesis of novel ruthenium-azole complexes and antioxidant properties

Öz

In this study, two novel dichloro-(1-alkylimidazoline)-(p-cymene)ruthenium(II), 3 and dichloro-(1-alkylbenzimidazole)-(p-cymene)ruthenium(II), 4 complexes have been synthesized and characterized
by spectroscopic
techniques. In vitro antioxidant
activities of new metal complexes have been investigated by inhibition properties
of 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl (^•OH) and superoxide (O₂^-.) radicals.
Additionally, total antioxidant activity of each metal
complexes was also determined. It was found that total antioxidant activity and
DPPH, hydroxyl and superoxide radicals scavenging
activities of compound 3 are more
efficient than compound 4.

 

 

Anahtar Kelimeler

Imidazoline; Benzimidazole; Ruthenium; DPPH; Hydroxyl Radical; Superoxide Radical; Antioxidant Activity

Kaynakça

• [1] İ. Gülçin, M. Oktay, Ö. İ. Küfrevioğlu ve A. Aslan, «Determination of antioxidant activity of lichen Cetrariaislandica (L),» Ach. Ethnopharmacology, no. 79, pp. 325-329, 2002. [2] L. Packer, E. Cadenas ve K. Davies, «Free radicals and exercise: An introduction,» Free Radical. Biol. Med., no. 44, p. 123, 2008. [3] P. Cerutti, «Oxy-Radical and Cancer,» Lancet, no. 344, pp. 862-863, 1994. [4] R. Dean, S. Gieges ve M. Davies, « Reactive species and their accumulation on radical-damaged proteins,» Trends Biochem Sci., cilt 18, no. 11, pp. 437-441, 1993. [5] A. Diplock, C. Rice-Evans ve R. Burdon, « Is There a Significant Role for Lipid Peroxidation in The Causation of Malignancy and for Antioxidants in Cancer Prevention?,» Cancer Res., cilt 7, no. 54, pp. 1952-1956, 1994. [6] M. Genestra, «Oxyl radicals, redox-sensitive signalling cascades and antioxidants.,» Cell. Signal , no. 19, p. 1807, 2007. [7] U. Mercan, «Toksikolojide Serbest Radikallerin Önemi,» YYU Vet. Fak. Derg., cilt 15, no. 1-2, pp. 91-96, 2004. [8] D. Bagchi, M. Bagchi, S. Stohs, D. Das, S. Ray, C. Kuszynski, S. Joshi ve H. Pruess, «Free radicals and grape seed proanthocyanidin extract: Importance in human health and disease prevention,» Toxicology, no. 148, pp. 187-197, 2000. [9] K. Datta, S. Sinha ve P. Chattopadhyay, « Reactive oxygen species in health and disease,» Nat. Med. J. India, no. 13, pp. 304-310, 2000. [10] F. Saczewski, E. Dziemidowicz-Borys, P. Bednarski ve M. Gdaniec, «Synthesis, Crystal Structure, Cytotoxic and Superoxide Dismutase Activities of Copper(II) Complexes of N-(4,5-Dihydroimidazol-2-yl)azoles,» Arch. Pharm. Chem. Life Sci., no. 340, pp. 333-338, 2007. [11] I. Stepanenko, B. Cebrian-Losanto, V. Arion, A. Krokhin, A. Nazarov ve B. Keppler, «The Complexes [OsCl2(azole)2(dmso)2] and [OsCl2(azole)(dmso)3]: Synthesis, Structure, Spectroscopic Properties and Catalytic Hydration of Chloronitriles,» Eur. J. Inorg. Chem., no. 400-411, 2007. [12] O. Schott, J. Ferrando-Soria, A. Bentama, S. Stiriba, J. Pasan, C. Ruiz-Perez, M. Andruh, F. Lloret ve M. Julve, «Chromium(III) complexes