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酮基聚甲炔：一类具有出色光谱特性的多功能染料，用于单光子和双光子显微镜成像。

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

作者信息

Pascal Simon, Denis-Quanquin Sandrine, Appaix Florence, Duperray Alain, Grichine Alexei, Le Guennic Boris, Jacquemin Denis, Cuny Jérôme, Chi San-Hui, Perry Joseph W, van der Sanden Boudewijn, Monnereau Cyrille, Andraud Chantal, Maury Olivier

机构信息

ENS Lyon , Université de Lyon 1 , CNRS Laboratoire de chimie de l'ENS Lyon , UMR 5182 CNRS, 46 allée d'Italie , 69364 Lyon , France . Email:

Univ. Grenoble Alpes , Grenoble Institut des Neurosciences , GIN, Inserm , U836 , F-38000 Grenoble , France.

出版信息

Chem Sci. 2017 Jan 1;8(1):381-394. doi: 10.1039/c6sc02488b. Epub 2016 Aug 3.

DOI:10.1039/c6sc02488b
PMID:28451183
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5365052/
Abstract

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 ( 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.

摘要

酮-七甲川衍生物的合成已扩展到各种新的对称和不对称结构，包括前所未有的双阴离子酮-聚甲川。对这些新染料的光谱行为进行了系统而深入的研究，结果表明与质子溶剂形成氢键相互作用是远红光光谱区域荧光量子产率显著提高的原因。分子动力学模拟进一步证实了这些强氢键相互作用的存在。这些双偶极聚甲川在近红外区域表现出较大的双光子吸收（TPA）截面（以GM为单位），使其成为近红外到近红外双光子显微镜成像应用的理想候选物。我们证明，亲水/疏水平衡的分子工程能够靶向不同的细胞成分，如细胞质或细胞膜。添加适当的取代基可使分子具有高水溶性，从而为血管造影提供高效的双光子探针。

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