Synthesis of Silicon-Substituted Hemicyanines for Multimodal SWIR Imaging

East, Amanda; Lee, Michael C.; Smaga, Lukas P.; Chang, Jiang; Mallojjala, Sharath Chandra; Hirschi, Jennifer S.; Chan, Jefferson

doi:10.1021/acs.orglett.2c03382

Cited by 11 publications

(9 citation statements)

References 36 publications

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“…As another example, HDs are a series of popular hemicyanine dyes which emit in the NIR-I region; 52,53 Chan and co-workers found that, by replacing the oxygen atom of HD dyes in the terminal donor part with the SiMe 2 group, the emission wavelength of Si-HDs would redshift about 350 nm to the NIR-II region. 54 Since the 1930s, researchers have observed the phenomenon of J-aggregation with a narrow absorption band turning to a longer wavelength compared with the monomer absorption band and a nearly resonant fluorescence (tiny Stokes shift) with a narrow band. 55 For many J-aggregates, bathochromic shifts beyond 100 nm are observed, attributed to excited states formed by extended domains of coherently coupled molecular transition dipoles.…”

Section: Wavelength Extension Principles Of Polymethine Fluorophoresmentioning

confidence: 99%

“…For instance, the oxygen atoms of the symmetric polymethine fluorophore IR-971 was substituted by sulfur atom, resulting in an approximately 90 nm bathochromic shift. As another example, HDs are a series of popular hemicyanine dyes which emit in the NIR-I region; , Chan and co-workers found that, by replacing the oxygen atom of HD dyes in the terminal donor part with the SiMe 2 group, the emission wavelength of Si-HDs would redshift about 350 nm to the NIR-II region …”

Section: Design Principles Of Polymethine Fluorophoresmentioning

confidence: 99%

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Molecular Design of NIR-II Polymethine Fluorophores for Bioimaging and Biosensing

Ren

Yuan

et al. 2023

Chemical & Biomedical Imaging

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Organic polymethine fluorophores with emission in the NIR-II window (1000–1700 nm) are receiving enormous attention in biomolecular medicine and bioimaging, attributed to the high absorption coefficients, bright NIR-II emission, excellent biocompatibility, and molecule adjustability. Recently, researchers have devoted significant effort to designing and improving NIR-II polymethine fluorophores and making notable progress in the NIR-II fluorescence imaging performance. This review summarizes recent developments in the molecular engineering design mentality of polymethine fluorophores and probes and highlights their extensive bioimaging and biosensing applications. Furthermore, we elucidate the potential challenges and perspectives of these NIR-II polymethine dyes in chemical and biomedicine imaging, which may stimulate the further development of high-performance NIR-II polymethine dye contrast agents for their future clinical applications.

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Section: Wavelength Extension Principles Of Polymethine Fluorophoresmentioning

confidence: 99%

Section: Design Principles Of Polymethine Fluorophoresmentioning

confidence: 99%

Molecular Design of NIR-II Polymethine Fluorophores for Bioimaging and Biosensing

Ren

Yuan

et al. 2023

Chemical & Biomedical Imaging

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“…For example, Chan’s group shifted the wavelengths of hemicyanine fluorophores by heteroatom substitution strategies, which can be used to visualize liver and tumors through multimodal shortwave infrared (SWIR, 900–1700 nm) imaging. 38 Furthermore, Miao’s group constructed several NIR-II fluorophores by modifying the donor–π–acceptor for visualizing amyloid-β in vivo (Figure 12 ). 39…”

Section: Construction Of Hemicyanine Fluorophores In the Nir-ii Regionmentioning

confidence: 99%

Near-Infrared Hemicyanine Fluorophores with Optically Tunable Groups: A ‘Leap Forward’ for in Vivo Sensing and Imaging

Huang

Wang

et al. 2023

Synlett

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Hemicyanine dyes, with a tunable optical site and high wavelength tailorability, are of great importance in the field of sensing and diagnosis. With the first discovery of the near-infrared (NIR, 650–900 nm) fluorescent dyes CS and HD by our group, remarkable progress has been made in the development of hemicyanine-based probes for in vivo imaging and detecting. In this review, we summarize the key contributions made by our group in developing long-wavelength (650–1700 nm) hemicyanines and using them to construct functional probes. Finally, potential drawbacks and prospects of hemicyanine dyes/probes are also discussed.

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“…A wide range of biomarkers ranging from the production of ROS to increased activity of certain liver enzymes has been associated with liver damage. By taking advantage of these changes, the diversity of activatable probes suitable for molecular imaging of the liver has greatly expanded. − …”

Section: Liver Imagingmentioning

confidence: 99%

Activity-Based Photoacoustic Probes for Detection of Disease Biomarkers beyond Oncology

Lee

Landers

Chan

2023

ACS Bio Med Chem Au

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The earliest activity-based photoacoustic (PA) probes were developed as diagnostic agents for cancer. Since this seminal work over a decade ago that specifically targeted matrix metalloproteinase-2, PA instrumentation, dye platforms, and probe designs have advanced considerably, allowing for the detection of an impressive list of cancer types. However, beyond imaging for oncology purposes, the ability to selectively visualize a given disease biomarker, which can range from aberrant enzymatic activity to the overproduction of reactive small molecules, is also being exploited to study a myriad of noncancerous disease states. In this review, we have assembled a collection of recent papers to highlight the design principles that enable activity-based sensing via PA imaging with respect to biomarker identification and strategies to trigger probe activation under specific conditions.

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Synthesis of Silicon-Substituted Hemicyanines for Multimodal SWIR Imaging

Cited by 11 publications

References 36 publications

Molecular Design of NIR-II Polymethine Fluorophores for Bioimaging and Biosensing

Molecular Design of NIR-II Polymethine Fluorophores for Bioimaging and Biosensing

Near-Infrared Hemicyanine Fluorophores with Optically Tunable Groups: A ‘Leap Forward’ for in Vivo Sensing and Imaging

Activity-Based Photoacoustic Probes for Detection of Disease Biomarkers beyond Oncology

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