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The impurities of biological dyes: their detection, removal, occurrence and histological significance—a review

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References

  • Abrahams, D. H. &Edelstein, S. M. (1964). A new method for the analysis of ancient dyes textiles.Am. Dyestuff Reptr. 53, 19–25.

    Google Scholar 

  • Anwar, M. H., Norman, S., Anwar, B. &Laplaca, P. (1963). Electrophoretic study of synthetic food dyes.J. chem. Educ. 40, 537–8.

    Google Scholar 

  • Arshid, F. M., Connelly, R. F., Desai, J. N., Fulton, R. G., Giles, C. H. &Kefalis, J. C. (1954). A study of certain natural dyes. 2. The structure of the metallic lakes of brazilwood and logwood colouring matters.J. Soc. Dyers Colour. 70, 402–12.

    Google Scholar 

  • Arshid, F. M., Desai, H. F., Giles, C. H. &McLintock, G. K. (1953). Quantitative analysis of azo and other dyes and intermediates.J. Soc. Dyers Colour. 69, 11–18.

    Google Scholar 

  • Asquith, R. S., Peters, A. T. &Wallace, F. (1968). Application of Craig countercurrent extraction techniques to the purification of dyes.J. Soc. Dyers Colour,84, 225–9.

    Google Scholar 

  • Baitsholts, A. D. &Ardell, R. E. (1967). Thin layer chromatography with precoated alumina sheets. I. General properties.J. Chromat. 30, 493–501.

    Google Scholar 

  • Ball, J. &Jackson, D. S. (1953). Histological, chromatographic and spectrophotometric studies of Toluidine Blue.Stain Technol. 28, 33–40.

    PubMed  Google Scholar 

  • Banny, T. M. &Clark, G. (1950). The new domestic Cresyl Echt Violet.Stain Technol. 25, 195–6.

    PubMed  Google Scholar 

  • Beck, F., Spenser, B. &Baxter, J. S. (1960). Effect of Trypan, Blue on rat embryos.Nature, Lond. 187, 605–7.

    Google Scholar 

  • Beers, R. F. (1960). Inhibition and activation of polynucleotide phosphorylase by Acridine Orange.J. biol. Chem. 235, 726–32.

    PubMed  Google Scholar 

  • Bellin, J. S. &Ronayne, M. E. (1966). Chromatographic analysis of photosensitizing dyes.J. Chromat. 24, 131–40.

    Google Scholar 

  • Berger, J. A., Meyniel, G. &Petit, J. (1962). First attempts at thin layer ion exchange chromatography.C.r. Acad. Sci. Paris 255, 1116–18.

    PubMed  Google Scholar 

  • Beswick, T. S. L. (1958). The Einarson Gallocyanin-lake staining technique.J. Path. Bact. 76, 598–600.

    PubMed  Google Scholar 

  • Bird, C. L. &Stancey, G. P. (1961). The effect of temperature and pH on the adsorption of basic dyes by wool.J. Soc. Dyers Colour. 77, 244–6.

    Google Scholar 

  • Bocci, V. (1961). Distribution and fate of Rose Bengal.Nature Lond. 189, 584–5.

    Google Scholar 

  • Bogoslovsky, B. M. (1955). A method of purification of direct and acid dyes and a new method for the determination of their purity.Chem. Abstr. (1955),49, 13651 (Abstract of paper inZhur. Priklad. Chim. 28, 659–63).

    Google Scholar 

  • Bonneau, R., Faure, J. &Jussot-Dubien, J. (1967). Purification of the thiazine dyes Azurs A, B & C by a partition method.Tantala 14, 121–2.

    Google Scholar 

  • Boulton, J., Delph, A. E., Fothergill, F. &Morton, T. H. (1933). Quantitative research on the dyeing of viscose yarns.J. Text. Inst. 24, 113–28.

    Google Scholar 

  • Brakke, M. K. (1955). Zone electrophoresis of dyes, proteins and viruses in densitygradient columns of sucrose solutions.Archs Biochem. Biophys. 55, 175–90.

    Google Scholar 

  • Brown, J. C. (1960). Paper chromatography of synthetic dyes.J. Soc. Dyers Colour. 76, 536–42.

    Google Scholar 

  • Brown, R. B. &Jordan, H. (1923). Estimation of dyestuffs by titration.J. Soc. Dyers Colour. 39, 203–28.

    Google Scholar 

  • Bruns, G. &Beerhalter, H. (1955). Dye analysis. The fluorochrome mixture Thioflavine S.Acta histochem. 1, 254–71.

    PubMed  Google Scholar 

  • Buchanan, J. H. &Corfield, M. C. (1967). An easily constructed apparatus for two dimensional paper electrophoresis.J. Chromat. 31, 274–8.

    Google Scholar 

  • Burger, C. L. (1967). The interaction of dyes with ion exchange resins.J. Chromat,26, 334–6.

