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New Trends in Fluorescent Reporters in Biology

  • L. Della CianaEmail author
Chapter
First Online:
Part of the Springer Series on Fluorescence book series (SS FLUOR, volume 18)

Abstract

Fluorescent dyes play a prominent role in the detection and quantification of components in biological samples. Analytical methods based on fluorescent dyes include fluorescence microscopy, fluorescent immunoassays, nucleic acid assays, flow cytometry, and fluorescent imaging. During the past decade, most research effort by synthetic chemistry companies focused on three different areas: (a) improvement of existing cyanine dyes, (b) development of new dyes with large Stokes-shifts (LSS), and (c) development of dye assemblies, namely, fluorescent conjugated polymers (FCP) and fluorescent dye-doped silica nanoparticles (FSNP).

Keywords

4,4-Difluoro-4-bora-3a,4a-diaza-indacene (BODIPY) Cyanines Flow cytometry Fluorescent conjugated polymers (FCP) Fluorescent dye-doped silica nanoparticles (FSNP) Förster resonance energy transfer (FRET) InGaN (indium gallium nitride) InGaP (indium gallium phosphide) Large stokes-shift (LSS) dyes Laser diode excitation Major histocompatibility complex (MHC) Multicolor panels Near infrared (NIR) Plasma protein binding (PPB) 
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References

