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Generalizable synthesis of bioresponsive near-infrared fluorescent probes: sulfonated heptamethine cyanine prototype for imaging cell hypoxia.


ABSTRACT: Continued advancement in bioresponsive fluorescence imaging requires new classes of activatable fluorescent probes that emit near-infrared fluorescence with wavelengths above 740 nm. Heptamethine cyanine dyes (Cy7) have suitable fluorescence properties but it is challenging to create activatable probes because Cy7 dyes have a propensity for self-aggregation and fluorescence quenching. A new synthetic strategy is employed to create a generalizable class of hydrophilic bioresponsive near-infrared fluorescent probes with appended sulfonates that provide excellent physiochemical properties. A prototype version is triggered by nitroreductase enzyme to undergo self-immolative cleavage with a large enhancement in fluorescence signal at 780 nm and the probe enables microscopic imaging of cell hypoxia with "turn on" fluorescence. Near-infrared fluorescence imaging of hypoxia is potentially useful in many different areas of biomedical research and clinical treatment.

SUBMITTER: Atkinson KM 

PROVIDER: S-EPMC8121178 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Generalizable synthesis of bioresponsive near-infrared fluorescent probes: sulfonated heptamethine cyanine prototype for imaging cell hypoxia.

Atkinson Kirk M KM   Morsby Janeala J JJ   Kommidi Sai Shradha Reddy SSR   Smith Bradley D BD  

Organic & biomolecular chemistry 20210501 18


Continued advancement in bioresponsive fluorescence imaging requires new classes of activatable fluorescent probes that emit near-infrared fluorescence with wavelengths above 740 nm. Heptamethine cyanine dyes (Cy7) have suitable fluorescence properties but it is challenging to create activatable probes because Cy7 dyes have a propensity for self-aggregation and fluorescence quenching. A new synthetic strategy is employed to create a generalizable class of hydrophilic bioresponsive near-infrared  ...[more]

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