105
Views
8
CrossRef citations to date
0
Altmetric
Original Papers

Inaccurate chemical structures of dyes and fluorochromes found in the literature can be problematic for teaching and research

&
Pages 52-60 | Accepted 12 Apr 2010, Published online: 26 May 2010

References

  • Abrahart EN (1968) Dyes and their Intermediates. Pergamon Press, London, New York. 234–236.
  • Allen RLM (1971) Colour Chemistry. Thomas Nelson, Melbourne, Australia. 58, 199, 200.
  • Baliga R, Crothers DM(2000) On the kinetics of distamycin binding to its target sites on duplex DNA. Proc. Nat. Acad. Sci. USA 97: 7814–7818.
  • Bertolesi GE, Trigoso CI, Espada J, Stockert JC (1995) Cytochemical application of tris(2,2′-bipyridine)ruthenium(II): fluorescence reaction with sulfated polyanions of mast cell granules. J. Histochem. Cytochem. 43: 537–543.
  • Bradley PG, Kress N, Hornberger BA, Dallinger RF, Woodruff WH (1981) Vibrational spectroscopy of the electronically excited state. 5. Time-resolved resonance Raman study of tris(bipyridine)ruthenium(II) and related complexes. Definitive evidence for the “localized” MLCT state. J. Am. Chem. Soc. 103: 7441–7446.
  • Bruni A, Fasulo MP, Tosi B, Dall'Olio G, Vannini GL (1976) Fluorogenic detection of primary amines in plant histochemistry with fluorescamine: a comparative study on the effects of coagulant and non-coagulant fixatives. Histochemistry 48: 269–281.
  • Cameron DW, Deutscher DJ, Feutrill GI, Griffiths PG (1981) Chemistry of the Coccoidea. VIII. Synthesis of the ancient dyestuff kermesic acid and of related anthraquinones. Aust. J. Chem. 34: 2401–2421.
  • Chen X, Ramakrishnan B, Sundaralingam M (1997) Crystal structures of the side-by-side binding of distamycin to AT-containing DNA octamers d(ICITACIC) and d(ICATATIC). J. Mol. Biol. 267: 1157–1170.
  • Cooksey C (2009) Historic dyes and how to identify them. Biotech. & Histochem. 84: 123–134.
  • Cooksey C (2010) Hematoxylin and related compounds – an annotated bibliography concerning their origin, properties, chemistry, and certain applications. Biotech. & Histochem. 85: 65–82.
  • Cuéllar T, Gosálvez J, Del Castillo P, Stockert JC (1991) Fluram induces species-dependent C and G bands in mammalian chromosomes, revealing heterogeneous distribution of chromosomal proteins. Genome 34: 772776.
  • Dapson RW (2005) Dye-tissue interactions: mechanisms, quantification and bonding parameters for dyes used in biological staining. Biotech. & Histochem. 80: 49–72.
  • Dapson RW (2007) The history, chemistry and modes of action of carmine and related dyes. Biotech. & Histochem. 82: 173–187.
  • Frank M, Dapson RW, Wickersham TW, Kiernan JA (2007) Certification procedures for nuclear fast red (Kernechtrot) CI 60760. Biotech. & Histochem. 82: 35–39.
  • Gadgil DD, Rama Rao AV, Venkataraman K (1968). Structure of kermesic acid. Tetrahedron Lett. 18: 2223–2227.
  • Gordon PF, Gregory P (1987) Organic Chemistry in Colour. Springer-Verlag, Berlin, New York. 3, 164.
  • Green FJ (1990) The Sigma-Aldrich Handbook of Stains, Dyes and Indicators. Aldrich Chemical Co. Milwaukee, WI.
  • Gupta AK (2005) The Complete Book on Natural Dyes and Pigments. Board of Consultants and Engineers of the National Institute of Industrial Research, Asia Pacific Business Press, Delhi, India. 330–332.
