2β-甲氧羰基-3β-(3'-[(123)I]碘苯基)托烷([(123)I]YP256)作为一种血清素转运体放射性示踪剂的合成、放射性标记及狒狒单光子发射计算机断层显像成像
Synthesis, radiolabeling and baboon SPECT imaging of 2beta-carbomethoxy-3beta-(3'-[(123)I]iodophenyl)tropane ([(123)I]YP256) as a serotonin transporter radiotracer.
作者信息
Bois Frederic, Baldwin Ronald M, Amici Louis, Al-Tikriti Mohammed S, Kula Nora, Baldessarini Ross, Innis Robert B, Staley Julie K, Tamagnan Gilles D
机构信息
Yale University, School of Medicine, VA Connecticut HCS (116A2), West Haven, CT 06516, USA.
出版信息
Nucl Med Biol. 2008 Jan;35(1):53-9. doi: 10.1016/j.nucmedbio.2007.09.002.
Abstract
To develop a potential SPECT probe to evaluate the integrity of the serotoninergic system (5-HTT) whose dysfunction is linked to several disease conditions such as Parkinson's disease, Alzheimer's disease and depression, we report the synthesis, radiolabeling and in vivo baboon imaging of 2beta-carbomethoxy-3beta-(3'-[(123)I]iodophenyl) tropane (YP256, 6). The radiolabeling was performed by iododestannylation using sodium [(123)I]iodide and peracetic acid. Although the ligand displayed high selectivity for 5-HTT over dopamine transporter in vitro, SPECT imaging in baboons did not reveal selective 5-HTT accumulation in brain in vivo.
摘要
为开发一种潜在的单光子发射计算机断层扫描（SPECT）探针，以评估血清素能系统（5-HTT）的完整性，该系统功能障碍与帕金森病、阿尔茨海默病和抑郁症等多种疾病相关，我们报告了2β-甲氧羰基-3β-（3'-[（123）I]碘苯基）托烷（YP256，6）的合成、放射性标记及在狒狒体内的成像。放射性标记通过使用[（123）I]碘化钠和过氧乙酸进行碘去锡化反应来完成。尽管该配体在体外对5-HTT的选择性高于多巴胺转运体，但在狒狒体内进行的SPECT成像并未显示出其在脑内有选择性的5-HTT蓄积。
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本文引用的文献
1
Neuroimaging of the serotonin reuptake site requires high-affinity ligands.对5-羟色胺再摄取位点进行神经成像需要高亲和力配体。
Synapse. 2007 Nov;61(11):882-8. doi: 10.1002/syn.20443.
2
Targeting proteins in vivo: in vitro guidelines.体内蛋白质靶向：体外指南。
Nucl Med Biol. 2006 Feb;33(2):161-4. doi: 10.1016/j.nucmedbio.2006.01.010.
3
Synthesis and amine transporter affinities of novel phenyltropane derivatives as potential positron emission tomography (PET) imaging agents.
Bioorg Med Chem Lett. 2004 Nov 15;14(22):5635-9. doi: 10.1016/j.bmcl.2004.08.049.
4
In vivo measurement of the serotonin transporter with (S)-([18F]fluoromethyl)-(+)-McN5652.用(S)-([¹⁸F]氟甲基)-(+)-McN5652对5-羟色胺转运体进行体内测量。
Neuropsychopharmacology. 2003 Nov;28(11):2010-9. doi: 10.1038/sj.npp.1300281.
5
Synthesis of S-([18F]fluoromethyl)-(+)-McN5652 as a potential PET radioligand for the serotonin transporter.
Nucl Med Biol. 2001 Oct;28(7):857-63. doi: 10.1016/s0969-8051(01)00248-7.
6
Imaging the serotonin transporter with positron emission tomography: initial human studies with [11C]DAPP and [11C]DASB.用正电子发射断层扫描成像5-羟色胺转运体：用[11C]DAPP和[11C]DASB进行的初步人体研究。
Eur J Nucl Med. 2000 Nov;27(11):1719-22. doi: 10.1007/s002590000365.
7
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Nucl Med Biol. 2000 Aug;27(6):547-56. doi: 10.1016/s0969-8051(00)00129-3.
8
In vivo quantification of brain serotonin transporters in humans using [11C]McN 5652.使用[11C] McN 5652对人类大脑中5-羟色胺转运体进行体内定量分析。
J Nucl Med. 2000 Sep;41(9):1465-77.
9
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Bioorg Med Chem Lett. 2000 May 15;10(10):1113-5. doi: 10.1016/s0960-894x(00)00185-2.
10
Evaluation of serotonergic transporters using PET and [11C](+)McN-5652: assessment of methods.使用正电子发射断层扫描（PET）和[11C](+)McN-5652评估血清素转运体：方法评估
J Cereb Blood Flow Metab. 2000 Feb;20(2):253-62. doi: 10.1097/00004647-200002000-00005.
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