基于二酮吡咯并吡咯键接前药的合成及光动力治疗性能  

Synthesis and Photodynamic Therapy of Key-linker Prodrugs Based on Diketopyrrolopyrrole and Pyrrole

作　　者：姚杰 傅妮娜 YAO Jie;FU Nina(Nanjing University of Posts and Telecommunications,School of Materials Science and Engineering,Institute of Information Materials and Nanotechnology,Nanjing 210023,China)

机构地区：[1]南京邮电大学材料科学与工程学院,信息材料与纳米技术研究院,江苏南京210023

出　　处：《广州化学》2025年第1期74-77,I0004,共5页Guangzhou Chemistry

基　　金：浙江省柔性电子重点实验室开放基金资助项目(项目编号2023FE003)。

摘　　要：以二酮吡咯并吡咯(DPP)为核心受体单元,使用三苯胺硼酸、4-羟甲基苯硼酸等原料,通过Suzuki反应合成了TPA-DPP与TPA-DPP-OH,再利用酯化反应将二硫酸酐和抗癌药物紫杉醇(PTX)连接,合成PTX-SSCOOH,最后采用脱水缩合反应将TPA-DPP-OH与PTX-SS-COOH键接,合成了键接药物的光敏剂DPP-SS-PTX。利用核磁共振氢谱、高分辨质谱确认了其化学结构。使用共沉淀法制备了纳米颗粒,通过光谱表征测试了纳米颗粒的光动力潜力,利用透射电子显微镜(TEM)、激光粒度仪(Zet-PALS)表征了纳米颗粒的形貌和尺寸。结果表明,纳米颗粒单线态氧产率为28%,DPP-SS-PTX纳米颗粒呈球形且粒径均匀,平均粒径约为130 nm。通过体外细胞实验评估了其治疗潜力,结果表明DPP-SS-PTX NPs生物相容性好,具有良好的光动力治疗能力。Using diketopyrrolopyrrole(DPP)as the core acceptor unit,TPA-DPP and TPA-DPP-OH were synthesized through Suzuki reactions with raw materials such as triphenylamine boronic acid and 4-hydroxymethylphenylboronic acid.Subsequently,PTX-SSCOOH was synthesized by connecting disulfide anhydride and the anticancer drug paclitaxel(PTX)through esterification.Finally,the photosensitizer DPP-SS-PTX,with the drug conjugated,was synthesized by coupling TPA-DPP-OH and PTX-SS-COOH through a dehydration condensation reaction.Its chemical structure was confirmed using nuclear magnetic resonance spectroscopy and highresolution mass spectrometry.Nanoparticles were prepared using a co-precipitation method and characterized for their morphology and size using transmission electron microscopy(TEM)and laser particle size analyzer(Zet-PALS).The results showed that the nanoparticles exhibited a singlet oxygen yield of 28%,with DPP-SS-PTX nanoparticles displaying a spherical shape and uniform particle size,averaging around 130 nm.The therapeutic potential was evaluated through in vitro cell experiments,demonstrating that DPP-SS-PTX NPs exhibited good biocompatibility and effective photodynamic therapy capabilities.

关 键 词：二酮吡咯并吡咯(DPP) 紫杉醇 纳米粒子 光动力治疗 

分 类 号：TQ247[化学工程—有机化工]