Synthesis of fluorine-18 labeled rhodamine B: A potential PET myocardial perfusion imaging agent.
Synthesis of fluorine-18 labeled rhodamine B: A potential PET myocardial perfusion imaging agent.
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DOI：
10.1016/j.apradiso.2009.08.013
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发表时间：
2010-01
影响因子：
1.6
通讯作者：
Packard, Alan B.
中科院分区：
文献类型：
--
作者：
Heinrich, Tobias K.;Gottumukkala, Vijay;Snay, Erin;Dunning, Patricia;Fahey, Frederic H.;Treves, S. Ted;Packard, Alan B.
人们对开发 18F 标记的 PET 心肌灌注剂非常感兴趣。罗丹明染料与最常用的单光子心肌灌注剂 99mTc-MIBI 具有多种特性，这表明 18F 标记的罗丹明染料可能对此应用有用。除了像 99mTc-MIBI 这样的亲脂性阳离子外，罗丹明染料还已知会在心肌中积聚，并且是 Pgp（与 MDR1 多药耐药性有关的蛋白质）的底物。作为确定 18F 标记的罗丹明是否可用作 PET 心肌灌注剂的第一步，我们的目标是开发制备 18F 标记化合物的合成方法，以便可以在体内对其进行评估。选择罗丹明 B 作为开发合成的原型化合物，因为罗丹明 B 的胺部分上的乙基取代基可以保护它们免受副反应的影响，从而无需包含（并随后除去）保护基团。使用乙二醇二甲苯磺酸酯与 Kryptofix 2.2.2、K2CO3 和 [18F]NaF 在乙腈中反应制备的甲苯磺酸[18F]氟乙酯，将罗丹明 B 内酯与[18F]甲苯磺酸氟乙酯在乙腈中于 165°C 加热 30 分钟，合成罗丹明 B 的 2'-[18F]氟乙酯10分钟。在90°C。产品经半制备型HPLC纯化，得到放射化学纯度>97%的2'-[18F]-氟乙酯，比活度为1.3GBq/μmol，分离衰变校正收率为35%，总合成时间为90分钟。
There is considerable interest in developing an 18F-labeled PET myocardial perfusion agent. Rhodamine dyes share several properties with 99mTc-MIBI, the most commonly used single-photon myocardial perfusion agent, suggesting that an 18F-labeled rhodamine dye might prove useful for this application. In addition to being lipophilic cations, like 99mTc-MIBI, rhodamine dyes are known to accumulate in the myocardium and are substrates for Pgp, the protein implicated in MDR1 multidrug resistance. As the first step in determining whether 18F-labeled rhodamines might be useful as myocardial perfusion agents for PET, our objective was to develop synthetic methods for preparing the 18F-labeled compounds so that they could be evaluated in vivo. Rhodamine B was chosen as the prototype compound for development of the synthesis because the ethyl substituents on the amine moieties of rhodamine B protect them from side reactions, thus eliminating the need to include (and subsequently remove) protecting groups. The 2′-[18F]fluoroethyl ester of rhodamine B was synthesized by heating rhodamine B lactone with [18F]fluoroethyltosylate in acetonitrile at 165°C for 30 min.using [18F]fluoroethyl tosylate, which was prepared by the reaction of ethyleneglycol ditosylate with Kryptofix 2.2.2, K2CO3, and [18F]NaF in acetonitrile for 10 min. at 90°C. The product was purified by semi-preparative HPLC to produce the 2′-[18F]-fluoroethylester in >97% radiochemical purity with a specific activity of 1.3 GBq/μmol, an isolated decay corrected yield of 35%, and a total synthesis time of 90 min.
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DOI：
10.1007/s002590050403
发表时间：
1999-04-01
期刊：
EUROPEAN JOURNAL OF NUCLEAR MEDICINE
影响因子：
--
作者：
De Moerloose, B;Van de Wiele, C;Dierckx, RA
通讯作者：
Dierckx, RA
影响因子：
3.1
作者：
VORA, MM;DHALLA, M
通讯作者：
DHALLA, M
影响因子：
9.3
作者：
Madar, Igal;Ravert, Hayden;Becker, Lewis
通讯作者：
Becker, Lewis
影响因子：
2.4
作者：
Wallhaus, TR;Lacy, J;Stone, CK
通讯作者：
Stone, CK
影响因子：
3.1
作者：
Yoon, YH;Jeong, JM;Lee, MC
通讯作者：
Lee, MC