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Norcyanine-Carbamates Are Versatile Near-Infrared Fluorogenic Probes

2021; American Chemical Society; Volume: 143; Issue: 15 Linguagem: Inglês

10.1021/jacs.1c02112

1943-2984

Syed Muhammad Usama, Fuyuki Inagaki, Hisataka Kobayashi, Martin J. Schnermann,

Photoreceptor and optogenetics research

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.