  • Håkanson R, Larsson LI, Sundler F (1974) Fluorescamine: a novel reagent for the histochemical detection of amino groups. Histochemistry 39: 15–23.
  • Haugland RP (2002) Handbook of Fluorescent Probes and Research Chemicals. 9th Molecular Probes, Eugene OR.
  • Horobin RW (1982) Histochemistry. An Explanatory Outline of Histochemistry and Biophysical Staining. Gustav Fischer, Stuttgart, New York. 149.
  • Horobin RW, Kiernan JA (2002) Conn's Biological Stains. A Handbook of Dyes, Stains and Fluorochromes for Use in Biology and Medicine. 10th BIOS Scientific Publishers, Oxford.
  • Islam SA, Neidle S, Gandecha BM, Partridge M, Patterson LH, Brown JR (1985) Comparative computer graphics and solution studies of the DNA interaction of substituted anthraquinones based on doxorubicin and mitoxantrone. J. Med. Chem. 28: 857–864.
  • Jeffrey GA (1997) An Introduction to Hydrogen Bonding. Oxford University Press, UK. 33–55, 194–201.
  • Karlsson HJ, Eriksson M, Perzon E, Åkerman B, Lincoln P, Westman G (2003) Groove-binding unsymmetrical cyanine dyes for staining of DNA: syntheses and characterization of the DNA-binding. Nucl. Acids Res. 31: 6227–6234.
  • Kelényi G (1967) On the histochemistry of azo group-free thiazole dyes. J. Histochem. Cytochem. 15: 172–180.
  • Krebs MR, Bromley EH, Donald AM (2005) The binding of thioflavin-T to amyloid fibrils: localisation and implications. J. Struct. Biol. 149: 30–37.
  • LeVine H (1993) Thioflavin T interaction with synthetic Alzheimer's disease beta-amyloid peptides: detection of amyloid aggregation in solution. Protein Sci. 2: 404–410.
  • Lillie RD (1977) H. J. Conn's Biological Stains, 9th Williams and Wilkins, Baltimore. 369–371, 476–479.
  • Lojda Z (1965) Remarks on the histochemical demonstration of dehydrogenases. II. Intracellular localization. Folia Morphol. 13: 84–97.
  • Loontiens FG, Regenfuss P, Zechel A, Dumortier L, Clegg RM (1990) Binding characteristics of Hoechst 33258 with calf thymus DNA, poly[d(A-T)], and d(CCGGA ATTCCGG): multiple stoichiometries and determination of tight binding with a wide spectrum of site affinities. Biochemistry 29: 9029–9039.
  • Mikheikin AL, Zhuze AL, Zasedatelev AS (2000) Binding of symmetrical cyanine dyes into the DNA minor groove. J. Biomol. Struct. Dyn. 18: 59–72.
  • Mrksich M, Dervan PB (1993) Antiparallel side-by-side heterodimer for sequence-specific recognition in the minor groove of DNA by a distamycin/1-methylimidazole-2-carboxamide-netropsin pair. J. Am. Chem. Soc. 115: 2572–2576.
  • Pelton JG, Wemmer DE (1990) Binding modes of distamycin A with d(CGCAAATTTGCG)2 determined by two-dimensional NMR. J. Am. Chem. Soc. 112: 1393–1399.
  • Pindur U, Jansen M, Lemster T (2005) Advances in DNA-ligands with groove binding, intercalating and/or alkylating activity: chemistry, DNA binding and biology. Curr. Med. Chem. 12: 2805–2847.
  • Pinna-Senn E, Lisanti JA, Ortiz MI, Dalmasso G, Bella JL, Gosálvez J, Stockert JC (2000) Specific heterochromatic banding of metaphase chromosomes using Nuclear Yellow. Biotech. & Histochem. 75: 132–140.
  • Pjura PE, Grzeskowiak K, Dickerson RE (1987) Binding of Hoechst 33258 to the minor groove of B-DNA. J. Mol. Biol. 197: 257–271.
