基于单体-激基缔合物荧光转换的免洗细胞膜荧光探针

doi:10.6023/cjoc202511022

研究论文

基于单体-激基缔合物荧光转换的免洗细胞膜荧光探针

郭百淋^a, 王赛女^a, 雷炳新^b, 王恩举^*,a

^a热带药用资源化学教育部重点实验室, 海南省热带药用植物化学重点实验室, 海南师范大学化学与化工学院, 海南海口 571158;
^b广西先进结构材料与碳中和重点实验室,广西高校环境友好材料及生态修复重点实验室,广西民族大学材料与环境学院, 广西南宁 530105

收稿日期:2025-11-27 修回日期:2026-01-08
基金资助:
广西先进结构材料与碳中和重点实验室开放课题基金(GXAMCN24-3).

A Wash-Free Cell Membrane Fluorescent Probe Based on Monomer-Excimer Conversion

Guo Bailin^a, Wang Sainv^a, Lei Bingxin^b, Enju^*,a

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158;
^bSchool of Materials and Environment, Guangxi Key Laboratory of Advanced Structural Materials and Carbon Neutralization, Guangxi Colleges and Universities Key Laboratory of Eco-friendly Materials and Ecological Restoration, Guangxi Minzu University, Nanning 530105

Received:2025-11-27 Revised:2026-01-08
Contact: ^*E-mail: enjuwang@163.com
Supported by:
open research fund program of guangxi key laboratory of advanced structural materials and carbon neutralization (No.GXAMCN24-3).

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摘要/Abstract

相较于单体荧光,激基缔合物荧光具有更大的斯托克斯位移、更宽的发射谱带及更长的发射波长,在生物成像领域展现出显著优势。本文开发了一种基于芘的激基缔合物型荧光探针（BAPI）,该探针在稀溶液（二甲亚砜或水）中呈现微弱的单体荧光,随着浓度增加,逐渐转变为强激基缔合物荧光。值得注意的是,在表面活性剂溶液中,即使BAPI浓度很低,也仅能观察到激基缔合物荧光。这表明当BAPI单体从水相迁移至胶束内部时,会自发形成激基缔合物。基于这一特性,BAPI被成功应用于细胞膜荧光成像,表现出一系列优异性能：斯托克斯位移大（129 nm）、荧光量子产率高（在二甲亚砜中 Φ=75.66%）、细胞毒性低、内化速度快（约5分钟）及免洗成像。

关键词: 细胞膜, 荧光探针, 激基缔合物, 免洗成像, 芘

Excimers, characterized by their large Stokes shifts, broad emission profiles, and longer emission wavelengths compared to monomers, offer significant advantages for bioimaging. Herein, we developed a pyrene-based excimer-forming fluorescent probe (BAPI) for wash-free cell membrane imaging. In dilute dimethyl sulfoxide or aqueous solutions, BAPI exhibits weak monomer emission, which transitions to strong excimer emission as the concentration increases. Notably, in various surfactant-containing aqueous solutions, exclusive excimer emission was observed even at very low concentrations. This indicates that BAPI molecules at low-concentration conditions, undergo a monomer-to-excimer conversion upon migrating from the aqueous phase into micelles. Capitalizing on this property, BAPI serves as an effective membrane-targeting probe with several distinct advantages, including a large Stokes shift (129 nm), high fluorescence efficiency (Φ=75.66% in DMSO), low cytotoxicity, rapid cellular internalization (~5 min), and wash-free imaging capability.

Key words: cell membrane, fluorescent probe, excimer, wash-free imaging, pyrene

引用此文

郭百淋, 王赛女, 雷炳新, 王恩举. 基于单体-激基缔合物荧光转换的免洗细胞膜荧光探针[J]. 有机化学, doi: 10.6023/cjoc202511022.

Guo Bailin, Wang Sainv, Lei Bingxin, Enju. A Wash-Free Cell Membrane Fluorescent Probe Based on Monomer-Excimer Conversion[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202511022.

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