Cyanine-based [18F]F-C-glycosyl dual imaging probe: synthesis, physico-chemical characterization, in vitro binding evaluation and direct [18F]fluorination†
Abstract
The design and synthesis of 18F-radiolabelled and fluorescent dual imaging agents allowing bimodal PET/FLI imaging is a current challenge. We report herein the development of a cyanine-based [18F]F-C-glycosyl dual imaging probe for fluorescence imaging (FLI) and a robust [18F]F–C bond for positron emission tomography (PET) imaging. Interestingly, the proposed strategy allows a late-stage coupling of the probe with various vectors, successfully illustrated by conjugation to c(RGDfK) via CuAAC for αvβ3 integrin targeting. As attested by the in vitro evaluation, the novel dual agent demonstrates affinity for αvβ3 integrins in the nanomolar range (IC50 = 398 nM). This fluorescent dual agent was fully characterized by photophysical measurements (λabs/λem = 643/660 nm, Φfluo = 0.13) and by NMR spectroscopy, revealing some significant chemical shift modifications of the cyanine polymethine chain depending on the counter anion. A mesylated derivative of the cyanine-containing probe allowed the successful direct 18F-radiolabelling with a radiochemical yield of 18%. The 18F-radiolabelled fluorescent probe, obtained via [18F]F–C bond formation, allows subsequent vector introduction for in vivo targeting, opening a broad scope of applications in imaging modalities and therapy.
![Graphical abstract: Cyanine-based [18F]F-C-glycosyl dual imaging probe: synthesis, physico-chemical characterization, in vitro binding evaluation and direct [18F]fluorination](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=D2NJ06134A&imageInfo.ImageIdentifier.Year=2023)
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