Stains-all

Short description: Dye

Stains-all

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

CAS Number

* 7423-31-6

3D model (JSmol)

* Interactive image

PubChem CID

* 6364602

UNII |

* 4MB06G6N2I

SMILES

* 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

Chemical formula

| C30H27BrN2S2
Molar mass | 559.58 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

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

## 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. et al. (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.
5. ↑ 5.0 5.1 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. PMID 15866501.
6. ↑ 6.0 6.1 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. PMID 12481260.
7. ↑ 7.0 7.1 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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*[CID]: Compound ID