with 2-(20-pyridyl)imidazole: Synthesis, crystal structure and magneti cproperties,» Inorganica Chimica Acta, no. 376, pp. 358-366, 2011. [13] S. Rathinasamy, S. Karki, S. Bhattacharya, L. Lakshmanan Manikandan, S. Prabakaran, M. Malaya Gupta ve U. Mazumder, «Synthesis and anticancer activity of certain mononuclear Ru (II) Complexes.,» SURESH Journal of Enzyme Inhibition and Medicinal Chemistry, cilt 5, no. 21, pp. 501-507, 2006. [14] A. Abdel Rahman, A. Mahmoud, G. El-Naggar ve H. El-Sherief, «Synthesis and biological activity of some new benzimidazolyl-azetidin-2-ones and-thiazolidin-4-one,» Die Pharmazie , no. 38, pp. 589-590, 1983. [15] R. Coburn, M. Clark, R. Evans ve R. Genco, «Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases,» J. Med. Chem., no. 30, pp. 205-208, 1987. [16] V. Khairnar, S. Lockhande, M. Patel ve B. Khadse, Bull. Haffkine Inst, Chemical Abstracts, no. 95, pp. 67-70, 1980. [17] I. İslam, R. Skibo ve D. Alberts, «Structure-activity studies of antitumor agents based on pyrrolo [1, 2-a] benzimidazoles: new reductive alkylating DNA cleaving agents,» J. Med Chem, no. 34, pp. 2954-2961, 1991. [18] L. Kruse, D. Ladd, F. McCabe, S. Mong, L. Faucette ve R. Johnson, «Synthesis, tubulin binding, antineoplastic evaluation, and structure-activity relationship of oncodazole analogs,» J. Med. Chem., no. 32, pp. 409-417, 1989. [19] V. Habernickel, «Alkyl-5-heterocyclic-benzimidazolyl-carbamate Derivatives,» Drugs Made in Germany , no. 35, p. 97, 1992. [20] T. Fukuda, T. Saito, S. Tajima, K. Shimohara ve K. Ito, «Alkyl-5-heterocyclic-benzimidazolyl-carbamate Derivatives,» Arzneim-Forsch./Drug Res, no. 34, pp. 805-810, 1984. [21] T. Fukuda, Y. Morimoto, R. Lemura, T. Kawashima, G. Tsukamoto ve K. Ito, «Efffects of 1 -(2-ethoxyethyl)-2-(4-methyl-1 -homopiperazinyl)-benzimidazole difumarate (KB-2413), a new antiallergic, on chemical mediators,» Arzneim-Forsch./Drug Res., no. 34, pp. 801-805, 1984. [22] B. Can-Eke, B. Püsküllü, E. Büyükbingöl ve M. İşcan, «A study on the antioxidant capacities of some benzimidazoles in rat tissues,» Chem.-Biol. Inter, no. 113, pp. 65-77, 1998. [23] E. Üstün, M. Çöl Ayvaz, M. Sönmez Çelebi, G. Aşçı, S. Demir ve İ. Özdemir, «Structure, CO-releasing property, electrochemistry, DFT calculation, and antioxidant activity of benzimidazole derivatives substituted [Mn(CO)3(bpy)L]PF6 type novel manganese complexes,» İnorganicaChimica Acta, no. 450, pp. 182-189, 2016. [24] E. Üstün, Ş. Koç, S. Demir ve İ. Özdemir, «Carbon monoxide-releasing properties and DFT/TDDFT analiysis of [Mn(CO)3(bpy)L]PF6type novel manganese complexes,» Journal of Organometallic Chemistry, cilt 815, pp. 16-22, 2016. [25] M. Cuendet, K. Hostettmann ve O. Potterat, «Iridoid Glucosides with Free Radical Scavenging Properties from Fagraeablumei,» Helv. Chim. Acta, no. 80, pp. 1144-1152, 1997. [26] E. Kunchandy ve M. Rao, «Oxygen Radical Scavenching Activity of Curcumin,» Int. J. Pharmacol., no. 