Ketone Incorporation Extends the Emission Properties of the Xanthene Scaffold Beyond 1000 nm.
Journal
Photochemistry and photobiology
ISSN: 1751-1097
Titre abrégé: Photochem Photobiol
Pays: United States
ID NLM: 0376425
Informations de publication
Date de publication:
03 2022
03 2022
Historique:
received:
10
09
2021
accepted:
18
10
2021
pubmed:
23
10
2021
medline:
10
5
2022
entrez:
22
10
2021
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 34676539
doi: 10.1111/php.13544
pmc: PMC10503429
mid: NIHMS1925130
doi:
Substances chimiques
Fluorescent Dyes
0
Ketones
0
Xanthenes
0
Types de publication
Journal Article
Research Support, N.I.H., Intramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
325-333Subventions
Organisme : CCR NIH HHS
ID : HHSN261200800001C
Pays : United States
Organisme : NCI NIH HHS
ID : HHSN261200800001E
Pays : United States
Organisme : Intramural NIH HHS
ID : ZIA BC011564
Pays : United States
Informations de copyright
© 2021 American Society for Photobiology.
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