메뉴 건너뛰기




Volumn 27, Issue 3, 2003, Pages 125-134

Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes

Author keywords

[No Author keywords available]

Indexed keywords

5,6 DIHYDROXYINDOLE; 5,6 DIHYDROXYINDOLE 2 CARBOXYLIC ACID; AMPHETAMINE; BENZOYLECGONINE; CATECHOL; COCAINE; EUMELANIN; MELANIN; N ACETYLAMPHETAMINE; PHEOMELANIN; UNCLASSIFIED DRUG;

EID: 12444315623     PISSN: 01464760     EISSN: None     Source Type: Journal    
DOI: 10.1093/jat/27.3.125     Document Type: Article
Times cited : (40)

References (47)
  • 1
    • 0018751746 scopus 로고
    • Studies on the mechanism of drugbinding to melanin
    • B. Larsson and H. Tjalve. Studies on the mechanism of drugbinding to melanin. Biochem. Pharmacol. 28: 1181-1187 (1979).
    • (1979) Biochem. Pharmacol. , vol.28 , pp. 1181-1187
    • Larsson, B.1    Tjalve, H.2
  • 2
    • 0020457371 scopus 로고
    • Studies of the mechanism of chloroquine binding to synthetic DOPA-melanin
    • K.B. Stepien and T. Wilczok. Studies of the mechanism of chloroquine binding to synthetic DOPA-melanin. Biochem. Pharmacol. 31: 3359-3365 (1982).
    • (1982) Biochem. Pharmacol. , vol.31 , pp. 3359-3365
    • Stepien, K.B.1    Wilczok, T.2
  • 3
    • 0012985179 scopus 로고
    • Melanin-producing cells
    • Academic Press, San Diego, CA
    • G. Prota. Melanin-producing cells. In Melanins and Melanogenesis. Academic Press, San Diego, CA, 1992, pp 14-33.
    • (1992) Melanins and Melanogenesis , pp. 14-33
    • Prota, G.1
  • 4
    • 0032972834 scopus 로고    scopus 로고
    • Human melanocytes grown in epidermal equivalents transfer their melanin to follicular outer root sheath keratinocytes
    • A. Limat, D. Salomon, P. Carraux, J.H. Saurat, and T. Hunziker. Human melanocytes grown in epidermal equivalents transfer their melanin to follicular outer root sheath keratinocytes. Arch. Dermatol. Res. 291: 325-332 (1999).
    • (1999) Arch. Dermatol. Res. , vol.291 , pp. 325-332
    • Limat, A.1    Salomon, D.2    Carraux, P.3    Saurat, J.H.4    Hunziker, T.5
  • 6
    • 0015444699 scopus 로고
    • The melanin affinity of chloroquine and chlorpromazine studied by whole body autoradiography
    • N.G. Lindquist and S. Ullberg. The melanin affinity of chloroquine and chlorpromazine studied by whole body autoradiography. Acta Pharmacol. Toxicol. (Copenh.) 2: 1-32 (1972).
    • (1972) Acta Pharmacol. Toxicol. (Copenh.) , vol.2 , pp. 1-32
    • Lindquist, N.G.1    Ullberg, S.2
  • 7
    • 0027619954 scopus 로고
    • Interaction between chemicals and melanin
    • B.S. Larsson. Interaction between chemicals and melanin. Pigment Cell Res. 6: 127-133 (1993).
    • (1993) Pigment Cell Res. , vol.6 , pp. 127-133
    • Larsson, B.S.1
  • 8
    • 0017067810 scopus 로고
    • Binding characteristics of drugs to synthetic levodopa melanin
    • K. Shimada, R. Baweja, T. Sokoloski, and P.N. Patil. Binding characteristics of drugs to synthetic levodopa melanin. J. Pharm. Sci. 65: 1057-1060 (1976).
    • (1976) J. Pharm. Sci. , vol.65 , pp. 1057-1060
    • Shimada, K.1    Baweja, R.2    Sokoloski, T.3    Patil, P.N.4
  • 9
    • 0025261904 scopus 로고
    • Changes in the antibacterial activity of melanin-bound drugs
    • M. Fukuda and K. Sasaki. Changes in the antibacterial activity of melanin-bound drugs. Ophthalmic Res. 22: 123-127 (1990).
