1,012
Views
0
CrossRef citations to date
0
Altmetric
Articles

Classification and naming of polymethine dyes used as staining agents for microscopy. A short guide for biomedical investigators

ORCID Icon & ORCID Icon

References

  • Actien-Gesellschaft für Anilin-Fabrikation in Berlin. 1903 Jun 5. Verfahren zur Darstellung sensibilisierend wirkender Farbstoffe der Cyaninenreihe. DE 155541.
  • Adams EQ, Haller HL. 1920. Kryptocyanines. A new series of photosensitizing dyes. J Am Chem Soc. 42:2661–2663. doi: 10.1021/ja01457a026.
  • Brooker LGS, Keyes GH, Heseltine DW. 1951. Color and constitution. XI. Anhydronium bases of p-hydroxystyryl dyes as solvent polarity indicators. J Am Chem Soc. 73:5350–5356. doi: 10.1021/ja01155a097.
  • D’Alessandro S, Priefer R. 2020. Non-porphyrin dyes used as photosensitizers in photodynamic therapy. J Drug Deliv Sci Technol. 60:101979. doi: 10.1016/j.jddst.2020.101979.
  • Farbwerke H. 1905 Jul 22. Verfahren zur Darstellung von blauen Farbstoffen der Chinolingruppe. DE 172118.
  • Fischer O, Scheibe G. 1920. Beitrag zur Kenntnis der Chinocyanine. J Prakt Chem. 100:86–90. doi: 10.1002/prac.19201000107.
  • Fromherz P, Hübener G, Kuhn B, Hinner MJ. 2008. ANNINE-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity. Eur Biophys J. 37:509–514. doi: 10.1007/s00249-007-0210-y.
  • Gregory P. 1990. Classification of dyes by chemical structure. In: Waring D, Hallas G, Eds. The chemistry and application of dyes. Plenum Press, New York, NY; p. 36–38. doi: 10.1007/978-1-4684-7715-3_2.
  • Hamer FM. 1964. The cyanine dyes and related compounds. In: Weissberger A, Ed. The chemistry of heterocyclic compounds. Vol. 18. Interscience, New York, NY; p. 34. doi: 10.1002/9780470186794.
  • Han J, Burgess K. 2009. Fluorescent indicators for intracellular pH. Chem Rev. 110:2709–2728. doi: 10.1021/cr900249z.
  • Herzfeld KF, Sklar AL. 1942. Colour and constitution of polymethine dyes. Rev Mod Phys. 14:294–302. doi: 10.1103/RevModPhys.14.294.
  • Hofmann AW. 1863. Researches on some of the artificial colouring matters. – No. I. On the composition of the blue derivatives of the tertiary monoamines derived from cinchonine. Proc Roy Soc. 12:410–418. doi: 10.1098/rspl.1862.0085.
  • Horobin RW, Kiernan JA, Eds. 2002. Conn’s biological stains: a handbook of dyes, stains and fluorochromes for use in biology and medicine. 10th ed. Bios, Oxford.
  • Kiernan JA. 2001. Classification and naming of dyes, stains and fluorochromes. Biotech Histochem. 76:261–277. doi: 10.1080/bih.76.5-6.261.278.
  • König W. 1922. Über die Konstitution der Pinacyanole, ein Beitrag zur Chemie der Chinocyanine. Ber Dtsch Chem Ges. 55:3293–3313. doi: 10.1002/cber.19220550942.
  • König W. 1925. Über “vinylenhomologe” Indol- und Pyrrol-Farbstoffe. Angew Chem. 38:743–748. doi: 10.1002/ange.19250383504.
  • König W. 1926. Über den Begriff der “Polymethinfarbstoffe” und eine davon ableitbare allgemeine Farbstoff-Formel als Grundlage einer neuen Systematik der Farbenchemie. J Prakt Chem. 112:1–36. doi: 10.1002/prac.19261120101.
  • Liu T, Huo F, Yin C, Li JF, Niu L. 2015. A highly selective fluorescence sensor for cysteine/homocysteine and its application in bioimaging. RSC Adv. 5:28713–28716. doi: 10.1039/C5RA03011K.
