Enhanced radiosyntheses of [11C]raclopride and [11C]DASB using ethanolic loop chemistry

Nuclear Medicine and Biology

Volumn 40, Issue 1, 2013, Pages 109-116

  Shao, Xia ^a   Schnau, Paul L ^a   Fawaz, Maria V ^a   Scott, Peter J H ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

Carbon 11 radiochemistry; Flow chemistry; Positron emission tomography

Indexed keywords

ALCOHOL; ASCORBIC ACID; CARBON DASB C 11; ORGANIC SOLVENT; RACLOPRIDE C 11; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; 3 AMINO 4 (2 DIMETHYLAMINOMETHYLPHENYLSULFANYL)BENZONITRILE; 3-AMINO-4-(2-DIMETHYLAMINOMETHYLPHENYLSULFANYL)BENZONITRILE; ANILINE DERIVATIVE; RACLOPRIDE; SULFIDE;

ARTICLE; CONTROLLED STUDY; DOSIMETRY; ETHANOLIC LOOP CHEMISTRY; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHYLATION; PH; PURIFICATION; QUALITY CONTROL; RADIATION DOSE; RADIATION RESPONSE; RADIOASSAY; RADIOCHEMISTRY; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS; CHEMISTRY; METHODOLOGY;

ANILINE COMPOUNDS; CHEMISTRY TECHNIQUES, SYNTHETIC; ETHANOL; RACLOPRIDE; RADIOCHEMISTRY; RADIOPHARMACEUTICALS; SULFIDES;

EID: 84871927275     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.09.008     Document Type: Article

References (26)

1. C-Pro. J Label Compd Radiopharm 2011, 54:819-838.
2. Shao X., Kilbourn M.R. A simple modification of GE Tracerlab FX C Pro for preparation of [11C] carfentanil and [11C]raclopride. Appl Radiat Isot 2009, 67:6002-6605.
3. 11C]-iodomethane: a remarkably simple captive solvent method. Nucl Med Biol 2000, 27:529-532.
4. 11C]-methylation reactions. J Label Compd Radiopharm 2009, 52:490-492.
5. 11C]methyl triflate. Appl Radiat Isot 2001, 55:17-22.
6. 11C-labeled stilbene derivatives as Aβ-aggregate-specific PET imaging agents for Alzheimer's disease. Nucl Med Biol 2003, 30:565-571.
7. 11C]carfentanil. J Label Compd Radiopharm 2003, 46:837-842.
8. 11C]-6-OH-BTA-1). J Label Compd Radiopharm 2004, 47:679-682.
9. Lu S.Y., Hong J., Musachio J.L., CF T., VE S., Wikström H.V., Pike V.W. Alternative methods for labeling the 5-HT1A receptor agonist, 1-[2-(4-fluorobenzoylamino)ethyl]-4-(7-methoxynaphthyl)piperazine (S14506), with carbon-11 or fluorine-18. J Label Compd Radiopharm 2005, 48:971-981.
10. Le Bars D., Malleval M., Bonnefoi F., Tourvieille C. Simple synthesis of [1-11C]acetate. J Label Compd Radiopharm 2006, 49:263-267.
11. Musachio J.L., Hong J., Ichise M., Seneca N., Brown A.K., Liow J.S., Halldin C., Innis R.B., Pike V.W., He R., Zhou J., Kozikowski A.P. Development of new brain imaging agents based upon nocaine-modafinil hybrid monoamine transporter inhibitors. Bioorg Med Chem Lett 2006, 16:3101-3104.
12. Reske S.N., Blumstein N.M., Neumaier B., Gottfried H.W., Finsterbusch F., Kocot D., Möller P., Glatting G., Perner S. Imaging prostate cancer with 11C-choline PET/CT. J Nucl Med 2006, 47:1249-1254.
13. 11C]Flumazenil: captive solvent synthesis combined with purification by analytical sized columns. J Label Compd Radiopharm 2007, 50:19-24.
14. 11C]DAA1106. Nucl Med Biol 2007, 34:439-446.
15. Briard E., Zoghbi S.S., Imaizumi M., Gourley J.P., Shetty H.U., Hong J., Cropley V., Fujita M., Innis R.B., Pike V.W. Synthesis and evaluation in monkey of two sensitive 11C-labeled aryloxyanilide ligands for imaging brain peripheral benzodiazepine receptors in vivo. J Med Chem 2008, 51:17-30.
16. Jarkas N., Voll R.J., Williams L., Votaw J.R., Owens M., Goodman M.M. Synthesis and in vivo evaluation of halogenated N, N-dimethyl-2-(2'-amino-4'-hydroxymethylphenylthio)benzylamine derivatives as PET serotonin transporter ligands. J Med Chem 2008, 51:271-281.
17. Donohue S.R., Krushinski J.H., Pike V.W., Chernet E., Phebus L., Chesterfield A.K., Felder C.C., Halldin C., Schaus J.M. Synthesis, ex vivo evaluation, and radiolabeling of potent 1,5-diphenylpyrrolidin-2-one cannabinoid subtype-1 receptor ligands as candidates for in vivo imaging. J Med Chem 2008, 51:5833-5842.
18. Gómez V., Gispert J.D., Amador V., Llop J. New method for routine production of L-[methyl-11C]methionine: in loop synthesis. J Label Compd Radiopharm 2008, 51:83-86.
19. Studenov A.R., Jivan S., Adam M.J., Ruth T.J., Buckley K.R. Studies of the mechanism of the in-loop synthesis of radiopharmaceuticals. Appl Radiat Isot 2004, 61:1195-1201.
20. ICH Harmonised Tripartite Guideline. Impurities: Guideline for Residual Solvents Q3C(R5). 2011:1-29.
21. Chapter <823> Positron Emission Tomography Drugs for Compounding, Investigational, and Research Uses. USP 35 - NF 50 2012:398-406.
22. Effenberger F. Electrophilic reagents - recent developments and their preparative application. Angew Chem Int Ed 1980, 19:151-230.
23. N2 reaction. Org Lett 2008, 10:61-64.
24. N2/E2 branching in protic solvents: a mechanistic study. Bull Korean Chem Soc 2009, 30:1535-1538.
25. 11C]-labelled radiopharmaceuticals: reversal of the retention order of products and precursors. J Label Compd Radiopharm 2009, 52:177-181.
26. Scott P.J.H., Hockley B.G., Kung H.F., Manchanda R., Zhang W., Kilbourn M.R. Studies into radiolytic decomposition of fluorine-18 labeled radiopharmaceuticals for positron emission tomography. Appl Radiat Isot 2009, 67:88-94.