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

Article

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.

Attributes

Attribute NameValues
Creator
  • Dong-Hao Li

  • Cynthia L. Schreiber

  • Bradley D. Smith

Journal or Work Title
  • Angewandte Chemie Int. Edition

Volume
  • 59

First Page
  • 12154

Last Page
  • 12161

Publication Date
  • 2020-07

Subject
  • AMI HT Spectral Imaging

  • IVIS Lumina

Publisher
  • Wiley-VCH GmbH

Date Created
  • 2022-11-22

Language
  • English

Departments and Units
Record Visibility Public
Content License
  • All rights reserved

Digital Object Identifier

doi:10.1002/anie.202004449

This DOI is the best way to cite this article.

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