Ether Rhodamines with Enhanced Hydrophilicity, Fluorogenicity, and Brightness for Super-Resolution Imaging DOI Open Access

Xiangning Fang,

Qinglong Qiao,

Z W Li

и другие.

bioRxiv (Cold Spring Harbor Laboratory), Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

ABSTRACT Rhodamine dyes are widely used fluorophores in super-resolution fluorescence imaging due to their exceptional optical properties and “aggregation-disaggregation” induced fluorogenic activation. However, excessive lipophilicity often reduces brightness aqueous environments causes off-target staining, limiting effectiveness high-resolution imaging. To address these challenges, we introduce an ether-decorated N-terminal modification strategy for rhodamine silicon-rhodamine (Si-rhodamine), replacing conventional N-alkyl groups. The ether chains enhance water solubility, decrease aggregate size, improve fluorogenicity across a wide concentration range. Their flexible, hydrophilic structure forms protective shield around the xanthene core, minimizing dye-water interactions reducing quenching. Additionally, inductive effect of decreases electron-donating strength amino groups, suppressing quenching caused by twisted intramolecular charge transfer (TICT). These modifications collectively increase quantum yields ER ESiR from 0.35 0.19 (for tetraethyl-substituted analogs) 0.70 0.41, respectively. Probes derived exhibit outstanding fluorogenicity, enhanced signal-to-noise ratios, improved resolution complex environments, demonstrating superior performance advanced techniques such as structured illumination microscopy (SIM), stimulated emission depletion (STED) microscopy, single-molecule localization (SMLM). This work introduces innovative fluorophore design, offering significant advancements applications.

Язык: Английский

Twisted intramolecular charge transfer (TICT) and twists beyond TICT: from mechanisms to rational designs of bright and sensitive fluorophores DOI
Chao Wang, Weijie Chi, Qinglong Qiao

и другие.

Chemical Society Reviews, Год журнала: 2021, Номер 50(22), С. 12656 - 12678

Опубликована: Янв. 1, 2021

The twisted intramolecular charge transfer (TICT) mechanism and twists beyond TICT have guided the creation of numerous bright sensitive fluorophores. We reviewed structure–property relationships these dyes with representative examples.

Язык: Английский

Процитировано

423

Rigid and Photostable Shortwave Infrared Dye Absorbing/Emitting beyond 1200 nm for High-Contrast Multiplexed Imaging DOI

Ruwei Wei,

Yan Dong, Xueli Wang

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(22), С. 12013 - 12022

Опубликована: Май 22, 2023

The shortwave infrared (SWIR) spectral region beyond 1200 nm offers optimal tissue penetration depth and has broad potential in diagnosis, therapy, surgery. Here, we devised a novel class of fluorochromic scaffold, i.e., tetra-benzannulated xanthenoid (EC7). EC7 absorbs/emits maximally at 1204/1290 CH2Cl2 exhibits an unparalleled molar absorptivity 3.91 × 105 cm–1 M–1 high transparency to light 400–900 nm. It also exhibited resistance toward both photobleaching symmetry breaking due its unique structural rigidity. is feasible for vivo bioimaging particularly suitable couple with the shorter-wavelength analogues high-contrast multiplexing. High-contrast dual-channel intraoperative imaging hepatobiliary system three-channel intestine, stomach, vasculature were showcased. benchmark fluorochrome facile biomedical exploitation SWIR

Язык: Английский

Процитировано

60

Plasmon-enhanced fluorescence sensors for food and environmental samples monitoring DOI
Kamal Singh, Armando J. L. Pombeiro, Ismayil M. Garazade

и другие.

Microchemical Journal, Год журнала: 2024, Номер 197, С. 109888 - 109888

Опубликована: Янв. 4, 2024

Язык: Английский

Процитировано

30

Stable Super‐Resolution Imaging of Lipid Droplet Dynamics through a Buffer Strategy with a Hydrogen‐Bond Sensitive Fluorogenic Probe DOI
Jie Chen, Chao Wang, Wenjuan Liu

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(47), С. 25104 - 25113

Опубликована: Сен. 14, 2021

Although super-resolution imaging offers an opportunity to visualize cellular structures and organelles at the nanoscale level, heterogeneity unpredictability still pose a significant challenge in dynamic of live cells. It is thus vital develop better-performing more photostable probes for long-term imaging. Herein, we report probe, LD-FG, lipid droplet (LD) dynamics using structured illumination microscopy (SIM). LD-FG allows wash-free LDs, owing hydrogen-bond sensitive fluorogenic response. The replacement photobleached by intact probe molecules outside LDs ensures long-time stability fluorescence With this buffering fast unpredictable processes can be visualized. Using two LD coalescence modes were discovered. also allowed us propose new model maturation during adipocyte differentiation, i.e., followed slow ripening step. excellent performance makes buffer strategy effective method designing fluorescent cell

Язык: Английский

Процитировано

102

BODIPY 493 acts as a bright buffering fluorogenic probe for super-resolution imaging of lipid droplet dynamics DOI
Jie Chen, Wenjuan Liu,

Xiangning Fang

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 33(12), С. 5042 - 5046

Опубликована: Апрель 3, 2022

Язык: Английский

Процитировано

47

A TICS-fluorophore based probe for dual-color GSH imaging DOI
Wenjuan Liu, Jie Chen, Qinglong Qiao

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 33(11), С. 4943 - 4947

Опубликована: Апрель 5, 2022

Язык: Английский

Процитировано

46

SIM imaging resolves endocytosis of SARS-CoV-2 spike RBD in living cells DOI Creative Commons
Miao Lü,

Chunyu Yan,

Yingzhu Chen

и другие.

Cell chemical biology, Год журнала: 2023, Номер 30(3), С. 248 - 260.e4

Опубликована: Март 1, 2023

Язык: Английский

Процитировано

24

Xanthene-Based NIR organic phototheranostics agents: Design strategies and biomedical applications DOI
Xiao‐Yun Ran, Yuanfeng Wei, Yanling Wu

и другие.

Journal of Materials Chemistry B, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Near-infrared fluorescence imaging is key in biological exploration. Short emission wavelengths of xanthene dyes limit their use. Structural modifications shift emissions to the NIR-I/II range, enhancing biomedical applications.

Язык: Английский

Процитировано

1

Haloform-type reaction combined with the spirocyclic ring-opening of rhodamines affording a fluorescent probe for imaging hypochlorous acid in living organisms DOI
Yanjun Cao,

Penghua He,

Lei Wu

и другие.

Sensors and Actuators B Chemical, Год журнала: 2024, Номер 407, С. 135384 - 135384

Опубликована: Фев. 10, 2024

Язык: Английский

Процитировано

9

Comparison of rhodamine 6G, rhodamine B and rhodamine 101 spirolactam based fluorescent probes: A case of pH detection DOI
Fei Deng, Dongsheng Sun,

Shixu Yang

и другие.

Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy, Год журнала: 2021, Номер 268, С. 120662 - 120662

Опубликована: Ноя. 26, 2021

Язык: Английский

Процитировано

40