Design of Cell Membrane-Targeted Two-Photon Excited Bioorthogonal Near-Infrared Fluorogenic Probes.
- 1State Key Laboratory of Bioactive Substances and Function of Natural Medicine, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, P. R. China.
- 2Theranostics and Translational Research Center, Institute of Clinical Medicine, Department of Nuclear Medicine, Peking Union Medical College Hospital, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100730, China.
Abstract
The cell membrane is the critical cell component that protects cell integrity and mediates intercellular communication. In this contribution, we develop a cell membrane-targeted bioorthogonally activatable fluorogenic probe, DCM-Tz3, by incorporating the tetrazine motif into the dicyanomethylene-4H-chromone scaffold. Upon inverse electron-demand Diels-Alder reaction, the resulting cycloadduct (DCM-Pz3) exhibits a high fluorescence turn-on ratio, near-infrared emission, and significant solvatochromic effects. Notably, DCM-Pz3 presents a two-photon excitation property with a high two-photon absorption cross-section of 113 GM. Density functional theory calculation reveals the fluorescence OFF-ON switching mechanism of the probe. Importantly, we successfully applied the combination of DCM-Tz3 and the cyclooctyne for NIR fluorescence labeling of the cell membrane in both one-photon and two-photon patterns in living cells under wash-free conditions. This work provides a valuable cell membrane imaging tool with high specificity, laying the foundation for exploring cell membrane-based biological processes.
Related
- Bioorthogonal, twice-clickable fluorogenic probes for two-photon live-cell microscopy
- Reassignment of the Near-Infrared Absorption of Dioxidized Rare-Earth Porphyrin Double-Decker Complexes: Identification of a Nearly Dark Lowest Excited State
- Electric field-dependent excited-state twisting in donor–acceptor thiazolothiazole dyes establishes a new class of cell membrane voltage sensors
- Nanomaterial-genetics enables near-infrared-driven genetically targeted neuromodulation
- A GRPR-targeted near-infrared fluorescent probe for precise tumor imaging and intraoperative surgical navigation
BibTeX
@article{zhang2026design,
title = {{Design of Cell Membrane-Targeted Two-Photon Excited Bioorthogonal Near-Infrared Fluorogenic Probes.}},
author = {Rongrong Zhang and Yingchi Liu and Xuemei Du and Hong Yang and Yulin Tian},
journal = {Chemical \& biomedical imaging},
year = {2026},
month = jun,
doi = {10.1021/cbmi.6c00053},
url = {https://europepmc.org/article/MED/42953706},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - Design of Cell Membrane-Targeted Two-Photon Excited Bioorthogonal Near-Infrared Fluorogenic Probes.
AU - Rongrong Zhang
AU - Yingchi Liu
AU - Xuemei Du
AU - Hong Yang
AU - Yulin Tian
PY - 2026
DA - 2026/06/01
JO - Chemical & biomedical imaging
DO - 10.1021/cbmi.6c00053
UR - https://europepmc.org/article/MED/42953706
AB - The cell membrane is the critical cell component that protects cell integrity and mediates intercellular communication. In this contribution, we develop a cell membrane-targeted bioorthogonally activatable fluorogenic probe, DCM-Tz3, by incorporating the tetrazine motif into the dicyanomethylene-4H-chromone scaffold. Upon inverse electron-demand Diels-Alder reaction, the resulting cycloadduct (DCM-Pz3) exhibits a high fluorescence turn-on ratio, near-infrared emission, and significant solvatochromic effects. Notably, DCM-Pz3 presents a two-photon excitation property with a high two-photon absorption cross-section of 113 GM. Density functional theory calculation reveals the fluorescence OFF-ON switching mechanism of the probe. Importantly, we successfully applied the combination of DCM-Tz3 and the cyclooctyne for NIR fluorescence labeling of the cell membrane in both one-photon and two-photon patterns in living cells under wash-free conditions. This work provides a valuable cell membrane imaging tool with high specificity, laying the foundation for exploring cell membrane-based biological processes.
SN - 2832-3637
ER -