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Novel indole-BODIPY photosensitizers based on iodine promoted intersystem crossing enhancement for lysosome-targeted imaging and photodynamic therapy
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2021-09-02 , DOI: 10.1039/d1nj03628a Miao Liu 1 , Chengjun Wang 1, 2 , Ying Qian 1
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2021-09-02 , DOI: 10.1039/d1nj03628a Miao Liu 1 , Chengjun Wang 1, 2 , Ying Qian 1
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In this work, we report the new lysosome-targeting indole-BODIPY derivatives BDP-Lys, IBDP-Lys, and I2BDP-Lys. BDP-Lys dye was designed for fluorescence imaging through introduction of an indole-containing morpholine moiety to a BODIPY core. Monoiodine and diiodine were incorporated into BDP-Lys dye to develop the photosensitizers IBDP-Lys and I2BDP-Lys. The maximum absorption (λabs) for IBDP-Lys and I2BDP-Lys displayed a redshift at approximately 11 nm and 27 nm, respectively, compared with the BDP-Lys dye (λabs = 504 nm). Similarly, the maximum emission also exhibited a redshift. The fluorescence quantum yield (ΦF) of IBDP-Lys (ΦF = 0.37%) and I2BDP-Lys (ΦF = 0.71%) was much lower than that of BDP-Lys dye (ΦF = 7.48%). The singlet oxygen quantum yields were measured as 43.10% for IBDP-Lys and 71.00% for I2BDP-Lys, which were higher than the iodine-free dye BDP-Lys. The theoretical calculation reasonably explains that iodine atoms promoted the intersystem crossing (ISC) process, and di-iodine further enhanced the ISC in indole-BODIPY dyes. Moreover, monoiodine photosensitizer IBDP-Lys was able to balance the generation of singlet oxygen and biocompatibility in cancer treatment. IBDP-Lys exhibited low dark toxicity (cell viability >90%), satisfactory biocompatibility, and precise lysosome targeting, with a Pearson coefficient of 0.93. The IBDP-Lys photosensitizer also was able to kill tumour cells. Considering the above results, the novel structure of indole-BODIPY photosensitizers could serve as a potential platform for lysosome-targeted imaging and photodynamic therapy.
中文翻译：
基于碘的新型吲哚-BODIPY 光敏剂促进溶酶体靶向成像和光动力治疗的系统间交叉增强
在这项工作中，我们报告了新的溶酶体靶向吲哚-BODIPY 衍生物 BDP-Lys、IBDP-Lys 和 I 2 BDP-Lys。BDP-Lys 染料设计用于通过将含有吲哚的吗啉部分引入 BODIPY 核心进行荧光成像。将一碘和二碘加入 BDP-Lys 染料中以开发光敏剂 IBDP-Lys 和 I 2 BDP-Lys。与 BDP-Lys 染料（λ abs = 504 nm）相比，IBDP-Lys 和 I 2 BDP-Lys的最大吸收（λ abs）分别在约 11 nm 和 27 nm 处显示出红移。同样，最大发射也表现出红移。IBDP-Lys ( Φ F )的荧光量子产率 ( Φ F )F = 0.37%) 和 I 2 BDP-Lys ( Φ F = 0.71%) 远低于 BDP-Lys 染料 ( Φ F = 7.48%)。IBDP-Lys 的单线态氧量子产率为 43.10%，I 2为 71.00%BDP-Lys，高于无碘染料 BDP-Lys。理论计算合理地解释了碘原子促进了系统间交叉（ISC）过程，二碘进一步增强了吲哚-BODIPY染料中的系统间交叉（ISC）过程。此外，单碘光敏剂 IBDP-Lys 能够平衡单线态氧的产生和癌症治疗中的生物相容性。IBDP-Lys 表现出低暗毒性（细胞活力 >90%）、令人满意的生物相容性和精确的溶酶体靶向，Pearson 系数为 0.93。IBDP-Lys 光敏剂也能够杀死肿瘤细胞。考虑到上述结果，吲哚-BODIPY 光敏剂的新型结构可以作为溶酶体靶向成像和光动力治疗的潜在平台。
更新日期：2021-09-15
中文翻译：
基于碘的新型吲哚-BODIPY 光敏剂促进溶酶体靶向成像和光动力治疗的系统间交叉增强
在这项工作中，我们报告了新的溶酶体靶向吲哚-BODIPY 衍生物 BDP-Lys、IBDP-Lys 和 I 2 BDP-Lys。BDP-Lys 染料设计用于通过将含有吲哚的吗啉部分引入 BODIPY 核心进行荧光成像。将一碘和二碘加入 BDP-Lys 染料中以开发光敏剂 IBDP-Lys 和 I 2 BDP-Lys。与 BDP-Lys 染料（λ abs = 504 nm）相比，IBDP-Lys 和 I 2 BDP-Lys的最大吸收（λ abs）分别在约 11 nm 和 27 nm 处显示出红移。同样，最大发射也表现出红移。IBDP-Lys ( Φ F )的荧光量子产率 ( Φ F )F = 0.37%) 和 I 2 BDP-Lys ( Φ F = 0.71%) 远低于 BDP-Lys 染料 ( Φ F = 7.48%)。IBDP-Lys 的单线态氧量子产率为 43.10%，I 2为 71.00%BDP-Lys，高于无碘染料 BDP-Lys。理论计算合理地解释了碘原子促进了系统间交叉（ISC）过程，二碘进一步增强了吲哚-BODIPY染料中的系统间交叉（ISC）过程。此外，单碘光敏剂 IBDP-Lys 能够平衡单线态氧的产生和癌症治疗中的生物相容性。IBDP-Lys 表现出低暗毒性（细胞活力 >90%）、令人满意的生物相容性和精确的溶酶体靶向，Pearson 系数为 0.93。IBDP-Lys 光敏剂也能够杀死肿瘤细胞。考虑到上述结果，吲哚-BODIPY 光敏剂的新型结构可以作为溶酶体靶向成像和光动力治疗的潜在平台。
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