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Article Dans Une Revue Chemical Science Année : 2017

Keto-polymethines: a versatile class of dyes with outstanding spectroscopic properties for in cellulo and in vivo two-photon microscopy imaging

Simon Pascal
Sandrine Denis-Quanquin
Jérôme Cuny
Cyrille Monnereau

Résumé

The synthesis of keto-heptamethine derivatives has been expanded to various new symmetrical and asymmetrical structures, including an unprecedented di-anionic keto-polymethine. The spectroscopic behavior of these new dyes has been systematically and thoroughly investigated, revealing that the formation of hydrogen bond interactions with protic solvents is responsible for a dramatic enhancement of the fluorescence quantum yield in the far-red spectral region. The existence of these strong hydrogen-bond interactions was further confirmed by molecular dynamics simulations. These bis-dipolar polymethines exhibit large two-photon absorption (TPA) cross-sections (σ2 in GM) in the near-infrared, making them ideal candidates for NIR-to-NIR two-photon microscopy imaging applications. We demonstrate that the molecular engineering of the hydrophilic/hydrophobic balance enables targeting of different cellular components, such as cytoplasm or cell membranes. Addition of appropriate substituents provides the molecule with high-water-solubility, affording efficient two-photon probes for angiography.
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Dates et versions

hal-01419954 , version 1 (20-03-2017)

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Simon Pascal, Sandrine Denis-Quanquin, Florence Appaix, Alain Duperray, Alexei Grichine, et al.. Keto-polymethines: a versatile class of dyes with outstanding spectroscopic properties for in cellulo and in vivo two-photon microscopy imaging. Chemical Science, 2017, 8 (1), pp.381 - 394. ⟨10.1039/C6SC02488B⟩. ⟨hal-01419954⟩
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