Synthesis of Unsaturated Precursors for Parahydrogen-Induced Polarization and Molecular Imaging of 1-(13)C-Acetates and 1-(13)C-Pyruvates via Side Arm Hydrogenation.
Synthesis of Unsaturated Precursors for Parahydrogen-Induced Polarization and Molecular Imaging of 1-(13)C-Acetates and 1-(13)C-Pyruvates via Side Arm Hydrogenation.
复制标题
通过侧臂氢化的1-（13）c-乙酸盐和1-（13）c-丙酮酸的非饱和前体的合成。
DOI：
10.1021/acsomega.8b00983
复制
发表时间：
2018-06-30
期刊：
影响因子：
4.1
通讯作者：
Chekmenev EY
中科院分区：
文献类型：
--
作者：
Chukanov NV;Salnikov OG;Shchepin RV;Kovtunov KV;Koptyug IV;Chekmenev EY
超极化形式的1- 13 C-乙酸酯和1- 13 C-戊酸酯用作许多疾病和病症的分子成像的诊断造影剂。在这里，我们报告的合成制备1- 13 C同位素富集和纯的溶剂乙酸酯和乙酸酯衍生的不饱和酯部分。报道的不饱和前体可用于1- 13 C-乙酸酯和1- 13 C-戊酸酯的NMR超极化通过仲氢诱导极化（PHIP）。在该PHIP变体中，不饱和酯部分的侧臂氢化（SAH）之后是通过磁场循环程序从新生仲氢质子到13 C核的极化转移，以实现13 C核自旋的超极化。本工作报告了PHIP-SAH前体的合成：1- 13 C-乙酸乙烯酯（55%产率）、1- 13 C-乙酸烯丙酯（70%产率）、1- 13 C-乙酸炔丙酯（45%产率）、1- 13 C-丙酮酸烯丙酯（60%产率）和1- 13 C-丙酮酸炔丙酯（35%产率）。PHIP-SAH 13 C超极化的可行性通过13 C NMR光谱验证：超极化的1 - 13 C-丙酮酸烯丙酯由1- 13 C-丙酮酸炔丙酯产生，其中13 C极化在CD 3 OD中为1.33%，在D2 O中为1.07%。13 C磁共振成像显示与超极化1- 13 C-丙酮酸在水介质中。
Hyperpolarized forms of 1-13C-acetates and 1-13C-pyruvates are used as diagnostic contrast agents for molecular imaging of many diseases and disorders. Here, we report the synthetic preparation of 1-13C isotopically enriched and pure from solvent acetates and pyruvates derivatized with unsaturated ester moiety. The reported unsaturated precursors can be employed for NMR hyperpolarization of 1-13C-acetates and 1-13C-pyruvates via parahydrogen-induced polarization (PHIP). In this PHIP variant, Side arm hydrogenation (SAH) of unsaturated ester moiety is followed by the polarization transfer from nascent parahydrogen protons to 13C nucleus via magnetic field cycling procedure to achieve hyperpolarization of 13C nuclear spins. This work reports the synthesis of PHIP-SAH precursors: vinyl 1-13C-acetate (55% yield), allyl 1-13C-acetate (70% yield), propargyl 1-13C-acetate (45% yield), allyl 1-13C-pyruvate (60% yield), and propargyl 1-13C-pyruvate (35% yield). Feasibility of PHIP-SAH 13C hyperpolarization was verified by 13C NMR spectroscopy: hyperpolarized allyl 1-13C-pyruvate was produced from propargyl 1-13C-pyruvate with 13C polarization of ∼3.2% in CD3OD and ∼0.7% in D2O. 13C magnetic resonance imaging is demonstrated with hyperpolarized 1-13C-pyruvate in aqueous medium.
登录
查看更多内容
影响因子：
2.2
作者：
Baer, Sebastien;Lange, Thomas;Hoevener, Jan-Bernd
通讯作者：
Hoevener, Jan-Bernd
DOI：
10.1007/s10334-013-0366-7
发表时间：
2013-10-01
影响因子：
2.3
作者：
Borowiak, Robert;Schwaderlapp, Niels;Hoevener, Jan-Bernd
通讯作者：
Hoevener, Jan-Bernd
影响因子：
2.2
作者：
Coffey, Aaron M.;Shchepin, Roman V.;Chekmenev, Eduard Y.
通讯作者：
Chekmenev, Eduard Y.
影响因子：
3.7
作者：
Barskiy, Danila A.;Salnikov, Oleg G.;Chekmenev, Eduard Y.
通讯作者：
Chekmenev, Eduard Y.
DOI：
10.1007/s10334-005-0007-x
发表时间：
2005-11-01
影响因子：
2.3
作者：
Bhattacharya, P;Harris, K;Ross, BD
通讯作者：
Ross, BD