Free-radical degradation of high-molar-mass hyaluronan induced by ascorbate plus cupric ions: Testing of stobadine and its two derivatives in function as antioxidants

General Physiology and Biophysics

Volumn 31, Issue 1, 2012, Pages 57-64

  Surovcikova Machova, Lubica ^a   Valachova, Katarina ^a   Banasova, Maria ^a   Snirc, Vladimir ^a   Priesolova, Elena ^b   Nagy, Milan ^b   Juranek, Ivo ^a   Soltes, Ladislav ^a  

^a INSTITUTE OF EXPERIMENTAL PHARMACOLOGY AND TOXICOLOGY   (Slovakia)

^b Faculty of Natural Sciences   (Slovakia)

Author keywords

ABTS assay; Glycosaminoglycans; Hexahydropyridoindole derivatives; Rotational viscometry; Weissberger oxidative system

Indexed keywords

2 ISOPROPYLOXYCARBONYL 8 METHOXY 2,3,4,4A,5,9B HEXAHYDRO 1H PYRIDO[4,3 B]INDOLINIUM; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); 2,2,3,3,8 PENTAMETHYL 2,3,4,4A,5,9B HEXAHYDRO 1H PYRIDO[4,3 B]INDOLINIUM; ALOSTERONE; ANTIEMETIC AGENT; ANTIHISTAMINIC AGENT; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; ASCORBIC ACID; AUROTHIOMALATE; BUCILLAMINE; CARBOLINE; CATION; COPPER CHLORIDE; DICARBINE; FREE RADICAL; HYALURONIC ACID; INDOLE DERIVATIVE; MEBHYDROLIN; NEUROLEPTIC AGENT; PYRIDONE DERIVATIVE; SCAVENGER; STOBADINE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD PRESSURE; CARDIOVASCULAR EFFECT; CHELATION; CHEMICAL STRUCTURE; DEGRADATION; DRUG EFFECT; ENANTIOMER; HYDROPHILICITY; HYPOTENSION; OXIDATION; VISCOMETRY; VISCOSITY;

ANTIOXIDANTS; ASCORBIC ACID; CARBOLINES; COPPER; FREE RADICALS; HYALURONIC ACID; MOLECULAR WEIGHT;

EID: 84858786150     PISSN: 02315882     EISSN: 13384325     Source Type: Journal    
DOI: 10.4149/gpb_2012_006     Document Type: Article

References (44)

