1,323
Views
20
CrossRef citations to date
0
Altmetric
Research Article

Antioxidant activity of indole-based melatonin analogues in erythrocytes and their voltammetric characterization

, , , , , & show all
Pages 1143-1155 | Received 28 Jul 2012, Accepted 28 Jul 2012, Published online: 20 Sep 2012

References

  • Singh RP, Sharad S, Kapur SJ. Free radicals and oxidative stress in neuro degenerative diseases: Relevance of dietary antioxidants. Ind Acad Clin Med 2004;4:218–225.
  • Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 2007;39:44–84.
  • Fresco P, Borges F, Diniz C, Marques MP. New insights on the anticancer properties of dietary polyphenols. Med Res Rev 2006;26:747–766.
  • Suzen S. (2007). Topics in Heterocyclic Chemistry, Bioactive Heterocycles V. In: Khan MTH, ed. Antioxidant activities of synthetic indole derivatives and possible activity mechanisms. Berlin, Heidelberg: Spinger-Verlag,; 11, 145–178.
  • Reiter RJ, Tan DX, Cabrera J, D’Arpa D, Sainz RM, Mayo JC et al. The oxidant/antioxidant network: role of melatonin. Biol Signals Recept 1999;8:56–63.
  • Korkmaz A, Reiter RJ, Tan DX, Manchester LC. Melatonin; from pineal gland to healthy food. Spatula 2011;1:33–36.
  • Cano A, Alcaraz O, Arnao MB. Free radical-scavenging activity of indolic compounds in aqueous and ethanolic media. Anal Bioanal Chem 2003;376:33–37.
  • Andreadou I, Tsantili-Kakoulidou A, Spyropoulou E, Siatra T. Reactions of indole derivatives with cardioprotective activity with reactive oxygen species. Comparison with melatonin. Chem Pharm Bull 2003;51:1128–1131.
  • Misik V, Ondrias K, Stasko A. EPR spectroscopy of free radical intermediates of antiarrhythmic-antihypoxic drug stobadine, a pyridoindole derivative. Life Sci 1999;65:1879–1881.
  • Suzen S, Bozkaya P, Coban T, Nebiogu D. Investigation of the in vitro antioxidant behaviour of some 2-phenylindole derivatives: discussion on possible antioxidant mechanisms and comparison with melatonin. J Enzyme Inhib Med Chem 2006;21:405–411.
  • Ates-Alagoz Z, Coban T, Suzen S. A Comparative study: evaluation of antioxidant activity of melatonin and some indole derivatives. Med Chem Res 2005;14:169–179.
  • Gürkök G, Coban T, Suzen S. Melatonin analogue new indole hydrazide/hydrazone derivatives with antioxidant behavior: synthesis and structure-activity relationships. J Enzyme Inhib Med Chem 2009;24:506–515.
  • Shirinzadeh H, Eren B, Gurer-Orhan H, Suzen S, Ozden S. Novel indole-based analogs of melatonin: synthesis and in vitro antioxidant activity studies. Molecules 2010;15:2187–2202.
  • Rajitha G, Saideepa N, Praneetha P. Synthesis and evaluation of N-(α-benzamidocinnamoyl) aryl hydrazone derivatives for anti-inflammatory and antioxidant activities. Ind J Chem 2011;50B:729–733.
  • Prathapa KJ, Himajaa M, Malib SV, Ranjithaa A, Karigarc A, Sikarwar M. Synthesis and antioxidant activity of novel ketone hydrazones bearing 5-(Pyridine-3-yl)-1,3,4-thiadiazole. J Pharm Res 2010;3:2460–2462.
  • Kumar PP, Rani BL. Synthesis and characterization of new Schiff bases containing pyridine moiety and their derivatives as antioxidant agents. Int J Chem Tech Research 2011;3:155–160.
  • Thangadurai TD, Gowri M, Natarajan K. Synthesis and characterisation of ruthenium(III) complexes containing monobasic bidentate Schiff bases and their biological activities. Synth React Inorg Met-org Chem 2002;32:329–343.
  • Belkheiri N, Bouguerne B, Bedos-Belval F, Duran H, Bernis C, Salvayre R et al. Synthesis and antioxidant activity evaluation of a syringic hydrazones family. Eur J Med Chem 2010;45:3019–3026.
  • Negre-Salvayre A, Coatrieux C, Ingueneau C, Salvayre R. Advanced lipid peroxidation end products in oxidative damage to proteins. Potential role in diseases and therapeutic prospects for the inhibitors. Br J Pharmacol 2008;153:6–20.
  • Yılmaz AD, Coban T, Suzen S. JSynthesis and antioxidant activity evaluations of melatonin-based analogue indole-hydrazide/hydrazone derivatives. J Enzyme Inhib Med Chem 2012;27:428–436.
  • Suzen S, Karaaslan C. Electrochemical behavior of biologically important indole derivatives. J Int Electrochem 2011;2011:1–10.
  • Kissinger PT, Heineman WR, eds. (1996). Laboratory techniques in electroanalytical chemistry. 2nd ed. New York: Marcel Dekker.
  • Wang J, ed. (1988). Electroanalytical techniques in clinical chemistry and laboratory medicine. New York: VCH Publisher Inc.