    • (1990) Ophthalmic Res. , vol.22 , pp. 123-127
    • Fukuda, M.1    Sasaki, K.2
  • 10
    • 0026089278 scopus 로고
    • Ototoxicity of cis-platinum and its relationship to eye colour
    • R.M. Barr-Hamilton, L.M. Matheson, and D.G. Keay. Ototoxicity of cis-platinum and its relationship to eye colour. J. Laryngol. Otol. 105: 7-11 (1991).
    • (1991) J. Laryngol. Otol. , vol.105 , pp. 7-11
    • Barr-Hamilton, R.M.1    Matheson, L.M.2    Keay, D.G.3
  • 11
    • 0029075088 scopus 로고
    • Differential effects of gentamicin on the distribution of cochlear function in albino and pigmented guinea pigs
    • J.W. Conlee, M.L. Bennett, and D.J. Creel. Differential effects of gentamicin on the distribution of cochlear function in albino and pigmented guinea pigs. Acta Otolaryngol. 115: 367-374 (1995).
    • (1995) Acta Otolaryngol. , vol.115 , pp. 367-374
    • Conlee, J.W.1    Bennett, M.L.2    Creel, D.J.3
  • 12
  • 13
    • 0022539310 scopus 로고
    • Selectivity of the parkinsonian neurotoxin MPTP: Toxic metabolite MPP+ binds to neuromelanin
    • R.J. D'Amato, Z.P. Lipman, and S.H. Snyder. Selectivity of the parkinsonian neurotoxin MPTP: toxic metabolite MPP+ binds to neuromelanin. Science 231: 987-989 (1986).
    • (1986) Science , vol.231 , pp. 987-989
    • D'Amato, R.J.1    Lipman, Z.P.2    Snyder, S.H.3
  • 15
    • 0023137046 scopus 로고
    • Characterization of the binding of N-methyl-4-phenylpyridine, the toxic metabolite of the parkinsonian neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, to neuromelanin
    • R.J. D'Amato, D.F. Benham, and S.H. Snyder. Characterization of the binding of N-methyl-4-phenylpyridine, the toxic metabolite of the parkinsonian neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, to neuromelanin. J. Neurochem. 48: 653-658 (1987).
    • (1987) J. Neurochem. , vol.48 , pp. 653-658
    • D'Amato, R.J.1    Benham, D.F.2    Snyder, S.H.3
  • 17
    • 0022515129 scopus 로고
    • Interactions of the 1-methyl-4-phenyl-2,3-dihydropyridinium species with synthetic dopamine-melanin
    • E.Y. Wu, K. Chiba, A.J. Trevor, and N. Castagnoli, Jr. Interactions of the 1-methyl-4-phenyl-2,3-dihydropyridinium species with synthetic dopamine-melanin. Life Sci. 39: 1695-1700 (1986).
    • (1986) Life Sci. , vol.39 , pp. 1695-1700
    • Wu, E.Y.1    Chiba, K.2    Trevor, A.J.3    Castagnoli N., Jr.4
  • 18
    • 0031296810 scopus 로고    scopus 로고
    • Biosynthesis, structure, and function of neuromelanin and its relation to Parkinson's disease: A critical update
    • M. d'Ischia and G. Prota. Biosynthesis, structure, and function of neuromelanin and its relation to Parkinson's disease: a critical update. Pigment Cell Res. 10: 370-376 (1997).
    • (1997) Pigment Cell Res. , vol.10 , pp. 370-376
    • D'Ischia, M.1    Prota, G.2
  • 19
    • 0027672938 scopus 로고
    • Neuromelanin: A key to Parkinson's disease
    • G. Prota and M. d'Ischia. Neuromelanin: a key to Parkinson's disease. Pigment Cell Res. 6: 333-335 (1993).
