2-[(18)F]氟腺苷的高效放射性合成：通往2-[(18)F]氟嘌呤核苷的新途径。
Efficient radiosynthesis of 2-[(18)f]fluoroadenosine: a new route to 2-[(18)f]fluoropurine nucleosides.
作者信息
Marchand Patrice, Lorilleux Christophe, Gilbert Gwénaëlle, Gourand Fabienne, Sobrio Franck, Peyronnet Damien, Dhilly Martine, Barré Louisa
机构信息
Laboratoire de Développements Méthodologiques en Tomographie par Emission de Positons, CEA/DSV/I2BM, CI-NAPS UMR 6232, Université de Caen Basse Normandie, Cyceron, Caen, France.
出版信息
ACS Med Chem Lett. 2010 May 28;1(6):240-3. doi: 10.1021/ml100055m. eCollection 2010 Sep 9.
Abstract
An efficient method to incorporate the fluorine-18 radionuclide in 2-nitropurine-based nucleosides was developed. The nucleophilic radiofluorination of the labeling precursor with [(18)F]KF under aminopolyether-mediated conditions (Kryptofix 2.2.2/K2CO3) followed by deprotection was straightforward and, after formulation, gave 2-[(18)F]fluoroadenosine, ready for injection with a radiochemical yield of 45 ± 5%, a radiochemical purity of >98%, and a specific radioactivity up to 148 GBq/μmol. A micropositron emission tomography imaging and biodistribution study on rodents was reported.
摘要
开发了一种在基于2-硝基嘌呤的核苷中引入氟-18放射性核素的有效方法。在氨基聚醚介导的条件下（穴醚2.2.2/碳酸钾），标记前体与[¹⁸F]KF进行亲核放射性氟化，随后进行脱保护，过程简便，制剂后得到2-[¹⁸F]氟腺苷，可供注射，放射化学产率为45±5%，放射化学纯度>98%，比活度高达148 GBq/μmol。报道了对啮齿动物的微型正电子发射断层扫描成像和生物分布研究。
相似文献
1
Efficient radiosynthesis of 2-[(18)f]fluoroadenosine: a new route to 2-[(18)f]fluoropurine nucleosides.2-[(18)F]氟腺苷的高效放射性合成：通往2-[(18)F]氟嘌呤核苷的新途径。
ACS Med Chem Lett. 2010 May 28;1(6):240-3. doi: 10.1021/ml100055m. eCollection 2010 Sep 9.
2
Synthesis and evaluation of no-carrier-added 8-cyclopentyl-3-(3-[(18)F]fluoropropyl)-1-propylxanthine ([(18)F]CPFPX): a potent and selective A(1)-adenosine receptor antagonist for in vivo imaging.
J Med Chem. 2002 Nov 7;45(23):5150-6. doi: 10.1021/jm020905i.
3
Fully automated radiosynthesis of 2-[18F]fludarabine for PET imaging of low-grade lymphoma.全自动[18F]氟达拉滨正电子发射断层扫描显像用于低级别淋巴瘤的 PET 成像。
Mol Imaging Biol. 2014 Feb;16(1):28-35. doi: 10.1007/s11307-013-0657-4.
4
Synthesis of [¹¹C]PBR06 and [¹⁸F]PBR06 as agents for positron emission tomographic (PET) imaging of the translocator protein (TSPO).[¹¹C]PBR06 和 [¹⁸F]PBR06 的合成作为正电子发射断层扫描 (PET) 成像转位蛋白 (TSPO) 的示踪剂。
Steroids. 2011 Nov;76(12):1331-40. doi: 10.1016/j.steroids.2011.06.012. Epub 2011 Jul 3.
5
Optimization of a Nucleophilic Two-Step Radiosynthesis of 6--(2-[F]fluoroethyl)-6--desmethyl-diprenorphine ([F]FE-DPN) for PET Imaging of Brain Opioid Receptors.优化亲核两步法放射性合成 6--(2-[F]氟乙基)-6--去甲二苯并庚辛因 ([F]FE-DPN)，用于脑阿片受体的 PET 成像。
Int J Mol Sci. 2023 Aug 24;24(17):13152. doi: 10.3390/ijms241713152.
6
Improved Automated Radiosynthesis of [F]Dolutegravir: Toward Clinical Applications.[F]度鲁特韦的改进型自动化放射性合成：迈向临床应用
ACS Omega. 2024 Sep 27;9(40):41732-41741. doi: 10.1021/acsomega.4c05893. eCollection 2024 Oct 8.
7
Facile F labeling of non-activated arenes via a spirocyclic iodonium(III) ylide method and its application in the synthesis of the mGluR PET radiopharmaceutical [F]FPEB.通过螺环碘化𬭩(III)叶立德方法实现非活化芳环的简便 F 标记及其在 mGluR PET 放射性药物 [F]FPEB 合成中的应用。
Nat Protoc. 2019 May;14(5):1530-1545. doi: 10.1038/s41596-019-0149-3. Epub 2019 Apr 12.
8
cGMP production of the radiopharmaceutical [ F]MK-6240 for PET imaging of human neurofibrillary tangles.用于人类神经原纤维缠结PET成像的放射性药物[F]MK-6240的cGMP生产。
J Labelled Comp Radiopharm. 2017 May 15;60(5):263-269. doi: 10.1002/jlcr.3496. Epub 2017 Mar 23.
9
An Efficient Automated Radiosynthesis and Bioactivity Confirmation of VMAT2 Tracer [F]FP-(+)-DTBZ.一种高效自动化合成 VMAT2 示踪剂 [F]FP-(+)-DTBZ 并进行生物活性确证的方法。
Mol Imaging Biol. 2020 Apr;22(2):265-273. doi: 10.1007/s11307-019-01379-6.
