Ketone Incorporation Extends the Emission Properties of the Xanthene Scaffold Beyond 1000 nm.

Autor: Daly HC; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, USA., Matikonda SS; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, USA., Steffens HC; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, USA., Ruehle B; Division Biophotonics, Federal Institute of Materials Research and Testing (BAM), Berlin, Germany., Resch-Genger U; Division Biophotonics, Federal Institute of Materials Research and Testing (BAM), Berlin, Germany., Ivanic J; Advanced Biomedical Computational Science, Frederick National Laboratory for Cancer Research, Leidos Biomedical Research Inc., Frederick, MD, USA., Schnermann MJ; Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, USA.
Jazyk: angličtina
Zdroj: Photochemistry and photobiology [Photochem Photobiol] 2022 Mar; Vol. 98 (2), pp. 325-333. Date of Electronic Publication: 2021 Nov 19.
DOI: 10.1111/php.13544
Abstrakt: Imaging in the shortwave-infrared region (SWIR, λ = 1000-2500 nm) has the potential to enable deep tissue imaging with high resolution. Critical to the development of these methods is the identification of low molecular weight, biologically compatible fluorescent probes that emit beyond 1000 nm. Exchanging the bridging oxygen atom on the xanthene scaffold (C10' position) with electron withdrawing groups has been shown to lead to significant redshifts in absorbance and emission. Guided by quantum chemistry computational modeling studies, we investigated the installation of a ketone bridge at the C10' position. This simple modification extends the absorbance maxima to 860 nm and the emission beyond 1000 nm, albeit with reduced photon output. Overall, these studies demonstrate that broadly applied xanthene dyes can be extended into the SWIR range.
(© 2021 American Society for Photobiology.)
Databáze: MEDLINE
Externí odkaz: