Water soluble indodicarbocyanine dyes based on 2,3-dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

Маркова, Л. И.; Fedyunyayeva, Iryna A.; Povrozin, Yevgen A.; Semenova, O.; Khabuseva, S.U.; Terpetschnig, Ewald; Patsenker, L. D.

doi:10.1016/j.dyepig.2012.09.007

Cited by 17 publications

(11 citation statements)

References 28 publications

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“…Known indolium salts 7 (11) and 8 (8) were prepared by alkylation of the corresponding indoles 4 and 6 with 1,3propanesultone. Pre-activation of the Vilsmeier type reagent 9 with acetic anhydride was followed by addition of the indolium salt 7 (1.5:1 molar ratio) and acetic acid using standard procedures (12)(13)(14)(15). After 4 h of stirring at reflux temperature, acetic acid was evaporated and the residue was washed with ethyl acetate several times to remove the unreacted reagent 9.…”

Section: Resultsmentioning

confidence: 99%

Minimization of self‐quenching fluorescence on dyes conjugated to biomolecules with multiple labeling sites via asymmetrically charged NIR fluorophores

Zhegalova

Zhou

et al. 2014

Contrast Media & Molecular

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Self-aggregation of dyes even at low concentrations pose a considerable challenge in preparing sufficiently bright molecular probes for in vivo imaging, particularly in the conjugation of near infrared cyanine dyes to polypeptides with multiple labeling sites. Such self-aggregation leads to a significant energy transfer between the dyes resulting in severe quenching and low brightness of the targeted probe. To address this problem, we designed a novel type of dye with an asymmetrical distribution of charge. Asymmetrical distribution prevents the chromophores from π-stacking thus minimizing the energy transfer and fluorescence quenching. The conjugation of the dye to polypeptides showed only a small presence of an H-aggregate band in the absorption spectra and, hence, a relatively high quantum efficiency.

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Section: Resultsmentioning

confidence: 99%

Minimization of self‐quenching fluorescence on dyes conjugated to biomolecules with multiple labeling sites via asymmetrically charged NIR fluorophores

Zhegalova

Zhou

et al. 2014

Contrast Media & Molecular

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“…S1, ESI †). 17 The increased number of sulfonate groups in Cy3 dyes improved their photophysical properties. Initially, we expected that the ameliorated photophysical properties of GB2-Cy3-S1 and GB2-Cy3-S2 might lead to an improved version of glucose bioprobes compared to the original GB2-Cy3.…”

mentioning

confidence: 99%

Impact of molecular charge on GLUT-specific cellular uptake of glucose bioprobes and in vivo application of the glucose bioprobe, GB2-Cy3

Park

et al. 2014

Chem. Commun.

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“…Sulfo-cyanine-5-alkyne acid 5a ( n SO 3 – = 1) was prepared by reaction of 4 , which was prepared as described previously, with intermediate 3a in pyridine and DMF. Likewise, sulfo-cyanine-5-alkyne acid 5b ( n SO 3 – = 2) was prepared by reaction of 4 with intermediate 3b , which was prepared by the procedure outlined in the literature. , …”

Section: Resultsmentioning

confidence: 99%

Optimizing the Biodistribution of Radiofluorinated Barbiturate Tracers for Matrix Metalloproteinase Imaging by Introduction of Fluorescent Dyes as Pharmacokinetic Modulators

et al. 2020

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Dysregulated expression or activation of matrix metalloproteinases (MMPs) is observed in many kinds of life-threatening diseases. Therefore, MMP imagingfor example, with radiolabeled MMP inhibitors (MMPIs)potentially represents a valuable tool for clinical diagnostics using noninvasive single photon emission computed tomography (SPECT) or positron emission tomography (PET) imaging. Despite numerous preclinical imaging approaches, translation to a clinical setting has not yet been successful. We introduce and oppose three potential radiofluorinated MMP-targeted imaging probes, modified by the introduction of pentamethine cyanine (Cy5) dyes and therefore containing both radio-as well as fluorescent label with respect to their capability to assess MMP activity in vivo by means of scintigraphic (PET) and/or fluorescent (NIRF) imaging. New hybrid MMPI tracer candidates, structurally based on radiofluorinated pyrimidine-2,4,6-triones (barbiturates) from previous approaches, were synthesized by convenient two-step syntheses. In the first step, Cy5 dyes, varying in the number of sulfonate groups (n SO 3 − = 1, 2, or 4) and bearing an additional "clickable" alkyne moiety, were coupled to the barbiturate MMPI by amide formation. In the second step, the [ 18 F]fluoride radiolabel was introduced into the resulting Cy5 dye conjugates by "radio-click" chemistry. Biodistribution studies of these hybrid tracer candidates were assessed and compared in C57BL/6 mice by PET as well as fluorescence imaging. MMP activity was imaged in a MMP-positive mouse model of irritant contact dermatitis (ICD) by PET and sequential fluorescence reflectance imaging (FRI), respectively. In vivo data were validated by scintillation counting, gelatin zymography, and MMP-histology. Three new potential hybrid MMP imaging probes were prepared, differing essentially in the number of sulfonate groups, introduced by Cy5 dye components. Although the hydrophilicity of these compounds was substantially increased, 10a (n SO 3 − = 1) and 10b (n SO 3 − = 2) were still rapidly eliminated via unfavorable hepatobiliary pathways, as observed in earlier approaches. Only 11 (n SO 3 − = 4) showed delayed in vivo clearance and a shift towards higher renal elimination. In the chosen mouse model of ICD, only 11 (n SO 3 − = 4) significantly accumulated in the inflamed mouse ear, which could be precisely visualized by means of PET and FRI.

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Water soluble indodicarbocyanine dyes based on 2,3-dimethyl-3-(4-sulfobutyl)-3H-indole-5-sulfonic acid

Cited by 17 publications

References 28 publications

Minimization of self‐quenching fluorescence on dyes conjugated to biomolecules with multiple labeling sites via asymmetrically charged NIR fluorophores

Minimization of self‐quenching fluorescence on dyes conjugated to biomolecules with multiple labeling sites via asymmetrically charged NIR fluorophores

Impact of molecular charge on GLUT-specific cellular uptake of glucose bioprobes and in vivo application of the glucose bioprobe, GB2-Cy3

Optimizing the Biodistribution of Radiofluorinated Barbiturate Tracers for Matrix Metalloproteinase Imaging by Introduction of Fluorescent Dyes as Pharmacokinetic Modulators

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