Advertisement

Analytical and Bioanalytical Chemistry

, Volume 386, Issue 5, pp 1201–1214 | Cite as

New chromogenic and fluorogenic reagents and sensors for neutral and ionic analytes based on covalent bond formation–a review of recent developments

  • Gerhard J. Mohr
Review

Abstract

To date, hydrogen bonding and Coulomb, van der Waals and hydrophobic interactions are the major contributors to non-covalent analyte recognition using ionophores, ligands, aptamers and chemosensors. However, this article describes recent developments in the use of (reversible) covalent bond formation to detect analyte molecules, with special focus on optical signal transduction. Several new indicator dyes for analytes such as amines and diamines, amino acids, cyanide, formaldehyde, hydrogen peroxide, organophosphates, nitrogen oxide and nitrite, peptides and proteins, as well as saccharides have become available. New means of converting analyte recognition into optical signals have also been introduced, such as colour changes of chiral nematic layers. This article gives an overview of recent developments and discusses response mechanisms, selectivity and sensitivity.

Keywords

Chemosensor Optical probe Optical sensor Biomolecules Chemical warfare agents 

Notes

Acknowledgement

This work was supported by the Heisenberg Fellowship MO 1062/1-1 and research grant MO 1062/2-1 of Deutsche Forschungsgemeinschaft. This support is gratefully acknowledged.

