Photocatalytic actions of the pesticide metabolite 2-hydroxyquinoxaline: Destruction of antioxidant vitamins and biogenic amines - Implications of organic redox cycling

Redox Report

Volumn 9, Issue 5, 2004, Pages 279-288

  Behrends, Andreas ^a   Hardeland, Rüdiger ^a   Ness, Heiko ^a   Grube, Sascha ^a   Poeggeler, Burkhard ^a   Haldar, Chandana ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b BANARAS HINDU UNIVERSITY   (India)

Author keywords

2 hydroxyquinoxaline; Biogenic amines; Photocatalysis; Quinalphos; Redox cycling; Vitamins

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; 2 HYDROXYQUINOXALINE; ADRENOCHROME; ALCOHOL; ALPHA TOCOPHEROL; ANTHRANILIC ACID DERIVATIVE; ASCORBIC ACID; BIOGENIC AMINE; CATECHOLAMINE; DIMER; DOPAMINE; HYDROXYL RADICAL; INDOLEAMINE; MELATONIN; N ACETYL 5 METHOXYKYNURENAMINE; PESTICIDE; QUINALPHOS; SEROTONIN; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CIRCADIAN RHYTHM; DIMERIZATION; ENZYME METABOLISM; INCUBATION TIME; INTOXICATION; LIGHT EXPOSURE; OLIGOMERIZATION; OXIDATION REDUCTION REACTION; PHOTOCATALYSIS; PRIORITY JOURNAL; TOXICITY TESTING;

AMINES; ANTIOXIDANTS; ASCORBIC ACID; CATALYSIS; CATECHOLAMINES; DIMERIZATION; DOPAMINE; ETHANOL; FREE RADICAL SCAVENGERS; KYNURAMINE; LIGHT; MELATONIN; MODELS, CHEMICAL; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; PIPERAZINES; QUINOXALINES; SEROTONIN; SPECTROPHOTOMETRY; TIME FACTORS; ULTRAVIOLET RAYS; VITAMIN E; VITAMINS;

EID: 11044229199     PISSN: 13510002     EISSN: None     Source Type: Journal    
DOI: 10.1179/135100004225006759     Document Type: Article

References (47)

