甘氨酸-氟硼荧近红外荧光分子探针的合成及性能测试

摘要

将一种具有近红外荧光性能的氟硼荧染料（BDDIPY）作为显影基团，制成新型的检测肿瘤细胞的近红外荧光分子探针。首先以氟硼二吡咯烷（BOD）为起始原料，通过缩合反应，将具有强供电子作用的N-苯基亚氨基二苄引入到氟硼荧中，得到了荧光光谱处于近红外区的氟硼荧化合物，接着用N-羟基琥珀酰亚胺为活化剂，将具有肿瘤亲和力的甘氨酸引入到荧光基团-氟硼荧（BDDIPY），最终得到甘氨酸-氟硼荧近红外荧光探针，并对其结构进行了核磁和质谱表征，并进行了光学和生物学性能测试。实验结果显示：甘氨酸-氟硼荧近红外荧光分子探针的荧光发射波长大于700 nm，与肺癌细胞（GLC-82）具有较好的亲和力，达到23.65，是一个具有良好应用前景的检测肿瘤细胞的近红外荧光分子探针。

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	董雪
	张杰
	王坤朋
	方硕
	刘洋
	孟舒献
	冯亚青

关键词：氟硼荧；甘氨酸；肿瘤成像；荧光分子探针

Abstract：

In this paper, we used a BDDIPY with near-infrared fluorescent properties as imaging group to produce a new type of near infrared fluorescence molecular probe for detecting tumor cells. Firstly, BOD was used as the starting materials, and then introduced N-phenyl iminodibenzyl with strong electron-donating ability into the BDDIPY dye through condensation reaction. Then we gained the glycine-BDDIPY compound which has the near-infrared fluorescence spectrum. Next, with N-hydroxy succinimide as an activator,glycine methyl ester was introduced into the BDDIPY. Finally we get a biocompatible glycine-BDDIPY molecular fluorescent probe which having affinity with tumors. All the intermediates and target products were characterized by ¹H NMR and MALDI-TOF. These BODIPYs were tested to characterize their optical and biological properties. Experimental results showed that the fluorescence emission wavelength of glycine-BDDIPY is longer than 700 nm. And it had a good affinity with lung cancer cells at about 23.65. This indicates that glycine-BDDIPY has a good application prospect for detecting tumor cells.

Keywords： BODIPY； glycine； tumor imaging； fluorescence molecular probe

Received 2015-04-07;

Corresponding Authors: 孟舒献,E-mail:msxmail@tju.edu.cn。 Email: msxmail@tju.edu.cn

About author: 董雪(1989-),女,硕士研究生,现从事分子荧光探针方面的研究。

引用本文:

董雪, 张杰, 王坤朋, 方硕, 刘洋, 孟舒献, 冯亚青.甘氨酸-氟硼荧近红外荧光分子探针的合成及性能测试[J]. 化学工业与工程, 2017,34(2): 27-34

Dong Xue, Zhang Jie, Wang Kunpeng, Fang Shuo, Liu Yang, Meng Shuxian, Feng Yaqing.Synthesis and Properties Study of the Near-Infrared Fluorescence Molecular Probe Glycine-BDDIPY[J]. Chemcial Industry and Engineering, 2017,34(2): 27-34

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