1. Cheng Z., Moore J., Yu L. (2006): High-throughput relative DPPH radical scavenging capacity assay. J. Agric. Food Chem. 54, 7429-7436 http://dx.doi.org/10.1021/jf0611668 (Pubitemid 44645754)
2. Horáková L., Schaur R. J., Balgavý P., Egger G. (1995): Interaction of the pyridoindole stobadine with alkoxyl and stable free radicals. Redox Rep. 1, 369-372
3. Horáková L., Schaur R. J., Balgavý P. (1996): The crocin assay for the determination of relative rate constants of alkoxyl radical reactions with the pyridoindole stobadine and with other antioxidants. Redox Rep. 2, 401-405
4. Hrabárová E., Valachová K., Rapta P., Šoltés L. (2010): An alternative standard for Trolox-equivalent antioxidant-capacity estimation based on thiol antioxidants. Comparative 2,2'-azinobis[3-ethylbenzothiazoline- 6-sulfonic acid] decolorization and rotational viscometry study regarding hyaluronan degradation. Chem. Biodivers. 7, 2191-2200
5. Hung D. (2008): Hydrogenated pyrido [4,3-b] indoles such as Dimebon for treating canine cognitive dysfunction syndrome. US Patent No. 2007/020483
6. Ivachtchenko A. V., Mitkin O. D., Kadieva M. G., Tkachenko S. E. (2010): The synthesis and physiological activity of 2,3,4,5-tetrahydro- 1H-pyrido[4,3-b]indoles. Rus. Chem. Rev. 79, 285-306 http://dx.doi.org/10.1070/ RC2010v079n04ABEH004122
7. Ivashchenko A. A., Ivachtchenko A. V., Tkachenko S. Y., Frolov E. B., Mitkin O. D., Kravchenko D. V., Okun I. M., Savchuk N. F., Lavrovsky Y. (2010): Substituted 2,3,4,5-tetrahydro-1H- pyrido[4,3-b] indoles, methods for the production and use thereof. EP2145887A2
8. Juránek I., Horáková L., Račková L., Štefek M. (2010): Antioxidants in treating pathologies involving oxidative damage: An update on medicinal chemistry and biological activity of stobadine and related pyridoindoles. Curr. Med. Chem. 17, 552-570 http://dx.doi.org/10.2174/092986710790416317
9. Kagan V. E., Tsuchiya M., Serbinova E., Packer L., Sies H. (1993): Interaction of the pyridoindole stobadine with peroxyl, superoxide and chromanoxyl radicals. Biochem. Pharmacol. 45, 393-400 http://dx.doi.org/10.1016/ 0006-2952(93)90075-8 (Pubitemid 23042638)
10. Kittová M., Gibala P., Dřímal J. (1985): Antiarrhythmic and hemodynamic effects of derivatives of pyridoindole (DH 1011) on experimental models of disorders of rhythm and heart function. Bratisl. Lek. Listy 84, 542-549 (in Slovak)
11. Kogan G., Šoltés L., Stern R., Gemeiner P. (2007): Hyaluronic acid: A natural biopolymer with a broad range of biomedical and industrial applications. Biotechnol. Lett. 29, 17-25 http://dx.doi.org/10.1007/ s10529-006-9219-z (Pubitemid 44950153)
12. Kongtawelert P., Ghosh P. (1989): An enzyme-linked immunosorbent- inhibition assay for quantitation of hyaluronan (hyaluronic acid) in biological fluids. Anal. Biochem. 178, 367-372 http://dx.doi.org/10.1016/0003-2697(89) 90654-4 (Pubitemid 19125358)
13. Magalhaes L. M., Segundo M. A., Reis S., Lima J. L. F. C. (2008): Methodological aspects about in vitro evaluation of antioxidant properties. Anal. Chim. Acta 613, 1-19 http://dx.doi.org/10.1016/j.aca.2008.02.047
14. Ondriáš K., Mišík V., Gergel' D., Staško A. (1989): Lipid peroxidation of phosphatidylcholine liposomes depressed by the calcium channel blockers nifedipine and verapamiI and by the antiarrhythmic-antihypoxic drug stobadine. Biochim. Biophys. Acta 1003, 238-245 (Pubitemid 19150994)
15. Orviský E., Šoltés L., Stančí ková M., Vyletelová Z., Juránek I. (1994): Assessment of antioxidative properties of hydrophilic xenobiotics on the basis of inhibition of the radical degradation of hyaluronan by reactive oxygen species. CS Patent No. 2764 (in Slovak)