    Google Scholar 

  • Byrne, J. M. (1963). Electrophoresis of acid dyes.Q. Jl. microsc. Sci. 104, 441–3.

    Google Scholar 

  • Cain, J. C. &Thorpe, J. F. (1933).The Synthetic Dyestuffs, 7th Ed. London: Griffin.

    Google Scholar 

  • Callan, T. &Henderson, J. A. R. (1922). Estimation of the vitro group in aromatic organic compounds.J. Soc. chem. Ind., Lond. 41, 157T-164T.

    Google Scholar 

  • Chamberlin, E. M., Powell, B. F., Williams, D. E. &Conn, J. (1962). The structure of commercial Pyronin B.J. org. Chem. 27, 2263–4.

    Google Scholar 

  • Christman, J. F. &Cunningham, G. L. (1953). Chromatography and biological stains. 5. The isolation and spectral analysis of orange fat-staining component of Sudan 3.Stain Technol. 28, 275–7.

    PubMed  Google Scholar 

  • Christman, J. F. &Trubey, R. H. (1952). Chromatography and biological stains. I. Paper chromatography as a means of determining purity and dye content of Sudans 3 & 4.Stain Technol. 27, 53–60.

    PubMed  Google Scholar 

  • Christman, J. F. &Werner, H. J. (1953). Chromatography and biological stains. 4. Preparation of a suitable fat stain from commercial Sudan 3.Stain Technol. 28. 259–64.

    PubMed  Google Scholar 

  • Coats, E. &Rigg, B. (1961). Complex formation-data for Solochrome Violet R. 1. Ionisation constants.Trans. Faraday Soc. 57, 1088–92.

    Google Scholar 

  • Conn, H. J. (1961).Biological Stains. 7th Ed. Baltimore: Williams & Wilkins.

    Google Scholar 

  • Conn, H. J. &Holmes, W. C. (1928). Certain factors influencing the staining properties of fluorescein derivatives.Stain Technol. 3, 94–104.

    Google Scholar 

  • Copius-Peereboom, J. W. &Beekes, H. W. (1965). Thin-layer chromatography of dyestuffs on polyamide and ‘silver nitrate’ layers.J. Chromat. 20, 43–7.

    Google Scholar 

  • Corey, S. H. &Mckinney, R. M. (1962). Chromatography of Nitrofluoresceines, Aminofluoresceins and Fluorescein isothiocyanates.Analyt. Biochem. 4, 57–68.

    Google Scholar 

  • Criddle, W. J., Moody, G. J., &Thomas, J. D. R. (1964). Thin film electrophoresis. 1. The electrophoretic behaviour of coal-tar food colours on paper and thin films.J. Chromat. 16, 350–9.

    Google Scholar 

  • Dallas, M. S. J. (1968). Precision in the direct densitometry of coloured compounds on thin layers.J. Chromat. 33, 337–46.

    Google Scholar 

  • Davidek, J. &Janicek, G. (1964). Chromatography of fat soluble food dyes on thin starch layers with stationary non-polar phases.J. Chromat. 15, 542–5.

    Google Scholar 

  • Davidek, J., Pokorny, J. &Janicek, G. (1961).Z. Lebensmittlunters. u. Forsch. 116, 13.

    Google Scholar 

  • Dawson, T. L. (1964). The reaction mechanism and fixation of monochloro-s-trazine dyes on cellulose using tertiary amine catalysts.J. Soc. Dyers Colour. 80, 134–43.

    Google Scholar 

  • De Deyne, V. J. R. &Vetters, A. F. (1967). Techniques to reduce errors in quantitative thin-layer chromatography using elution.J. Chromat. 31, 261–2.

    Google Scholar 

  • Demetriou, J. A., Macias, F. M., Mcarthur, M. J. &Beattie, J. M. (1968). Gel filtration chromatography of fluorescent phenolic and heterocyclic compounds.J. Chromat. 34, 342–50.

    Google Scholar 

  • Dobres, H. L. &Moats, W. A. (1968). Qualitative analysis by thin-layer chromatography of some common dyes used in biological staining.Stain Technol. 43, 27–30.

    PubMed  Google Scholar 

  • Dose, K. &Krause, G. (1962). Preparative electrophoresis on Sephadex.Naturwissenschaften 49, 349.

    Google Scholar 

  • Drawert, H. (1955). Fluorescent vital staining with supposed ‘Magdala Red’.Flora, Fena 142, 479–88.

    Google Scholar 

  • Drawert, H. (1956). The uptake of dyes. Vital staining. InHandb. PflPhysiol. (ed. W. Ruhland),2, 252–89. Berlin: Springer.

    Google Scholar 

  • Durrum, E. L. (1951). Continuous electrophoresis and ionophoresis on filter paper.J. Am. chem. Soc. 73, 4875–80.

    Google Scholar 

  • Egerton, G. S., Gleadle, J. M. &Uffindell, N. D. (1967). Purification of organic dyes, particularly of the Anthraquinone series.J. Chromat. 26, 62–71.

