Bromination from the macroscopic level to the tracer radiochemical level: (76)Br radiolabeling of aromatic compounds via electrophilic substitution.
Bromination from the macroscopic level to the tracer radiochemical level: (76)Br radiolabeling of aromatic compounds via electrophilic substitution.
复制标题
从宏观水平到示踪放射化学水平的溴化：通过亲电取代对芳香族化合物进行(76)Br放射性标记。
DOI：
10.1021/bc800313c
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发表时间：
2009
影响因子：
4.7
通讯作者：
Welch,MichaelJ
中科院分区：
文献类型：
--
作者：
Zhou,Dong;Zhou,Haibing;Jenks,CarlC;Lewis,JasonS;Katzenellenbogen,JohnA;Welch,MichaelJ
用溴离子对雌激素受体β（ERβ）选择性配体4-（5-乙酰氧基-7-溴苯并恶唑-2-基）苯乙酸酯进行了无载体（NCA）~（76）Br标记。通过修饰离去基团（从Bu 3Sn到Me 3Sn）和向反应混合物中加入甲醇，通过有机锡前体分子的氧化亲电脱锡实现标记。在有效溴化剂方面探索了小规模宏观与示踪剂水平放射化学条件下氧化溴化反应之间的差异，这在很大程度上取决于放射化学溴化过程中溶剂的性质，以及反应中痕量水平的高反应性杂质的潜在干扰，这些杂质在NCA水平上竞争所需的溴化。我们的意见，我们的发展，成功的放射性溴化示踪剂的NCA规模的实验方案，应适用于合成其他放射性溴标记的有机化合物的潜在利益的PET放射性药物和放射治疗剂。
No-carrier-added (NCA)76Br labeling of 4-(5-acetoxy-7-bromobenzoxazol-2-yl)phenyl acetate, a diacetate-protected estrogen-receptor beta (ERβ) selective ligand, was carried out successfully using [76Br]bromide ion. The labeling was achieved via oxidative electrophilic destannylation of an organotin precursor molecule by modification of the leaving group (from Bu3Sn to Me3Sn) and the addition of methanol to the reaction mixture. The differences between the oxidative bromination reaction under small-scale macroscopic vs tracer level radiochemical conditions were explored in terms of effective brominating agents, which depend greatly on the nature of the solvent during the radiochemical bromination, and the potential interference by trace levels of highly reactive impurities in the reaction that compete for the desired bromination at the NCA level. Our observations, and our development of experimental protocols for successful radiobromination at the tracer NCA-scale, should be applicable to the synthesis of other radiobromine-labeled organic compounds of potential interest as PET radiopharmaceuticals and radiotherapy agents.