An improved synthesis of 1'-[18F]fluoroethyl-β-D-lactose ([18F]-FEL) for positron emission tomography imaging of pancreatic cancer.
An improved synthesis of 1'-[18F]fluoroethyl-β-D-lactose ([18F]-FEL) for positron emission tomography imaging of pancreatic cancer.
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DOI：
10.1002/jlcr.3042
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发表时间：
2013-06-15
影响因子：
1.8
通讯作者：
Alauddin, Mian M.
中科院分区：
文献类型：
--
作者：
Turkman, Nashaat;Gelovani, Juri G.;Alauddin, Mian M.
早期，我们报道了乙基-β-D-吡喃半乳糖基-（1，4 ′）-2′-脱氧-2 ′-[18 F]氟-β-D-吡喃葡萄糖苷（Et-[18 F]FDL）和1′-[18 F]氟乙基-β-D-乳糖（[18 F]-FEL）用于胰腺癌正电子发射断层扫描（PET）的合成。Et-[18F]FDL需要前体，其涉及11个步骤来合成并且产生总体低收率。合成[18F]-FEL的前体需要四个步骤，但这些前体产生的放射化学产率低。在这里，我们报告了新的前体和改进的合成[18 F]-FEL。以乳糖为原料，经4步反应合成了2个前体1′-（甲磺酰基）乙基-2 ′，3 ′，6 ′，2，3，4，6-七-O-乙酰基-β-D-乳糖2a和1′-（对硝基苯磺酰基）乙基-2 ′，3 ′，6 ′，2，3，4，6-七-O-乙酰基-β-D-乳糖2b。使用K18 F/kryptofix进行放射性同位素反应，并通过HPLC纯化粗产物[18F]-3。[18 F]-3碱性水解生成1′-[18 F]氟乙基-β-D-乳糖[18 F]-4，将其中和，用盐水稀释，在0.22 μm过滤器上过滤，并通过放射性TLC进行分析。[18F]-4（d. c.）2a和2b的回收率分别为21%（n = 6）和65%（n = 6），放射化学纯度> 99%，比活度为55.5GBq/μmol。合成时间为轰击结束后90-95分钟。改进了[18 F]FEL的合成方法，获得了高产率、高纯度和高比活性的[18 F]FEL。用该方法制备的前体2b可用于临床应用的商业合成模块中的高产率自动化生产。
Earlier, we reported syntheses of ethyl-β-D-galactopyranosyl-(1,4′)-2′-deoxy-2′-[18F]fluoro-β-D-glucopyranoside (Et-[18F]FDL) and 1′-[18F]fluoroethyl-β-D-lactose ([18F]-FEL) for positron emission tomography (PET) of pancreatic carcinoma. Et-[18F]FDL requires a precursor, which involves 11 steps to synthesize and produces overall low yields. Synthesis of precursors for [18F]-FEL requires four steps, but those precursors produced low radiochemical yields. Here, we report new precursors and an improved synthesis of [18F]-FEL. Two precursors, 1′-(methanesulfonyl)ethyl-2′,3′,6′,2,3,4,6-hepta-O-acetyl-β-D-lactose 2a and 1′-(p-nitrophenyl-sulfonyl)ethyl-2′,3′,6′,2,3,4,6-hepta-O-acetyl-β-D-lactose 2b, were synthesized from lactose in four steps. Radiofluorination reactions were performed using K18F/kryptofix and the crude product [18F]-3 was purified by HPLC. Basic hydrolysis of [18F]-3 produced 1′-[18F]fluoroethyl-β-D-lactose [18F]-4, which was neutralized, diluted with saline, filtered on a 0.22-μm filter, and analyzed by radio-TLC. The average radiochemical yields of [18F]-4 (d. c.) from 2a and 2b were 21% (n = 6) and 65% (n = 6), respectively, with > 99% radiochemical purity and specific activity of 55.5 GBq/μmol. Synthesis time was 90–95 min from the end of bombardment. An improved synthesis of [18F]FEL has been achieved in high yields, with high purity and specific activity. Precursor 2b with this method should be applicable for high yield automated production in a commercial synthesis module for clinical application.
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影响因子：
3.7
作者：
Flores LG;Bertolini S;Yeh HH;Young D;Mukhopadhyay U;Pal A;Ying Y;Volgin A;Shavrin A;Soghomonyan S;Tong W;Bornmann W;Alauddin MM;Logsdon C;Gelovani JG
通讯作者：
Gelovani JG
影响因子：
3.5
作者：
CHRISTA, L;FELIN, M;SEVE, AP
通讯作者：
SEVE, AP
影响因子：
8
作者：
Cavard, C;Terris, B;Perret, C
通讯作者：
Perret, C
影响因子：
7.5
作者：
Fukushima, N;Koopmann, J;Goggins, M
通讯作者：
Goggins, M
DOI：
10.1111/j.1432-1033.2004.04302.x
发表时间：
2004-10-01
期刊：
EUROPEAN JOURNAL OF BIOCHEMISTRY
影响因子：
--
作者：
Demaugre, F;Philippe, Y;Brechot, C
通讯作者：
Brechot, C