    Google Scholar 

  • Emery, A. J., Knapp Hazen, F. &Stotz, E. (1950). Spectrophotometric characteristics and assay of biological stains. 3. The Xanthenes.Stain. Technol. 25, 201–8.

    PubMed  Google Scholar 

  • Emery, A. J. &Stotz, E. (1953). Spectrophotometric characteristics and assay of biological stains. 4. The Phenyl Methane dyes.Stain Technol. 28, 235–44.

    PubMed  Google Scholar 

  • Engle, R. L. &Dempsey, E. W. (1954). The separation of Orcein into four fractions by chromatography and the staining qualities of each fraction.J. Histochem. Cytochem. 2, 9–20.

    PubMed  Google Scholar 

  • Evans, E. E. &Walls, K. W. (1952). The separation of biological stains by filter paper electrophoresis.J. Bact. 63, 422–3.

    PubMed  Google Scholar 

  • Felton, L. C. &McMillion, C. R. (1961). Chromatographically pure Fluorescein and Tetramethylrhodamine isothiocyanates.Analyt. Biochem. 2, 178–80.

    PubMed  Google Scholar 

  • Fernando, J., Morgan, W. S. &Hausser, J. W. (1967). Structure of Neutral Red and other 2,8-substituted aminophenazines.J. org. Chem. 32, 1120–3.

    PubMed  Google Scholar 

  • Fredericsson, B., Laurent, T. C. &Lüning, B (1958). Decomposition of Sudan Black B causing an artifact in the staining of lipids.Stain Technol. 33, 155–8.

    PubMed  Google Scholar 

  • French, R. W. (1927). Extinction coefficients of dyes.Stain Technol. 2, 124–5.

    Google Scholar 

  • Frodyma, M. M., Frei, R. W. &Williams, D. J. (1964). The application of spectral reflectance to thin-layer chromatography.J. Chromat. 13, 61–8.

    Google Scholar 

  • Frommhagen, L. H. &Spendlove, R. S. (1962). The staining properties of human serum proteins conjugated with purified Fluorescein isothiocyanate.J. Immun. 89, 124–31.

    PubMed  Google Scholar 

  • Giles, C. H. &Greczek, J. J. (1962). A review of methods of purifying and analysing water soluble dyes.Text. Res. J. 32, 506–15.

    Google Scholar 

  • Gill, J. E. (1967). Partition and ion-exchange thin layer chromatography of watersoluble fluorescent compounds.J. Chromat. 26, 315–19.

    Google Scholar 

  • Goldman, J. G. &Goodall, R. R. (1968). Quantitative analysis on thin layer chromatograms: A theory for light adsorption methods with an experimental verification.J. Chromat. 32, 24–42.

    Google Scholar 

  • Green, F. J. (1966). Polychromasia of Cresyl Violet dyes; a chemical explanation of variation in pre-world war 2 products.Stain Technol. 41, 223–8.

    PubMed  Google Scholar 

  • Grossmann, H. &Wagner, H. (1968). Electrophoresis and thin layer gel-filtration of Nitro BT.J. Chromat. 35, 301–3.

    Google Scholar 

  • Gupta, V. S., Kraft, S. C. &Samuelson, J. S. (1967). Purification and properties of Acriflavine, Proflavine and related compounds.J. Chromat. 26, 158–63.

    Google Scholar 

  • Hais, I. M. &Malek, K. (editors). (1963).Paper Chromatography. A Comprehensive Treatise, 3rd Ed. New York: Academic Press.

    Google Scholar 

  • Hanig, I. &Koch, L. (1963). Quantitative paper chromatography of D & C Red No. 21 (tetrabromofluorescein).J. Ass. off. agric. Chem. 46, 1010–13.

    Google Scholar 

  • Herdon, J. F., Touchstone, J. C., White, G. R. &Davis, C. N. (1963). Horizontal chromatography accelerating apparatus. Separation of dyes and indicators.Analyt. Chem. 35, 238–40.

    Google Scholar 

  • Holmes, F. H. (1958). The absorption spectrum and substantivity to cotton of Congo Red and related structures.Trans. Faraday Soc. 43, 1166–71.

    Google Scholar 

  • Holmes, W. C. (1927). Subsidiary dyes in Methylene Blue.Stain Technol. 2, 71–3.

    Google Scholar 

  • Holmes, W. C. (1928). The spectrophotometric evaluation of mixtures of Methylene Blue and Trimethyl Thionin.Stain Technol. 3, 45–8.

    Google Scholar 

  • Holmes, W. C. &French, R. W. (1926). The oxidation products of Methylene Blue.Stain Technol. 1, 17–26.

    Google Scholar 

  • Holmes, W. C., Martin, C. G. &Peterson, A. R. (1932). Eosin B.Stain Technol. 7, 121–7.

