메뉴 건너뛰기




Volumn 11, Issue 1, 2006, Pages 15-24

Reactions of the melatonin metabolite N1-acetyl-5- methoxykynuramine (AMK) with the ABTS cation radical: Identification of new oxidation products

Author keywords

ABTS cation radical; AMK; Kynuramines; Melatonin

Indexed keywords

AROMATIC AMINE; AROMATIC AMINO ACID; DIMER; KYNURAMINE; MELATONIN; N 1 ACETYL 5 METHOXYKYNURAMINE; NITROGEN; OLIGOMER; SCAVENGER; SULFONIC ACID DERIVATIVE; TETRAMER; UNCLASSIFIED DRUG;

EID: 33745190395     PISSN: 13510002     EISSN: 13510002     Source Type: Journal    
DOI: 10.1179/135100006X100977     Document Type: Article
Times cited : (27)

References (37)
  • 1
    • 0000872314 scopus 로고    scopus 로고
    • Melatonin: Multiple functions in signaling and protection
    • Altmeyer P, Hoffmann K, Stücker M. (eds) Berlin: Springer
    • 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.
    • (1997) Skin Cancer and UV Radiation , pp. 186-198
    • Hardeland, R.1
  • 2
    • 0006128323 scopus 로고    scopus 로고
    • High physiological levels of melatonin in the bile of mammals
    • Tan D-X, Manchester LC, Reiter RJ et al. High physiological levels of melatonin in the bile of mammals. Life Sci 1999; 65: 2523-2529.
    • (1999) Life Sci , vol.65 , pp. 2523-2529
    • Tan, D.-X.1    Manchester, L.C.2    Reiter, R.J.3
  • 3
    • 0037246752 scopus 로고    scopus 로고
    • Melatonin - A hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin
    • Tan D-X, Manchester LC, Hardeland R et al. Melatonin - a hormone, a tissue factor, an autocoid, a paracoid, and an antioxidant vitamin. J Pineal Res 2003; 34: 75-78.
    • (2003) J Pineal Res , vol.34 , pp. 75-78
    • Tan, D.-X.1    Manchester, L.C.2    Hardeland, R.3
  • 5
    • 27644552995 scopus 로고    scopus 로고
    • Antioxidative protection by melatonin - Multiplicity of mechanisms from radical detoxification to radical avoidance
    • Hardeland R. Antioxidative protection by melatonin - Multiplicity of mechanisms from radical detoxification to radical avoidance. Endocrine 2005; 27: 119-130.
    • (2005) Endocrine , vol.27 , pp. 119-130
    • Hardeland, R.1
  • 6
    • 0027429994 scopus 로고
    • The significance of the metabolism of the neurohormone melatonin: Antioxidative protection and formation of bioactive substances
    • 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.
    • (1993) Neurosci Biobehav Rev , vol.17 , pp. 347-357
    • Hardeland, R.1    Reiter, R.J.2    Poeggeler, B.3    Tan, D.-X.4
  • 7
    • 0002979059 scopus 로고
    • Melatonin: A potent, endogenous hydroxyl radical scavenger
    • Tan D-X, Chen L-D, Poeggeler B et al. Melatonin: a potent, endogenous hydroxyl radical scavenger. Endocr J 1993; 1: 57-60.
    • (1993) Endocr J , vol.1 , pp. 57-60
    • Tan, D.-X.1    Chen, L.-D.2    Poeggeler, B.3
  • 8
    • 0031845040 scopus 로고    scopus 로고
    • Oxidative damage in the central nervous system: Protection by melatonin
    • Reiter RJ. Oxidative damage in the central nervous system: Protection by melatonin. Prog Neurobiol 1998; 56: 359-384.
    • (1998) Prog Neurobiol , vol.56 , pp. 359-384
    • Reiter, R.J.1
  • 9
    • 0037198063 scopus 로고    scopus 로고
    • Reactive oxygen and nitrogen species and cellular and organismal decline: Amelioration with melatonin
    • Reiter RJ, Tan D-X, Burkhardt S. Reactive oxygen and nitrogen species and cellular and organismal decline: amelioration with melatonin. Mech Ageing Dev 2002; 123: 1007-1019.
