Melatonin and synthetic analogs as antioxidants

Current Drug Delivery

Volumn 10, Issue 1, 2013, Pages 71-75

  Suzen, Sibel ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

Antioxidant; Free radical; Indole; Melatonin; Synthesis

Indexed keywords

2 PHENYLINDOLE DERIVATIVE; ANTIOXIDANT; INDOLE; INDOLE 3 PROPIONAMIDE; INDOLE AMINE TRIAZOLE; INDOLEPROPIONIC ACID; MELATONIN; STOBADINE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; CYTOTOXICITY; HUMAN; PRIORITY JOURNAL; REVIEW;

ANIMALS; ANTIOXIDANTS; HUMANS; MELATONIN;

EID: 84875282051     PISSN: 15672018     EISSN: 18755704     Source Type: Journal    
DOI: 10.2174/1567201811310010013     Document Type: Review

References (34)

1. Singh, R. P.; Sharad, S.; Kapur, S. Free Radicals and Oxidative Stress in Neurodegenerative Diseases: Relevance of Dietary Anti- oxidants. J. Ind. Acad. Clin. Med., 2004, 5, 218-25.
2. Suzen, S. Antioxidant activities of synthetic indole derivatives and possible activity mechanisms. Berlin Heidelberg: Spinger-Verlag, 145-178, 2007.
3. Ahmed, R. G. Is there a balance between oxidative stress and anti-oxidant defence system during development? Med. J. Islamic World Acad. Sci., 2005, 15, 55-63.
4. Suzen, S. Recent developments of melatonin related antioxidant compounds. Comb. Chem. High Throughput Screen, 2006, 9, 409-419.
5. Ohkawa, H.; Ohishi, N., Yagi, K. Assay of lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal. Biochem., 1979, 95, 351-358.
6. Thaipong, K.; Boonprakob, U.; Crosby, K.; Cisneros-Zevallos, L.; Byrne, D. H. Comparison of ABTS, DPPH, FRAP and ORAC assays for estimating antioxidant activity from guava fruit extracts. J. Food Comp. Anal., 2006, 19, 669-675.
7. Zhan, C. D.; Sindhu, R. K.; Pang, J., Ehdaie, A., Vaziri, N. D. J. Hypertens., 2004, 22, 2025-33.
8. Gherghel, D.; Griffiths, H. R., Hilton, E. J.; Cunliffe, I. A., Hosking S. L. Systemic reduction in glutathione levels occurs in patients with primary open-angle glaucoma. Invest. Ophthalmol. Vis. Sci., 2005, 46, 877-883.
9. Betteridge, D. J. What is oxidative stress? Metabolism, 2000, 49, 3-8.
10. Reiter, R. J. Pineal melatonin: cell biology of its synthesis and of its physiological interactions. Endocr. Rev., 1991, 12, 151-80.
11. Reiter, R. J.; Tan, D.X.; Manchester, L. C.; Calvo, J.R. Antioxida- tive capacity of melatonin. In Handbook of antioxidants, 2nd edn. Cadenas E, Packer L, ed, pp 565-613. Marcel Dekker, New York, 2002.
12. Kennaway, D.J.; Wright, H. Melatonin and circadian rhythms. Curr. Top. Med. Chem., 2002, 2, 199-209.
13. Blask, D.E.; Sauer, L.A.; Dauchy, R. T. Melatonin as a chronobi-otic/anticancer agent: cellular, biochemical, and molecular mechanisms of action and their implications for circadian-based cancer therapy. Curr. Top. Med. Chem., 2002, 2, 113-32.
14. Guerrero, J. M.; Reiter, R. J. Melatonin-Immune System Relationships. Curr. Top. Med. Chem., 2002, 2, 167-80.
15. Cuzzocrea, S.; Reiter, R. J. Pharmacological Actions of Melatonin in Acute and Chronic Inflammation. Curr. Top. Med. Chem., 2002, 2, 153-65.
16. Tan, D. X.; Reiter, R. J.; Manchester, L. C.; Yan, M. T.; El-Sawi, M.; Sainz, R. M.; Mayo, J. C.; Kohen, R.; Allegra, M.; Hardeland, R. Chemical and Physical Properties and Potential Mechanisms: Melatonin as a Broad Spectrum Antioxidant and Free Radical Scavenger. Curr. Top. Med. Chem., 2002, 2, 181-97.
