Epicocconone

Epicocconone is a long Stokes' shift fluorogenic natural product found in the fungus Epicoccum nigrum.[1] Though weakly fluorescent in water (green emission, 520 nm) it reacts covalently yet reversibly with primary amines such as those in proteins to yield a product with a strong orange-red emission (610 nm).[2] Epicoconone is notable because it the first covalent/reversible/turn-on fluorophore to be discovered and is a natural product with a new fluorescent scaffold. It is also cell membrane permeable, unlike many other fluorophores, and subsequently can be used in in vivo (live cell) applications.[2] Additionally, this dye can be used as a sensitive total protein stain for 1D and 2D electrophoresis,[3] quantitative determination of protein concentration,[4] making it a powerful loading control for Western blots.[5]

Epicocconone
Chemical structure of epicocconone
Names
Preferred IUPAC name
(6S,9aS)-6-(Hydroxymethyl)-3-[(1Z,4E,6E,8E)-1-hydroxy-3-oxodeca-1,4,6,8-tetraen-1-yl]-9a-methyl-5,6-dihydro-2H-furo[3,2-g][2]benzopyran-2,9(9aH)-dione
Other names
Deep Purple

Lava Purple

Lightning Fast
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C23H22O7/c1-3-4-5-6-7-8-15(25)11-19(26)20-18-10-14-9-16(12-24)29-13-17(14)21(27)23(18,2)30-22(20)28/h3-8,10-11,13,16,24,26H,9,12H2,1-2H3/b4-3+,6-5+,8-7+,19-11-/t16-,23-/m0/s1
    Key: JKMBMIMLVFMXRW-LYYFRFARSA-N
  • InChI=1/C23H22O7/c1-3-4-5-6-7-8-15(25)11-19(26)20-18-10-14-9-16(12-24)29-13-17(14)21(27)23(18,2)30-22(20)28/h3-8,10-11,13,16,24,26H,9,12H2,1-2H3/b4-3+,6-5+,8-7+,19-11-/t16-,23-/m0/s1
    Key: JKMBMIMLVFMXRW-LYYFRFARBG
  • C/C=C/C=C/C=C/C(=O)/C=C(/C1=C2C=C3C[C@H](OC=C3C(=O)[C@]2(OC1=O)C)CO)\O
Properties
C23H22O7
Molar mass 410.422 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthetic variant

In addition to the natural variant from the fungus, there are several synthetic analogs.[6] With respect to protein staining properties there are few differences between natural and synthetic analogs.

Reaction

[7]

References
  1. Bell, P. J. L.; Karuso, P. (2003). "Epicocconone, A Novel Fluorescent Compound from the Fungus Epicoccum nigrum". Journal of the American Chemical Society. 125 (31): 9304–9305. doi:10.1021/ja035496+. PMID 12889954.
  2. Choi, H. -Y.; Veal, D. A.; Karuso, P. (2005). "Epicocconone, A New Cell-Permeable Long Stokes' Shift Fluorescent Stain for Live Cell Imaging and Multiplexing". Journal of Fluorescence. 16 (4): 475–482. doi:10.1007/s10895-005-0010-7. PMID 16328703.
  3. MacKintosh, J. A.; Choi, H. Y.; Bae, S. H.; Veal, D. A.; Bell, P. J.; Ferrari, B. C.; Van Dyk, D. D.; Verrills, N. M.; Paik, Y. K.; Karuso, P (2003). "A fluorescent natural product for ultra sensitive detection of proteins in one-dimensional and two-dimensional gel electrophoresis". Proteomics. 3 (12): 2273–88. doi:10.1002/pmic.200300578. PMID 14673778.
  4. MacKintosh, J. A.; Veal, D. A.; Karuso, P. (2005). "Fluoroprofile, a fluorescence-based assay for rapid and sensitive quantitation of proteins in solution". Proteomics. 5 (18): 4673–4677. doi:10.1002/pmic.200500095. PMID 16267819.
  5. Moritz, C. P.; Marz, S. X.; Reiss, R; Schulenborg, T; Friauf, E (2014). "Epicocconone staining: A powerful loading control for Western blots". Proteomics. 14 (2–3): 162–8. doi:10.1002/pmic.201300089. PMID 24339236.
  6. Peixoto, P. A.; Boulangé, A; Ball, M; Naudin, B; Alle, T; Cosette, P; Karuso, P; Franck, X (2014). "Design and synthesis of epicocconone analogues with improved fluorescence properties". Journal of the American Chemical Society. 136 (43): 15248–56. doi:10.1021/ja506914p. PMID 25271695.
  7. Coghlan, Daniel R.; Mackintosh, James A.; Karuso, Peter (2005-05-17). "Mechanism of Reversible Fluorescent Staining of Protein with Epicocconone". Organic Letters. American Chemical Society (ACS). 7 (12): 2401–2404. doi:10.1021/ol050665b. ISSN 1523-7060.
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