    • (2002) Mech Ageing Dev , vol.123 , pp. 1007-1019
    • Reiter, R.J.1    Tan, D.-X.2    Burkhardt, S.3
  • 10
    • 2342535627 scopus 로고    scopus 로고
    • Melatonin as an antioxidant: Biochemical mechanisms and pathophysiological implications in humans
    • Reiter RJ, Tan D-X, Mayo JC et al. Melatonin as an antioxidant: biochemical mechanisms and pathophysiological implications in humans. Acta Biochim Pol 2003; 50: 1129-1146.
    • (2003) Acta Biochim Pol , vol.50 , pp. 1129-1146
    • Reiter, R.J.1    Tan, D.-X.2    Mayo, J.C.3
  • 11
    • 10744224028 scopus 로고    scopus 로고
    • 1-acetyl-5-methoxykynuramine (AMK): Scavenging of free radicals and prevention of protein destruction
    • 1-acetyl-5-methoxykynuramine (AMK): scavenging of free radicals and prevention of protein destruction. Redox Report 2003; 8: 205-213.
    • (2003) Redox Report , vol.8 , pp. 205-213
    • Ressmeyer, A.-R.1    Mayo, J.C.2    Zelosko, V.3
  • 14
    • 0141876062 scopus 로고    scopus 로고
    • Circadian rhythms, oxidative stress and antioxidative defense mechanisms
    • Hardeland R, Coto-Montes A, Poeggeler B. Circadian rhythms, oxidative stress and antioxidative defense mechanisms. Chronobiol Int 2003; 20: 921-962.
    • (2003) Chronobiol Int , vol.20 , pp. 921-962
    • Hardeland, R.1    Coto-Montes, A.2    Poeggeler, B.3
  • 15
    • 1042302727 scopus 로고    scopus 로고
    • Mitochondrial regulation by melatonin and its metabolites
    • Acuna-Castroviejo D, Escames G, Leon J et al. Mitochondrial regulation by melatonin and its metabolites. Adv Exp Med Biol 2003; 527: 549-557.
    • (2003) Adv Exp Med Biol , vol.527 , pp. 549-557
    • Acuna-Castroviejo, D.1    Escames, G.2    Leon, J.3
  • 17
    • 0035487508 scopus 로고    scopus 로고
    • 2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant
    • 2-formyl-5-methoxykynuramine, a biogenic amine and melatonin metabolite, functions as a potent antioxidant. FASEB J 2001; 15: 2294-2296.
    • (2001) FASEB J , vol.15 , pp. 2294-2296
    • Tan, D.-X.1    Manchester, L.C.2    Burkhardt, S.3
  • 18
    • 0032982508 scopus 로고    scopus 로고
    • Antioxidant activity applying an improved ABTS cation radical decolorization assay
    • Re R, Pellegrini N, Proteggente A et al. Antioxidant activity applying an improved ABTS cation radical decolorization assay. Free Radic Biol Med 1999; 26: 1231-1237.
    • (1999) Free Radic Biol Med , vol.26 , pp. 1231-1237
    • Re, R.1    Pellegrini, N.2    Proteggente, A.3
  • 19
    • 0037404895 scopus 로고    scopus 로고
    • Mechanistic and comparative studies of melatonin and classic antioxidants in terms of their interactions with the ABTS cation radical
    • Tan D-X, Hardeland R, Manchester LC et al. Mechanistic and comparative studies of melatonin and classic antioxidants in terms of their interactions with the ABTS cation radical. J Pineal Res 2003; 34: 249-259.
    • (2003) J Pineal Res , vol.34 , pp. 249-259
    • Tan, D.-X.1    Hardeland, R.2    Manchester, L.C.3
  • 20
    • 0024153421 scopus 로고
    • Structure-activity studies of melatonin analogues in prepubertal male rats
    • 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.
    • (1988) Aust J Biol Sci , vol.41 , pp. 393-400
    • Kennaway, D.J.1    Hugel, H.M.2    Clarke, S.3
  • 21
    • 1542497812 scopus 로고
