Access to Diverse Activatable Heptamethine Cyanine Probes with Low Intrinsic Fluorescence via 5‐ exo‐trig Cyclization Strategy for High‐Contrast Bioimaging In Vivo
Abstract
The conversion of conventional “always‐on” cyanine dyes into activatable NIR probes with low inherent fluorescence remains challenging, resulting in poor imaging contrast and nonspecific response in vivo. We herein report a 5‐ exo‐trig cyclization strategy to create diverse activatable heptamethine cyanine probes with “zero” intrinsic background fluorescence for high‐contrast bioimaging. This intramolecular ring‐closure approach imparts a built‐in switch to regulate the fluorescence of cyanine dyes, which predominantly exist in the nonfluorescent closed‐loop form at pH over 5.0 and are not affected by environmental polarity and protein interaction, thereby reducing false‐positive fluorescent signals. Upon reaction with various biomarkers, including methylglyoxal (MGO), hydroxyl radical (·OH), and adenosine triphosphate (ATP), they could rapidly transform into fluorescent open‐loop structures, showing significant NIR fluorescence enhancement (up to 184‐fold). Furthermore, we extended this strategy to develop a variety of NIR‐II ATP‐activatable cyanine probes for the first time, as well as a theranostic probe 57 using host–guest chemistry. Probe 57 not only sensitively monitored ATP levels in inflammatory bowel disease (IBD) with a high signal‐to‐background ratio of 48/1, but it also precisely detected extracellular ATP in stools. This work opens a new avenue to develop stimuli‐responsive NIR cyanine probes for improving disease diagnosis.
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Cy-57 achieved highly sensitive ATP monitoring in inflammatory bowel disease with an SBR of 48:1.
“It achieved highly sensitive ATP monitoring in inflammatory bowel disease (IBD) with an SBR of 48:1.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [206]
Upon activation by target biomarkers MGO, •OH, and ATP, these probes showed 109-137-fold fluorescence enhancement at 940 nm, yielding high SBRs of 28:1, 13:1, and 38:1, respectively.
“Upon activation by the target biomarkers, including methylglyoxal (MGO), hydroxyl radicals (•OH), and adenosine triphosphate (ATP), these probes showed 109–137-fold fluorescence enhancement at 940 nm, yielding high SBRs of 28:1, 13:1, and 38:1, respectively.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [206]
Xiong et al. engineered three activatable cyanine probes (Cy-29, Cy-30, and Cy-31) featuring diverse reactive groups.
“Xiong et al. rationally engineered three activatable cyanine probes (Cy-29, Cy-30, and Cy-31) featuring diverse reactive groups (Fig. 15a)206.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [206]
These activatable cyanine probes demonstrated excellent performance across multiple live models, highlighting significant potential for advancing disease diagnosis and multiplexed detection of biomarkers.
“Collectively, these probes demonstrated excellent performance across multiple live models, highlighting their significant potential for advancing disease diagnosis and multiplexed detection of biomarkers in complex biological environments.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [206]
Leveraging host-guest chemistry, researchers developed a dual-responsive NIR-II theranostic probe Cy-57 capable of simultaneous sensing of ATP and ROS.
“Furthermore, leveraging host-guest chemistry, the researchers developed a dual-responsive NIR-II theranostic probe (Cy-57) capable of simultaneous sensing of ATP and ROS.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [206]
Cy-57 enabled precise therapeutic intervention and non-invasive detection of extracellular ATP in fecal samples.
“This capability enabled precise therapeutic intervention and non-invasive detection of extracellular ATP in fecal samples.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [206]
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- Authors
- Wu, F., Zheng, B., Qiu, X., Hu, T., Yang, Y., Yang, K., Zhou, B., Ma, Q., Pang, D., & Xiong, H.
- Affiliations
- Nankai University (CN)
- Research Center for Analytical Sciences Tianjin Key Laboratory of Biosensing and Molecular Recognition Frontiers Science Center for New Organic Matter College of Chemistry Nankai University 94 Weijin Road, Nankai District Tianjin 300071 China
- Corresponding author
- Xiong, Hu
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2025-06-02
- Volume
- 64
- Issue
- 31
- Pages
- e202423059-e202423059
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W4410832237
- Cited by
- 18
- References
- 56
- Citations by year
- 2026: 12 · 2025: 6
- FWCI
- 4.56
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (22422407, 22174078)
- Fundamental Research Funds for the Central Universities (020–63253156)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Biomedical Engineering › Nanoplatforms for cancer theranostics
- Keywords
- heptamethine cyanine dyes, activatable fluorescent probes, 5-exo-trig cyclization, intramolecular ring closure, NIR-II fluorescence, host-guest chemistry, theranostic probes, inflammatory bowel disease, hydroxyl radical detection
- MeSH terms
- Adenosine Triphosphate, Animals, Carbocyanines, Cyclization, Fluorescence, Fluorescent Dyes, Humans, Molecular Structure, Mice, Optical Imaging
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