1. Teixeira H, Proença P, Alvarenga M et al. Pesticide intoxications in the centre of Portugal: three years' analysis. Forensic Sci Int 2004; 143: 199-204.
2. Chatterjee S, Ray A, Bagchi P, Deb C. Estrogenic effects of aldrin and quinalphos in rats. Bull Environ Contam Toxicol 1992; 48: 125-130.
3. Ray A, Chatterjee S, Ghosh S et al. Quinalphos-induced suppression of spermatogenesis, plasma gonadotrophins, testicular testosterone production, and secretion in adult rats. Environ Res 1992; 57: 181-189.
4. Debnath D, Mandal TK. Study of quinalphos (an environmental oestrogenic insecticide) formulation (Ekalux 25 E.C.)-induced damage of testicular tissues and antioxidant defence systems in Sprague-Dawley albino rats. J Appl Toxicol 2000; 20: 197-204.
5. Sarkar R, Mhanakumar KP, Chowdhury M. Effects of an organo-phosphate pesticide, quinalphos, on the hypothalamo-pituitary-gonadal axis in adult male rats. J Reprod Fertil 2000; 118: 29-38.
6. Hardeland R. Melatonin: multiple functions in signaling and protection. In: Altmeyer P, Hoffmann K, Stücker M. (eds) Skin Cancer and UV Radiation, Berlin: Springer, 1997; 186-198.
7. Hardeland R. New actions of melatonin and their relevance to biometeorology. Int J Biometeorol 1997; 41: 47-57.
8. Guerrero JM, Reiter RJ. Melatonin-immune system relationships. Curr Top Med Chem 2: 167-179.
9. Haldar C. Apoptosis, cancer, immunity and melatonin. In: Haldar C, Singaravel M, Maitra SK, (eds) Treatise on Pineal Gland and Melatonin, Enfield: Science Publishers, 2002; 535-542.
10. Hardeland R, Reiter RJ, Poeggeler B, Tan D-X. The significance of the metabolism of the neurohormone melatonin: antioxidative protection and formation of bioactive substances. Neurosci Biobehav Rev 1993; 17: 347-357.
11. Tan D-X, Chen LD, Poeggeler B et al. Melatonin: a potent, endogenous hydroxyl radical scavenger. Endocr J 1993; 1 57-60.
12. Hardeland R, Fuhrberg B. Ubiquitous melatonin - presence and effects in unicells, plants and animals. Trends Comp Biochem Physiol 1996; 2: 25-45.
13. Poeggeler B, Reiter RJ, Hardeland R et al. Melatonin and structurally-related, endogenous indoles act as potent electron donors and radical scavengers in vitro. Redox Report 1996; 2: 179-184.
14. Tan D-X, Reiter RJ, Manchester LC et al. Chemical and physical properties and potential mechanisms: melatonin as a broad spectrum antioxidant and free radical scavenger Curr Top Med Chem 2002; 2: 181-1917.
15. Burkhardt S, Hardeland R, Poeggeler B. Various forms of oxidative stress strongly diminish 5-methoxylated indoleamines in Gonyaulax polyedra. In: Hardeland R. (ed) Biological Rhythms and Antioxidative Protection, Göttingen: Cuvillier, 1997; 98-102.
16. Hardeland R, Burkhardt S, Antolín I et al. Melatonin and 5-methoxytryptamine in the bioluminescent dinoflagellate Gonyaulax polyedra: restoration of the circadian glow peak after suppression of indoleamine biosynthesis or oxidative stress. Adv Exp Med Biol 1999; 460: 387-390.
17. Hardeland R, Coto-Montes A, Burkhardt S, Zsizsik BK. Circadian rhythms and oxidative stress in non-vertebrate organisms. In: Vanden Driessche T, Guisset J-L. Petiau-de Vries G. (eds) The Redox State and Circadian Rhythms, Dordrecht: Kluwer, 2000; 121-140.
18. Hardeland R, Coto-Montes A, Poeggeler B. Circadian rhythms, oxidative stress and antioxidative defense mechanisms. Chronobiol Int 2003; 20: 921-962.
19. Gupta A, Gupta A, Shukla GS. Effects of neonatal quinalphos exposure and subsequent withdrawal on free radical generation and antioxidative defenses in developing rat brain. J Appl Toxicol 1998; 18: 71-77.
20. Dwivedi PD, Das M, Khanna SK. Role of cytochrome P-450 in quinalphos toxicity: effect on hepatic and brain antioxidant enzymes in rats. Food Chem Toxicol 1998; 36: 437-444.
21. Rupa DS, Reddy PP, Reddi OS. Frequencies of chromosomal aberrations in smokers exposed to pesticides in cotton fields. Mutat Res 1989; 222: 37-41.
22. Rupa DS, Reddy PP, Reddi OS. Cytogeneticity of quinalphos and methyl parathion in human peripheral lymphocytes. Hum Exp Toxicol 1990; 9: 385-387.
23. Rupa DS, Reddy PP, Reddi OS. Cytogenetic effects of quinalphos in mice. Food Chem Toxicol 1991; 29: 115-117.