58, pp. 237-240, 1990. [27] H. Ohkawa, N. Ohishi ve K. Yagi, «Assay for lipid Peroxides in Animal Tissuesby Thiobarbituric Acid Reaction,» Anal. Biochem., no. 95, pp. 351-358, 1979. [28] T. Imanari, M. Hirota, M. Miyazaki, K. Hayakawa ve Z. Tamura, «Improved assa ymethod fo rsuperoxide dismutase,» Igaku No Ayumi, no. 101, pp. 496-497, 1977. [29] P. Prieto, M. Pineda ve M. Aguilar, «Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E,» Anal Biochem., no. 269, pp. 337-341, 1999. [30] I. Koleva, T. vanBeek, J. Linssen, A. de Groot ve L. Evstatieva, « Screening of plant extracts fo rantioxidant activity: a comparative study on three testing methods,» Phytochemical Analysis, no. 13, pp. 8-17, 2002. [31] L. Macdonald-Wicks, L. Wood ve M. Garg, «Methodology For The Determination Of Biologica lAntioxidan tCapacity İn Vitro,» A Review, J. Sci. FoodAgric., no. 86, pp. 2046-2056. [32] R. Scalzo, «Organic Acids İnfluence On DPPH Scavenging By Ascorbic Acid,» FoodChem., no. 107, pp. 40-43, 2008. [33] E. Menteşe, F. Yılmaz, N. Baltaş, O. Bekircan ve B. Kahveci, «Synthesis and antioxidan tactivities of some new tri heterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings,» J. Enzyme Inhib. Med. Chem., cilt 30, no. 3, pp. 435-441, 2015. [34] R. Krishan Arora, N. Kaur, Y. Bansaln ve G. Bansal, «Nove lcoumarin–benzimidazole derivatives as antioxidants and safe ranti-
• inflammatory agents,» Acta Pharmaceutica Sinica B, cilt 5, no. 4, pp. 368-375, 2014. [35] E. Menteşe, S. Ülker ve B. Kahveci, «Synthesıs And Study Of Α-Glucosıdase Inhıbıtory, Antımıcrobıa lAnd Antıoxıdant Actıvıtıes Of
• Some Benzımıdazole Derıvatıves ContaınıngTrıazole, Thıadıazole, Oxadıazole, And Morpholıne Rıngs,» Chemistry of Heterocyclic Compounds, cilt 50, no. 12, 2015. [36] Y. Liu, Z. Liang, X. Hong, Z. Li, J. Yao ve H. Huang, «Synthesis, characterization, cytotoxicity, apoptotic inducing activity, cellula ruptake, interaction of DNA binding and antioxidant
• activity studies of ruthenium(II) complexes,» İnorganica Chimica Acta, no. 387, pp. 117-124, 2012.
• [37] S. Selvamurugan, P. Viswanathamurti, A. Endo, T. Hashimito ve K. Natarajan, «Synthesis, spectral characterization, atioxidant, anticancer in vitro, and NA cleavage studies of a series of ruthenium(II) complexes bearing Schiff base ligands,» Journal of CoordinationChemistry, no. 22, pp. 4052-4066, 2013. [38] L. Xu, X. Yang-Yin, Z. Nan-Jing, L. Zhen-Hua, J. He, H. Hong-Liang ve L. Yun-Jun, «DNA-binding and photo cleavage, cytotoxicity, apoptosis and antioxidan tactivity studies of ruthenium(II) complexes,» Transition Met Chem., no. 37, pp. 197-205, 2012. [39] J. Wood, S. Senthilmohan ve A. Peskin, «“Antioxidant Activity Of Procyanidin-Containing Plant Extract At Different Phs.,» Food Chemistry, no. 77, pp. 115-161, 2002. [40] G. Kılcıgil, C. Kuş, E. Özdamar, B. Eke ve M. İşcan, «Synthesis and Antioxidant Capacities of Some New Benzimidazole Derivatives,» Arch., Pharm, no. 340, pp. 607-611, 2007.