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Dynamic Combinatorial Libraries for the Development of Synthetic Receptors and Sensors

  • Sijbren Otto
  • Kay Severin
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 277)

Abstract

Dynamic combinatorial libraries are mixtures of compounds that continuously interchange their subunits, resulting in a thermodynamically controlled product distribution. Such mixtures are responsive to their environment. Thus, introducing a guest or analyte into a mixture of potential receptors will result in a change in the product distribution in response to molecular recognition events. One way of utilizing this response is for the discovery of new synthetic receptors. We show several examples where new receptors have been identified from the increase in their concentration in the dynamic mixture after introducing a guest. Alternatively, rather than focusing on one particular species in the complex mixture, the response of the entire library can be used as a reporter on the nature of the guest. We show how libraries made from building blocks that are UV-Vis or fluorescently active can act as sensors. When analyzed with chemometrics methods, sensor DCLs can give remarkable results.

Combinatorial chemistry Molecular recognition Sensors Systems chemistry Synthetic receptors  Thermodynamic control 

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References

  1. 1.
    Karan C, Miller BL (2000) Drug Discov Today 5:67 PubMedCrossRefGoogle Scholar
  2. 2.
    Lehn J-M, Eliseev AV (2001) Science 291:2331 PubMedCrossRefGoogle Scholar
  3. 3.
    Ramström O, Lehn J-M (2002) Nat Rev Drug Discov 1:26 PubMedCrossRefGoogle Scholar
  4. 4.
    Rowan SJ, Cantrill SJ, Cousins GRL, Sanders JKM, Stoddart JF (2002) Angew Chem Int Ed 41:898 CrossRefGoogle Scholar
  5. 5.
    Ramström O, Bunyapaiboonsri T, Lohmann S, Lehn J-M (2002) Biochim Biophys Acta 1572:178 PubMedGoogle Scholar
  6. 6.
    Otto S (2003) Curr Opin Drug Discov Dev 6:509 Google Scholar
  7. 7.
    Cheeseman JD, Corbett AD, Gleason JL, Kazlauskas RJ (2005) Chem Eur J 11:1708 CrossRefGoogle Scholar
  8. 8.
    de Bruin B, Hauwert P, Reek JNH (2006) Angew Chem Int Ed 45:2660 CrossRefGoogle Scholar
  9. 9.
    Corbett PT, Leclaire J, Vial L, West KR, Wietor J-L, Sanders JKM, Otto S (2006) Chem Rev 106:3652 PubMedCrossRefGoogle Scholar
  10. 10.
    Otto S, Furlan RLE, Sanders JKM (2002) Curr Opin Chem Biol 6:321 PubMedCrossRefGoogle Scholar
  11. 11.
    Sanders JKM (2004) Philos Trans R Soc Lond Ser A Math Phys Eng Sci 362:1239 CrossRefADSGoogle Scholar
  12. 12.
    Otto S (2005) J Mater Chem 15:3357 CrossRefMathSciNetGoogle Scholar
  13. 13.
    Grote Z, Scopelliti R, Severin K (2003) Angew Chem Int Ed 42:3821 CrossRefGoogle Scholar
  14. 14.
    Severin K (2004) Chem Eur J 10:2565 CrossRefGoogle Scholar
  15. 15.
    Saur I, Severin K (2005) Chem Commun, p 1471 Google Scholar
  16. 16.
    Corbett PT, Otto S, Sanders JKM (2004) Chem Eur J 10:3139 CrossRefGoogle Scholar
  17. 17.
    Corbett PT, Sanders JKM, Otto S (2005) J Am Chem Soc 127:9390 PubMedCrossRefGoogle Scholar
  18. 18.
    Nishinaga T, Tanatani A, Oh KC, Moore JS (2002) J Am Chem Soc 124:5934 PubMedCrossRefGoogle Scholar
  19. 19.
    Lüning U (2004) J Incl Phenom Macrocycl Chem 49:81 CrossRefGoogle Scholar
  20. 20.
    Storm O, Lüning U (2002) Chem-Eur J 8:793 CrossRefGoogle Scholar
  21. 21.
    Gonzalez-Alvarez A, Alfonso I, Lopez-Ortiz F, Aguirre A, Garcia-Granda S, Gotor V (2004) Eur J Org Chem, p 1117 Google Scholar
  22. 22.
    Gonzalez-Alvarez A, Alfonso I, Gotor V (2006) Chem Commun, p 2224 Google Scholar
  23. 23.
    Nguyen R, Huc I (2003) Chem Commun, p 942 Google Scholar
  24. 24.
    Cousins GRL, Poulsen SA, Sanders JKM (1999) Chem Commun, p 1575 Google Scholar
  25. 25.
