Synthesis of N-succinimidyl 4-[18F] fluorobenzoate, an agent for labeling proteins and peptides with 18F
Synthesis of N-succinimidyl 4-[18F] fluorobenzoate, an agent for labeling proteins and peptides with 18F
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DOI：
10.1038/nprot.2006.264
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发表时间：
2006-01-01
期刊：
影响因子：
14.8
通讯作者：
Zalutsky, Michael R.
中科院分区：
文献类型：
--
作者：
Vaidyanathan, Ganesan;Zalutsky, Michael R.
本方案描述了合成N-琥珀酰亚胺基4-[F-18]氟苯甲酸酯（[F-18]SFB）的分步程序，[F-18]SFB是一种广泛用于用正电子发射放射性核素F-18标记蛋白质和肽的试剂。还描述了用于合成未标记的SFB和季盐前体4-甲酰基-N，N，N-三甲基苯铵三氟甲烷磺酸盐的方案。对于[F-18] SFB合成，首先将季盐转化为4-[F-18]氟苯甲醛。后者的氧化提供4-[F-18]氟苯甲酸，通过用N，N-二琥珀酰亚胺基碳酸酯处理将其转化为[F-18] SFB。用这种方法，[F-18] SFB的衰变校正放化产率为30%~ 35%，比放射性为11-12 GBq μ mol（-1）。从[F-18]氟化物的递送开始，所需的总合成和纯化时间为约80分钟。[F-18] SFB仍然是用F-18标记蛋白质和肽的最佳试剂，因为其具有良好的缀合产率和代谢稳定性。
This protocol describes the step-by-step procedure for the synthesis of N-succinimidyl 4-[F-18] fluorobenzoate ([F-18]SFB), an agent widely used for labeling proteins and peptides with the positron-emitting radionuclide F-18. The protocols for the synthesis of unlabeled SFB and the quaternary salt precursor 4- formyl-N, N, N-trimethyl benzenaminium trifluoromethane sulfonate also are described. For the [F-18] SFB synthesis, the quaternary salt is first converted to 4-[F-18]fluorobenzaldehyde. Oxidation of the latter provides 4-[F-18] fluorobenzoic acid, which is converted to [F-18] SFB by treatment with N,N-disuccinimidyl carbonate. Using this method, [F-18] SFB can be synthesized in decay-corrected radiochemical yields of 30%-35% and a specific radioactivity of 11-12 GBq mu mol(-1). The total synthesis and purification time required is about 80 min, starting from delivery of the [F-18] fluoride. [F-18] SFB remains an optimal reagent for labeling proteins and peptides with F-18 because of good conjugation yields and metabolic stability.