Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Bilbao, Spain.
Departamento de Química Orgánica, Facultad de CC. Químicas, Universidad Complutense de Madrid, Madrid, Spain.
Photochem Photobiol. 2020 May;96(3):458-477. doi: 10.1111/php.13232. Epub 2020 Apr 20.
This minireview is devoted to honoring the memory of Dr. Thomas Dougherty, a pioneer of modern photodynamic therapy (PDT). It compiles the most important inputs made by our research group since 2012 in the development of new photosensitizers based on BODIPY chromophore which, thanks to the rich BODIPY chemistry, allows a finely tuned design of the photophysical properties of this family of dyes to serve as efficient photosensitizers for the generation of singlet oxygen. These two factors, photophysical tuning and workable chemistry, have turned BODIPY chromophore as one of the most promising dyes for the development of improved photosensitizers for PDT. In this line, this minireview is mainly related to the establishment of chemical methods and structural designs for enabling efficient singlet oxygen generation in BODIPYs. The approaches include the incorporation of heavy atoms, such as halogens (iodine or bromine) in different number and positions on the BODIPY scaffold, and also transition metal atoms, by their complexation with Ir(III) center, for instance. On the other hand, low-toxicity approaches, without involving heavy metals, have been developed by preparing several orthogonal BODIPY dimers with different substitution patterns. The advantages and drawbacks of all these diverse molecular designs based on BODIPY structural framework are described.
这篇综述旨在纪念现代光动力疗法(PDT)的先驱 Thomas Dougherty 博士。它汇集了我们研究小组自 2012 年以来在基于 BODIPY 生色团的新型光敏剂开发方面所做的最重要的贡献,BODIPY 生色团得益于丰富的 BODIPY 化学,可以精细设计该染料家族的光物理性质,使其成为产生单线态氧的有效光敏剂。这两个因素,光物理调谐和可行的化学,使 BODIPY 生色团成为开发用于 PDT 的改良光敏剂最有前途的染料之一。在这方面,本篇综述主要涉及建立化学方法和结构设计,以实现 BODIPY 中有效的单线态氧生成。这些方法包括在 BODIPY 支架上不同位置和数量引入卤素(碘或溴)等重原子,以及通过与 Ir(III) 中心络合引入过渡金属原子。另一方面,通过制备具有不同取代模式的几个正交 BODIPY 二聚体,开发了不涉及重金属的低毒性方法。描述了所有基于 BODIPY 结构框架的这些不同分子设计的优缺点。