Norcyanine-Carbamates Are Versatile Near-Infrared Fluorogenic Probes.
Syed Muhammad UsamaFuyuki InagakiHisataka KobayashiMartin J SchnermannPublished in: Journal of the American Chemical Society (2021)
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 in vivo 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.
Keyphrases
- fluorescence imaging
- living cells
- fluorescent probe
- photodynamic therapy
- small molecule
- high resolution
- drug release
- squamous cell carcinoma
- single molecule
- small cell lung cancer
- molecular docking
- human health
- cancer therapy
- risk assessment
- nucleic acid
- drug delivery
- health information
- transcription factor
- sensitive detection
- gram negative
- climate change