17. Reiter, R. J.; Tan, D. X., Osuna, C., Gitto, E. Actions of melatonin in the reduction of oxidative stress. A review. J. Biomed. Sci., 2000, 7, 444-58.
18. Cano, A.; Alcaraz, O.; Arnao, M. B. Free radicalscavenging activity of indolic compounds in aqueous and ethanolic media.Anal. Bioanal. Chem., 2003, 376, 33-37.
19. 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.
20. Misik, V.; Ondrias, K.; Stasko, A. EPR spectroscopy of free radical intermediates of antiarrhythmic-antihypoxic drug stobadine, a pyri-doindole derivative. Life Sci., 1999, 65, 1879-1881.
21. Suzen, S.; Bozkaya, P.; Coban, T.; Nebiogu, D. Investigation of 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.
22. 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.
23. Das-Evcimen, N.; Yildirm, O.; Suzen, S. Relationship between aldose reductase and superoxide dismutase Inhibition capacities of indole-based analogs of melatonin derivatives. Arch. Biol. Sci., Belgrade 2009, 61, 675-681.
24. Suzen, S.; Demircigil, T.; Buyukbingol, E.; Ozkan, S. A. Electro-analitical 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.
25. Suzen, S.; Ates-Alagöz, Z.; Demircigil, B. T.; Ozkan, S. A. Synthesis and Analytical Evaluation by Voltammetric Studies of Some New Indole-3-propionic acid Derivatives FARMACO 2001, 56, 835-840.
26. Gurkok, G.; Coban, T.; Suzen, S. Melatonin analogue new indole hydrazide/hydrazone derivatives with antioxidant behavior: synthesis and discussion on structure activity relationships. J. Enzyme Inhib. Med. Chem., 2009, 24, 506-515.
27. Shirinzadeh, H.; Eren, B.; Gurer-Orhan, H.; Suzen, S., Ozden, S. Synthesis and Investigation of Electrochemical Behaviour of N-Methylindole-3-Carboxaldehyde Izonicotinoyl Hydrazone Molecules 2010, 15, 2187-2202.
28. Karaaslan, C; Tekiner-Gülba, B.; Ozcan, S.; Gurer-Orhan, H.; Suzen, S. Antioxidant activity of indole-based melatonin analogues in erythrocytes and their voltammetric characterization. J. Enzym Inh. Med. Chem., 2012, in press.
29. Yilmaz, A. D.; Coban, T.; Suzen, S. J. Synthesis and antioxidant activity evaluations of melatonin-based analogue indole-hydrazide/hydrazone derivatives. Enzyme Inhib. Med. Chem., 2012, 27, 428-36.
30. Poeggeler, B.; Thuermann, S.; Dose, A.; Schoenke, M.; Burkhardt, S.; Hardeland, R. J. Pineal Res., 2002, 33, 20-30.
31. Poeggeler, B.; Pappolla, M. A.; Hardeland, R.; Rassoulpour, A.; Hodgkins, P. S.; Guidetti, P. Melatonin's unique radical scavenging properties - roles of its functional substituents as revealed by a comparison with its structural analogs. J. Pineal Res. Brain Res., 1999, 815, 382-388.
32. Barros, S. B. M.; Simizu, K.; Junqueira, V. B. C. liver lipid peroxidation- related parameters after short-term administraoon of hei{dotless}cachlorocydohexane isomers lo rats. Toxicol. Lett., 1991, 56, 137-144.
33. Reiter, R. J. Cytoprotective properties of melatonin: Presumed association with oxidative damage and aging. Nutrition, 1998, 14, 691-696.
34. Bradbury, A. F.; Smyth, D. G. Enzyme catalysed peptide amida-tion: isolation of a stable intermediate formed by reaction of the amidating enzyme with an imino acid. Eur. J. Biochem., 1987, 169, 579-584.