10
Microfluidic radiosynthesis and biodistribution of [18 F] 2-(5-fluoro-pentyl)-2-methyl malonic acid.[18F]2-(5-氟戊基)-2-甲基丙二酸的微流控放射性合成及生物分布
J Labelled Comp Radiopharm. 2013 May 15;56(5):289-94. doi: 10.1002/jlcr.3016. Epub 2013 Feb 12.
引用本文的文献
1
State of the art procedures towards reactive [F]fluoride in PET tracer synthesis.正电子发射断层显像（PET）示踪剂合成中针对活性[F]氟化物的先进程序。
EJNMMI Radiopharm Chem. 2023 Oct 12;8(1):28. doi: 10.1186/s41181-023-00203-5.
2
Fluorinated carbohydrates for F-positron emission tomography (PET).氟代碳水化合物用于正电子发射断层扫描（PET）。
Chem Soc Rev. 2023 Jun 6;52(11):3599-3626. doi: 10.1039/d3cs00037k.
3
18F-labelled intermediates for radiosynthesis by modular build-up reactions: newer developments.用于模块化合成反应进行放射性合成的18F标记中间体：新进展
Biomed Res Int. 2014;2014:812973. doi: 10.1155/2014/812973. Epub 2014 Jun 23.
4
2-[18F]fludarabine, a novel positron emission tomography (PET) tracer for imaging lymphoma: a micro-PET study in murine models.2-[18F]氟达拉滨，一种新型正电子发射断层扫描（PET）示踪剂用于淋巴瘤成像：在鼠模型中的 micro-PET 研究。
Mol Imaging Biol. 2014 Feb;16(1):118-26. doi: 10.1007/s11307-013-0659-2.
5
Fully automated radiosynthesis of 2-[18F]fludarabine for PET imaging of low-grade lymphoma.全自动[18F]氟达拉滨正电子发射断层扫描显像用于低级别淋巴瘤的 PET 成像。
Mol Imaging Biol. 2014 Feb;16(1):28-35. doi: 10.1007/s11307-013-0657-4.
本文引用的文献
1
Preparation and biological evaluation of 2-amino-6-[18F]fluoro-9-(4-hydroxy-3-hydroxy-methylbutyl) purine (6-[18F]FPCV) as a novel PET probe for imaging HSV1-tk reporter gene expression.新型PET探针2-氨基-6-[¹⁸F]氟-9-(4-羟基-3-羟甲基丁基)嘌呤(6-[¹⁸F]FPCV)的制备及其用于成像单纯疱疹病毒1型胸苷激酶(HSV1-tk)报告基因表达的生物学评价
Nucl Med Biol. 2007 Aug;34(6):717-25. doi: 10.1016/j.nucmedbio.2007.06.005.
2
Biodistribution and PET imaging of [(18)F]-fluoroadenosine derivatives.[(18)F] -氟腺苷衍生物的生物分布及正电子发射断层显像
Nucl Med Biol. 2007 Apr;34(3):267-72. doi: 10.1016/j.nucmedbio.2006.12.009. Epub 2007 Feb 22.
3
Structure-activity relationship for nucleoside analogs as inhibitors or substrates of adenosine kinase from Mycobacterium tuberculosis. I. Modifications to the adenine moiety.结核分枝杆菌腺苷激酶抑制剂或底物核苷类似物的构效关系。I. 腺嘌呤部分的修饰。
Biochem Pharmacol. 2006 Jun 14;71(12):1671-82. doi: 10.1016/j.bcp.2006.03.006. Epub 2006 Mar 10.
4
Adenosine receptors as therapeutic targets.腺苷受体作为治疗靶点。
Nat Rev Drug Discov. 2006 Mar;5(3):247-64. doi: 10.1038/nrd1983.
5
Role of central and peripheral adenosine receptors in the cardiovascular responses to intraperitoneal injections of adenosine A1 and A2A subtype receptor agonists.中枢和外周腺苷受体在腹腔注射腺苷A1和A2A亚型受体激动剂后心血管反应中的作用。
Br J Pharmacol. 2005 Mar;144(5):642-50. doi: 10.1038/sj.bjp.0706043.
6
Tracer adenosine: a novel myocardial flow marker.示踪剂腺苷：一种新型心肌血流标志物。
J Nucl Med. 2003 Apr;44(4):641-8.
7
Molecular imaging with PET--the future challenges.正电子发射断层显像（PET）分子成像——未来的挑战
Br J Radiol. 2002 Nov;75 Spec No:S6-15. doi: 10.1259/bjr.75.suppl_9.750006.
8
Nucleic acid related compounds. 116. Nonaqueous diazotization of aminopurine nucleosides. Mechanistic considerations and efficient procedures with tert-butyl nitrite or sodium nitrite.核酸相关化合物。116. 氨基嘌呤核苷的非水重氮化。用亚硝酸叔丁酯或亚硝酸钠的机理考量及有效方法。
J Org Chem. 2002 Sep 20;67(19):6788-96. doi: 10.1021/jo0204101.
9
Molecular imaging of cancer with positron emission tomography.正电子发射断层扫描在癌症分子成像中的应用
Nat Rev Cancer. 2002 Sep;2(9):683-93. doi: 10.1038/nrc882.
10
The biological application of small animal PET imaging.小动物正电子发射断层扫描成像的生物学应用。
Nucl Med Biol. 2001 Jul;28(5):585-93. doi: 10.1016/s0969-8051(01)00213-x.
Zotero 插件