References

  1. 1.
    Mohr GJ (2004) Chem Eur J 10:1083–1090CrossRefGoogle Scholar
  2. 2.
    Mohr GJ (2005) Sens Actuators B 107:2–13CrossRefGoogle Scholar
  3. 3.
    Wetzl BK, Yarmoluk SM, Craig DB, Wolfbeis OS (2004) Angew Chem 116:5515–5517CrossRefGoogle Scholar
  4. 4.
    Höfelschweiger BK, Dürkop A, Wolfbeis OS (2005) Anal Biochem 344:122–129CrossRefGoogle Scholar
  5. 5.
    Comes M, Marcos MD, Martinez-Manez R, Sancenon F, Soto J, Villaescusa LA, Amoros P, Beltran D (2004) Adv Mater 16:1783–1786CrossRefGoogle Scholar
  6. 6.
    Comes M, Marcos MD, Martinez-Manez R, Millan MC, Ros-Lis JV, Sancenon F, Soto J, Villaescusa LA (2006) Chem Eur J 12:2162–2170CrossRefGoogle Scholar
  7. 7.
    Basurto S, Torroba T, Comes M, Martinez-Manez R, Sancenon F, Villaescusa L, Amoros P (2005) Org Lett 7:5469–5472CrossRefGoogle Scholar
  8. 8.
    Secor K, Plante J, Avetta C, Glass T (2005) J Mater Chem 15:4073–4077CrossRefGoogle Scholar
  9. 9.
    Tanaka F, Mase N, Barbas CF (2004) Chem Commun 1762–1763Google Scholar
  10. 10.
    Sasaki S, Monma G, Citterio D, Yamada K, Suzuki K (2005) Chimia 59:204–208CrossRefGoogle Scholar
  11. 11.
    Rohand T, Baruah M, Qin W, Boens N, Dehan W (2006) Chem Commun 266–268Google Scholar
  12. 12.
    Oguri S, Mizusawa A, Kamada M, Kohori M (2006) Anal Chim Acta 558:326–331CrossRefGoogle Scholar
  13. 13.
    Ros-Lis JV, Martinez-Manez R, Soto J (2005) Chem Commun 5260–5262Google Scholar
  14. 14.
    Badugu R, Lakowicz JR, Geddes CD (2005) J Am Chem Soc 127:3635–3641CrossRefGoogle Scholar
  15. 15.
    Badugu R, Lakowicz JR, Geddes CD (2005) Dyes Pigments 64:49–55CrossRefGoogle Scholar
  16. 16.
    Trupp S, Schweitzer A, Mohr GJ (2006) Microchim Acta 153:127–131CrossRefGoogle Scholar
  17. 17.
    Mohr GJ, Lehmann F, Grummt UW, Spichiger UE (1997) Anal Chim Acta 344:215–225CrossRefGoogle Scholar
  18. 18.
    Mohr GJ, Demuth C, Spichiger UE (1998) Anal Chem 70:3868–3873CrossRefGoogle Scholar
  19. 19.
    Mohr GJ, Tirelli N, Spichiger UE (1999) Anal Chem 71:1534–1539CrossRefGoogle Scholar
  20. 20.
    Chung YM, Raman B, Kim DS, Ahn KH (2006) Chem Commun 186–188Google Scholar
  21. 21.
    Tomasulo M, Raymo FM (2005) Org Lett 7:4633–4636CrossRefGoogle Scholar
  22. 22.
    Tomasulo M, Sortino S, White AJP, Raymo FM (2006) J Org Chem 71:744–753CrossRefGoogle Scholar
  23. 23.
    Garcia F, Garcia JM, Garcia-Acosta B, Martinez-Manez R, Sancenon F, Soto J (2005) Chem Commun 2790–2792Google Scholar
  24. 24.
    Sivakumar K, Xie F, Cash BM, Long S, Barnhill HN, Wang Q (2004) Org Lett 6:4603–4606CrossRefGoogle Scholar
  25. 25.
    Kawamura K, Kerman K, Fujihara M, Nagatani N, Hashiba T, Tamiya E (2005) Sens Actuators B 105:495–501CrossRefGoogle Scholar
  26. 26.
    Toda K, Yoshioka KI, Mori K, Hirata S (2005) Anal Chim Acta 531:41–49CrossRefGoogle Scholar
  27. 27.
    Salahuddin S, Renaudet O, Reymond JL (2004) Org Biomol Chem 2:1471–1475CrossRefGoogle Scholar
  28. 28.
    Chang MCY, Pralle A, Isacof EY, Chang CJ (2004) J Am Chem Soc 126:15392–15393Google Scholar
  29. 29.
    Xu K, Tang B, Huang H, Yang G, Chen Z, Li P, An L (2005) Chem Commun 5974–5976Google Scholar
  30. 30.
    Maeda H, Fukuyasu Y, Yoshida S, Fukuda M, Sueki K, Matsuno H, Yamauchi Y, Yoshida K, Hirata K, Miyamoto K (2004) Ang Chem 116:2443–2445CrossRefGoogle Scholar
  31. 31.
    Gomes A, Fernandes E, Lima JLFC (2006) J Fluoresc 16:119–139CrossRefGoogle Scholar
  32. 32.
    Bru M, Burguete MI, Galindo F, Luis SV, Marin MJ, Vigara L (2006) Tetrahedron Lett 47:1787–1791CrossRefGoogle Scholar
  33. 33.
    Zguris J, Pishko MV (2006) Sens Actuators B 115:503–509CrossRefGoogle Scholar
  34. 34.
    Ilhan F, Tyson DS, Meador MA (2004) Chem Mater 16:2978–2980CrossRefGoogle Scholar
  35. 35.
    Bencic-Nagale S, Sternfeld T, Walt DR (2006) J Am Chem Soc 128:5041–5048CrossRefGoogle Scholar
  36. 36.
    Dale TJ, Rebek J (2006) J Am Chem Soc 128:4500–4501CrossRefGoogle Scholar
  37. 37.
    Saimaru H, Masuda M, Toriumi C, Santa T, Ichikawa E, Takamura N, Imai K (2005) J Mater Chem 15:2865–2872CrossRefGoogle Scholar
  38. 38.
    Cao H, Heagy MD (2004) J Fluoresc 14:569–584CrossRefGoogle Scholar
  39. 39.
    Fang H, Kaur G, Wang B (2004) J Fluoresc 14:481–488CrossRefGoogle Scholar
  40. 40.
    Shinkai S, Takeuchi M (2004) Biosens Bioelectron 20:1250–1259CrossRefGoogle Scholar
  41. 41.
    Badugu R, Lakowicz JR, Geddes CD (2006) Dyes Pigments 68:159–163CrossRefGoogle Scholar
  42. 42.
    Badugu R, Lakowicz JR, Geddes CD (2003) J Fluoresc 13:371–374CrossRefGoogle Scholar
  43. 43.
    Zhao J, Davidson MG, Mahon MF, Kociok-Köhn G, James TD (2004) J Am Chem Soc 126:16179–16186CrossRefGoogle Scholar
  44. 44.
    Tamaoki N (2001) Adv Mater 13:1135–1147CrossRefGoogle Scholar
  45. 45.
    Dickert FL, Haunschild A, Hofmann P (1994) Fresenius J Anal Chem 350:577–581CrossRefGoogle Scholar
  46. 46.
    Winterbottom DA, Narayanaswamy R, Raimundo IM (2003) Sens Actuators B 90:52–57CrossRefGoogle Scholar
  47. 47.
    Kirchner N, Zedler L, Mayerhöfer TG, Mohr GJ (2006) Chem Commun 1512–1514Google Scholar

Copyright information

© Springer-Verlag 2006

Authors and Affiliations

  1. 1.Institute of Physical ChemistryFriedrich Schiller University of JenaJenaGermany

Personalised recommendations