    • (1993) Pigment Cell Res. , vol.6 , pp. 333-335
    • Prota, G.1    D'Ischia, M.2
  • 20
  • 22
    • 0031670791 scopus 로고    scopus 로고
    • The incorporation of drugs into hair: Relationship of hair color and melanin concentration to phencyclidine incorporation
    • M.H. Slawson, D.G. Wilkins, and D.E. Rollins. The incorporation of drugs into hair: relationship of hair color and melanin concentration to phencyclidine incorporation. J. Anal. Toxicol. 22: 406-413 (1998).
    • (1998) J. Anal. Toxicol. , vol.22 , pp. 406-413
    • Slawson, M.H.1    Wilkins, D.G.2    Rollins, D.E.3
  • 23
    • 0029845210 scopus 로고    scopus 로고
    • Detection of stanozolol in hair by negative ion chemical ionization mass spectrometry
    • K. Hold, D. Wilkins, D. Crouch, D. Rollins, and R. Maes. Detection of stanozolol in hair by negative ion chemical ionization mass spectrometry. J. Anal. Toxicol. 20: 345-349 (1996).
    • (1996) J. Anal. Toxicol. , vol.20 , pp. 345-349
    • Hold, K.1    Wilkins, D.2    Crouch, D.3    Rollins, D.4    Maes, R.5
  • 24
    • 10144251766 scopus 로고    scopus 로고
    • In vitro binding studies of drugs to hair: Influence of melanin and lipids on cocaine binding to Caucasoid and Africoid hair
    • R.E. Joseph, Jr., T.P. Su, and E.J. Cone. In vitro binding studies of drugs to hair: influence of melanin and lipids on cocaine binding to Caucasoid and Africoid hair. J. Anal. Toxicol. 20: 338-344 (1996).
    • (1996) J. Anal. Toxicol. , vol.20 , pp. 338-344
    • Joseph R.E., Jr.1    Su, T.P.2    Cone, E.J.3
  • 25
    • 0033964992 scopus 로고    scopus 로고
    • Statistical examination of hair color as a potential biasing factor in hair analysis
    • T. Mieczkowski and R. Newel. Statistical examination of hair color as a potential biasing factor in hair analysis. Forensic Sci. Int. 107: 13-38 (2000).
    • (2000) Forensic Sci. Int. , vol.107 , pp. 13-38
    • Mieczkowski, T.1    Newel, R.2
  • 26
    • 0033981905 scopus 로고    scopus 로고
    • Hair analysis for drugs of abuse. Hair color and race differentials or systematic differences in drug preferences?
    • C.K. Kelly, T. Mieczkowski, S.A. Sweeney, and J.A. Bourland. Hair analysis for drugs of abuse. Hair color and race differentials or systematic differences in drug preferences? Forensic Sci. Int. 107: 63-86 (2000).
    • (2000) Forensic Sci. Int. , vol.107 , pp. 63-86
    • Kelly, C.K.1    Mieczkowski, T.2    Sweeney, S.A.3    Bourland, J.A.4
  • 27
    • 0031051749 scopus 로고    scopus 로고
    • A comparison of phenobarbital and codeine incorporation into pigmented and nonpigmented rat hair
    • S.P. Gygi, D.G. Wilkins, and D.E. Rollins. A comparison of phenobarbital and codeine incorporation into pigmented and nonpigmented rat hair. J. Pharm. Sci. 86: 209-214 (1997).
    • (1997) J. Pharm. Sci. , vol.86 , pp. 209-214
    • Gygi, S.P.1    Wilkins, D.G.2    Rollins, D.E.3
  • 28
    • 0034996101 scopus 로고    scopus 로고
    • Amphetamine and N-acetylamphetamine incorporation into hair: An investigation of the potential role of drug basicity in hair color bias
    • C.R. Borges, D.G. Wilkins, and D.E. Rollins. Amphetamine and N-acetylamphetamine incorporation into hair: an investigation of the potential role of drug basicity in hair color bias. J. Anal. Toxicol. 25: 221-227 (2001).
    • (2001) J. Anal. Toxicol. , vol.25 , pp. 221-227
    • Borges, C.R.1    Wilkins, D.G.2    Rollins, D.E.3
  • 29
    • 0034718178 scopus 로고    scopus 로고
    • Isolation and characterization of mammalian eumelanins from hair and irides
    • L. Novellino, A. Napolitano, and G. Prota. Isolation and characterization of mammalian eumelanins from hair and irides. Biochim. Biophys. Acta 1475: 295-306 (2000).
