Stains-all

Last updated
Stains-all
Stains-all.svg
Names
Preferred IUPAC name
1-Ethyl-2-[(1E,3Z)-3-(1-ethylnaphtho[1,2-d][1,3]thiazol-2(1H)-ylidene)-2-methylprop-1-en-1-yl]naphtho[1,2-d][1,3]thiazol-1-ium bromide
Other names
DBTC; Carbocyanin DBTC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.028.225 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 231-047-7
PubChem CID
UNII
  • InChI=1S/C30H27N2S2.BrH/c1-4-31-27(33-25-16-14-21-10-6-8-12-23(21)29(25)31)18-20(3)19-28-32(5-2)30-24-13-9-7-11-22(24)15-17-26(30)34-28;/h6-19H,4-5H2,1-3H3;1H/q+1;/p-1
    Key: MPBRYMWMMKKRGC-UHFFFAOYSA-M
  • CCN1/C(=C/C(=C/C2=[N+](C3=C(S2)C=CC4=CC=CC=C43)CC)/C)/SC5=C1C6=CC=CC=C6C=C5.[Br-]
Properties
C30H27BrN2S2
Molar mass 559.58 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stains-all is a carbocyanine dye, which stains anionic proteins, nucleic acids, anionic polysaccharides and other anionic molecules. [1] [2]

Contents

Properties

Stains-all is metachromatic and changes its color dependent on its contact to other molecules. [3] The detection limit for phosphoproteins is below 1 ng after one hour of staining, [4] for anionic polysaccharides between 10 and 500 ng. [5] [6] Highly anionic proteins are stained blue, proteoglycans purple and anionic proteins pink. [7] RNA is stained blueish-purple with a detection limit of 90 ng and DNA is stained blue with a detection limit of 3 ng. [8]

Stains-all is light sensitive, therefore the staining is performed in the absence of light and photographed immediately. Staining of proteins can be improved by a subsequent silver stain. [7] The analogue Ethyl-Stains-all has similar properties as stains-all, with differences in solubility and staining properties. [9]

Applications

Stains-all stains nucleic acids, anionic proteins, anionic polysaccharides such as alginate and pectinate, [10] hyaluronic acid and dermatan sulfate, [5] heparin, heparan sulfate and chondroitin sulfate. [6] It is used in SDS-PAGE, agarose gel electrophoresis and histologic staining, e.g. staining of growth lines in bones. [11]

References

  1. ↑ Green, M. R.; Pastewka, J. V.; Peacock, A. C. (1973). "Differential staining of phosphoproteins on polyacrylamide gels with a cationic carbocyanine dye". Analytical Biochemistry. 56 (1): 43–51. doi:10.1016/0003-2697(73)90167-x. PMID   4128675.
  2. ↑ Myers, Jody M.; Veis, Arthur; Sabsay, Boris; Wheeler, A.P. (1996). "A Method for Enhancing the Sensitivity and Stability of Stains-All for Phosphoproteins Separated in Sodium Dodecyl Sulfate–Polyacrylamide Gels". Analytical Biochemistry. 240 (2): 300–302. doi:10.1006/abio.1996.0361. PMID   8811925.
  3. ↑ Sharma, Y.; Rao, C. M.; Rao, S. C.; Krishna, A. G.; Somasundaram, T.; Balasubramanian, D. (1989). "Binding site conformation dictates the color of the dye stains-all. A study of the binding of this dye to the eye lens proteins crystallins". The Journal of Biological Chemistry. 264 (35): 20923–7. doi: 10.1016/S0021-9258(19)30024-9 . PMID   2480348.
  4. ↑ Cong, W. T.; Ye, W. J.; Chen, M.; Zhao, T.; Zhu, Z. X.; Niu, C.; Ruan, D. D.; Ni, M. W.; Zhou, X.; Jin, L. T. (2013). "Improved staining of phosphoproteins with high sensitivity in polyacrylamide gels using Stains-All". Electrophoresis. 34 (24): 3277–86. doi:10.1002/elps.201300328. PMID   24114871. S2CID   1412613.
  5. 1 2 NVolpi, N.; MacCari, F.; Titze, J. (2005). "Simultaneous detection of submicrogram quantities of hyaluronic acid and dermatan sulfate on agarose-gel by sequential staining with toluidine blue and Stains-All". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 820 (1): 131–5. doi:10.1016/j.jchromb.2005.03.028. hdl: 11380/310191 . PMID   15866501.
  6. 1 2 Volpi, N.; MacCari, F. (2002). "Detection of submicrogram quantities of glycosaminoglycans on agarose gels by sequential staining with toluidine blue and Stains-All". Electrophoresis. 23 (24): 4060–6. doi:10.1002/elps.200290021. hdl: 11380/310673 . PMID   12481260. S2CID   22945783.
  7. 1 2 Goldberg, H. A.; Warner, K. J. (1997). "The staining of acidic proteins on polyacrylamide gels: Enhanced sensitivity and stability of "Stains-all" staining in combination with silver nitrate". Analytical Biochemistry. 251 (2): 227–33. doi:10.1006/abio.1997.2252. PMID   9299020.
  8. ↑ Sigma-Aldrich: MSDS Stains-All ~95%, accessed May 16, 2015.
  9. ↑ Green, M. R.; Pastewka, J. V. (1979). "The cationic carbocyanine dyes Stains-all DBTC, and Ethyl-Stains-all, DBTC-3,3',9 triethyl". The Journal of Histochemistry and Cytochemistry. 27 (3): 797–9. doi: 10.1177/27.3.90067 . PMID   90067.
  10. ↑ Krishna, A. G.; Sharma, Y. (1991). "Conformation of alginate and pectate chains monitored by the binding of the dye stains-all". Indian Journal of Biochemistry & Biophysics. 28 (1): 30–3. PMID   1711507.
  11. ↑ Gruber, H. E.; Mekikian, P. (1991). "Application of stains-all for demarcation of cement lines in methacrylate embedded bone". Biotechnic & Histochemistry. 66 (4): 181–4. doi:10.3109/10520299109109966. PMID   1716999.
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