    Google Scholar 

  • Holmes, W. C. &Peterson, A. R. (1930). The analysis of Neutral Red R and of the Pyronins.Stain Technol. 5, 91–6.

    Google Scholar 

  • Holmes, W. C. &Scanlan, J. T. (1927). The evaluation of Ethyl Eosin.Stain Technol. 2, 101–3.

    Google Scholar 

  • Horobin, R. W. (1968a). Simple preparative thin layer chromatography.J. Chromat. 37, 354–6.

    Google Scholar 

  • Horobin, R. W. (1968b). A simple method for desalting biological dyes. (Manuscript in preparation).

  • Horobin, R. W. &Murgatroyd, L. B. (1967). A comparison of rapid electrophoretic and chromatographic methods for the investigation of common histological dyes.Histochemie 11, 141–51.

    PubMed  Google Scholar 

  • Horobin, R. W. &Murgatroyd, L. B. (1968a). The composition and properties of Gallocyanin-chrome alum stains.Histochem. J. 1, 36–54.

    Google Scholar 

  • Horobin, R. W. & Murgatroyd, L. B. (1968b). Analysis and purification of Pyronin and Rhodamin dyes. (Manuscript in preparation).

  • Horobin, R. W. &Williams, M. A. (1967). Agar gel electrophoresis: an advantageous technique for the investigation of certain biological stains.Stain Technol. 42, 137–42.

    PubMed  Google Scholar 

  • Jackson, J. H. E. &Turner, H. A. (1952). The desorption of a direct cotton dye from cellulosic fibres.J. Soc. Dyers Colour. 68, 345–52.

    Google Scholar 

  • Jencks, W. P., Durrum, E. L. &Jetton, M. R. (1955). Paper electrophoresis as a quantitative method: the staining of serum lipoproteins.J. clin. Invest. 34, 1437–48.

    PubMed  Google Scholar 

  • Jirsa, M. &Hykes, P. (1966). The use of Sephadex for the desalting of dyes.J. Chromat. 21, 122–3.

    Google Scholar 

  • Jirsa, M. &Rahan, P. (1962). Metabolism of Rose Bengal.Nature, Lond. 195, 1100–1.

    Google Scholar 

  • Kamikura, M. (1966). Thin-layer chromatography of synthetic dyes. 4. Separation and identification of water soluble dyes. 1. On the developing solvent and condition of activation of silica gel.Chem. Abstr. (1967),66, 66715 (Abstract of paper inShakuhin Eiseigaku Zassli. 7, 338–42).

    Google Scholar 

  • Kasten, F. H. (1967). Cytochemical studies with Acridine Orange and the influence of dye contaminants in the staining of nucleic acids.Int. Rev. Cytol. 21, 141–202.

    PubMed  Google Scholar 

  • Kasten, F. H., Burton, V. &Lofland, S. (1962). Schiff-type reagents in cytochemistry. 2. Detection of primary amine impurities in Pyronin B & Y(G).Stain Technol. 37, 277–91.

    PubMed  Google Scholar 

  • Kasten, F. H. &Sandritter, W. (1962). Crystal Violet contamination of Methyl Green and purification of Methyl Green—A historical note.Stain Technol. 37, 253–4.

    PubMed  Google Scholar 

  • Kay, W. W., &Whitehead, R. (1941). The role of impurities and mixtures of isomers in the staining of fat by commercial Sudans.J. Path. Bact. 53, 279–84.

    Google Scholar 

  • Kelenyi, G. (1967). On the histochemistry of azo group-free thiazole dyes.J. Histochem. Cytochem. 15, 172–80.

    PubMed  Google Scholar 

  • Kelly, J. W. (1958a). Paper chromatography of anionic disazo dyes, especially Trypan Blue and its red impurity.Stain Technol. 33, 79–88.

    PubMed  Google Scholar 

  • Kelly, J. W. (1958b). Staining reactions of some anionic disazo dyes and histochemical properties of the red impurity in Trypan Blue.Stain Technol. 33, 89–94.

    PubMed  Google Scholar 

  • Kelly, J. W., Feagans, W. M., Parker, J. C. &Porterfield, J. M. (1964). Studies on the mechanism of Trypan Blue-induced congenital malformations. I. Dye fraction and foetal abnormalities.Exper. mol. Path. 3, 262–78.

    Google Scholar 

  • Kirchner, J. G. (1967).Thin-Layer Chromatography. New York: Interscience.

    Google Scholar 

  • Kitahara, S. &Hiyama, H. (1955). Paper chromatography of the reduction products of dyes from benzidine and its derivatives.J. chem. Soc. Japan 58, 620–5.

    Google Scholar 

  • Knapp, F., Emery, A. J. &Stotz, E. (1950). Spectrophotometric characteristics and assay of biological stains. 2. The Thiazins.Stain Technol. 25, 62–8.

    Google Scholar 

  • Knecht, E. &Hibbert, E. (1925).New Reduction Methods in Volumetric Analysis, 2nd Ed. London: Longmans, Green & Co.

