Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging

Emily D Cosco; Justin R Caram; Oliver T Bruns; Daniel Franke; Rachael A Day; Erik P Farr; Moungi G Bawendi; Ellen M Sletten

doi:10.1002/anie.201706974

Flavylium Polymethine Fluorophores for Near- and Shortwave Infrared Imaging

Angew Chem Int Ed Engl. 2017 Oct 9;56(42):13126-13129. doi: 10.1002/anie.201706974. Epub 2017 Sep 14.

Authors

Emily D Cosco¹, Justin R Caram², Oliver T Bruns², Daniel Franke², Rachael A Day¹, Erik P Farr¹, Moungi G Bawendi², Ellen M Sletten¹

Affiliations

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.
² Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.

PMID: 28806473
DOI: 10.1002/anie.201706974

Abstract

Bright fluorophores in the near-infrared and shortwave infrared (SWIR) regions of the electromagnetic spectrum are essential for optical imaging in vivo. In this work, we utilized a 7-dimethylamino flavylium heterocycle to construct a panel of novel red-shifted polymethine dyes, with emission wavelengths from 680 to 1045 nm. Photophysical characterization revealed that the 1- and 3-methine dyes display enhanced photostability and the 5- and 7-methine dyes exhibit exceptional brightness for their respective spectral regions. A micelle formulation of the 7-methine facilitated SWIR imaging in mice. This report presents the first polymethine dye designed and synthesized for SWIR in vivo imaging.

Keywords: fluorescent dyes; imaging agents; near-infrared; polymethines; shortwave infrared.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.