Synthesis of isotopomers of l-DOPA and dopamine labeled with hydrogen isotopes in the side chain

Journal of Radioanalytical and Nuclear Chemistry

Volumn 281, Issue 3, 2009, Pages 365-370

  Pajak M ^a   Kanska M ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

Deuterium; Dopamine; L DOPA; Labeling; Tritium

Indexed keywords

DEUTERIUM; DOPAMINE; LEVODOPA; TRITIUM; TYROSINE DECARBOXYLASE;

ARTICLE; DECARBOXYLATION; ENZYME SYNTHESIS; HYDROXYLATION; ISOTOPE LABELING; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 70349971603     PISSN: 02365731     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10967-009-0012-z     Document Type: Article

References (25)

1. MA Medina JL Urdiales C Rodriguez-Caso FJ Ramirez F Sanchez-Jimenez 2003 Biogenic amines and polyamines: similar biochemistry for different physiological missions and biomedical application Crit. Rev. Biochem. Mol. Biol. 38 23 59 10.1080/713609209 1:CAS:528:DC%2BD3sXisFakt7k%3D
2. O Hornykiewicz 2002 L-DOPA from a biologically inactive amino acid, to a successful therapeutic agent Amino Acids 23 65 70 10.1007/s00726-001-0111-9 1:CAS:528:DC%2BD38Xns1Gns7o%3D
3. B Thomas FM Beal 2007 Parkinson's disease Hum. Mol. Genet. 16 R183 R194 10.1093/hmg/ddm159 1:CAS:528:DC%2BD2sXht1KntLfN
4. LJ Siever MD Kenneth 2004 The pathophysiology of schizophrenia disorders: perspectives from the spectrum Am. J. Psychiatry 161 398 413 10.1176/appi.ajp.161.3.398 (Pubitemid 38326093)
5. R Ceravolo D Volterrani G Gambaccini S Bernardini C Rossi C Logi G Tognoni G Manca G Mariani U Bonuccelli L Murri 2004 Presynaptic nigro-striatal function in a group of Alzheimer's disease patients with parkinsonism: evidence from a dopamine transporter imaging study J. Neural. Transm. 111 1065 1073 10.1007/s00702-004-0140-0 1:CAS:528:DC%2BD2cXls1ant7c%3D
6. J Li M Zhu AB Manning-Bog DADI Monte AL Fink 2004 Dopamine and L-DOPA disaggregate amyloid fibrils: implications for Parkinson's and Alzheimer's disease FASEB J. 18 962 964 10.1096/fj.04-2273com 1:CAS:528:DC%2BD2cXkslWisbs%3D (Pubitemid 39610507)
7. MB Mattammal JH Haring HD Chung G Raghu R Strong 1995 An endogenous dopaminergic neurotoxin: implication for Parkinson's disease Neurodegeneration 4 271 281 10.1016/1055-8330(95)90016-0 1:STN:280:DyaK287jtVyluw%3D%3D
8. I Lamensdorf G Eisenhofer J Harvey-White A Nechustan K Kirk IJ Kopin 2000 3,4-Dihydroxyphenylacetaldehyde potentiates the toxic effects of metabolic stress in PC12 cells Brain Res. 868 191 201 10.1016/S0006-8993(00)02309-X 1:CAS:528:DC%2BD3cXktVSgtLs%3D (Pubitemid 30347515)
9. SW Li T-S Lin S Minteer WJ Burke 2001 3,4-Dihydroxyphenylacetaldehyde and hydrogen peroxide generate a hydroxyl radical: Possible role in Parkinson's disease pathogenesis Mol. Brain Res. 93 1 7 10.1016/S0169-328X(01)00120-6 1:CAS:528:DC%2BD3MXmt1yhurs%3D (Pubitemid 32786896)
10. WJ Burke SW Li EA Williams R Nonneman DS Zahm 2003 3,4- Dihydroxyphenylacetaldehyde is the toxic dopamine metabolite in vivo: implications for Parkinson's disease pathogenesis Brain Res. 989 205 213 10.1016/S0006-8993(03)03354-7 1:CAS:528:DC%2BD3sXnvFSht7k%3D (Pubitemid 37211424)