    Google Scholar 

  • Kramer, H. &Windrum, G. M. (1955). The metachromatic staining reaction.J. Histochem. Cytochem. 3, 227–37.

    PubMed  Google Scholar 

  • Kubin, R. H., Grodsky, G. M. &Corbone, J. V. (1960). Investigation of Rose Bengal conjugation.Proc. Soc. exp. Biol. Med. 104, 650–3.

    PubMed  Google Scholar 

  • Kurnick, N. B. (1955). Pyronin Y in the Methyl-Green-Pyronin histological stain.Stain Technol. 30, 213–30.

    PubMed  Google Scholar 

  • Kutt, H., Lockwood, D. &McDowell, F. (1959a). The lipid and protein staining properties of Sudan 2, 3 and 4 and their components.Stain Technol. 34, 197–202.

    PubMed  Google Scholar 

  • Kutt, H., Lockwood, D. &McDowell, F. (1959b). Decomposition of Sudan Black B by ultraviolet light and gases; its lipid and protein staining properties.Stain Technol. 34, 203–8.

    PubMed  Google Scholar 

  • Kutt, H. &Tsaltas, T. T. (1959). The staining properties of Oil Red O and a method of partial purification of the commercial product.Clin. Chem. 5, 149–60.

    PubMed  Google Scholar 

  • Labor, G. C. &Martin, S. L. (1959). Studies on haematoxylin and haematein, the colouring principles of logwood. I. Absorption spectra of pure compounds in various solvents and a spectrophotometric method of analysis for haematoxylin and haematein.J. Soc. Dyers Colour. 75, 513–17.

    Google Scholar 

  • Latta, T. (1954). B.Sc. Thesis, Glasgow University. Cited by Giles, C. H. & Greczek, J. J. inText. Res. J. (1962),32, 506–17.

  • Lederer, E. &Lederer, M. (1954).Chromatography: A Review of Principles and Applications. Amsterdam: Elsevier.

    Google Scholar 

  • Leske, R. (1967). Paper chromatographic analysis of fluorescent labelling dyes.Acta histochem.Supplement 7, 185–90.

    Google Scholar 

  • Liebmann, R. (1967). Multilayer chromatography in difficult separations.Angew. Chem. (International Edition)6, 374.

    Google Scholar 

  • Lillie, R. D. (1965).Histopathologic Technic and Practical Histochemistry, 3rd Ed. New York: Blakiston.

    Google Scholar 

  • Lima, F. W. &Pieroni, R. R. (1959). Paper chromatographic separation of components of Rose Bengal labelled with iodine-131.Nature, Lond. 184, 1065.

    Google Scholar 

  • Lima-De-Faria, A. &Bose, S. (1954). Comparative analysis of Aceto-Carmine solutions.Caryologia,6, Supplement, 652–3.

    Google Scholar 

  • Lloyd, J. B. &Beck, F. (1963). An evaluation of acid disazo dyes by chloride determination and paper chromatography.Stain Technol. 38, 165–71.

    PubMed  Google Scholar 

  • Lloyd, J. B. &Beck, F. (1964). The identification of some acid disazo dyes by paper electrophoresis of their reduction products.Stain Technol. 39, 7–12.

    PubMed  Google Scholar 

  • Loev, B. & Goodman, M. M. (1967). Dry-column chromatography: A preparative chromatographic technique with the resolution of thin-layer chromatography.Chemy Ind., 2026–32.

  • Longley, J. B. (1952). Effectiveness of Schiff variants in the periodic acid-Schiff and Feulgen neucleal techniques.Stain Technol. 27, 161–9.

    PubMed  Google Scholar 

  • Maurina, F. A. &Deahl, N. (1943). A study of assay methods for Methylene Blue.J. Am. pharm. Ass. Scientific Edition 32, 301–6.

    Google Scholar 

  • Mckinney, R. M., Spillane, J. T. &Pearse, G. W. (1964). Determination of purity of Fluorescein isothiocyanates.Analyt. Biochem. 7, 74–86.

    Google Scholar 

  • Mcneil, C. (1960). The separation and identification of commercial dyes by paper chromatography. I. Acid dyes.J. Soc. Dyers Colour. 76, 272–5.

    Google Scholar 

  • Mehta, C. D. &Shah, K. H. (1966). Purification of reactive dyes.Indian J. appl. Chem. 24, 122–4.

    Google Scholar 

  • Mitchell, P. (1950). Crystallisation of Congo Red.Nature, Lond. 165, 772–3.

    Google Scholar 

  • Murakami, M., Yoshino, T. &Harasawa, S. (1967). Separation and acid equilibria of Xylenol Orange and Semi-Xylenol Orange.Tantala 14, 1293–1307.

    Google Scholar 

  • Musso, H. (1960). Orcein and Litmus pigments: constitutional elucidation and constitutional proof by synthesis.Planta med. 8, 432–46.

