［<sup>18</sup>F］F-DOPA合成方法的研究进展

成伟华; 郭飞虎; 邓雪松; 秦祥宇; 樊红强; 胡骥

doi:10.11665/j.issn.1000-5048.20190313

［¹⁸F］F-DOPA合成方法的研究进展

原子高科股份有限公司

基金项目: 中核集团青年英才计划资助项目(No.20180821-GK009) ^#成伟华,郭飞虎对本论文的贡献相同

计量
- 文章访问数: 679
- HTML全文浏览量: 1
- PDF下载量: 1146
出版历程
- 刊出日期: 2019-06-24

Research progress of synthetic methods of ［¹⁸F］F-DOPA

摘要

摘要: 6-［¹⁸F］氟-3，4-二羟基-L-苯丙氨酸(［¹⁸F］F-DOPA)作为帕金森病的诊断试剂已应用30多年。目前应用的亲电合成方法存在着放化产率(RCY)低、比活度(SA)低等缺点，而近年来亲核取代合成［¹⁸F］F-DOPA的方法以无载体的［¹⁸F］F^-作为亲核进攻试剂，可以克服以上缺点。本文综述了近年来报道的［¹⁸F］F-DOPA亲核取代合成的新方法。
- 6-［¹⁸F］氟-3,4-二羟基-L-苯丙氨酸 /
- 亲核取代 /
- 氟化反应 /
- 放射化学合成
Abstract: ［¹⁸F］6-fluoro-3, 4-dihydroxy-L-phenylalanine(［¹⁸F］F-DOPA)has been used as a radiotracer for Parkinson′s disease over 30 years. The previously reported electrophilic synthesis method has low radiochemical yield(RCY), low specific activity(SA)and other defects. Recent reported nucleophilic synthesis of ［¹⁸F］F-DOPA could overcome the disadvantages. In this paper, the nucleophilic synthetic methods for ［¹⁸F］F-DOPA are reviewed.
- ［¹⁸F］6-fluoro-3,4-dihydroxy-L-phenylalanine /
- nucleophilic substitution /
- fluorination /
- radiochemical synthesis

HTML全文

参考文献(29)

