n-Hexyl side chain engineering: Crafting NIR-II AIEgens with balanced fluorescence-photothermal performance for precision tumor ablation

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-05-23 DOI:10.1016/j.dyepig.2025.112911

Binbin Wu , Qin Zhang , Min Chen , Hongchen Zhang , Lulu Zheng , Xingyu Peng , Shihua Wang , Yun-Yun Quan , Lingtian Wang , Zu-Sheng Huang , Xiaoxia Ye

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引用次数: 0

Abstract

Photothermal therapy (PTT) has gained significant attention as a promising cancer treatment due to its low systemic toxicity, minimal invasiveness, and other advantages. Aggregation-induced emission luminogens (AIEgens) with second near-infrared (NIR-II) fluorescence have emerged as ideal photothermal agents (PTAs), offering key benefits such as high biosafety, excellent biocompatibility, and precise tumor theranostics. Nevertheless, achieving an optimal balance between radiation-mediated NIR-II fluorescence imaging and non-radiation NIR-PTT poses a considerable challenge in designing efficient NIR-II AIEgens. In this work, we employed side chain engineering by strategically grafting n-hexyl onto the π-bridge of a conjugated D-π-A-π-D structure, leading to the development of four new AIEgens (BQ1∼BQ4). These compounds feature 6,7-diphenyl- [1,2,5] thiadiazolo [3,4-g] quinoxaline as the acceptor, thiophene as the π-bridge, and phenothiazine as the donor. This molecular design enables precise regulation of backbone distortion, effectively balancing fluorescence emission and photothermal conversion. Among them, BQ1, BQ3, and BQ4 exhibited strong fluorescence, longer emission wavelengths, and superior photothermal conversion efficiencies (PCEs) (59.2 %, 57.8 %, 52 % respectively), whereas BQ2, with greater molecular distortion, showed a lower PCE of 33.4 %. Notably, BQ1 nanoparticles demonstrated outstanding photothermal conversion, prolonged tumor retention, strong resistance to photobleaching in vitro and in vivo, and NIR-II imaging capability at 1055 nm. This study introduces a novel strategy for optimizing NIR-II/AIE PTAs through precise conformational control via strategic n-hexyl positioning, which remains unreported to date.

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正己基侧链工程：制作具有平衡荧光光热性能的NIR-II AIEgens，用于精确肿瘤消融

光热疗法（PTT）因其全身毒性低、侵袭性小等优点而成为一种很有前景的癌症治疗方法。具有第二近红外（NIR-II）荧光的聚集诱导发射发光原（AIEgens）已成为理想的光热剂（PTAs），具有高生物安全性，优异的生物相容性和精确的肿瘤治疗等关键优点。然而，在辐射介导的NIR-II荧光成像和非辐射NIR-PTT之间实现最佳平衡对设计高效的NIR-II aigens提出了相当大的挑战。在这项工作中，我们采用侧链工程，将n-己基巧妙地接枝到共轭D-π-A-π-D结构的π桥上，从而开发了四种新的AIEgens （BQ1 ~ BQ4）。这些化合物以6,7-二苯基-[1,2,5]噻二唑[3,4-g]喹啉为受体，噻吩为π桥，吩噻嗪为供体。这种分子设计能够精确调节主干畸变，有效地平衡荧光发射和光热转换。其中，BQ1、BQ3和BQ4具有较强的荧光性、较长的发射波长和较高的光热转换效率（PCE）（分别为59.2%、57.8%和52%），而分子畸变较大的BQ2的PCE较低，为33.4%。值得注意的是，BQ1纳米颗粒表现出出色的光热转化，长时间的肿瘤保留，体外和体内强烈的光漂白抗性，以及1055 nm的NIR-II成像能力。本研究介绍了一种新的策略，通过战略性正己基定位来精确控制NIR-II/AIE PTAs的构象，这是迄今为止尚未报道的。

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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.