Epicocconon

from Wikipedia, the free encyclopedia
Structural formula
Structure of Epicocconon
General
Surname Epicocconon
other names
  • (6 S , 9a S ) -3 - ((1 Z , 4 E , 6 E , 8 E ) -1-hydroxy-3-oxodeca-1,4,6,8-tetraenyl) -6- (hydroxymethyl) - 9a-methyl-5,6-dihydro-9a H -furo [3.2- g ] isochromene-2,9-dione ( IUPAC )
  • Beljian Red
  • Lightning Fast
  • Deep Purple
  • Lava Purple
  • LavaCell
Molecular formula C 23 H 22 O 7
External identifiers / databases
CAS number 371163-96-1
PubChem 10223268
ChemSpider 8398759
Wikidata Q1346935
properties
Molar mass 410.42 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Epicocconon is a fluorescent dye from the fungus Epicoccum nigrum .

Properties and use

The water-soluble epicocconone fluoresces slightly greenish (λ em = 520 nm) in its protonated form, after binding a protein the maximum fluorescence shifts to a wavelength of 605 nm. The absorption maximum is 395 nm. When adding base , a proton is given off. However, the resulting anion loses the ability to fluoresce:

Epicocconone pks.svg

The dye can react with primary amines. This is used in biochemistry in the context of protein characterization in order to stain proteins , in particular when determining the quantity in solutions, for tracking proteolysis , in SDS-PAGE , in 2D gel electrophoresis with in-gel digestion and mass spectrometric analysis, and as Loading control for Western blots ( detection limit 1 ng after 40 minutes). The staining is reversible and compatible with immunostaining or mass spectrometry . An intense, red-fluorescent enamine forms during the reaction . However, if the proteins are in a too basic environment, the enamine product is deprotonated and loses its fluorescent properties.

Epicocconone protein.svg

Synthetic variant

Epicoccum nigrum (dark)

In addition to the natural variant from the mushroom, the dye now also exists as a synthetic product. Regarding the coloring properties of proteins, there are no differences between the natural and synthetic variants.

Web links

Individual evidence

  1. ↑ interchim.fr: product sheet (PDF; 370 kB), accessed on December 29, 2012.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ^ PJ Bell, P. Karuso: Epicocconone, a novel fluorescent compound from the fungus epicoccumnigrum. In: Journal of the American Chemical Society. Volume 125, Number 31, August 2003, pp. 9304-9305, doi : 10.1021 / ja035496 + , PMID 12889954 .
  4. ↑ JA Mackintosh, DA Veal, P. Karuso: Fluoroprofile, a fluorescence-based assay for rapid and sensitive quantitation of proteins in solution. In: Proteomics. Volume 5, Number 18, December 2005, pp. 4673-4677, doi: 10.1002 / pmic.200500095 , PMID 16267819 .
  5. ↑ JA Mackintosh, HY Choi, SH Bae, DA Veal, PJ Bell, BC Ferrari, DD Van Dyk, NM Verrills, YK Paik, P. Karuso: A fluorescent natural product for ultra sensitive detection of proteins in one-dimensional and two- dimensional gel electrophoresis. In: Proteomics. Volume 3, Number 12, December 2003, pp. 2273-2288, doi: 10.1002 / pmic.200300578 , PMID 14673778 .
  6. ↑ JA Mackintosh, DA Veal, P. Karuso: Fluoroprofile, a fluorescence-based assay for rapid and sensitive quantitation of proteins in solution. In: Proteomics. Volume 5, Number 18, December 2005, pp. 4673-4677, doi: 10.1002 / pmic.200500095 , PMID 16267819 .
  7. ↑ P. Karuso, AS Crawford, DA Veal, GB Scott, HY Choi: Real-time fluorescence monitoring of tryptic digestion in proteomics. In: Journal of proteome research. Volume 7, Number 1, January 2008, pp. 361-366, doi: 10.1021 / pr0704480 , PMID 18052032 .
  8. ↑ a b Hubert Rehm , Thomas Letzel: The experimenter: protein biochemistry / proteomics . 6th edition, Spektrum Akademischer Verlag, Heidelberg 2009. ISBN 978-3-8274-2312-2 . Pp. 18, 28.
  9. ↑ DR Coghlan, JA Mackintosh, P. Karuso: Mechanism of reversible fluorescent staining of protein with epicocconone. In: Organic letters. Volume 7, Number 12, June 2005, pp. 2401-2404, doi: 10.1021 / ol050665b , PMID 15932208 .
  10. ↑ NS Tannu, G. Sanchez-Brambila, P. Kirby, TM Andacht: Effect of staining reagent on peptide mass fingerprinting from in-gel trypsin digestions: a comparison of SyproRuby and DeepPurple. In: Electrophoresis. Volume 27, Number 15, August 2006, pp. 3136-3143, doi: 10.1002 / elps.200500740 PMID 16800026 .
  11. ↑ a b C. P. Moritz, SX Marz, R. Reiss, T. Schulenborg, E. Friauf: Epicocconone staining: a powerful loading control for Western blots. In: Proteomics , Volume 14, Number 1-2, February 2014, pp 162-168, doi: 10.1002 / pmic.201300089 PMID 24339236 .
  12. ↑ DR Coghlan et al.  : Mechanism of reversible fluorescent staining of protein with epicocconone . In: Org Lett. 7, No. 12, 2005, pp. 2401-2404, PMID 15932208 .
  13. ^ A. Boulange, PA Peixoto, X. Franck: Diastereoselective IBX oxidative dearomatization of phenols by remote induction: towards the epicocconone core framework. In: Chemistry. Volume 17, number 37, September 2011, pp. 10241-10245, doi: 10.1002 / chem . 201101681 PMID 21809405 .