  • Hart HP. (1990). Electroanalysis of biologycally important compounds. England: Ellis Horwood Ltd.
  • Vire JC, Kauffmann JM. Curr. Top. Trends in electrochemistry in drug analysis. Electrochem 1994;3:493–515.
  • Süzen S, Ates-Alagöz Z, Demircigil BT, Ozkan SA. Synthesis and analytical evaluation by voltammetric studies of some new indole-3-propionamide derivatives. Farmaco 2001;56:835–840.
  • Suzen S, Demircigil T, Buyukbingol E, Ozkan SA. Electroanalitical evaluation and determination of 5-(3′-indolyl)-2-thiohydantoin derivatives by voltammetric studies: possible relevance to in vitro metabolism. New J Chem 2003;27:1007–1011.
  • Bozkaya P, Dogan B, Suzen S, Nebioglu D, Ozkan SA. Determination and investigation of electrochemical behaviour of 2-phenylindole derivatives: discussion on possible mechanistic pathways. Can J Anal Sci Spec 2006;51:125–139.
  • Shirinzadeh H, Yılmaz AD, Gumustas M, Suzen S, Ozden S, Ozkan SA. Electrochemical behavior of indole-3-carboxaldehyde izonicotinoyl hydrazones: discussion on possible biological behavior. Chem High T Synt 2010;13:619–627.
  • Kidwai M, Negi N, Gupta SD. Synthesis and antifertility activity of 1,5-diaryl-3-(3’-indolyl)formazans. Chem Pharm Bull 1994;42:2363–2364.
  • Lautraite S, Bigot-Lasserre D, Bars R, Carmichael N. Optimisation of cell-based assays for medium throughput screening of oxidative stress. Toxicol In Vitro 2003;17:207–220.
  • Hassoun EA, Roche VF, Stohs JS. Release of enzymes by ricin from macrophages and Chinese hamster ovary cells in culture. Toulouse Med 1993;3:119–129.
  • Moss DW, Henderson AR, Kochmar JR. (1986). Enzymes. In: Tietz NW, ed. Textbook of clinical chemistry. Philadelphia: WB Saunders, 619–663.
  • Barros SB, Simizu K, Junqueira VB. Liver lipid peroxidation-related parameters after short-term administration of hexachlorocyclohexane isomers to rats. Toxicol Lett 1991;56:137–144.
  • Suzen S, Ozkan SA. (2011). Medicinal and pharmaceutical applications and prospects of electrochemistry. In: Ozkan SA, ed. Electroanalytical methods in pharmaceutical analysis and their validation. NHB Publishing, ISBN: 978-0-9664286-7-4.
  • Kul D, Gumustas M, Uslu B, Ozkan SA. Electroanalytical characteristics of antipsychotic drug ziprasidone and its determination in pharmaceuticals and serum samples on solid electrodes. Talanta 2010;82:286–295.
  • Altun Y, Dogan-Topal B, Uslu B, Ozkan SA. Anodic behavior of sertindole and its voltammetric determination in pharmaceuticals and human serum using glassy carbon and boron-doped diamond electrodes. Electrochim Acta 2009;54:1893–1903.
  • Laviron E, Roullier C, Degrand J. A multilayer model for the study of space distributed redox modified electrodes: Part II. Theory and application of linear potential sweep voltammetry for a simple reaction. Electroanal Chem 1980;112:11–23.
  • Goyal RN, Kumar RN, Signhal NK. Oxidation chemistry and biochemistry of indole and effect of its oxidation product in albino mice. Bioelectrochem Bioenerg 1998;45:47–53.
  • Ozkan SA, Uslu B, Aboul-Enein HY. Voltammetric investigation of tamsulosin. Talanta 2003;61:147–156.
  • Demircan S, Ozkan SA, Kır S. Electroanalytical characterization of verapamil and its voltammetric determination in pharmaceuticals and human serum. Anal Lett 2007;40:1177–1195.
  • Jennings P, Jones AC, Mount AR, Thomson AD. Electrooxidation of 5-substituted indoles. J Chem Soc Faraday Trans 1997;93:3791–3797.
  • Enache TA, Oliveira-Brett AM. Pathways of electrochemical oxidation of indolic compounds. Electroanalysis 2011;23:1337–1344.
  • Somers KRF, Kryachko ES, Ceulemans A. Theoretical study of indole: protonation, indolyl radical, tautomers of indole, and its interaction with water. Ceulemans Chem Phys 2004;301:61–79.
  • Grimshow J, ed. (2000). Electrochemical reactions and mechanisms in organic chemistry. 1st ed. Amsterdam: Elsevier.
  • Lund H, Hammerich O. (2001). Organic electrochemistry. 4th ed. New York: Marcel Dekker.
  • Dekker M. (1997). Analytical Method Development and Validation. In: Swartz ME, Krull IS, eds. New York: Marcel Dekker, Inc.
  • Ermer J, Miller JHMcB. (2005) Method validation in pharmaceutical analysis. 1st ed. Weinheim, Germany: Wiley-VCH.
  • Cossum PA. Role of the red blood cell in drug metabolism. Biopharm Drug Dispos 1988;9:321–336.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.