16. Puré E., Assoian R. K. (2009): Rheostatic signaling by CD44 and hyaluronan. Cell. Signal. 21, 651-655 http://dx.doi.org/10.1016/j.cellsig.2009. 01.024
17. Račková L., Štefek M., Májeková M. (2002): Structural aspects of antioxidant activity of substituted pyridoindoles. Redox Rep. 7, 207-214 http://dx.doi.org/10.1179/135100002125000578
18. Rapta P., Valachová K., Gemeiner P., Šoltés L. (2009): High-molar -mass hyaluronan behavior during testing its radical scavenging capacity in organic and aqueous media: Effects of the presence of manganese(II) ions. Chem. Biodivers. 6, 162-169 http://dx.doi.org/10.1002/cbdv. 200800075
19. Rapta P., Valachová K., Zalibera M., Šnirc V., Šoltés L. (2010): Hyaluronan degradation by reactive oxygen species. Scavenging effect of the hexahydropyridoindole stobadine and two of its derivatives. In: Monomers, Oligomers, Polymers, Composites and Nanocomposites Research: Synthesis, Properties and Applications. (Eds. R. A. Pethrick, P. Petkov, A. Zlatarov, G. E. Zaikov and S. K. Rakovsky), pp. 113-126, Nova Science Publishers, New York
20. Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C. (1999): Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 26, 1231-1237 http://dx.doi.org/10. 1016/S0891-5849(98)00315-3 (Pubitemid 29262709)
21. Schoenfeld P. (2005): Efficacy of current drug therapies in irritable bowel syndrome: What works and does not work. Clin. North. Am. 34, 319-335 (Pubitemid 40615959)
22. Stankovská M., Šoltés L. (2010): Oxidative degradation of hyaluronan: Is melatonin an antioxidant or prooxidant. In: Monomers, Oligomers, Polymers, Composites and Nanocomposites Research: Synthesis, Properties and Applications. (Eds. R. A. Pethrick, P. Petkov, A. Zlatarov, G. E. Zaikov and S. K. Rakovsky), pp. 59-67, Nova Science Publishers, New York
23. Staško A., Ondriáš K., Mišík V. (1990): Stobadine - a novel scavenger of free radicals. Chem. Pap. 44, 493-500
24. Steenken S., Sundquist A. R., Jovanovic S. V., Crockett R., Sies H. (1992): Antioxidant activity of the pyridoindole stobadine. Pulse radiolytic characterization of one-electron-oxidized stobadine and quenching of singlet molecular oxygen. Chem. Res. Toxicol. 5, 355-360 http://dx.doi.org/10.1021/ tx00027a006
25. Stern R. (2003): Devising a pathway for hyaluronan catabolism: Are we there yet? Glycobiology 13, 105-115 http://dx.doi.org/10.1093/glycob/cwg112
26. Stern R., Kogan G., Jedrzejas M. J., Šoltés L. (2007): The many ways to cleave hyaluronan. Biotechnol. Adv. 25, 537-557 http://dx.doi.org/10.1016/j.biotechadv.2007.07.001 (Pubitemid 47464847)
27. Šoltés L., Bezek Š., Ujházy E., Bauer V. (2000): Extraction and chromatographic separation methods in pharmacokinetic studies of Stobadine - an indole-related antioxidant and free-radical scavenger. Biomed. Chromatogr. 14, 188-201 (Pubitemid 30255906)
28. Šoltés L., Stankovská M., Kogan G., Gemeiner P., Stern R. (2005): Contribution of oxidative-reductive reactions to high-molecular-weight hyaluronan catabolism. Chem. Biodivers. 2, 1242-1245 http://dx.doi.org/10.1002/cbdv.200590094 (Pubitemid 41404123)
29. Šoltés L., Stankovská M., Brezová V., Schiller J., Arnhold J., Kogan G., Gemeiner P. (2006): Hyaluronan degradation by copper(II) chloride and ascorbate: Rotational viscometric, EPR spin-trapping, and MALDI-TOF mass spectrometric investigations. Carbohydr. Res. 341, 2826-2834 (Pubitemid 44692666)
30. Šoltés L. Stankovská M., Kogan G., Mendichi R., Volpi N., Sasinková V., Gemeiner P. (2007a): Degradation of high-molar-mass hyaluronan by an oxidative system comprising ascorbate, Cu(II), and hydrogen peroxide: Inhibitory action of antiinflammatory drugs - Naproxen and acetylsalicylic acid. J. Pharm. Biomed. Anal. 44, 1056-1063 (Pubitemid 47239301)