    Google Scholar 

  • Nash, N., Allen, P., Bevenue, A., &Beckman, H. (1963). A technique for the recovery of compounds from thin-layer chromatography strips for infra-red analysis.J. Chromat. 12, 421–3.

    Google Scholar 

  • Neal, S. M. &Hanson, J. (1932). The true weight of Benzopurpurin 4B, and the electrical conductivity of its aqueous solutions.Nature, Lond. 129, 761.

    Google Scholar 

  • Nerenberg, C. &Fischer, R. (1963). Purification of Thionin, Azur A, Azur B and Methylene Blue.Stain Technol. 38, 75–84.

    Google Scholar 

  • Ney, M. (1967). Carmine dyes and Archil.Dt. LebensmittRdsch. 63, 167–70.

    Google Scholar 

  • Nietruch, F. &Preschler, K.-E. (1967). Purity testing of parafuchsine dyes. Appraisal of their utility for sulphur dioxide determination.Z. analyt. Chem. 231, 29–34.

    Google Scholar 

  • Olin, J. S. (1966). The use of infrared spectroscopy in the examination of paintings and ancient artifacts.Instrum. News. 17, No. 2, 1 & 4–5.

    Google Scholar 

  • Ortman, R., Forbes, W. F. &Balasubramanian (1966). Concerning the staining properties of aldehyde basic fuchsin.J. Histochem. Cytochem. 14, 104–11.

    PubMed  Google Scholar 

  • Palmer, R. W. &Lillie, R. D. (1965). Spectroscopic and staining studies of the ripening and overripening of aluminium hematoxylins.Histochemie 5, 44–54.

    PubMed  Google Scholar 

  • Parrish, J. R. (1968). Chromatography of food dyes on Sephadex.J. Chromat. 33, 542–3.

    Google Scholar 

  • Parsons, J. S. &Seaman, W. (1955). Coulometric titration of dyes with externally generated titanous ion.Analyt. Chem. 27, 210–12.

    Google Scholar 

  • Pastuska, G. &Trinks, H. (1962). Investigations using thin-layer electrophoresis.Chemikerzeitung 86, 135–8.

    Google Scholar 

  • Paul, M. H. &Durrum, E. L. (1952). Ionophoresis in non-aqueous systems.J. Am. chem. Soc. 74, 4721–2.

    Google Scholar 

  • Payne, R. W. (1934). Determination of basic dyes by precipitation with phosphotungstic acid.J. Soc. Dyers Colour. 50, 320.

    Google Scholar 

  • Persijn, J.-P. (1961). Improved solvents for paper chromatography of Thiazine stains.Stain Technol. 36, 27–29.

    PubMed  Google Scholar 

  • Person, P. (1966). Turbid system spectrophotometry with the Perkin-Elmer Model 450.Instrum. News. 17, No. 2, 13–15.

    Google Scholar 

  • Persson, B. H. (1952). Studies on connective tissue ground substance.Acta Soc. Med. upsal. 58, Supplement 2, 1–104.

    Google Scholar 

  • Peters, R. H., Petropoulos, J. H. &McGregor, R. (1961). A study of the diffusion of dyes in polymer films by a microdensitometric technique.J. Soc. Dyers Colour. 77, 704–14.

    Google Scholar 

  • Pollard, F. H., Nickless, G., Samuelson, T. J. &Anderson, R. G. (1964). Thin-film chromatography of some azo-dyestuffs.J. Chromat. 16, 231–3.

    Google Scholar 

  • Porro, T. J., Dadik, S. P., Green, M. &Morse, H. T. (1963). Fluorescence and absorption spectra of biological dyes.Stain Technol. 38, 37–48.

    PubMed  Google Scholar 

  • Pristoupil, T. I. &Kramdova, M. (1968). Membrane chromatography of dyes on nitrocellulose filters.J. Chromat. 34, 21–5.

    Google Scholar 

  • Przybylowicz, E. P., Staudenmeyer, W. J., Perry, E. S., Baitsholts, A. D. &Tischer, T. N. (1965). Precoated sheets for thin layer chromatography.J. Chromat. 20, 506–13.

    Google Scholar 

  • Pucar, Z. (1960). Continuous electrophoresis and two dimensional electrophoresis-chromatography.J. Chromat. 4, 261–318.

    Google Scholar 

  • Puchtler, H., Sweat, F. &Doss, N. O. (1964). A one-hour phosphotungstic acid-hematoxylin stain.Am. J. clin. Path. 40, 334–7.

    Google Scholar 

  • Puchtler, H., Sweat, F. &Levine, M. (1962). On the binding of Congo Red by amyloid.J. Histochem. Cytochem. 10, 355–63.

    Google Scholar 

  • Purdy, S. J. & Truter, E. V. (1962). The weight-area relationship in thin film chromatography.Chemy Ind. 506–7.

  • Raban, P. (1963). Adsorption chromatography of direct azo dyes.Nature, Lond. 199, 596–7.