    • Ueber das Verhalten des Phenylhydroxylamins gegen alkoholische Schwefelsäure und gegen Anilin
    • Bamberger E, Lagutt J. Ueber das Verhalten des Phenylhydroxylamins gegen alkoholische Schwefelsäure und gegen Anilin. Chem Ber 1898; 31: 1500-1508.
    • (1898) Chem Ber , vol.31 , pp. 1500-1508
    • Bamberger, E.1    Lagutt, J.2
  • 22
    • 0035920620 scopus 로고    scopus 로고
    • Solvent free permanganate oxidations
    • Shaabani A, Lee DG. Solvent free permanganate oxidations. Tetrahedron Lett 2001; 34: 5833-5836.
    • (2001) Tetrahedron Lett , vol.34 , pp. 5833-5836
    • Shaabani, A.1    Lee, D.G.2
  • 23
    • 0000789186 scopus 로고
    • Cooperative effect of acid sites in the photocyclization of azobenzene within the zeolite microenvironment
    • Corma A, Garcia H., Iborra S et al. Cooperative effect of acid sites in the photocyclization of azobenzene within the zeolite microenvironment. J Am Chem Soc 1993; 115: 2177-2180.
    • (1993) J Am Chem Soc , vol.115 , pp. 2177-2180
    • Corma, A.1    Garcia, H.2    Iborra, S.3
  • 24
    • 0000863564 scopus 로고    scopus 로고
    • Modification of photochemical reactivity by Nafion, photocyclization and photochemical cis-trans isomerization of azobenzene
    • Tung C-H, Guan J-Q. Modification of photochemical reactivity by Nafion, photocyclization and photochemical cis-trans isomerization of azobenzene. J Org Chem 1996; 61: 9417-9421.
    • (1996) J Org Chem , vol.61 , pp. 9417-9421
    • Tung, C.-H.1    Guan, J.-Q.2
  • 25
    • 0028893764 scopus 로고
    • Catalytic oxidative aromatic cyclizations with palladium
    • Aekermark B, Oslob JD, Heuschert U. Catalytic oxidative aromatic cyclizations with palladium. Tetrahedron Lett 1995; 36: 1325-1326.
    • (1995) Tetrahedron Lett , vol.36 , pp. 1325-1326
    • Aekermark, B.1    Oslob, J.D.2    Heuschert, U.3
  • 26
    • 3242780140 scopus 로고    scopus 로고
    • 1,1′-Biazulene derivatives. Synthesis and reactions
    • [Chem. Abstr. 138:303954]
    • Razus AC, Birzan L, Nae S et al. 1,1′-Biazulene derivatives. Synthesis and reactions. ARKIVOC 2002; 142-153. [Chem. Abstr. 138:303954.]
    • (2002) ARKIVOC , pp. 142-153
    • Razus, A.C.1    Birzan, L.2    Nae, S.3
  • 27
    • 0032829442 scopus 로고    scopus 로고
    • Identification of highly elevated levels of melatonin in bone marrow: Its origin and significance
    • Tan D-X, Manchester LC, Reiter RJ et al. Identification of highly elevated levels of melatonin in bone marrow: its origin and significance. Biochim Biophys Acta 1999; 1472: 206-214.
    • (1999) Biochim Biophys Acta , vol.1472 , pp. 206-214
    • Tan, D.-X.1    Manchester, L.C.2    Reiter, R.J.3
  • 28
    • 0001925353 scopus 로고    scopus 로고
    • Ubiquitous melatonin - Presence and effects in unicells, plants and animals
    • Hardeland R, Fuhrberg B. Ubiquitous melatonin - Presence and effects in unicells, plants and animals. Trends Comp Biochem Physiol 1996; 2: 25-45.
    • (1996) Trends Comp Biochem Physiol , vol.2 , pp. 25-45
    • Hardeland, R.1    Fuhrberg, B.2
  • 29
    • 0033367025 scopus 로고    scopus 로고
    • Melatonin and 5-methoxytryptamine in non-metazoans
    • Hardeland R. Melatonin and 5-methoxytryptamine in non-metazoans. Reprod Nutr Dev 1999; 39: 399-408.
    • (1999) Reprod Nutr Dev , vol.39 , pp. 399-408
    • Hardeland, R.1
  • 30
    • 0021277141 scopus 로고
    • N-Acetyl-5-methoxy kynurenamine, a brain metabolite of melatonin, is a potent inhibitor of prostaglandin biosynthesis
