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pH-Activatable Singlet Oxygen-Generating Boron-dipyrromethenes (BODIPYs) for Photodynamic Therapy and Bioimaging.
Journal of Medicinal Chemistry ( IF 6.8 ) Pub Date : 2020-01-22 , DOI: 10.1021/acs.jmedchem.9b01873
Sebastian Radunz 1 , Stefanie Wedepohl 2 , Mathilde Röhr 1 , Marcelo Calderón 2, 3, 4 , Harald Rune Tschiche 5 , Ute Resch-Genger 1
Affiliation  

Singlet oxygen can severely damage biological tissue, which is exploited in photodynamic therapy (PDT). In PDT, the effective range is limited by the distribution of the photosensitizer (PS) and the illuminated area. However, no distinction is made between healthy and pathological tissue, which can cause undesired damage. This encouraged us to exploit the more acidic pH of cancerous tissue and design pH-controllable singlet oxygen-generating boron-dipyrromethene (BODIPY) dyes. A pH sensitivity of the dyes is achieved by the introduction of an electronically decoupled, photoinduced electron transfer (PET)-capable subunit in meso-position of the BODIPY core. To favor triplet-state formation as required for singlet oxygen generation, iodine substituents were introduced at the chromophore core. The resulting pH-controlled singlet oxygen-generating dyes with pKa values in the physiological range were subsequently assessed regarding their potential as pH-controlled PS for PDT. Using HeLa cells, we could successfully demonstrate markedly different pH-dependent cytotoxicities upon illumination.

中文翻译:

用于光动力疗法和生物成像的pH活化单线态产氧双吡啶酮(BODIPYs)。

单线态氧会严重破坏生物组织,这在光动力疗法(PDT)中得到了利用。在PDT中,有效范围受光敏剂(PS)和照明区域的分布限制。但是,在健康组织和病理组织之间没有区别,后者会引起不良的损害。这鼓励我们利用癌组织的更酸性pH值,并设计可控制pH值的单线态氧生成硼二吡咯亚甲基(BODIPY)染料。染料的pH敏感性是通过在BODIPY核的介观位置引入电解耦的,具有光致电子转移(PET)功能的亚基实现的。为了促进单线态氧生成所需的三线态形成,在生色团核心处引入了碘取代基。随后评估所得pKa值在生理范围内的pH受控的单线态产氧染料,其作为PDT的pH受控的PS的潜力。使用HeLa细胞,我们可以成功地证明照明后pH依赖性细胞毒性显着不同。
更新日期:2020-02-06
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