  1. 1.
    Strekowski L, Lipowska M, Patonay G (1992) Substitution reactions of a nucleofugal group in heptamethine cyanine dyes. Synthesis of an isothiocyanato derivative for labeling of proteins with a near-infrared chromophore. J Org Chem 57:4578–4580CrossRefGoogle Scholar
  2. 2.
    Mujumdar RB, Ernst LA, Mujumdar SR, Lewis CJ, Waggoner AS (1993) Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters. Bioconjug Chem 4:105–111CrossRefGoogle Scholar
  3. 3.
    Hermanson GT (2013) Bioconjugate techniques. Academic Press, LondonGoogle Scholar
  4. 4.
    Leung WY, Cheung CY, Yue S (2010) Modified carbocyanine dyes and their conjugates. US Pat 7820824Google Scholar
  5. 5.
    Licha K, Riefke B, Semmler W, Speck U, Hilger CS (2010) Near infrared imaging agent. US Pat 7655217Google Scholar
  6. 6.
    Brush CK, He K, Czerney PT, Wenzel M (2011) Hydrophilic labels for biomolecules. US Pat 7951959Google Scholar
  7. 7.
    Hermanson G, Czerney PT, Desai S, Wenzel MS, Dworecki BR, Lehmann FG, Nlend MC (2016) Cyanine compounds. US Pat Appl 15/042328Google Scholar
  8. 8.
    Romanov N, Anastasi C, Liu X (2015) Dyes for labelling molecular ligands. US Patent 9085698Google Scholar
  9. 9.
    Schweder BG, Wenzel MS, Frank WG, Lehmann FG, Czerney PT (2016) Marker dyes for UV and short wave excitation with high stokes shift based on benzoxazoles. US Pat 9453010Google Scholar
  10. 10.
    Diwu Z, Dubrovsky T, Abrams B, Liao J, Meng Q (2013) Reactive heterocycle-substituted 7-hydroxycoumarins and their conjugates. US Pat 8431416Google Scholar
  11. 11.
    Jin X, Uttamapinant C, Ting AY (2011) Synthesis of 7-aminocoumarin by Buchwald–Hartwig cross coupling for specific protein labeling in living cells. Chembiochem 12:65–70CrossRefGoogle Scholar
  12. 12.
    Wang HY, Leung WY, Mao F (1997) Sulfonated derivatives of 7-aminocoumarin. US Pat 5696157Google Scholar
  13. 13.
    Jansen TP, Rodeghiero G, Foglietta D, Perciaccante R, Della Ciana L (2017) Novel coumarin dyes and conjugates thereof. US Pat Appl 15/458801Google Scholar
  14. 14.
    Haugland RP (2013) The handbook: a guide to fluorescent probes and labeling technologies, 11th edn. Invitrogen Corp., EugeneGoogle Scholar
  15. 15.
    Buller G, Liu J, Yue S, Bradford JA (2017) Violet laser excitable dyes and their method of use. US Pat 9644099Google Scholar
  16. 16.
    Czerney P, Wenzel M, Schweder B, Lehmann F (2009) Compounds based on polymethines. US Pat 7563907Google Scholar
  17. 17.
    Zilles A, Drexhage KH, Kemnitzer NU, Arden-Jacob J, Hamers-Schneider M (2017) Amine-substituted tricyclic fluorescent dyes. US Pat 9651490Google Scholar
  18. 18.
    Moriarty RD, Martin A, Adamson K, O’Reilly E, Mollard P, Forster RJ, Keyes TE (2014) The application of water soluble, mega-Stokes-shifted BODIPY fluorophores to cell and tissue imaging. J Microsc 253:204–218CrossRefGoogle Scholar
  19. 19.
    Bertolino CA, Caputo G, Barolo C, Viscardi G, Coluccia S (2006) Novel heptamethine cyanine dyes with large stokes’ shift for biological applications in the near infrared. J Fluoresc 16:221–225CrossRefGoogle Scholar
  20. 20.
    Della Ciana L, Gretz N, Perciaccante R, Rodeghiero F, Geraci S, Huang J, Herrera Pérez Z, Pill J, Weinfurter S (2015) US Pat Appl 14/713,459Google Scholar
  21. 21.
    Huang J, Weinfurter S, Daniele C, Perciaccante R, Federica R, Della Ciana L, Pill J, Gretz N (2017) Zwitterionic near infrared fluorescent agents for noninvasive real-time transcutaneous assessment of kidney function. Chem Sci 8:2652–2660CrossRefGoogle Scholar
  22. 22.
    Gaylord BS, Hong JW, Fu TJ, Sun, CJ, Baldocchi R (2013) Fluorescent methods and materials for directed biomarker signal amplification. US Pat 8354239Google Scholar
  23. 23.
    Liu B, Wang C, Zhan R, Bartholomew GP, Hong JW, Wheeler JM, Gaylord BS (2015) Signal amplified biological detection with conjugated polymers US Pat 8969509Google Scholar
  24. 24.
    Chattopadhyay PK, Gaylord B, Palmer A, Jiang N, Raven MA, Lewis G, Roederer M (2012) Brilliant violet fluorophores: a new class of ultrabright fluorescent compounds for immunofluorescence experiments. Cytometry A 81:456–466CrossRefGoogle Scholar