    Google Scholar 

  • Randerath, K. (trans. D. D. Libman) (1966).Thin Layer Chromatography, 2nd Ed. New York & London: Academic Press.

    Google Scholar 

  • Rebek, M. &Semlitisch, M. K. (1961). Preparation of pure Crystal Violet Base by ion-exchange.Mh. Chem. 92, 214–18.

    Google Scholar 

  • Rentsch, G. &Wittekind, D. (1967). The labelling of proteins with fluorescent fractions of Fluorescein isothiocyanate.Acta histochem.Supplement 7, 191–8.

    Google Scholar 

  • Rettie, G. H. &Haynes, C. G. (1964). Thin-layer chromatography and its application to dyes.J. Soc. Dyers Colour. 80, 629–40.

    Google Scholar 

  • Ribeiro, P. L., Mitidieri, E. &Affonso, U. R. (trans. C. Cole) (1961).Paper Electrophoresis: A Review of Methods and Results. Amsterdam: Elsevier.

    Google Scholar 

  • Rice, D. D. (1967). A direct transfer technique for preparing micropellets from thin layer chromatograms for infrared identification.Analyt. Chem. 39, 1906–7.

    Google Scholar 

  • Richardson, R. W. (1951). Selective diffusion into ion-exchange resins. A new method for the purification of the direct cotton dyes.J. chem. Soc. 190–14.

  • Robinson, C. &Mills, H. A. T. (1931). The colloid chemistry of dyes: the aqueous solutions of Benzopurpurine 4B and its Isomer prepared from m-tolidine, Part 1,Proc. R. Soc. A. 131, 576–95.

    Google Scholar 

  • Robinson, R. L. &Bacsich, P. (1958). Improving the staining qualities of Toluidine Blue.Stain Technol. 33, 171–3.

    PubMed  Google Scholar 

  • Rose, R. E. (1933).J. ind. Engng Chem. 25, 1029. Cited by Giles, C. H. & Greczek, J. J. inText Res. J. (1962),32, 506–15.

    Google Scholar 

  • Rosenthal, S. I., Puchtler, H. &Sweat, F. (1965). Paper chromatography of dyes.Archs Path. 80, 190–6.

    Google Scholar 

  • Rottiers, P. B. (1953). Spectrophotometry of dyes. 1. Methyl Green. 2. Pyronin.Stain Technol. 28, 265–73.

    PubMed  Google Scholar 

  • Ruiz, I. S. L. & Laroche, C. (1963). Thin-layer chromatography of synthetic dyes.Bull. Soc. chim. Fr. 1594–7.

  • Schott, H. (1964). Ultrafiltration of non-ionic detergent solutions.J. Phys. Chem., Ithaca 68, 3612–18.

    Google Scholar 

  • Scott, J. E. (1967). On the mechanism of the Methyl Green-Pyronin stain for nucleic acids.Histochemie 9, 30–47.

    PubMed  Google Scholar 

  • Seki, M. (1932). The physical chemistry of histological dyes. 1. Electrophoresis of acid and basic dyes, and the staining of silica by acid and basic dyes.Folia anat. jap. 10, 621–34.

    Google Scholar 

  • Seki, M. (1933a). The physical chemistry of histological dyes. Carmine dyes.Folia anat. jap. 11, 1–13.

    Google Scholar 

  • Seki, M. (1933b). The physical chemistry of histological dyes. 4. The hematein dyes.Folia anat. jap. 11, 15–36.

    Google Scholar 

  • Seki, M. (1933c). The physical chemistry of histological dyes. 6. Investigations on Orcein.Folia anat. jap. 11, 391–403.

    Google Scholar 

  • Shapiro, J. (1961). Freezing out, a safe technique for concentration of dilute solutions.Science, N.Y. 133, 2063–4.

    Google Scholar 

  • Sheludko, A., Konstantinov, G. &Tsvetanov, K. (1959). Electrophoresis of dyes in the gelatin layer of photographic film.Kolloid Zh. 21, 747–53. Cited byChem. Abstr. (1961),55, 6217.

    Google Scholar 

  • Sibatini, A. (1952). Differential staining of nucleic acids. 1. Methyl Green-Pyronin.Cytologia 16, 315–24.

    Google Scholar 

  • Singh, C. (1963). Heterogeneity and metachromasy of some commercial anionic dyes.Stain Technol. 38, 103–10.

    PubMed  Google Scholar 

  • Smith, W. F. &Eddy, K. L. (1966). Liquid-liquid partition chromatography with the system chloroform-benzene-nitromethane.J. Chromat. 22, 296–302.

    Google Scholar 

  • Smyth, J. D. (1953). Standardisation of Methyl Green for specific staining of eggshell material in a trematode.Q. Jl. microsc. Sci. 94, 243–6.

    Google Scholar 

  • Spenser, R. D. &Beggs, B. H. (1966). Thin-layer chromatography on silica gel: quantitative analysis by direct ultraviolet spectrophotometry.J. Chromat. 21, 52–66.