11. A Toninello P Pietrangeli U De Marchi M Salvi B Mondovi 2006 Amine oxidases in apoptosis and cancer Biochim. Biophys. Acta 1765 1 13 1:CAS:528:DC%2BD2MXht12ku7%2FO
12. MC Summers R Markovic JP Klinman 1979 Stereochemistry and kinetic isotope effects in the bovine plasma amine oxidase catalyzed oxidation of dopamine Biochemistry 18 1969 1979 10.1021/bi00577a019 1:CAS:528:DyaE1MXhvF2msLk%3D (Pubitemid 9173554)
13. MF Farnum JP Klinman 1986 Stereochemical probes of bovine plasma amine oxidase: evidence for mirror image processing and a syn abstraction of hydrogens from C-1 and C-2 of dopamine Biochemistry 25 6028 6036 10.1021/bi00368a029 1:CAS:528:DyaL28Xls1Ortr8%3D (Pubitemid 17204037)
14. PH Yu 1988 Three types of stereospecificity and the kinetic deuterium isotope effect in the oxidative deamination of dopamine as catalyzed by different amine oxidases Biochem. Cell Biol. 66 853 861 1:CAS:528: DyaL1MXjs1SgtA%3D%3D
15. Cook, P.F. (ed.): Enzyme mechanism from isotope effects. CRC press, Boca Raton, Ann Arbor, Boston, London (1991)
16. M Paja̧k M Kańska 2006 Synthesis of isotopomers of dopamine labeled with deuterium or tritium J. Label. Comp. Radiopharm. 49 1061 1067 10.1002/jlcr.1123 (Pubitemid 46141415)
17. M Paja̧k M Kańska 2009 Enzymatic synthesis of dopamine ring labeled with hydrogen isotopes J. Radioanal. Nucl. Chem. 279 455 458 10.1007/s10967-008-7335-z
18. E Panufnik M Kańska 2007 Enzymatic synthesis of isotopomers of tyramine labeled with deuterium and tritium J. Label. Comp. Radiopharm. 50 85 89 10.1002/jlcr.1160 1:CAS:528:DC%2BD2sXjvVOhs70%3D
19. SH Pomerantz 1964 Tyrosine hydroxylation catalyzed by mammalian tyrosinase: an improved method of assay Biochem. Biophys. Res. Commun. 16 188 194 10.1016/0006-291X(64)90359-6 1:CAS:528:DyaF2cXktF2ns7Y%3D
20. VJ Hearing TM Ekel 1976 Mammalian tyrosinase Biochem. J. 157 549 557 1:CAS:528:DyaE2sXjvFCjtQ%3D%3D
21. H Claus H Decker 2006 Bacterial tyrosinases Syst. Appl. Microbiol. 29 3 14 10.1016/j.syapm.2005.07.012 1:CAS:528:DC%2BD28Xjt1Krs7s%3D (Pubitemid 43102498)
22. HC Dunathan 1971 Stereochemical aspects of pyridoxal phosphate catalysis Adv. Enzymol. Relat. Areas Mol. Biol. 35 79 134 10.1002/9780470122808.ch3 1:CAS:528:DyaE38XmvFemsg%3D%3D
23. JC Vederas ID Reingold HW Sellers 1979 Stereospecificity of sodium borohydride reduction of tyrosine decarboxylase from Streptococcus faecalis J. Biol. Chem. 254 5053 5057 1:CAS:528:DyaE1MXkslSrsLw%3D
24. Battersby, A.R., Chrystal, E.J.T., Staunton, J.: Studies of enzyme-mediated reactions. Part 12. Stereochemical course of the decarboxylation of (2S)-tyrosine to tyramine by microbial, mammalian, and plant systems. J. Chem. Soc. Perkin I 31-42 (1980)
25. JM Perel DK Dawson PG Dayton LI Goldberg 1972 α,α'- and β,β'-Deuterium-labeled dopamine. Synthesis and pharmacologic actions J. Med. Chem. 15 714 716 10.1021/jm00277a005 1:CAS:528:DyaE38XkvVelu74%3D