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Kostenko, O. M.; Dmitrieva, S. Yu.; Tolmachev, O.I.; Yarmoluk, S. M.

doi:10.1023/a:1016844330051

Cited by 13 publications

(10 citation statements)

References 1 publication

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“…17,18 Typically, polymers have to be labeled with fluorescent tags to examine their cellular processing. 19 Cyanine dyes are among the most widely used dyes for labeling of naturally occurring (e.g., peptides, 20 proteins, 21 and nucleic acids 22 ) and synthetic (e.g., drugs, 23 polymers, 24 and particles 25 ) materials. In recent years, these dyes have found widespread applications in biomedical imaging because of their high extinction coefficients and adjustable emission maxima.…”

Section: ■ Introductionmentioning

confidence: 99%

Tuning Cellular Interactions of Carboxylic Acid-Side-Chain-Containing Polyacrylates: The Role of Cyanine Dye Label and Side-Chain Type

et al. 2020

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Cellular uptake and intracellular targeting to specific organelles are key events in the cellular processing of nanomaterials. Herein, we perform a detailed structure–property relationship study on carboxylic acid-side-chain-bearing polyacrylates to provide design criteria for the manipulation of their cellular interactions. Redox-initiated reversible addition-fragmentation chain-transfer (RRAFT) polymerization of three tert-butyl-protected N-acylated amino ester-based acrylate monomers of different substitutions and degrees of polymerization (DPs) yielded defined and pH-responsive carboxylic acid-side-chain polymers upon deprotection (N-acetyl, DP 1: P(M1); N-propionyl, DP 1: P(E1), DP 2: P(E2)). Flow cytometry studies revealed time-dependent cell association with P(E2) > P(E1) > P(M1) at any given time point. Importantly, the type of cyanine dye used for labeling was found to significantly influence the cellular processing of the polymers. Changing the dye from Cy5 to its sulfonated version sulfoCy5 resulted in a much lower cellular association. Moreover, Cy5-labeled polymers were targeted to mitochondria, while sulfoCy5 modification caused a significant change in the cellular fate of polymers toward lysosome trafficking. This study highlights the importance of selecting a suitable dye but also demonstrates the possibilities for the rational design of organelle-specific targeting of carboxylated polyacrylates.

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Section: ■ Introductionmentioning

confidence: 99%

Tuning Cellular Interactions of Carboxylic Acid-Side-Chain-Containing Polyacrylates: The Role of Cyanine Dye Label and Side-Chain Type

et al. 2020

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“…a decade later , studying the kinetics of the reaction with gelatin, chymotrypsin, and lysine and triggering a number of research efforts that depended on reporter labels. For instance, heavy metal derivatives were suggested for X‐ray crystallography and pyrylium cyanine dyes for fluorescent labeling ; the latter were further developed for use in single‐molecule microscopy . Other researchers used pyrylium salts as reactive matrices for MALDI MS imaging or glycan analysis .…”

Section: Methodsmentioning

confidence: 99%

“…Although the pyrylium‐to‐product conversion was almost quantitative, the predicted red color was not observed, likely due to the formation of pyridine instead of pyridinium (R 2 = H, Scheme , Fig. ) . Only when labeling was performed at a high percentage of organic solvent (80% MeOH added to the dye dissolved in anhydrous DMF) and any further sample cleanup was omitted, yields ≥30% and color change could be achieved.…”

Section: Methodsmentioning

confidence: 99%

Pyrylium‐based dye and charge tagging in proteomics

Bayer

König

2016

Electrophoresis

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The pyrylium group is a selective reagent for ε-amino groups in proteins. In particular, for fluorescence labeling, a number of advantages over traditional N-hydroxysuccinimidyl ester chemistry were recognized such as the rapid prestaining procedure. Here, we have investigated the labeling reaction for the fluorogenic pyrylium dye Py-1 using liquid chromatography coupled to MS with the aim of determining its specificity and possible side products. Peptides containing no, one, and two lysine residue and a choice of no or one cysteine residue were labeled with Py-1 at yields > 30%. Gas phase fragmentation proved both labeling of lysine residues as well as that of the N-terminus also in peptides that contained a lysine residue. Evidence for cysteine labeling was not found, but several other products were detected such as the results of rearrangements with adjacent acidic amino acids. Apart from the use as a fluorogenic label, Py-1 recommends itself for N-terminal charge tagging as alternative to the commonly used quaternary ammonium salts. Predominantly a- and b-type ion series were observed for N-terminally labeled peptides. Further applications include chromophore tagging since the labeled product is not only fluorescent but also colored red.

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“…Herein we report an entirely new class of labels for gel electrophoresis and also for general protein quantitation. Pyrylium groups react with amines to form the respective pyridinium analogues 9. We have synthesized the new labels by attaching a pyrylium group to a small aromatic group (thereby forming one of the smallest blue and fluorescent chromophores known) and this resulted in the label Py‐1 .…”

Section: Photophysical Properties Of Stains Py‐1 Py‐3 and Py‐5 In Fmentioning

confidence: 99%

Chameleon Labels for Staining and Quantifying Proteins

et al. 2004

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Glowing marks: A new class of protein stains, the pyrylium dyes, undergo a strong color change (typically from blue to red, see picture) on covalently binding to proteins. While the free stains are almost nonfluorescent, the protein‐conjugated forms are highly fluorescent. The dyes do not alter the charge of a protein, and thus do not change its electrophoretic properties. The stains also can be used in quantitative protein assays.

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Cited by 13 publications

References 1 publication

Tuning Cellular Interactions of Carboxylic Acid-Side-Chain-Containing Polyacrylates: The Role of Cyanine Dye Label and Side-Chain Type

Tuning Cellular Interactions of Carboxylic Acid-Side-Chain-Containing Polyacrylates: The Role of Cyanine Dye Label and Side-Chain Type

Pyrylium‐based dye and charge tagging in proteomics

Chameleon Labels for Staining and Quantifying Proteins

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