    • Kelly RW, Amato F, Seamark RF. N-Acetyl-5-methoxy kynurenamine, a brain metabolite of melatonin, is a potent inhibitor of prostaglandin biosynthesis. Biochem Biophys Res Commun 1994; 121: 372-379.
    • (1994) Biochem Biophys Res Commun , vol.121 , pp. 372-379
    • Kelly, R.W.1    Amato, F.2    Seamark, R.F.3
  • 31
    • 22144498398 scopus 로고    scopus 로고
    • 1-acetyl-5-methoxykynuramine (AMK), in macrophages
    • 1-acetyl-5-methoxykynuramine (AMK), in macrophages. J Neuroimmunol 2005; 165: 139-149.
    • (2005) J Neuroimmunol , vol.165 , pp. 139-149
    • Mayo, J.C.1    Sainz, R.M.2    Tan, D.-X.3
  • 32
    • 29744434001 scopus 로고    scopus 로고
    • Kynurenamines as neural nitric oxide synthase inhibitors
    • Entrena A, Camacho ME, Carrion MD et al. Kynurenamines as neural nitric oxide synthase inhibitors. J Med Chem 2005; 48: 8174-8181.
    • (2005) J Med Chem , vol.48 , pp. 8174-8181
    • Entrena, A.1    Camacho, M.E.2    Carrion, M.D.3
  • 33
    • 0015944572 scopus 로고
    • In vitro and in vivo formation of two new metabolites of melatonin
    • Hirata F, Hayaishi O, Tokuyama T, Senoh S. In vitro and in vivo formation of two new metabolites of melatonin. J Biol Chem 1974; 249: 1311-1313.
    • (1974) J Biol Chem , vol.249 , pp. 1311-1313
    • Hirata, F.1    Hayaishi, O.2    Tokuyama, T.3    Senoh, S.4
  • 34
    • 0036142587 scopus 로고    scopus 로고
    • Melatonin enters the cerebrospinal fluid through the pineal recess
    • Tricoire H, Locatelli A, Chemineau P et al. Melatonin enters the cerebrospinal fluid through the pineal recess. Endocrinology 2002; 143: 84-90.
    • (2002) Endocrinology , vol.143 , pp. 84-90
    • Tricoire, H.1    Locatelli, A.2    Chemineau, P.3
  • 35
    • 0032417658 scopus 로고    scopus 로고
    • Tissue retention and subcellular distribution of continuously infused melatonin in rats under near physiological conditions
    • Messner M, Hardeland R, Rodenbeck A, Huether G. Tissue retention and subcellular distribution of continuously infused melatonin in rats under near physiological conditions. J Pineal Res 1998; 25: 251-259.
    • (1998) J Pineal Res , vol.25 , pp. 251-259
    • Messner, M.1    Hardeland, R.2    Rodenbeck, A.3    Huether, G.4
  • 36
    • 0034469065 scopus 로고    scopus 로고
    • Effects of continuous melatonin infusions on steady-state plasma melatonin levels, metabolic fate and tissue retention in rats under near physiological conditions
    • Messner M, Hardeland R, Rodenbeck A, Huether G. Effects of continuous melatonin infusions on steady-state plasma melatonin levels, metabolic fate and tissue retention in rats under near physiological conditions. Adv Exp Med Biol 1999; 467: 303-313.
    • (1999) Adv Exp Med Biol , vol.467 , pp. 303-313
    • Messner, M.1    Hardeland, R.2    Rodenbeck, A.3    Huether, G.4
  • 37
    • 0344285529 scopus 로고    scopus 로고
    • Chemistry and biology of melatonin oxidation
    • Haldar C, Singaravel M, Maitra SK. (eds) Enfield: Science Publishers (USA)
    • Hardeland R, Poeggeler B. Chemistry and biology of melatonin oxidation. In: Haldar C, Singaravel M, Maitra SK. (eds) Treatise on Pineal Gland and Melatonin. Enfield: Science Publishers (USA), 2002; 407-422.
    • (2002) Treatise on Pineal Gland and Melatonin , pp. 407-422
    • Hardeland, R.1    Poeggeler, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.