24. Babu GVAK, Reddy BR, Narasimha G, Sethunathar N. Persistence of quinalphos and occurrence of its primary metabolite in soils. Bull Environ Contam Toxicol 1998; 60: 724-731.
25. 14C carbaryl and quinalphos in soil under a groundnut crop (Arachis hypogaea L.) in semi-arid India. Chemosphere 2003; 53: 1023-1031.
26. Vasili Z, Drevenkar V, Rumenjak V et al. Urinary excretion of diethylphosphorus metabolites in persons poisoned by quinalphos or chlorpyrifos. Arch Environ Contam Toxicol 1992; 22 351-357.
27. Srivastava LP, Singh RP, Raizada RB. Phototoxicity of quinalphos under sunlight in vitro and in vivo. Food Chem Toxicol 1999; 37: 177-181.
28. Kennaway DJ, Hugel HM, Clarke S et al. Structure-activity studies of melatonin analogues in prepubertal male rats. Aust J Biol Sci 1988; 41: 393-400.
29. Burkhardt S, Poeggeler B, Tan D-X et al. Oxidation products formed from melatonin in various radical-generating systems. In: Hardeland R. (ed) Actions and Redox Properties of Melatonin and Other Aromatic Amino Acid Metabolites Göttingen: Cuvillier, 2001; 9-22.
30. Hardeland R, Ressmeyer A-R, Zelosko V et al. Metabolites of melatonin: formation and properties of the methoxylated kynuramines AFMK and AMK. In: Haldar C, Singh SS. (eds) Recent Advances in Endocrinology and Reproduction: Evolutionary, Biotechnological and Clinical Applications, Varanasi: Banaras Hindu University, 2004; 21-38.
31. Mueller U, Hardeland R, Poeggeler B et al. Pathways of melatonin catabolism in the dinoflagellate Gonyaulax polyedra. Biol Rhythm Res 2001; 32: 465.
32. Agozzino P, Avellone G, Bongiorno D et al. Melatonin: structural characterization of its non-enzymatic mono-oxygenate metabolite. J Pineal Res 2003; 35: 269-275.
33. 2. J Neural Transm Suppl 1990; 32: 249-257.
34. Schuff-Werner P, Splettstosser W, Schmidt F, Huether G. Serotonin acts as a radical scavenger and is oxidized to a dimer during the respiratory burst of human mononuclear and polymorphonuclear phagocytes. Eur J Clin Invest 1995; 25: 477-484.
35. Huether G, Fettkötter I, Keilhoff G, Wolf G. Serotonin acts as a radical scavenger and is oxidized to a dimer during the respiratory burst of activated microglia. J Neurochem 1997; 69 2096-2101.
36. 1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction. Redox Report 2003; 8: 205-213.
37. Srivastava AK, Gupta BN, Bihari V et al. Clinical, biochemical and neurobehavioural studies of workers engaged in the manufacture of quinalphos. Food Chem Toxicol 2000; 38: 65-69.
38. Jokanovic M. Studies on the delayed neurophathic and anticholinesterase potential of quinalphos (diethyl 2-quinoxalyl phosphorothionate) in hens. J Appl Toxicol 1993; 13: 337-339.
39. Ribeiro da Silva MAV, Matos MAR, Rio CMA et al. Thermochemical and theoretical studies of 2-hydroxyquinoxaline, 2,3-dihydroxyquinoxaline, and 2-hydroxy-3-methylquinoxaline. J Phys Chem A 2000; 104: 6644-6648.
40. Hardeland R, Burkhardt S, Antolín I et al. Bioluminescent dinoflagellates as test systems for various forms of cellular stress. Trends Comp Biochem Physiol 2004; 10: 19-29.
41. Uría H, Fuhrberg B, Poeggeler B et al. Photooxidation of melatonin. In: Hardeland R. (ed) Cell Biological Problems in Chronobiology, Göttingen: University of Gö ttingen, 1994; 89-99.
42. Hardeland R, Balzer I, Poeggeler B et al. On the primary functions of melatonin in evolution: mediation of photoperiodic signals in a unicell, photooxidation and scavenging of free radicals. J Pineal Res 1995; 18: 104-111.
43. 2-formyl-5-methoxykynurenine. J Pineal Res 2003; 35: 131-137. (Remark: Authors do not describe a substituted kynurenine, as mentioned in the title, but the kynuramine AFMK.)
44. Bindoli A, Rigobello MP. Galzigna L. Toxicity of aminochromes. Toxicol Lett 1989; 48: 3-20.
45. Smythies JR. Oxidative reactions and schizophrenia: a review-discussion. Schizophr Res 1997; 24: 357-364.
46. Rump AF, Schierholz J, Rosen R et al. Studies on the role of superoxide anion radicals for the cardiotoxicity of adrenochrome. Arzneimittelforschung 2001; 51: 964-970.
47. Behonick GS, Novak MJ, Nealley EW, Baskin SI. Toxicology update: the cardiotoxicity of the oxidative stress metabolites of catecholamines (aminochromes). J Appl Toxicol 2001; 21 ( Suppl1): S15-S22.