Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species

Journal of Pharmacy and Pharmacology

Volumn 55, Issue 7, 2003, Pages 1029-1039

  Panteleon, Vassiliki ^a   Marakos, Panagiotis ^a   Pouli, Nicole ^a   Mikros, Emmanuel ^a   Andreadou, Ioanna ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 7 [(2 ETHYNYLTRICYCLO[3,3,1,1 3,7]DECAN 2 YL)OXY]BENZO[B]PYRAN 2(2H) ONE; 9',10' DIHYDRO 10' HYDROXYSPIRO(CYCLOHEPTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; 9',10' DIHYDRO 10' HYDROXYSPIRO(CYCLOHEXANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; 9',10' DIHYDRO 10' HYDROXYSPIRO(CYCLOPENTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; 9',10' DIHYDRO 9',10' DIHYDROXYSPIRO(CYCLOHEPTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; 9',10' DIHYDRO 9',10' DIHYDROXYSPIRO(CYCLOHEXANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; 9',10' DIHYDRO 9',10' DIHYDROXYSPIRO(CYCLOPENTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; 9',10' DIHYDRO 9',10' DIHYDROXYSPIRO[TRICYCLO[3,3,1,1 3,7]DECANE 2,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN] 2'(2'H) ONE; 9',10' DIHYDROSPIRO(CYCLOHEPTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H),10' DIONE; 9',10' DIHYDROSPIRO(CYCLOHEXANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H),10' DIONE; 9',10' DIHYDROSPIRO(CYCLOPENTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H),10' DIONE; ADAMANTANE DERIVATIVE; ASCORBIC ACID; DIMETHYL SULFOXIDE; FREE RADICAL; HYDROXYL RADICAL; MANNITOL; PYRANOCOUMARIN DERIVATIVE; REACTIVE OXYGEN METABOLITE; SPIRO(CYCLOHEPTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; SPIRO(CYCLOHEXANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; SPIRO(CYCLOPENTANE 1,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN) 2'(2'H) ONE; SPIRO[TRICYCLO[3,3,1,1 3,7]DECAN 2,8'(8'H) PYRAN[2,3 H]BENZO[B]PYRAN 2'(2'H) ONE; SUPEROXIDE; UMBELLIFERONE; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

ANTIOXIDANT ACTIVITY; ARTICLE; CONCENTRATION (PARAMETERS); CONJUGATION; CONTROLLED STUDY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; OXIDATION; PATHOPHYSIOLOGY; PROTECTION; SCAVENGING SYSTEM;

ANTIOXIDANTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRANOCOUMARINS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0042666860     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/0022357021512     Document Type: Article

References (33)

