Construction of cyclic π-conjugated BODIPY derivatives using the molecular double-lock strategy for photothermal therapy

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-07-29 DOI:10.1016/j.dyepig.2025.113081

Fei Cheng , Taotao Qiang , Mingli Li , Baoshuai Wang , Kun Liu , Ke Li

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引用次数: 0

Abstract

The development of near-infrared BODIPY-based photothermal agents with high photothermal stability is of significant importance in the field of photothermal therapy (PTT). Therefore, we report a molecular double-lock strategy, which was employed to construct near-infrared cyclic π-conjugated BODIPY derivatives Ph-BDP-R and An-BDP-R. X-ray structural analysis confirms the synthetic feasibility of the molecular double-lock strategy. The lower spin-orbit coupling (SOC) constants (0.055 cm⁻¹ and 0.047 cm⁻¹), triplet lifetimes (3.68 ± 0.09 ns and 3.7 ± 0.2 ns), and singlet oxygen (¹O₂) quantum yields (15.2 % and 11.3 %) demonstrate that Ph-BDP-R and An-BDP-R possess weak intersystem crossing (ISC) abilities. The fluorescence quantum yields of 12.6 % and 10.1 % indicate that Ph-BDP-R and An-BDP-R exhibit lower radiative transition (RT) processes. Meanwhile, the formation of the intramolecular cyclic π-conjugated system allows Ph-BDP-R and An-BDP-R to exhibit higher photothermal stability, photothermal conversion efficiency and non-radiative transition (NRT) processes. To this end, nanoparticles An-BDP-R-NPs were constructed to enhance biocompatibility. The photothermal conversion capacity of An-BDP-R-NPs was tested using photothermal conversion experiments (808 nm light excitation), yielding a photothermal conversion efficiency of 42.1 %. CCK-8 assay results show that An-BDP-R-NPs possess low biotoxicity and strong photothermal cytotoxicity against tumor cells. The research results indicate that the molecular double-lock strategy can be used to construct near-infrared cyclic π-conjugated BODIPY derivatives with high photothermal stability and good photothermal killing efficiency against tumor cells. This provides a new method and reference for the development of near-infrared BODIPY-based photothermal agents with high photothermal stability.

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光热治疗用分子双锁策略构建环π共轭BODIPY衍生物

开发具有高光热稳定性的近红外bodipy光热剂在光热治疗（PTT）领域具有重要意义。因此，我们报道了一种分子双锁策略，用于构建近红外环π共轭BODIPY衍生物Ph-BDP-R和An-BDP-R。x射线结构分析证实了分子双锁策略的合成可行性。较低的自旋-轨道耦合（SOC）常数（0.055 cm−1和0.047 cm−1）、三重态寿命（3.68±0.09 ns和3.7±0.2 ns）和单重态氧（1O2）量子产率（15.2%和11.3%）表明Ph-BDP-R和An-BDP-R具有较弱的系统间交叉（ISC）能力。荧光量子产率分别为12.6%和10.1%，表明Ph-BDP-R和An-BDP-R具有较低的辐射跃迁（RT）过程。同时，分子内循环π共轭体系的形成使得Ph-BDP-R和An-BDP-R具有更高的光热稳定性、光热转换效率和非辐射跃迁过程。为此，构建了纳米颗粒An-BDP-R-NPs，以增强生物相容性。通过光热转换实验（808 nm光激发）测试了An-BDP-R-NPs的光热转换能力，光热转换效率为42.1%。CCK-8实验结果表明，An-BDP-R-NPs具有较低的生物毒性和较强的光热细胞毒性。研究结果表明，利用分子双锁策略可构建光热稳定性高、对肿瘤细胞光热杀伤效率好的近红外环π共轭BODIPY衍生物。这为开发具有高光热稳定性的近红外bodip基光热剂提供了新的方法和参考。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.