31. Šoltés L., Valachová K., Mendichi R., Kogan G., Arnhold J., Gemeiner P. (2007b): Solution properties of high-molar-mass hyaluronans: The biopolymer degradation by ascorbate. Carbohyd. Res. 342, 1071-1077 http://dx.doi.org/10.1016/j.carres.2007.02.018 (Pubitemid 46551992)
32. Štefek M., Beneš L. (1991): Pyridoindole stobadine is a potent scavenger of hydroxyl radicals. FEBS Lett. 294, 264-266 http://dx.doi.org/10.1016/0014-5793(91)81444-D
33. Štefek M., Masaryková M., Beneš L. (1992): Inhibition of cumene hydroperoxide induced lipid peroxidation by a novel pyridoindole antioxidant in rat liver microsomes. Pharmacol. Toxicol. 70, 407-411 http://dx.doi.org/10.1111/j.1600-0773.1992.tb00498.x
34. Štefek M., Trnková Z. (1996): The pyridoindole antioxidant stobadine prevents alloxan-induced lipid peroxidation by inhibiting its propagation. Pharmacol. Toxicol. 78, 77-81 http://dx.doi.org/10.1111/j.1600- 0773.1996.tb00183.x (Pubitemid 26042761)
35. Štolc S., Považanec F., Bauer V., Májeková M., Wilcox A. L., Šnirc V., Račková L., Sotníková R., Štefek M., Gáspárová Z., Gajdošíková A., Mihálová D., Alfoldi J. (2010): Pyridoindole derivatives with antioxidant properties: Their synthesis and use in therapeutic practice. SK Patent No. 287506 (in Slovak)
36. Valachová K., Rapta P., Kogan G., Hrabárová E., Gemeiner P., Šoltés L. (2009a): Degradation of high-molar-mass hyaluronan by ascorbate plus cupric ions: Effects of D-penicillamine addition. Chem. Biodivers. 6, 389-395 http://dx.doi.org/10.1002/cbdv.200800261
37. Valachová K., Kogan G., Gemeiner P., Šoltés L. (2009b): Hyaluronan degradation by ascorbate: Protective effects of manganese(II) chloride. In: Kinetics & Thermodynamics for Chemistry & Biochemistry. (Eds. E. M. Pearce, G. E. Zaikov and G. Kirshenbaum), pp. 201-215, Nova Science Publishers, New York
38. Valachová K., Hrabárová E., Dráfi F., Juránek I., Bauerová K., Priesolová E., Nagy M., Šoltés L. (2010a): Ascorbate and Cu(II)-induced oxidative degradation of high-molar-mass hyaluronan. Pro- and antioxidative effects of some thiols. Neuroendocrinol. Lett. 31 (Suppl. 2), 101-104
39. Valachová K., Kogan G., Gemeiner P., Šoltés L. (2010b): Protective effects of manganese(II) chloride on hyaluronan degradation by oxidative system ascorbate plus cupric chloride. Interdisc. Toxicol. 3, 26-34 http://dx.doi.org/10.2478/v10102-010-0001-7
40. Valachová K., Mendichi R., Šoltés L. (2010c): Effect of L-glutathione on high-molar-mass hyaluronan degradation by oxidative system Cu(II) plus ascorbate. In: Monomers, Oligomers, Polymers, Composites, and Nanocomposites. (Eds. R. A. Pethrick, P. Petkov, A. Zlatarov, G. E. Zaikov and S. K. Rakovsky), pp. 101-111, Nova Science Publishers, New York
41. Valachová K., Hrabárová E., Priesolová E., Nagy M., Baňasová M., Juránek I., Šoltés L. (2011): Free-radical degradation of high-molecular-weight hyaluronan induced by ascorbate plus cupric ions. Testing of bucillamine and its SA981-metabolite as antioxidants. J. Pharm. Biomed. Anal. 56, 664-670 http://dx.doi.org/10.1016/j. jpba.2011.06.015
42. Waitzinger J., Lenders H., Pabst G., Ulbrich E. (1995): Three explorative studies on the efficacy of the antihistamine mebhydroline (Omeril). Int. J. Clin. Pharmacol. Ther. 33, 373-383
43. Yakhontov L. N., Glushkov R. G. (1983). Synthetic Drugs. (Ed. A. G. Natradze), pp. 234-237, Meditsina Publishing House, Moscow (in Russian)
44. Yamazaki K., Fukuda K., Matsukawa M., Hara F., Yoshida K., Akagi M., Munakata H., Hamanishi C. (2003): Reactive oxygen species depolymerize hyaluronan: Involvement of the hydroxyl radical. Pathophysiology 9, 215-220 http://dx.doi.org/10.1016/S0928-4680(03)00024-5 (Pubitemid 37297866)