[1]	Sun T,Han SQ,Wang JW.Imaging theory,predominance and clinical applications of PET/CT[J].Chin J Med Phys(中国医学物理学杂志),2010,27(1):1581-1582.
[2]	Tang GH.Positron emission tomography imaging and drug development[J].Acta Pharm Sin(药学学报),2001,36(6):470-474.
[3]	Hoegerle S,Schneider B,Kraft A,et al.Imaging of a metastatic gastrointestinal carcinoid by F-18-DOPA positron emission tomography[J].Nuklearmedizin,1999,38(4):127-130.
[4]	Forsback S,Eskola O,Haaparanta M,et al.Electrophilic synthesis of 6-[¹⁸F] fluoro-L-DOPA using post-target produced [¹⁸F] F₂[J].Radiochim Acta,2008,96(12):845-848.
[5]	Dolle F,Demphel S,Hinnen F,et al.6-[¹⁸F]Fluoro-L-DOPA by radiofluorodestannylation:a short and simple synthesis of a new labelling precursor[J].J Labelled Compd Rad,1998,41(2):105-114.
[6]	Chang CW, Wang HE, Lin HM, et al. Robotic synthesis of 6-[¹⁸F] fluoro-L-dopa[J].Nucl Med Commun,2000,21(9):799-802.
[7]	de Vries EFJ,Luurtsema G,Brüssermann M,et al.Fully automated synthesis module for the high yield one-pot preparation of 6-[¹⁸F] fluoro-L-DOPA[J].Appl Radiat Isot,1999,51(4):389-394.
[8]	Luxen A,Perlmutter M,Bida GT,et al.Remote,semiautomated production of 6-[¹⁸F] fluoro-L-dopa for human studies with PET[J].Appl Radia Isot,1990,41(3):275-281.
[9]	Forsback S,Eskola O,Bergman J,et al.Alternative solvents for electrophilic synthesis of 6-[¹⁸F]fluoro-L-DOPA[J].J Labelled Compd Rad,2009,52(7):286-288.
[10]	Stenhagen IS,Kirjavainen AK,Forsback SJ,et al.[¹⁸F]Fluorination of an arylboronic ester using [¹⁸F] selectfluor bis(triflate):application to 6-[¹⁸F]fluoro-L-DOPA[J].Chem Commun,2013,49(14):1386-1388.
[11]	Lee E,Hooker J M,Ritter T.Nickel-mediated oxidative fluorination for PET with aqueous [¹⁸F] fluoride[J].J Am Chem Soc,2012,134(42):17456-17458.
[12]	Zlatopolskiy BD,Zischler J,Urusova EA,et al.A practical one-pot synthesis of positron emission tomography(PET)tracers via nickel-mediated radiofluorination[J].ChemistryOpen,2015,4(4):457-462.
[13]	DiMagno SG. Fluorination of aromatic ring systems: US,20110313170 A1 [P].2011-12-22.
[14]	Wang B,Qin L,Neumann KD,et al.Improved arene fluorination methodology for I(III)salts[J].Org Lett,2010,12(15):3352-3355.
[15]	Edwards R,Westwell AD,Daniels S,et al.Convenient synthesis of diaryliodonium salts for the production of [¹⁸F] F-DOPA[J].Eur J Org Chem,2015,2015(3):625-630.
[16]	Ichiishi N, Brooks AF, Topczewski JJ, et al. Copper-catalyzed [¹⁸F] fluorination of(mesityl)(aryl)iodonium salts[J].Org Lett,2014,16(12):3224-3227.
[17]	Rotstein BH,Stephenson NA,Vasdev N,et al.Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics[J].Nat Commun,2014,5:4365.
[18]	Satyamurthy N,Barrio JR.No-carrier-added nucleophilic [F-18] fluorination of aromatic compounds:US,8742139B2[P].2012-05-17.
[19]	Satyamurthy N,Barrio JR.Nucleophilic fluorination of aromatic compounds:US,8674101B2[P].2011-07-21.
[20]	Tredwell M, Preshlock SM, Taylor NJ, et al. A general copper-mediated nucleophilic ¹⁸F fluorination of arenes[J].Angew Chem Int Ed Engl,2014,53(30):7751-7755.
[21]	Makaravage KJ,Brooks AF,Mossine AV,et al.Copper-mediated radiofluorination of arylstannanes with [¹⁸F]KF[J].Org Lett,2016,18(20):5440-5443.
[22]	Tierling T,Hamacher K,Coenen HH.A new nucleophilic asymmetric synthesis of 6-[¹⁸ F]fluoro-DOPA[J].J Labelled Compd Rad,2001,44(S1):S146-S147.
[23]	Wagner FM,Ermert J,Coenen HH.Three-step,“one-pot” radiosynthesis of 6-fluoro-3,4-dihydroxy-l-phenylalanine by isotopic exchange[J].J Nucl Med,2009,50(10):1724-1729.
[24]	Yin DZ,Zhang L,Tang GH,et al.Enantioselective synthesis of no-carrier added(NCA)6-[¹⁸F] fluoro-L-Dopa[J].J Radioanal Nucl Ch,2003,257(1):179-185.
[25]	Libert LC,Franci X,Plenevaux AR,et al.Production at the Curie level of no-carrier-added 6-¹⁸F-fluoro-L-dopa[J].J Nucl Med,2013,54(7):1154-1161.
[26]	Lemaire C,Gillet S,Guillouet S,et al.Highly enantioselective synthesis of no-carrier-added 6-[¹⁸F]fluoro-L-dopa by chiral phase-transfer alkylation[J].Eur J Org Chem,2004,2004(13):2899-2904.
[27]	Lemaire C,Libert L,Plenevaux A,et al.Fast and reliable method for the preparation of ortho- and para-[¹⁸F]fluorobenzyl halide derivatives:key intermediates for the preparation of no-carrier-added PET aromatic radiopharmaceuticals[J].J Fluorine Chem,2012,138:48-55.
[28]	Fu HP,Zhang XJ,Ma GY,et al.Automatic synthesis of 18F-6-F-L-DOPA and its application in clinical PET imaging [J].J Isotopes(同位素),2018,31(5):298-303.
[29]	Wen FH,Zhang ZW,Ma H,et al.Full automated synthesis of 18F-FDOPA and preliminary PET/CT imaging [J].J Isotopes(同位素),2018,31(5):269-275.