    Google Scholar 

  • Sramek, J. (1964). Paper chromatography of dyes. 5. Paper chromatography of water soluble dyes.J. Chromat. 15, 57–64.

    Google Scholar 

  • Stahl, E. (1964). Gradient and low-temperature thin-layer chromatography.Angew. Chem. (International Edition)3, 784–91.

    Google Scholar 

  • Stahl, E. (Editor) (1965).Thin-Layer Chromatography, A Laboratory Handbook, 2nd Ed. New York & London: Academic Press.

    Google Scholar 

  • Stewart, A. (1951). The function of adsorbent activity in the chromatographic separation of certain Anthraquinone compounds. InDiscuss. Faraday Soc., No. 7, Chromatographic Analysis, pp. 65–79.

  • Stier, A. &Specht, W. (1963). Chromatographic investigation of xanthene dyes for histological staining after the method of Unna-Pappenheim.Naturwissenschaften 50, 549.

    Google Scholar 

  • Stotz, E., Conn, H. J., Knapp, F. &Emery, A. J. (1950). Spectrophotometric characteristics and assay of biological stains.Stain Technol. 25, 57–62.

    Google Scholar 

  • Stoward, P. J. (1967a). Studies in fluorescence histochemistry. 1. The demonstration of sulphomucin.Jl. R. microsc. Soc. 87, 215–35.

    Google Scholar 

  • Stoward, P. J. (1967b). Studies in fluorescence histochemistry. 2. The demonstration of periodate-reactive mucosubstances with pseudo Schiff reagents.Jl. R. microsc. Soc. 87, 237–46.

    Google Scholar 

  • Stutz, M. H., Ludemann, W. H. &Sass, S. (1968). Improved method for preparative chromatography.Analyt. Chem. 40, 258–9.

    Google Scholar 

  • Sumner, B. E. H. (1965). Experiments to determine the composition of Aldehyde-fuchsin solutions.Jl. R. microsc. Soc. 84, 181–7.

    Google Scholar 

  • Taylor, K. B. (1960a). Chromatographic separation and isolation of metachromatic thiazine dyes.J. Histochem. Cytochem. 8, 248–57.

    PubMed  Google Scholar 

  • Taylor, K. B. (1960b). Chromatography of Xanthene dyes.Nature, Lond. 185, 243–4.

    Google Scholar 

  • Taylor, K. B. (1961). The influence of the molecular structure of Thiazine and Oxazine dyes on their metachromatic properties.Stain Technol. 36, 73–83.

    PubMed  Google Scholar 

  • Terner, J. Y. (1966). Phosphotungstic acid-hematoxylin. Reactivityin vitro.J. Histochem. Cytochem. 14, 345–51.

    PubMed  Google Scholar 

  • Trotman, S. R. &Freabson, T. B. (1931). Quantitative analysis of dyestuffs.J. Soc. Dyers Colour. 47, 344–7.

    Google Scholar 

  • Trubey, R. H. &Christman, J. F. (1952). Chromatography and biological stains. 2. Column chromatographic separation of the colored materials in commercial Sudan 3.Stain Technol. 27, 87–92.

    PubMed  Google Scholar 

  • Venkataraman, K. (1952).The Chemistry of Synthetic Dyes, vol. 2 New York: Academic Press.

    Google Scholar 

  • Vickerstaff, T. (1954).The Physical Chemistry of Dyeing, 2nd Ed. London, Edinburgh: Oliver & Boyd.

    Google Scholar 

  • Visser, R., (1967). Continuous preparative thin-layer chromatography.Analytica chim. Acta.,38, 157–62.

    Google Scholar 

  • Werner, H. J. &Christman, J. F. (1952). Chromatography and biological stains. 3. Comparison of the fat staining efficiencies of fractions of commercial Sudan 3 separated by column chromatography.Stain Technol. 27, 93–6.

    PubMed  Google Scholar 

  • Winterstein, A. &Hegedus, B. (1960). The occurrence of retinence in nature.Hoppe-Seylers Z. physiol. Chem. 321, 97–106.

    PubMed  Google Scholar 

  • Wollenweber, P. (1962). Separation of dyes by thin-layer chromatography on cellulose layers.J. Chromat.,7, 557–60.

    Google Scholar 

  • Yarbo, C. L., Miller, B. &Anderson, C. E. (1954) Purifying pararoaniline for use in colourless Schiff reagents.Stain Technol. 29, 299–300.

    PubMed  Google Scholar 

  • Zwaan, J. &Van Dam, A. F. (1961). Rapid separation of fluorescent anti-sera and unconjugated dye.Acta histochem. 11, 306–8.

    PubMed  Google Scholar 

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Horobin, R.W. The impurities of biological dyes: their detection, removal, occurrence and histological significance—a review. Histochem J 1, 231–265 (1969). https://doi.org/10.1007/BF01081411

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