    Kubik S, Goddard R (1999) J Org Chem 64:9475 CrossRefGoogle Scholar
  26. 26.
    Cousins GRL, Furlan RLE, Ng Y-F, Redman JE, Sanders JKM (2001) Angew Chem Int Ed 40:423 CrossRefGoogle Scholar
  27. 27.
    Furlan RLE, Ng Y-F, Cousins GRL, Redman JE, Sanders JKM (2002) Tetrahedron 58:771 CrossRefGoogle Scholar
  28. 28.
    Roberts SL, Furlan RLE, Otto S, Sanders JKM (2003) Org Biomol Chem 1:1625 PubMedCrossRefGoogle Scholar
  29. 29.
    Furlan RLE, Cousins GRL, Sanders JKM (2000) Chem Commun, p 1761 Google Scholar
  30. 30.
    Lam RTS, Belenguer A, Roberts SL, Naumann C, Jarrosson T, Otto S, Sanders JKM (2005) Science 308:667 PubMedCrossRefADSGoogle Scholar
  31. 31.
    Otto S, Furlan RLE, Sanders JKM (2000) J Am Chem Soc 122:12063 CrossRefGoogle Scholar
  32. 32.
    Ramström O, Lehn J-M (2000) ChemBioChem 1:41 PubMedCrossRefGoogle Scholar
  33. 33.
    Otto S, Furlan RLE, Sanders JKM (2002) Science 297:590 PubMedCrossRefADSGoogle Scholar
  34. 34.
    Corbett PT, Tong LH, Sanders JKM, Otto S (2005) J Am Chem Soc 127:8902 PubMedCrossRefGoogle Scholar
  35. 35.
    Ngola SM, Kearney PC, Mecozzi S, Russell K, Dougherty DA (1999) J Am Chem Soc 121:1192 CrossRefGoogle Scholar
  36. 36.
    Kubik S, Goddard R, Kirchner R, Nolting D, Seidel J (2001) Angew Chem Int Ed 40:2648 CrossRefGoogle Scholar
  37. 37.
    Kubik S, Kirchner R, Nolting D, Seidel J (2002) J Am Chem Soc 124:12752 PubMedCrossRefGoogle Scholar
  38. 38.
    Otto S, Kubik S (2003) J Am Chem Soc 125:7804 PubMedCrossRefGoogle Scholar
  39. 39.
    Rodriguez-Docampo Z, Pascu SI, Kubik S, Otto S (2006) J Am Chem Soc 128:11206 PubMedCrossRefGoogle Scholar
  40. 40.
    Williams DH, Stephens E, O'Brien DP, Zhou M (2004) Angew Chem Int Ed 43:6596 CrossRefGoogle Scholar
  41. 41.
    Otto S (2006) Dalton Trans, p 2861 Google Scholar
  42. 42.
    Vial L, Ludlow RF, Leclaire J, Perez-Fernandez R, Otto S (2006) J Am Chem Soc 128:10253 PubMedCrossRefGoogle Scholar
  43. 43.
    Fuchs B, Nelson A, Star A, Stoddart JF, Vidal SB (2003) Angew Chem Int Ed 42:4220 CrossRefGoogle Scholar
  44. 44.
    Cacciapaglia R, Di Stefano S, Mandolini L (2005) J Am Chem Soc 127:13666 PubMedCrossRefGoogle Scholar
  45. 45.
    Albert KJ, Lewis NS, Schauer CL, Sotzing GA, Stitzel SE, Vaid TP, Walt DR (2000) Chem Rev 100:2595 PubMedCrossRefGoogle Scholar
  46. 46.
    Wright AT, Anslyn EV (2006) Chem Soc Rev 35:14 PubMedCrossRefGoogle Scholar
  47. 47.
    Giuseppone N, Lehn J-M (2004) J Am Chem Soc 126:11448 PubMedCrossRefGoogle Scholar
  48. 48.
    Giuseppone N, Fuks G, Lehn JM (2006) Chem Eur J 12:1723 CrossRefGoogle Scholar
  49. 49.
    Lehn JM (2005) Prog Polym Sci 30:814 CrossRefGoogle Scholar
  50. 50.
    Buryak A, Severin K (2005) Angew Chem Int Ed 44:7935 CrossRefGoogle Scholar
  51. 51.
    Jurs PC, Bakken GA, McClelland HE (2000) Chem Rev 100:2649 PubMedCrossRefGoogle Scholar
  52. 52.
    Buryak A, Severin K (2006) J Comb Chem 8:540 PubMedCrossRefGoogle Scholar
  53. 53.
    McCleskey SC, Floriano PN, Wiskur SL, Anslyn EV, McDevitt JT (2003) Tetrahedron 59:10089 CrossRefGoogle Scholar
  54. 54.
    Wiskur SL, Floriano PN, Anslyn EV, McDevitt JT (2003) Angew Chem Int Ed 42:2070 CrossRefGoogle Scholar
  55. 55.
    Anslyn EV, Collins BE, Wright AT (2007) Combining Molecular Recognition, Optical Detection, and Chemometric Analysis. Top Curr Chem, in this volume Google Scholar
  56. 56.
    James D, Scott SM, Ali Z, O'Hare WT (2005) Microchim Acta 149:1 CrossRefGoogle Scholar
  57. 57.
    Gouma P, Sberveglieri G, Dutta R, Gardner JW, Hines EL (2004) MRS Bull 29:697 PubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2007

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of CambridgeCambridgeUK
  2. 2.Institut des Sciences et Ingénierie ChimiquesÉcole Polytechnique Fédéralede LausanneLausanneSwitzerland

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