  • Prentø P (2009) Staining of macromolecules: possible mechanisms and examples. Biotech. & Histochem. 84: 139–158.
  • Puchtler H, Waldrop FS, Meloan SN (1983) Application of thiazole dyes to amyloid under conditions of direct cotton dyeing: correlation of histochemical and chemical data. Histochemistry 77: 431–445.
  • Rěha D, Kabeláč M, Ryjáček F, Šponer J, Šponer JE, Elstner M, Suhai S, Hobza P (2002) Intercalators. 1. Nature of stacking interactions between intercalators (ethidium, daunomycin, ellipticine, and 4′,6-diaminide-2-phenylindole) and DNA base pairs. Ab initio quantum chemical, density functional theory, and empirical potential study. J. Am. Chem. Soc. 124: 3366–3376.
  • Seidler E (1991) The tetrazolium-formazan system –design and histochemistry. Progr. Histochem. Cytochem. 24: 1–86.
  • Seifert JL, Connor RE, Kushon SA, Wang M, Armitage BA (1999) Spontaneous assembly of helical cyanine dye aggregates on DNA nanotemplates. J. Am. Chem. Soc. 121: 2987–2995.
  • Stiller D, Katenkamp D, Thoss K (1972) Staining mechanism of thioflavine T with special reference to the localization of amyloid. Acta Histochem. 42: 234–245.
  • Stockert JC (1994) Stereoscopy of computer-drawn molecular structures. Biochem. Educ. 22: 23–25.
  • Stockert JC (2000) Cytochemistry of mast cells: new fluorescence methods selective for sulfated glycosaminoglycans. Acta Histochem. 102: 259–272.
  • Stockert JC (2005) The horse eosinophil as a model leucocyte for morphological and cytochemical studies. Braz. J. Morphol. Sci. 22: 73–84.
  • Stockert JC, Trigoso CI (1993) Fluorescence of eosinophil leukocyte granules induced by the fluorogenic reagent 2methoxy2,4diphenyl3(2H)furanone. Blood Cells 19: 423–430.
  • Stockert JC, Blázquez A, Galaz S, Juarranz A (2008) A mechanism for the fluorogenic reaction of amino groups with fluorescamine and 2methoxy2,4-diphenyl3(2H)-furanone. Acta Histochem. 110: 333–340.
  • Sugden JK (2004) Photochemistry of dyes and fluorochromes used in biology and medicine: some physicochemical background and current applications. Biotech. & Histochem. 79: 71–90.
  • Udenfriend S, Stein S, Böhlen P, Dairman W, Leimgruber W, Weigele M (1972) Fluorescamine: a reagent for assay of amino acids, peptides, proteins and primary amines in the picomole range. Science 178: 871–872.
  • Volkova KD, Kovalska VB, Segers-Nolten GM, Veldhuis G, Subramanian V, Yarmoluk SM (2009) Explorations of the application of cyanine dyes for quantitative α-synuclein detection. Biotech. & Histochem. 84: 55–61.
  • Wagner SJ, Sripchenko A (2003) Investigation of photosensitizing dyes for pathogen reduction in red cell suspensions. Biotech. & Histochem. 78: 171–177.
  • Wang AHJ, Ughetto G, Quigley GJ, Rich A (1987) The interaction between an anthracycline antibiotic and DNA: molecular structure of daunomycin complexed to d(CpGpTpApCpG) at 1.2 Å resolution. Biochemistry 26: 1152–1163.
  • Weigele M, Tengi JP, De Bernardo SL, Czajkowski R, Leimgruber W (1976) Fluorometric reagents for primary amines. Synthesis of 2-alkoxy- and 2-acyloxy-3(2H)-furanones. J. Org. Chem. 41: 388–389.
  • Windholz M (1983) The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 10th. Merck & Co. Rahway, NJ. 760.
  • Yarmoluk SM, Kovalska MY, Losytskyy MY (2008) Symmetric cyanine dyes for detecting nucleic acids. Biotech. & Histochem. 83: 131–145.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.