  • Mills WH, Braunholtz WT. 1923. The cyanine dyes. Part VII. A new method of formation of the carbocyanines. The constitution of the thioisocyanines and of kryptocyanine. J Chem Soc Trans. 123:2804–2813. doi: 10.1039/CT9232302804.
  • Mills WH, Hamer FM. 1920. The cyanine dyes. Part III. The constitution of pinacyanol. J Chem Soc Trans. 117:1550–1562. doi: 10.1039/CT9201701550.
  • Mills WH, Odams RC. 1924. The cyanine dyes. Part VIII. Synthesis of a 2 : 4′-carbocyanine. Constitution of the dicyanines. J Chem Soc Trans. 125:1913–1921. doi: 10.1039/CT9242501913.
  • Mustroph H. 2020. Cyanine dyes. Phys Sci Rev. 5:20190145. doi: 10.1515/psr-2019-0145.
  • Mustroph H. 2021. Streptocyanine dyes. Phys Sci Rev. 6:137–147. doi: 10.1515/psr-2020-0198.
  • Mustroph H. 2022a. Correspondence on “cyanine dyes containing quinolinemoieties: history, synthesis, optical properties and applications”. Chem Eur J. 28:e202103714. doi: 10.1002/chem.202103714.
  • Mustroph H. 2022b. Bring back order in the polymethine dye medley: classification, structure and spectra. Dyes Pigm. 208:110783. doi: 10.1016/j.dyepig.2022.110783.
  • Pfaff G, Ed. 2022. Encyclopedia of color, dyes, pigments. De Gruyter, Berlin.
  • Pfautsch S, Renard J, Tjoilker MG, Salih A. 2015. Phloem as capacitor: radial transfer of water into xylem of tree stems occurs via symplastic transport in ray parenchyma. Plant Physiol. 167:963–971. doi: 10.1104/pp.114.254581.
  • Riester O. 1963. Polymethinfarbstoffe. In: Foerst W, Ed. Ullmanns Encyklopädie der technischen Chemie. 3rd ed. Urban & Schwarzenberg, München; p. 315.
  • Schnitzer G. 1861. Ueber Anilinroth und Chinolinblau. Chem Centr NF. 6:636–638.
  • Shapiro HM. 2000. Membrane potential estimation by flow cytometry. Methods. 21:271–279. doi: 10.1006/meth.2000.1007.
  • Spalteholz W. 1883. Ueber Farbstoffe aus dem Steinkohlentheerchinolin. Ber Dtsch Chem Ges. 16:1847–1852. doi: 10.1002/cber.18830160267.
  • Stockert JC, Blázquez-Castro A. 2017. Fluorescence microscopy in life sciences. Bentham Books, Sharjah. doi: 10.2174/97816810851801170101.
  • Suvarna SK, Layton T, Bancroft JD. 2019. Bancroft’s theory and practice of histological techniques. 8th ed. Elsevier, Amsterdam.
  • Towns A. 2019. Colorants: general survey. Phys Sci Rev. 4:20190008. doi: 10.1515/psr-2019-0008.
  • Tyutyulkov N, Fabian J, Mehlhorn A, Dietz F, Tadjer A. 1991. Polymethine dyes – structure and properties. St. Kliment Ohridski University Press, Sofia; p. 18.
  • von Babo LH. 1857. Ueber einige Zersetzungsprodukte des Cinchonins. J Prakt Chem. 72:73–88. doi: 10.1002/prac.18570720110.
  • Williams CG. 1857. Researches on chinoline and its homologues. Trans R Soc Edinb. 21:377–401. doi: 10.1017/S0080456800032208.
  • Williams CG. 1863. On the chinoline and leukoline series. J Chem Soc. 16:375–378. doi: 10.1039/JS8631600375.
  • Xiao Y, Rocha S, Kitts CC, Reymerd A, Beke-Somfaie T, Fredericka KK, Nordén B. 2020. Michler’s hydrol blue elucidates structural differences in prion strains. Proc Natl Acad Sci USA. 117:29677–29683. doi: 10.1073/pnas.2001732117.
  • Yaneva Z, Iva Nova D, Nevena Nikolova N, Toneva M. 2022. Organic dyes in contemporary medicinal chemistry and biomedicine. I. From the chromophore to the bioimaging/bioassay agent. Biotechnol Biotechnol Equip. 36:1–14. doi: 10.1080/13102818.2022.2039077.
  • Zollinger H. 2003. Color chemistry. 3rd ed. Wiley-VCH, Weinheim; p. 74.