Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squarine Dyes for Biological Imaging

Authors

William E. Meador, University of MississippiFollow
Shane A. Autry, University of Mississippi
Riley N. Besetti, University of Southern Mississippi
Jacqueline N. Gayton, University of MississippiFollow
Alex S. Flynt, University of Southern MississippiFollow
Nathan I. Hammer, University of MississippiFollow
Jared H. Delcamp, University of MississippiFollow

Document Type

Article

Publication Date

2-10-2020

Department

Biological Sciences

School

Biological, Environmental, and Earth Sciences

Abstract

Organic dyes that absorb and emit in the near-infrared (NIR) region are potentially noninvasive, high-resolution, and rapid biological imaging materials. Indolizine donor-based cyanine and squaraine dyes with water-solubilizing sulfonate groups were targeted in this study due to strong absorptions and emissions in the NIR region. As previously observed for nonwater-soluble derivatives, the indolizine group with water-solubilizing groups retains a substantial shift toward longer wavelengths for both absorption and emission with squaraines and cyanines relative to classically researched indoline donor analogues. Very high quantum yields (as much as 58%) have been observed with absorption and emission >700 nm in fetal bovine serum. Photostability studies, cell culture cytotoxicity, and cell uptake specificity profiles were all studied for these dyes, demonstrating exceptional biological imaging suitability.

Publication Title

The Journal of Organic Chemistry

Volume

85

Issue

6

First Page

4089

Last Page

4095

Recommended Citation

Meador, W. E., Autry, S. A., Besetti, R. N., Gayton, J. N., Flynt, A. S., Hammer, N. I., Delcamp, J. H. (2020). Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squarine Dyes for Biological Imaging. The Journal of Organic Chemistry, 85(6), 4089-4095.
Available at: https://aquila.usm.edu/fac_pubs/17414