    • (2000) Biochim. Biophys. Acta , vol.1475 , pp. 295-306
    • Novellino, L.1    Napolitano, A.2    Prota, G.3
  • 30
    • 0033670526 scopus 로고    scopus 로고
    • The incorporation of cocaine and metabolites into hair: Effects of dose and hair pigmentation
    • D.L. Hubbard, D.G. Wilkins, and D.E. Rollins. The incorporation of cocaine and metabolites into hair: effects of dose and hair pigmentation. Drug Metab. Dispos. 28: 1464-1469 (2000).
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 1464-1469
    • Hubbard, D.L.1    Wilkins, D.G.2    Rollins, D.E.3
  • 31
    • 0023891919 scopus 로고
    • Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihyroxyindole-2-carboxylic acid, and their O-methyl derivatives
    • K. Wakamatsu and S. Ito. Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihyroxyindole-2-carboxylic acid, and their O-methyl derivatives. Anal. Biochem. 170: 335-340 (1988).
    • (1988) Anal. Biochem. , vol.170 , pp. 335-340
    • Wakamatsu, K.1    Ito, S.2
  • 32
    • 0027380249 scopus 로고
    • Spectrophotometric assay of eumelanin in tissue samples
    • S. Ito, K. Wakamatsu, and H. Ozeki. Spectrophotometric assay of eumelanin in tissue samples. Anal. Biochem. 215: 273-277 (1993).
    • (1993) Anal. Biochem. , vol.215 , pp. 273-277
    • Ito, S.1    Wakamatsu, K.2    Ozeki, H.3
  • 33
    • 0019827747 scopus 로고
    • Synthesis and antitumor activity of cysteinyl-3,4-dihydroxyphenylalanines and related compounds
    • S. Ito, S. Inoue, Y. Yamamoto, and K. Fujite. Synthesis and antitumor activity of cysteinyl-3,4-dihydroxyphenylalanines and related compounds. J. Med. Chem. 24: 673-677 (1981).
    • (1981) J. Med. Chem. , vol.24 , pp. 673-677
    • Ito, S.1    Inoue, S.2    Yamamoto, Y.3    Fujite, K.4
  • 34
    • 0021914577 scopus 로고
    • Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid chromatography
    • S. Ito and K. Fujita. Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid chromatography. Anal. Biochem. 144: 527-536 (1985).
    • (1985) Anal. Biochem. , vol.144 , pp. 527-536
    • Ito, S.1    Fujita, K.2
  • 35
    • 0035283130 scopus 로고    scopus 로고
    • Relationship of melanin degradation products to actual melanin content: Application to human hair
    • C.R. Borges, J.C. Roberts, D.G. Wilkins, and D.E. Rollins. Relationship of melanin degradation products to actual melanin content: application to human hair. Anal. Biochem. 290: 116-125 (2001).
    • (2001) Anal. Biochem. , vol.290 , pp. 116-125
    • Borges, C.R.1    Roberts, J.C.2    Wilkins, D.G.3    Rollins, D.E.4
  • 36
    • 0000158743 scopus 로고
    • Synthesis of acetyl derivatives of some sympathomimetic amines
    • J. Halmekoski and P. Saarinen. Synthesis of acetyl derivatives of some sympathomimetic amines. Farmaseuttinen Aikakauslehti 75: 335-353 (1966).
    • (1966) Farmaseuttinen Aikakauslehti , vol.75 , pp. 335-353
    • Halmekoski, J.1    Saarinen, P.2
  • 37
    • 0029028062 scopus 로고
    • Development of a melanin-based highperformance liquid chromatography stationary phase and its use in the study of drug-melanin binding interactions
    • H. Ibrahim and A.F. Aubry. Development of a melanin-based highperformance liquid chromatography stationary phase and its use in the study of drug-melanin binding interactions. Anal. Biochem. 229: 272-277 (1995).
