Synthesis and application of 4-[18F] fluorobenzylamine: A versatile building block for the preparation of PET radiotracers

被引：25

作者：

Koslowsky, Ingrid ^{[1
]}

Mercer, John ^{[1
]}

Wuest, Frank ^{[1
]}

机构：

[1] Univ Alberta, Dept Oncol, Edmonton, AB T6G 1Z2, Canada

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 20期

关键词：

POSITRON-EMISSION-TOMOGRAPHY; DRUG DISCOVERY; F-18; OLIGONUCLEOTIDES; BOROHYDRIDE; DERIVATIVES; REDUCTION; CHEMISTRY; ANALOG; TIME;

D O I：

10.1039/c0ob00255k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthesis of 4-[F-18]fluorobenzylamine ([F-18]FBA) by means of transition metal-assisted sodium borohydride reduction of 4-[F-18]fluorobenzonitrile ([F-18]FBN) is described. This approach could successfully be extended to borohydride exchange resin (BER) enabling a viable option for use in automated syntheses. [F-18]FBA was used for the synthesis of 4-[F-18]fluorobenzylamine-based thiol group-reactive prosthetic groups 4-[F-18]fluorobenzyl-2-bromoacetamide ([F-18]FBBA) and 4-[F-18]fluorobenzylamidopropionyl maleimide ([F-18]FBAPM). [F-18]FBBA and [F-18]FBAPM were obtained in radiochemical yields of 75% and 55%, respectively. Feasibility of using [F-18]FBAPM as novel prosthetic group for peptide and protein labelling was demonstrated with cysteine-containing tripeptide glutathione (GSH). [F-18]FBBA was used for labelling of a fully phosphorothioated 20mer oligodesoxynucleotide (ODN).

引用

页码：4730 / 4735

页数：6

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