甘氨酸-氟硼荧近红外荧光分子探针的合成及性能测试  

Synthesis and Properties Study of the Near-Infrared Fluorescence Molecular Probe Glycine-BDDIPY

作　　者：董雪[1,2] 张杰[1,2] 王坤朋[1,2] 方硕[3] 刘洋[4] 孟舒献[1,2] 冯亚青[1,2] Dong Xue Zhang Jie Wang Kunpeng Fang Shuo Liu Yang Meng Shuxian Feng Yaqing(School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China Collaborative Innovation Center of Chemical Science and Engineering （Tianjin） , Tianjin 300072, China Tianjin LiSheng Pharmaceutical Co. Ltd, Tianjin 300111, China PET Center of Second Affiliated Hospital of Zhejiang University, School of Medicine, Hangzhou 310009, China)

机构地区：[1]天津大学化工学院,天津300072 [2]天津化学化工协同创新中心,天津300072 [3]天津力生制药股份有限公司,天津300111 [4]浙江大学医学院附属第二医院PET中心,杭州310009

出　　处：《化学工业与工程》2017年第2期27-34,共8页Chemical Industry and Engineering

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。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 iminodibenzy] with strong electron-dona- ting ability into the BDDIPY dye through condensation reaction. Then we gained the glycine-BDDIPY com- pound which has the near-infrared fluorescence spectrum. Next, with N-hydroxy succinimide as an activa- tor,glycine methyl ester was introduced into the BDDIPY. Finally we get a biocompatible glyeine-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.

关 键 词：氟硼荧 甘氨酸 肿瘤成像 荧光分子探针 

分 类 号：TQ11[化学工程—无机化工]