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NIR ditriphenylamine Indole-BODIPY photosensitizer: synthesis, photodynamic therapy in A549 cells and two-photon fluorescence imaging in zebrafish
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy ( IF 4.3 ) Pub Date : 2023-09-09 , DOI: 10.1016/j.saa.2023.123387
Ruibo Liu 1 , Ying Qian 1
Affiliation  

In this study, the ditriphenylamine Indole-BODIPY photosensitizer T2BDP-lyso was synthesized for near-infrared photodynamic therapy and two-photon fluorescence imaging. The photosensitizer T2BDP-lyso exhibits absorption above 700 nm and emission above 800 nm, respectively. Theoretical calculations show the energy gap from the excited state S1 to the excited state T2 is 0.14 eV, which indicated that the photosensitizer T2BDP-lyso could reach the triplet state by intersystem crossing from the singlet state. Under NIR light, the singlet oxygen yield of photosensitizer T2BDP-lyso was calculated to be 0.64 in CH2Cl2. The photosensitizer T2BDP-lyso can effectively produce reactive oxygen species in A549 cells and zebrafish under 660 nm light for 5 min. The photosensitizer T2BDP-lyso exhibited lower dark toxicity and higher phototoxicity (IC50 = 1.49 μM), as well as lysosomal targeting ability (Pearson coefficient = 0.89). In the AO/EB double staining assay simulating photodynamic therapy at the cellular level, 3 μM of T2BDP-lyso light for 10 min was effective in killing cancer cells. Moreover, the photosensitizer T2BDP-lyso has a large two-photon absorption cross section at 1050 nm, which was calculated to be 138.7 GM in THF by Z-scan method, and two-photon fluorescence imaging was performed in zebrafish. The above results indicate the potential application of the photosensitizer T2BDP-lyso in near-infrared photodynamic therapy and two-photon fluorescence imaging.



中文翻译:

近红外二三苯胺吲哚-BODIPY光敏剂:A549细胞的合成、光动力治疗和斑马鱼的双光子荧光成像

本研究合成了二三苯胺吲哚-BODIPY光敏剂T 2 BDP-lyso,用于近红外光动力治疗和双光子荧光成像。光敏剂T 2 BDP-lyso分别表现出700 nm以上的吸收和800 nm以上的发射。理论计算表明,激发态S 1到激发态T 2的能隙为0.14 eV,这表明光敏剂T 2 BDP-lyso可以通过系间窜越从单线态达到三线态。在近红外光下,计算光敏剂T 2 BDP-lyso在CH 2 Cl 2中的单线态氧产率为0.64 。光敏剂T 2 BDP-lyso在660 nm光下5分钟可以有效地在A549细胞和斑马鱼中产生活性氧。光敏剂T 2 BDP-lyso表现出较低的暗毒性和较高的光毒性(IC 50  = 1.49 μM)以及溶酶体靶向能力(Pearson系数 = 0.89)。在模拟细胞水平光动力疗法的AO/EB双染色测定中,3μM的T 2 BDP-lyso光持续10分钟可有效杀死癌细胞。此外,光敏剂T 2 BDP-lyso在1050 nm处具有较大的双光子吸收截面,通过Z扫描方法计算出其在THF中的吸收截面为138.7 GM,并在斑马鱼中进行了双光子荧光成像。上述结果表明光敏剂T 2 BDP-lyso在近红外光动力治疗和双光子荧光成像中的潜在应用。

更新日期:2023-09-09
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