Fluorescent labeling of drugs and simple organic compounds containing amine functional groups, utilizing dansyl chloride in Na2CO3 buffer
Fluorescent labeling of drugs and simple organic compounds containing amine functional groups, utilizing dansyl chloride in Na2CO3 buffer
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DOI：
10.1016/s1056-8719(01)00157-5
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发表时间：
2001-05-01
影响因子：
1.9
通讯作者：
Bartzatt, R
中科院分区：
文献类型：
--
作者：
Bartzatt, R
在碳酸钠缓冲液中，使用丹磺酰氯(Dns-Cl)荧光标记胺官能团，可检测1杯量的分析物。提出的方法允许伯胺、仲胺和叔胺在25℃的温度下丹化。叔胺的丹磺化涉及除去胺基的一个取代基(或分支)的化学反应。使用一摩尔工作浓度的Na2CO3，其pH值为11.0。异丙胺、二丙胺、二乙胺、三乙胺、三异辛胺和N，N-二甲基苯胺等化合物被用于从复杂的烷烃混合物中获得的样品的DNS-Cl标记。化合物对氯苯胺含有伯胺基团，在25℃为固体，在一摩尔碳酸钠缓冲液中迅速溶解，15分钟内丹磺化。将含有叔胺基团的海洛因从水溶液中提取到乙酸乙酯中，然后与双氯甲烷反应。局麻药苯佐卡因在15分钟内麻醉完毕。刚性环系中的叔胺基团，如咖啡因、士的宁和离子盐型的可卡因盐酸盐，在这些条件下不与dns-Cl反应。叔胺的反应时间为2小时或更短，具有伯胺和仲胺基团的化合物反应时间为15分钟。通过乙醚萃取反应水溶液，然后用丙酮和二氯甲烷等各种有机溶剂进行薄层层析，完成了从未反应的DNS-Cl中分离丹磺类化合物。(C)2002 Elsevier Science Inc.保留所有权利。
Fluorescent labeling of amine functional groups using dansyl chloride (DNS-Cl), and in sodium carbonate buffer, allowed the detection of 1 mug amounts of analytes. The methodology presented allows dansylation of primary, secondary, and tertiary amine groups at a temperature of 25degrees C. The dansylation of tertiary amines involves a chemical reaction which removes one substituent (or branch) of the amine group. A one molar working concentration of Na2CO3 is used, and is at pH 11.0. Compounds such as isopropylamine, dipropylamine, diethylamine, triethylamine, triisooctylamine, and N,N-dimethylaniline were labeled by use of DNS-Cl from samples obtained from a complex mixture of alkanes. The compound p-chloroaniline contains a primary amine group and is a solid at 25degrees, quickly dissolves in the one molar sodium carbonate buffer and is dansylated in 15 min. Heroin, which contains a tertiary amine group, was extracted into ethyl acetate from an aqueous solution, then reacted with DNS-Cl. Benzocaine, a local anesthetic, was dansylated in 15 min. Tertiary amine groups incorporated in a rigid ring system, such as for caffeine, strychnine, and the ionic salt form of cocaine hydrochloride did not react with DNS-Cl under these conditions. The reaction time for tertiary amines was 2 h or less, and 15 min for compounds having primary and secondary amine groups. Separation of the dansylated compounds from unreacted DNS-Cl was accomplished by diethyl ether extraction of the aqueous reaction solution, followed by thin layer chromatography using various organic solvents such as acetone and methylene chloride. (C) 2002 Elsevier Science Inc. All rights reserved.