  25. 25.
    Bonacchi S, Genovese D, Juri R, Montalti M, Prodi L, Rampazzo E, Zaccheroni N (2011) Luminescent silica nanoparticles: extending the frontiers of brightness. Angew Chem Int Ed 50:4056–4066CrossRefGoogle Scholar
  26. 26.
    Bae SW, Tan W, Hong JI (2012) Fluorescent dye-doped silica nanoparticles: new tools for bioapplications. Chem Commun 48:2270–2282CrossRefGoogle Scholar
  27. 27.
    Montalti M, Prodi L, Rampazzo E, Zaccheroni N (2014) Dye-doped silica nanoparticles as luminescent organized systems for nanomedicine. Chem Soc Rev 43:4243–4268CrossRefGoogle Scholar
  28. 28.
    Hench LL, West JK (1990) The sol-gel process. Chem Rev 90:33–72CrossRefGoogle Scholar
  29. 29.
    Stöber W, Fink A, Bohn E (1968) Controlled growth of monodisperse silica spheres in the micron size range. J Colloid Interface Sci 26:62–69CrossRefGoogle Scholar
  30. 30.
    Van Blaaderen A, Vrij A (1992) Synthesis and characterization of colloidal dispersions of fluorescent, monodisperse silica spheres. Langmuir 8:2921–2931CrossRefGoogle Scholar
  31. 31.
    Zanarini S, Rampazzo E, Della Ciana L, Marcaccio M, Marzocchi E, Montalti M, Paolucci F, Prodi L (2009) Ru(bpy)3 covalently doped silica nanoparticles as multicenter tunable structures for electrochemiluminescence amplification. J Am Chem Soc 131:2260–2267CrossRefGoogle Scholar
  32. 32.
    Bagwe RP, Yang C, Hilliard R, Tan W (2004) Optimization of dye-doped silica nanoparticles prepared using a reverse microemulsion method. Langmuir 20:8336–8342CrossRefGoogle Scholar
  33. 33.
    Zanarini S, Rampazzo E, Bonacchi S, Juris R, Marcaccio M, Montalti M, Paolucci F, Prodi L (2009) Iridium doped silica-PEG nanoparticles: enabling electrochemiluminescence of neutral complexes in aqueous media. J Am Chem Soc 131:14208–14209CrossRefGoogle Scholar
  34. 34.
    Yong KT, Roy I, Swihart MT, Prasad P (2009) Multifunctional nanoparticles as biocompatible targeted probes for human cancer diagnosis and therapy. J Mater Chem 19:4655–4672CrossRefGoogle Scholar
  35. 35.
    Van Blaaderen A, Imhof A, Hage W, Vrij A (1992) Three-dimensional imaging of submicrometer colloidal particles in concentrated suspensions using confocal scanning laser microscopy. Langmuir 8:1514–1517CrossRefGoogle Scholar
  36. 36.
    Verhaegh NA, Blaaderen AV (1994) Dispersions of rhodamine-labeled silica spheres: synthesis characterization, and fluorescence confocal scanning laser microscopy. Langmuir 10:1427–1438CrossRefGoogle Scholar
  37. 37.
    Herz E, Burns A, Bonner D, Wiesner U (2009) Large stokes-shift fluorescent silica nanoparticles with enhanced emission over free dye for single excitation multiplexing. Macromol Rapid Commun 30:1907–1910CrossRefGoogle Scholar
  38. 38.
    Wu C, Hong J, Guo X, Huang C, Lai J, Zheng J, Chen J, Mu X, Zhao Y (2008) Fluorescent core-shell silica nanoparticles as tunable precursors: towards encoding and multifunctional nano-probes. Chem Commun 6:750–752CrossRefGoogle Scholar
  39. 39.
    Fedorenko SV, Bochkova OD, Mustafina AR, Burilov VA, Kadirov MK, Holin CV, Nizameev IR, Skripacheva VV, Menshikova AY, Antipin IS, Konovalov AI (2010) Dual visible and near-infrared luminescent silica nanoparticles. Synthesis and aggregation stability. J Phys Chem C 114:6350–6355CrossRefGoogle Scholar
  40. 40.
    Wang L, Tan W (2006) Multicolor FRET silica nanoparticles by single wavelength excitation. Nano Lett 6:84–88CrossRefGoogle Scholar
  41. 41.
    Chen X, Estévez MC, Zhu Z, Huang YF, Chen Y, Wang L, Tan W (2009) Using aptamer-conjugated fluorescence resonance energy transfer nanoparticles for multiplexed cancer cell monitoring. Anal Chem 81:7009–7014CrossRefGoogle Scholar
  42. 42.
    Rampazzo E, Bonacchi S, Genovese D, Juris R, Montalti M, Paterlini V, Zaccheroni N, Dumas-Verdes C, Gilles C, Méallet-Renault R, Prodi L (2014) Pluronic-silica (PluS) nanoparticles doped with multiple dyes featuring complete energy transfer. J Phys Chem C 118:9261–9267CrossRefGoogle Scholar

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© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Cyanagen srlBolognaItaly

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