2,4,6-Tri-(<i>p</i>-methoxyphenyl)pyrylium Tetrafluoroborate

Balaban, A. T.

doi:10.1002/047084289x.rn00618

Cited by 4 publications

(4 citation statements)

References 42 publications

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“…The pyrylium salts were prepared according to the literature. 19,37,38 CAUTION: Since perchlorates may explode when they are heated or upon impact in dry form, they should be stored moist with water.…”

Section: Discussionmentioning

confidence: 99%

Pyridinium Cationic Lipids in Gene Delivery: A Structure−Activity Correlation Study

et al. 2004

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Three series of pyridinium cationic lipids useful as nonviral gene delivery agents were prepared by reaction of pyrylium salts with aminodiols, followed by acylation with fatty acyl chlorides. On the basis of this set of compounds, we undertook a comprehensive structure-activity relationship study at the level of the linker, hydrophobic anchor, and counterion in order to identify the structural elements that generate the highest transfection efficiency for this new type of cationic lipid. The results revealed that when formulated with cholesterol at a 1:1 molar ratio, the 1-(1,3-dimyristoyloxyprop-2-yl)-2,4,6-trimethylpyridinium, under the form of hexafluorophosphate (5AMyr) or chloride (5DMyr), was able to transfect NCI-H23 lung carcinoma with efficiencies surpassing classic DOTAP-based formulations and with lower cytotoxicity. Subsequent tests on other malignancies yielded similarly promising results.

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Section: Discussionmentioning

confidence: 99%

Pyridinium Cationic Lipids in Gene Delivery: A Structure−Activity Correlation Study

et al. 2004

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“…The great advantage of pyrylium salts’ application has been their commercial availability as well as cost-effectiveness. Furthermore, the compounds can be easily synthesized with a good yield by a one-pot cyclization of two equivalents of benzalacetophenone and one equivalent of benzaldehyde [ 67 , 68 , 69 ]. This fact prompted Waliczek and co-workers to prepare isotopically labeled 2,4,6-triphenylpyrylium (tetra-2,3,5,6- 13 C 4 ) and then apply it to the formation of isobaric peptides (2-plex) [ 70 ].…”

Section: Sensitivity Problemmentioning

confidence: 99%

Trends in the Design of New Isobaric Labeling Reagents for Quantitative Proteomics

et al. 2019

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Modern mass spectrometry is one of the most frequently used methods of quantitative proteomics, enabling determination of the amount of peptides in a sample. Although mass spectrometry is not inherently a quantitative method due to differences in the ionization efficiency of various analytes, the application of isotope-coded labeling allows relative quantification of proteins and proteins. Over the past decade, a new method for derivatization of tryptic peptides using isobaric labels has been proposed. The labels consist of reporter and balanced groups. They have the same molecular weights and chemical properties, but differ in the distribution of stable heavy isotopes. These tags are designed in such a way that during high energy collision induced dissociation (CID) by tandem mass spectrometry, the isobaric tag is fragmented in the specific linker region, yielding reporter ions with different masses. The mass shifts among the reporter groups are compensated by the balancing groups so that the overall mass is the same for all forms of the reagent. Samples of peptides are labeled with the isobaric mass tags in parallel and combined for analysis. Quantification of individual peptides is achieved by comparing the intensity of reporter ions in the tandem mass (MS/MS) spectra. Isobaric markers have found a wide range of potential applications in proteomics. However, the currently available isobaric labeling reagents have some drawbacks, such as high cost of production, insufficient selectivity of the derivatization, and relatively limited enhancement of sensitivity of the analysis. Therefore, efforts have been devoted to the development of new isobaric markers with increased usability. The search for new isobaric markers is focused on developing a more selective method of introducing a tag into a peptide molecule, increasing the multiplexicity of markers, lowering the cost of synthesis, and increasing the sensitivity of measurement by using ionization tags containing quaternary ammonium salts. Here, the trends in the design of new isobaric labeling reagents for quantitative proteomics isobaric derivatization strategies in proteomics are reviewed, with a particular emphasis on isobaric ionization tags. The presented review focused on different types of isobaric reagents used in quantitative proteomics, their chemistry, and advantages offer by their application.

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“…These compounds are commercially available, inexpensive and can be easily prepared with a good yield by a one-pot cyclization of e.g. two equivalents of benzalacetophenone and one equivalent of benzaldehyde272829. The proposed approach is particularly useful for analysis of tryptic peptides containing C-terminal lysine residue.…”

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confidence: 99%

Peptides Labeled with Pyridinium Salts for Sensitive Detection and Sequencing by Electrospray Tandem Mass Spectrometry

Waliczek

Kijewska

Setner

et al. 2016

Sci Rep

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Mass spectrometric analysis of trace amounts of peptides may be problematic due to the insufficient ionization efficiency resulting in limited sensitivity. One of the possible ways to overcome this problem is the application of ionization enhancers. Herein we developed new ionization markers based on 2,4,6-triphenylpyridinium and 2,4,6-trimethylpyridinium salts. Using of inexpensive and commercially available pyrylium salt allows selective derivatization of primary amino groups, especially those sterically unhindered, such as ε-amino group of lysine. The 2,4,6-triphenylpyridinium modified peptides generate in MS/MS experiments an abundant protonated 2,4,6-triphenylpyridinium ion. This fragment is a promising reporter ion for the multiple reactions monitoring (MRM) analysis. In addition, the fixed positive charge of the pyridinium group enhances the ionization efficiency. Other advantages of the proposed ionization enhancers are the simplicity of derivatization of peptides and the possibility of convenient incorporation of isotopic labels into derivatized peptides.

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2,4,6-Tri-(p-methoxyphenyl)pyrylium Tetrafluoroborate

Cited by 4 publications

References 42 publications

Pyridinium Cationic Lipids in Gene Delivery: A Structure−Activity Correlation Study

Pyridinium Cationic Lipids in Gene Delivery: A Structure−Activity Correlation Study

Trends in the Design of New Isobaric Labeling Reagents for Quantitative Proteomics

Peptides Labeled with Pyridinium Salts for Sensitive Detection and Sequencing by Electrospray Tandem Mass Spectrometry

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