    • (1995) Anal. Biochem. , vol.229 , pp. 272-277
    • Ibrahim, H.1    Aubry, A.F.2
  • 39
    • 0017745495 scopus 로고
    • Competitive binding between cocaine and various drugs to synthetic levodopa melanin
    • R. Baweja, T.D. Sokoloski, and P.N. Patil. Competitive binding between cocaine and various drugs to synthetic levodopa melanin. J. Pharm. Sci. 66: 1544-1547 (1977).
    • (1977) J. Pharm. Sci. , vol.66 , pp. 1544-1547
    • Baweja, R.1    Sokoloski, T.D.2    Patil, P.N.3
  • 40
    • 0000459322 scopus 로고
    • Interactions of melanin with metal ions: Electron spin resonance evidence for chelate complexes of metal ions with free radicals
    • C.C. Felix, J.S. Hyde, T. Sarna, and R.C. Sealy. Interactions of melanin with metal ions: Electron spin resonance evidence for chelate complexes of metal ions with free radicals. J. Am. Chem. Soc. 100: 3922-3926 (1978)
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3922-3926
    • Felix, C.C.1    Hyde, J.S.2    Sarna, T.3    Sealy, R.C.4
  • 41
    • 0031242561 scopus 로고    scopus 로고
    • Modeling drug-melanin interaction with theoretical linear solvation energy relationships
    • A.H. Lowrey, G.R. Famini, V. Loumbev, L.Y. Wilson, and J.M. Tosk. Modeling drug-melanin interaction with theoretical linear solvation energy relationships. Pigment Cell Res. 10: 251-256 (1997).
    • (1997) Pigment Cell Res. , vol.10 , pp. 251-256
    • Lowrey, A.H.1    Famini, G.R.2    Loumbev, V.3    Wilson, L.Y.4    Tosk, J.M.5
  • 42
    • 0033176168 scopus 로고    scopus 로고
    • Pheomelanin as a binding site for drugs and chemicals
    • U. Mars and B.S. Larsson. Pheomelanin as a binding site for drugs and chemicals. Pigment Cell Res. 12: 266-274 (1999).
    • (1999) Pigment Cell Res. , vol.12 , pp. 266-274
    • Mars, U.1    Larsson, B.S.2
  • 43
    • 0029909914 scopus 로고    scopus 로고
    • Hair analysis for drugs of abuse. XIII. Effect of structural factors on incorporation of drugs into hair: The incorporation rates of amphetamine analogs
    • Y. Nakahara and R. Kikura. Hair analysis for drugs of abuse. XIII. Effect of structural factors on incorporation of drugs into hair: the incorporation rates of amphetamine analogs. Arch. Toxicol. 70: 841-849 (1996).
    • (1996) Arch. Toxicol. , vol.70 , pp. 841-849
    • Nakahara, Y.1    Kikura, R.2
  • 45
    • 0345062348 scopus 로고    scopus 로고
    • Drug testing with alternative matrices II. Mechanisms of cocaine and codeine deposition in hair
    • R.E. Joseph, Jr., K.M. Hold, D.G. Wilkins, D.E. Rollins, and E.J. Cone. Drug testing with alternative matrices II. Mechanisms of cocaine and codeine deposition in hair. J. Anal. Toxicol. 23; 396-408 (1999).
    • (1999) J. Anal. Toxicol. , vol.23 , pp. 396-408
    • Joseph R.E., Jr.1    Hold, K.M.2    Wilkins, D.G.3    Rollins, D.E.4    Cone, E.J.5
  • 46
    • 0036284796 scopus 로고    scopus 로고
    • Influx and efflux of amphetamine and N-acetylamphetamine in keratinocytes, pigmented melanocytes, and nonpigmented melanocytes
    • C.R. Borges, S.D. Martin, L.J. Meyer, D.G. Wilkins, and D.E. Rollins. Influx and efflux of amphetamine and N-acetylamphetamine in keratinocytes, pigmented melanocytes, and nonpigmented melanocytes. J. Pharm. Sci. 91: 1523-1535 (2002).
    • (2002) J. Pharm. Sci. , vol.91 , pp. 1523-1535
    • Borges, C.R.1    Martin, S.D.2    Meyer, L.J.3    Wilkins, D.G.4    Rollins, D.E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.