使用对-[¹⁸F]氟苄胺合成抗肿瘤前列腺素δ⁷-PGA₁甲酯的¹⁸F标记类似物。

Synthesis of a F-18 labeled analog of antitumor prostaglandin delta 7-PGA1 methyl ester using p-[18F]fluorobenzylamine.

作者信息

Haradahira T, Hasegawa Y, Furuta K, Suzuki M, Watanabe Y, Suzuki K

机构信息

Division of Advanced Technology for Medical Imaging, National Institute of Radiological Sciences, Chiba, Japan.

出版信息

Appl Radiat Isot. 1998 Dec;49(12):1551-6. doi: 10.1016/s0969-8043(98)00051-7.

DOI:10.1016/s0969-8043(98)00051-7

PMID:9745691

Abstract

A fluorine-18 labeled analog of an antitumor prostaglandin delta 7-PGA1 methyl ester, 15-deoxy-13,14-dihydro-delta 7-PGA1 4-[18F]fluorobenzyl amide ([18F]3), was synthesized as a tracer candidate for detecting tumors with positron emission tomography. p-[18F]Fluorobenzylamine (p-[18F]FBnA) used as a labeled precursor for the synthesis of [18F]3 was prepared by fluorination of a 4-N, N, N-trimethylammonium-benzonitrile triflate with [18F]fluoride and subsequent reduction with borane-dimethylsulfide. Radiochemical yield and purity of p-[18F]FBnA obtained were 39-49% (decay uncorrected) and 91-96%, respectively, after C18 Sep-Pak purification. Treatment of p-[18F]FBnA with a 15-deoxy-13,14-dihydro-delta 7-PGA1 N-succinimidyl ester in acetonitrile and subsequent HPLC purification gave radiochemically pure (> 99%) [18F]3 with a 58% decay uncorrected yield. The total synthesis time was 70 min from the start of the radiosynthesis of p-[18F]FBnA.

摘要

合成了一种抗肿瘤前列腺素δ7-PGA1甲酯的氟-18标记类似物，即15-脱氧-13,14-二氢-δ7-PGA1 4-[18F]氟苄酰胺（[18F]3），作为正电子发射断层扫描检测肿瘤的示踪剂候选物。用作合成[18F]3的标记前体的对-[18F]氟苄胺（p-[18F]FBnA）是通过用[18F]氟化物对4-N，N，N-三甲基铵-苯甲腈三氟甲磺酸盐进行氟化，随后用硼烷-二甲硫醚还原而制备的。经C18 Sep-Pak纯化后，得到的p-[18F]FBnA的放射化学产率和纯度分别为39-49%（未校正衰变）和91-96%。在乙腈中用15-脱氧-13,14-二氢-δ7-PGA1 N-琥珀酰亚胺酯处理p-[18F]FBnA，随后进行HPLC纯化，得到放射化学纯（>99%）的[18F]3，未校正衰变产率为58%。从开始合成p-[18F]FBnA起，总合成时间为70分钟。