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

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

doi:10.1039/c6sc02488b

Cited by 46 publications

(57 citation statements)

References 72 publications

(43 reference statements)

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“…Polymethine dyes are functional compounds with a unique range of photophysical properties . They are widely used as sensitizers and light energy converters for passive Q‐switches and active laser media, nonlinear optical materials and information recording media, photovoltaic composites, and in biomedical studies ,.…”

Section: Introductionmentioning

confidence: 99%

“…Polymethine dyes are functional compounds with a unique range of photophysical properties. [1][2][3] They are widely used as sensitizers and light energy converters for passive Q-switches and active laser media, [4] nonlinear optical materials and information recording media, [5] photovoltaic composites, [6][7][8][9] and in biomedical studies. [10,11] The reason is that their characteristics can be tuned in an eminently wide range by varying their chemical structure and molecular environment as well as via formation of the dye supramolecular aggregates in solutions or on diverse substrates.…”

Section: Introductionmentioning

confidence: 99%

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Interaction of Polymethine Dyes with Detonation Nanodiamonds

et al. 2019

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Among cationic, anionic, and merocyanine polymethine dyes, the binding to detonation nanodiamond (DND) colloid particles in hydrosol occurs only for negatively charged dye species. This, in view of the positive ζ‐potential of the DND used in this study, suggests the predominance of electrostatic interactions over other intermolecular forces in such systems. Indeed, after decorating the merocyanine and the cationic dye by one and two negatively charged sulfopropyl groups, respectively, so that the net charge of their colored species becomes negative, the compounds also demonstrate affinity to the DND particles. In all cases, the binding of dyes to DND is accompanied by a decrease in fluorescence intensity and a bathochromic shift of their absorption and fluorescence bands. A quantitative study of the dyes adsorption on the DND nanoparticles as performed using the Küster‐Freundlich and Langmuir equations reveals some peculiarities of their attaching to the DND aggregates and allows estimating the specific area of the DND particles at a concentration of 0.0212 wt/vol %.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Interaction of Polymethine Dyes with Detonation Nanodiamonds

et al. 2019

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“…The Cy7N fluorophores were designed by introducing sulfonate functions to optimize their solubility in biological media, while the rigidity of the heptamethine skeleton was ensured by a tertbutyl cyclohexenyl framework, limiting fluorescence losses by nonradiative deexcitation. 24 The synthesis of the reference amino-heptamethine Cy7N 4 ( Figure 1A) and carboxyldiethylenglycolamine (CDE)-functionalized Cy7N 6 (CDE-Cy7N, Figure 1B) was carried out using classical condi-…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The fluorescence quantum yield is however noticeably decreased in water, as already reported for analogous polymethine derivatives. 24 Introduction of functional group on CDE-Cy7N 6 has no influence on the optical properties ( Figure S1). 23,24,26 Cy7N was chosen for its particularly interesting photophysical properties, 14,27 such as featuring sulfonate side-chains that provide good solubility in aqueous media which is a critical parameter for imaging.…”

Section: Bioconjugate Chemistrymentioning

confidence: 99%

Synthesis of the New Cyanine-Labeled Bacterial Lipooligosaccharides for Intracellular Imaging and in Vitro Microscopy Studies

et al. 2019

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Endotoxin (lipooligosaccharide, LOS, and lipopolysaccharide, LPS) is the major molecular component of Gram-negative bacteria outer membrane, and very potent proinflammatory substance. Visualizing and tracking the distribution of the circulating endotoxin is one of the fundamental approaches to understand the molecular aspects of infection with subsequent inflammatory and immune responses, LPS also being a key player in the molecular dialogue between microbiota and host. While fluorescently labeled LPS has previously been used to track its subcellular localization and colocalization with TLR4 receptor and downstream effectors, our knowledge on lipopolysaccharide (LOS) localization and cellular activity remains almost unexplored. In this study, LOS was labeled with a novel fluorophore, Cy7N, featuring a large Stokes-shifted emission in the deep-red spectrum resulting in lower light scattering and better imaging contrast. The LOS-Cy7N chemical identity was determined by mass spectrometry, and immunoreactivity of the conjugate was evaluated. Interestingly, its application to microscopic imaging showed a faster cell internalization compared to LPS-Alexa488, despite that it is also CD14-dependent and undergoes the same endocytic pathway as LPS toward lysosomal detoxification. Our results suggest the use of the new infrared fluorophore Cy7N for cell imaging of labeled LOS by confocal fluorescence microscopy, and propose that LOS is imported in the cells by mechanisms different from those responsible for LPS uptake.

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“…1 For example, two-photon microscopy using various symmetric and asymmetric keto-polymethine dyes was used to selectively image different cellular regions, such as the cytoplasm and cell membranes, through careful control of the hydrophilichydrophobic balance in the molecules. 2 Acedan-merocyanine dyes were used in two-photon microscopy for detecting fluctuations of enzymatically generated SO 2 derivatives in mitochondria of living HepG2 cells and rat liver tissues. 3 Two-photon imaging dyes based on lanthanides are also known.…”

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confidence: 99%

Two-Photon Excitation for Bone Imaging: A New Application for Lanthanide Luminescence

Bettencourt‐Dias

2016

Chem

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

Abstract: The keto-heptamethine family has been expanded to various symmetrical and asymmetrical structures.

Cited by 46 publications

References 72 publications

Interaction of Polymethine Dyes with Detonation Nanodiamonds

Interaction of Polymethine Dyes with Detonation Nanodiamonds

Synthesis of the New Cyanine-Labeled Bacterial Lipooligosaccharides for Intracellular Imaging and in Vitro Microscopy Studies

Two-Photon Excitation for Bone Imaging: A New Application for Lanthanide Luminescence

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