Sterically Shielded Heptamethine Cyanine Dyes for Bioconjugation and High Performance Near‐Infrared Fluorescence Imaging

Li, Dong‐Hao; Schreiber, Cynthia L.; Smith, Bradley D.

doi:10.1002/anie.202004449

Cited by 163Luminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionOptical Imaging and Spectroscopy Techniques

Sterically Shielded Heptamethine Cyanine Dyes for Bioconjugation and High Performance Near‐Infrared Fluorescence Imaging

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Li, Dong‐Hao, Schreiber, Cynthia L., Smith, Bradley D.·2020·Angewandte Chemie International Edition

DOI 10.1002/anie.202004449PMC PMC7473488

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Abstract

The near‐infrared window of fluorescent heptamethine cyanine dyes greatly facilitates biological imaging because there is deep penetration of the light and negligible background fluorescence. However, dye instability, aggregation, and poor pharmacokinetics are current drawbacks that limit performance and the scope of possible applications. All these limitations are simultaneously overcome with a new molecular design strategy that produces a charge balanced and sterically shielded fluorochrome. The key design feature is a meso‐aryl group that simultaneously projects two shielding arms directly over each face of a linear heptamethine polyene. Cell and mouse imaging experiments compared a shielded heptamethine cyanine dye (and several peptide and antibody bioconjugates) to benchmark heptamethine dyes and found that the shielded systems possess an unsurpassed combination of photophysical, physiochemical, and biodistribution properties that greatly enhance bioimaging performance.

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The common issue of low chemical stability and reduced fluorescence intensity of polymethines in an aqueous environment can be overcome by proper charge balancing and the introduction of steric shielding.
“The common issue of low chemical stability and reduced fluorescence intensity of polymethines in an aqueous environment can be overcome by proper charge balancing and the introduction of steric shielding.29,32,33”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [33]

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Mourot, B., Jacquemin, D., Siri, O., & Pascal, S. (2024) · The Chemical Record · doi:10.1002/tcr.202400183 · Cited by 16 · see citing works

Authors: Li, D., Schreiber, C. L., & Smith, B. D.
Affiliations: University of Notre Dame (US)
Corresponding author: Smith, Bradley D.
ORCID: Li, Dong‐Hao
Schreiber, Cynthia L.
Smith, Bradley D.
Venue: Angewandte Chemie International Edition
Publisher: Wiley
Published: 2020-05-11
Volume: 59
Issue: 29
Pages: 12154-12161
ISSN: 1433-7851 (ISSN-L)
1521-3773
DOI: 10.1002/anie.202004449
PMC: PMC7473488
OpenAlex: W3020002613
Cited by: 163
References: 71
Citations by year: 2026: 14 · 2025: 25 · 2024: 25 · 2023: 24 · 2022: 32 · 2021: 27 · 2020: 16
FWCI: 9.62
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations: Angewandte Chemie International Edition (publishedVersion)
PubMed (publishedVersion)
PubMed Central (acceptedVersion)
Figshare (submittedVersion, cc-by)
Funders: National Institute of General Medical Sciences (R01GM059078, T32GM075762, R35GM136212)
Topics: Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Optical Imaging and Spectroscopy Techniques
Keywords: heptamethine cyanine dyes, near-infrared fluorescence imaging, bioconjugation, dye aggregation, dye stability, tissue distribution, peptide conjugates, antibody conjugates, charge balance, photophysical properties
MeSH terms: Animals, Carbocyanines, Fluorescence, Fluorescent Dyes, Tissue Distribution, Molecular Structure, Spectroscopy, Near-Infrared, Cell Line, Tumor, Mice, Molecular Imaging, Optical Imaging

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Sterically Shielded Heptamethine Cyanine Dyes for Bioconjugation and High Performance Near‐Infrared Fluorescence Imaging

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