Group of Lead Compound, Department of Pharmacy, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, University of South China, Hengyang 421001, China.
Hubei Province Engineering and Technology Research Center for Fluorinated Pharmaceuticals, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China.
Org Biomol Chem. 2022 Apr 20;20(16):3335-3341. doi: 10.1039/d2ob00297c.
Dual-imaging agents with highly sensitive fluorescence (FL) imaging and highly selective fluorine-19 magnetic resonance imaging (F MRI) are valuable for biomedical research. At the same time, photosensitizers with a high reactive oxygen species (ROS) generating capability are crucial for photodynamic therapy (PDT) of cancer. Herein, a series of tetra-trifluoromethylated aza-boron dipyrromethenes (aza-BODIPYs) were conveniently synthesized from readily available building blocks and their physicochemical properties, including ultraviolet-visible (UV-Vis) absorption, FL emission, photothermal efficacy, ROS generating efficacy, and F MRI sensitivity, were systematically investigated. An aza-BODIPY with 12 symmetrical fluorines was identified as a potent FL-F MRI dual-imaging traceable photodynamic agent. It was found that the selective introduction of trifluoromethyl (CF) groups into aza-BODIPYs may considerably improve their UV absorption, FL emission, photothermal efficacy, and ROS generating properties, which lays the foundation for the rational design of trifluoromethylated aza-BODIPYs in biomedical applications.
具有高灵敏度荧光（FL）成像和高选择性氟-19 磁共振成像（F MRI）的双模式成像探针对于生物医学研究具有重要价值。同时，具有高活性氧（ROS）生成能力的光敏剂对于癌症的光动力治疗（PDT）至关重要。在此，本文从易得的原料出发，方便地合成了一系列四三氟甲基化的氮杂苯并二吡咯甲川（aza-BODIPY）染料，并系统地研究了其包括紫外-可见（UV-Vis）吸收、FL 发射、光热性能、ROS 生成能力和 F MRI 敏感性在内的物理化学性质。具有 12 个对称氟原子的 aza-BODIPY 被鉴定为一种有效的 FL-F MRI 双模式成像示踪光动力剂。研究发现，选择性地在 aza-BODIPY 中引入三氟甲基（CF）基团可以显著提高其 UV 吸收、FL 发射、光热性能和 ROS 生成能力，这为在生物医学应用中合理设计三氟甲基化 aza-BODIPY 奠定了基础。