1. Andreadou, I., Tsantili-Kakoulidou, A., Siatra-Papastaikoudi, T. (2000) Significant antioxidant properties of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole analogs. Res. Com. Biochem. Cell Mol. Biol. 4: 269-275
2. Andreadou, I., Tasouli, A., Iliodromitis, E., Tsantili-Kakoulidou, A., Papalois, A., Siatra, T., Kremastinos, D. (2002) Reduction of myocardial infarct size in rabbits by a novel indole derivative with antioxidant and free radical scavenging properties. Eur. J. Pharmacol. 453: 271-277
3. Barclay, R. C., Baskin, K. A., Dakin, K. A., Locke, S. J., Vinquist, M. R. (1990) The antioxidant activities of phenolic antioxidants in free-radical peroxidation of phospholipid membranes. Can. J. Chem. 68: 2258-2269
4. Bender, D. R., Kanne, D., Frazier, J. D., Rapoport, H. (1983) Synthesis and derivatization of 8-acetylpsoralens. Acetyl migrations during Claisen rearrangement. J. Org. Chem. 48: 2709-2719
5. Dinis, T. C. P., Madeira, V. M. C., Almeida, L. M. (1994) Action of phenolic derivatives (Acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys. 315: 161-169
6. Eguchi, S., Arasaki, M. (1988) Synthesis of novel carbo- and hetero-polycycles. Part 8. An efficient and convenient synthesis of adamantylidenevinylidenecyclopropane derivatives. J. Chem. Soc. Perkin 1: 1047-1050
7. Elstner, E. F., Schuff-Werner, P., Seidel, D. (1988) Deutsches Patentamt Nr. De 37, 15, 990A1, Offenlegungstag: 08, 12
8. Esterbauer, H., Cheesemann, K. H. (1987) Lipid peroxidation: Part II pathological implications. Chem. Phys. Lipids 45: 103-367
9. Halliwell, B. (1990) How to characterize a biological antioxidant. Free Rad. Res. Commun. 9: 1-32
10. Halliwell, B., Gutteridge, J. M. C. (1986) Oxygen free radicals and iron in relation to biology and medicine: Some problems and concepts. Arch. Biochem. Biophys. 246: 501-514
11. Hoult, J. R., Paya, M. (1996) Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol. 27: 713-722
12. Kabbe, H. J. (1978) Eine einfache synthese von 4-chromanonen. Synthesis 886-887
13. Kirkiacharian, S., Bakhchinian, R., Chidiak, H., Mazmanian, M., Planché, C. (1999) Activité antiradicalaire de dérivés substitués de la 4-hydroxycoumarine. Ann. Pharm. Fr. 57: 251-254
14. Kostakis, I. K., Pouli, N., Marakos, P., Mikros, E., Skaltsounis, A. L., Leonce, S., Atassi, G., Renard, P. (2001) Synthesis, cytotoxic activity, NMR study and stereochemical effects of some new pyrano[3,2-b]thioxanthen-6-ones and pyrano[2,3-c]-thioxanthen-7-ones. Bioorg. Med. Chem. 9: 2793-2802
15. Klein, S. M., Cohen, G., Cederbaum, A. I. (1981) Production of formaldehyde during metabolism of dimethyl sulfoxide by hydroxyl radical generating systems. Biochemistry 20: 6006-6012
16. Le Noble, W. J., Chiou, D.-M., Okaya, Y. (1979) Evidence for a Carbene-Anion pair. 1,4-Disubstituted adamantanes as a stereochemical probe. J. Am. Chem. Soc. 101: 3244-3251
17. Martín-Aragón, S., Benedi, J. M., Villar, A. M. (1997) Modifications on antioxidant capacity and lipid peroxidation in mice under fraxetin treatment. J. Pharm. Pharmacol. 49: 49-52
18. Martín-Aragón, S., Benedi, J. M., Villar, A. M. (1998) Effects of the antioxidant (6,7-dihydroxycoumarin) esculetin on the glutathione system and lipid peroxidation in mice. Gerontology 44: 21-25
19. Mikros, E., Mitaku, S., Skaltsounis, A. L., Libot, F., Tillequin, F., Koch, M. (1999) Stereochemical effects of some acronycine derivatives. Magn. Reson. Chem. 37: 498-506
20. Mohamadi, F., Richards, N. G. J., Guida, W. C., Liskamp, R., Lipton, M., Caufield, C., Chang, G., Hendrickson, T., Still, W. C. (1990) Macromodel - An integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comp. Chem. 11: 440-467
21. Paya, M., Halliwell, B., Hoult, J. R. (1992) Interactions of a series of coumarins with reactive oxygen species. Scavenging of superoxide, hypochlorous acid and hydroxyl radicals. Biochem. Pharmacol. 44: 205-214
22. Paya, M., Goodwin, P. A., De Las Heras, B., Hoult, J. R. (1994) Superoxide scavenging activity in leucocytes and absence of cellular toxicity of a series of coumarins. Biochem. Pharmacol. 48: 445-451
23. Prashant, A., Rao, S., Srinivas, S., Chowdary, K. S., Krishnan, V. S. H. (2001) Synthesis of some new 1,5-benzothiazepins containing 2H-1-benzopyran-2-one heterocycle. Heterocycl. Commun. 7: 61-66
24. Raj, H. G., Parmar, V. S., Jain, S. C., Goel, S., Himanshu, P., Malhotra, S., Singh, A., Olsen, C. E., Wengel, J. (1998) Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: Dioxygenated 4-methyl coumarins as superb antioxidant and radical scavenging agents. Biorg. Med. Chem. Lett. 6: 833-839
25. Rekka, E., Kourounakis, N. P. (1991) Effect of hydroxyethyl rutosides and related compounds on lipid peroxidation and free radical scavenging activity. Some structural aspects. J. Pharm. Pharmacol. 43: 486-491
26. Rice-Evans, C., Miller, N. J., Paganga, G. (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Rad. Biol. Med. 20: 933-956
27. Robak, J., Gryglewski, R. J. (1988) Flavonoids are scavengers of superoxide anions. Biochem. Pharmacol. 37: 837-841
28. Ross, R., Glomset, J. A. (1993) The pathogenesis of atherosclerosis: A perspective for the 1990s. Nature 362: 801-809
29. Sato, T., Kawamoto, A., Tamura, A., Tatsumi, Y., Fuji, T. (1992) Mechanism of antioxidant action of pueraria glycoside (PG)-1 (an isoflavonoid) and mangifezin (a xanthonoid). Chem. Pharm. Bull. 40: 721-724
30. Valencia-Islas, N., Abbas, H., Bye, R., Toscano, R., Mata, R. (2002) Phytotoxic compounds from Prionosciadium watsoni. J. Nat. Prod. 65: 828-834
31. 4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant. Tetrahedron Lett. 17: 1973-1976
32. Xiong, Q., Kadota, S., Tani, T., Namba, T. (1996) Antioxidative effects of phenylethanoids from Cistanche deserticola. Biol. Pharm. Bull. 19: 1580-1585
33. Yu, W., Liu, Z.-Q., Liu, Z.-L. (1999) Antioxidant effect of coumarin derivatives on free radical initiated and photosensitized peroxidation of linoleic acid in micelles. J. Chem. Soc. Perkin Trans. 2: 969-974