Norcyanine-Carbamates Are Versatile Near-Infrared Fluorogenic Probes.

J Am Chem Soc

Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702, United States.

Published: April 2021

AI Article Synopsis

  • Fluorogenic probes that emit in the near-infrared (NIR) region can provide important information about biological processes in living organisms.
  • A new class of these probes, called cyanine carbamates (CyBams), are created by modifying existing NIR compounds with responsive linkers that enhance their signal when certain conditions are met.
  • These CyBams demonstrated high efficiency in imaging specific enzyme activity in ovarian cancer models, suggesting they could be valuable for studying biological processes in live tissues and animals.

Article Abstract

Fluorogenic probes in the near-infrared (NIR) region have the potential to provide stimuli-dependent information in living organisms. Here, we describe a new class of fluorogenic probes based on the heptamethine cyanine scaffold, the most broadly used NIR chromophore. These compounds result from modification of heptamethine norcyanines with stimuli-responsive carbamate linkers. The resulting cyanine carbamates (CyBams) exhibit exceptional turn-ON ratios (∼170×) due to dual requirements for NIR emission: carbamate cleavage through 1,6-elimination and chromophore protonation. Illustrating their utility in complex settings, a γ-glutamate substituted CyBam was applied to imaging γ-glutamyl transpeptidase (GGT) activity in a metastatic model of ovarian cancer. Overall, CyBams have significant potential to extend the reach of fluorogenic strategies to intact tissue and live animal imaging applications.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9310664PMC
http://dx.doi.org/10.1021/jacs.1c02112DOI Listing

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