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Structure‐Activity Studies of Nitroreductase‐Responsive Near‐Infrared Heptamethine Cyanine Fluorescent Probes.
- Source :
- European Journal of Organic Chemistry; 6/20/2022, Vol. 2022 Issue 23, p1-10, 10p
- Publication Year :
- 2022
-
Abstract
- Two new classes of near‐infrared molecular probes were prepared and shown to exhibit "turn on" fluorescence when cleaved by the nitroreductase enzyme, a well‐known biomarker of cell hypoxia. The fluorescent probes are heptamethine cyanine dyes with a central 4'‐carboxylic ester group on the heptamethine chain that is converted by a self‐immolative fragmentation mechanism to a 4'‐caboxylate group that greatly enhances the fluorescence brightness. Each compound was prepared by ring opening of a Zincke salt. The chemical structures have either terminal benzoindolinenes or propargyloxy auxochromes, which provide favorable red‐shifted absorption/emission wavelengths and a hyperchromic effect that enhances the photon output when excited by 808 nm light. A fluorescent probe with terminal propargyloxy‐indolenines exhibited less self‐aggregation and was rapidly activated by nitroreductase with large "turn on" fluorescence; thus, it is the preferred choice for translation towards in vivo applications. [ABSTRACT FROM AUTHOR]
- Subjects :
- FLUORESCENT probes
CYANINES
MOLECULAR probes
CHEMICAL structure
FLUORESCENCE
PHOTONS
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2022
- Issue :
- 23
- Database :
- Complementary Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 157665253
- Full Text :
- https://doi.org/10.1002/ejoc.202200270