新型近红外非对称七甲川菁染料的设计与合成  

Design and synthesis of novel near-infrared asymmetric heptamethine eyanine dyes

作　　者：刘琳霞 胡曰富 杨佳丽 齐庆蓉[1] LIU Linxia;HU Yuefu;YANG Jiali;QI Qingrong(Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology,Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry,West China School of Pharmacy,Sichuan University,Chengdu,Sichuan,610041 P.R.China)

机构地区：[1]四川大学华西药学院靶向药物与释药系统教育部和四川省重点实验室、四川省植物来源药物工程实验室、四川省小分子药物精准化工程技术研究中心,四川成都610041

出　　处：《华西药学杂志》2023年第6期609-614,共6页West China Journal of Pharmaceutical Sciences

摘　　要：目的设计并合成3个结构新颖的非对称七甲川菁染料,初步研究其光学性质。方法采用“两步法”合成非对称七甲川菁染料;将2,3,3-三甲基-3H-吲哚与溴取代物反应生成季铵盐,季铵盐与过量缩合剂反应生成半菁中间体,纯化后的半菁中间体与另一种季铵盐缩合,得到目标产物,并测定目标产物在甲醇、二甲基亚砜和10%二甲基亚砜水溶液中的最大吸收和发射波长。结果与结论得到了3个非对称七甲川菁染料,其结构经^(1)HNMR、^(13)CNMR和HR-MS确证,在不同溶剂中的最大吸收和发射波长均在近红外区。该结果为后续小鼠活体成像和体内组织器官的近红外显像研究奠定了基础。OBJECTIVE To design and synthesize three asymmetrical heptamethine cyanine dyes with novel structures,and to preliminarily study their optical properties.METHODS Asymmetrical heptamethine cyanine dyes were synthesized by a“two-step method”.2,3,3-Trimethyl-3H-indole reacted with a bromine substituent to form a quaternary ammonium salt,and the quaternary ammonium salt was reacted with an excess condensing agent to form a hemicyanine intermediate.Then the purified hemicyanine intermediate was condensed with another quaternary ammonium salt to obtain the target product.The maximum absorption and emission wavelengths of the target products in three different solvents(methanol,DMSO and 10% DMSO aqueous solution)were measured.RESULTS and CONCLUSION Three target compounds were synthesized,and their structures were characterized by ^(1)HNMR,^(13)CNMR and HR-MS.Their maximum absorption and emission wavelengths in diferent solvents were in the near-infrared region.This study lays a certain foundation for the subsequent in vivo imaging of mice and the near-infrared imaging of tissues and organs in vivo.

关 键 词：近红外 七甲川菁染料 非对称 设计 合成 半菁法 紫外吸收 

分 类 号：R914[医药卫生—药物化学]