Fine-tuning the electronic structure of heavy-atom-free BODIPY photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy,Chemical Science

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Fine-tuning the electronic structure of heavy-atom-free BODIPY photosensitizers for fluorescence imaging and mitochondria-targeted photodynamic therapy
Chemical Science ( IF 7.6 ) Pub Date : 2020-03-17 , DOI: 10.1039/d0sc01171a
Sujie Qi ₁ , Nahyun Kwon ₁ , Yubin Yim ₁ , Van-Nghia Nguyen _{1,

2} , Juyoung Yoon ₁

Affiliation

Theranostics that combines both diagnosis and therapy into a single platform has recently emerged as a promising biomedical approach for cancer treatment; however, the development of efficient theranostic agents with excellent optical properties remains a challenge. Here, we report novel mitochondria-targeting BODIPY photosensitizers (R-BODs) that possess considerable singlet oxygen generation capabilities and good fluorescence properties for imaging-guided photodynamic therapy (PDT). The incorporation of sulfur atoms into the π-conjugated skeleton of BODIPY along with the introduction of different functional groups at the meso-position of the BODIPY core is essential for tuning the photophysical and photosensitizing properties. Notably, the MeOPh-substituted thiophene-fused BODIPY (MeO-BOD, R = p-methoxyphenyl) displayed the highest singlet oxygen generation capability (Φ_Δ ≈ 0.85 in air-saturated acetonitrile) and a moderate fluorescence quantum yield (Φ_f = 17.11). Furthermore, MeO-BOD showed good biocompatibility, low dark toxicity and superior fluorescence imaging properties in living cells. More importantly, the PDT efficacy of mitochondria-specific anchoring of MeO-BOD was remarkably amplified with an extremely low half-maximal inhibitory concentration (IC₅₀) value of 95 nM. We believe that the incorporation of an electron-donating group at the meso-position of the thiophene-fused BODIPY platform may be an effective approach for developing theranostic agents for precision cancer therapy.

中文翻译：

微调无重原子 BODIPY 光敏剂的电子结构，用于荧光成像和线粒体靶向光动力治疗

将诊断和治疗结合到一个平台中的治疗诊断学最近已成为一种有前途的癌症治疗生物医学方法。然而，开发具有优异光学特性的高效治疗诊断剂仍然是一个挑战。在此，我们报道了新型线粒体靶向BODIPY光敏剂（ R-BOD ），其具有相当大的单线态氧生成能力和良好的荧光特性，适用于成像引导光动力疗法（PDT）。将硫原子掺入BODIPY的 π 共轭骨架中，并在BODIPY核心的中间位引入不同的官能团，对于调节光物理和光敏性能至关重要。值得注意的是，MeOPh 取代的噻吩稠合BODIPY （ MeO-BOD ，R =对甲氧基苯基）表现出最高的单线态氧生成能力（在空气饱和乙腈中Φ _Δ ≈ 0.85）和中等的荧光量子产率（ Φ _f = 17.11））。此外， MeO-BOD在活细胞中表现出良好的生物相容性、低暗毒性和优异的荧光成像特性。更重要的是， MeO-BOD线粒体特异性锚定的 PDT 功效显着增强，半数抑制浓度 (IC ₅₀ ) 值极低，为 95 nM。我们相信，在噻吩稠合的BODIPY平台的中间位置掺入给电子基团可能是开发用于精准癌症治疗的治疗诊断剂的有效方法。

更新日期：2020-03-17

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