Skip to main content
SpringerLink
Log in

A Spectral and Molecular Dynamics Simulation Study of β-Cyclodextrin Inclusion Complexes with Solvatochromic Dyes Derived from Barbituric Acid

  • Published:
Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

The linear interaction energy (LIE) method was applied to the molecular-dynamics-simulation study of the interactions in water between β-cyclodextrin and two solvatochromic dyes derived from N,N-dimethylbarbituric acid, the 5-[(4-dimethylaminophenyl)methylene]- (1), and the 5-[bis(4-dimethylaminophenyl) methylene]-2,4,6-(1H,3H,5H)-pyrimidinetrione (2). Both compounds interact with β-CD by insertion of an aminophenyl ring into its hydrophobic cavity. Theoretical and spectral evidences point to a greater association of compound (1) than dye (2) with cyclodextrin in water.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. For a series of reviews on various aspects of CD inclusion complexes see Chem. Rev. 98 (1998)

  2. L. Liu Q.-X. Guo (2002) J. Incl. Phenom. Macroc. Chem 42 1 Occurrence Handle1:CAS:528:DC%2BD38XivFymsrc%3D

    CAS  Google Scholar 

  3. X.-M- Wanga H.-Y. Chena J.-D. Wangb (1994) Anal. Chim. Acta 290 349

    Google Scholar 

  4. M.C. Mahedero A.M. De la Peña A. Bautista J.J. Aaron (2002) J.Incl. Phenom. Macroc. Chem 42 61 Occurrence Handle1:CAS:528:DC%2BD38XivFyms7g%3D

    CAS  Google Scholar 

  5. M.S. Ibrahim I.S. Shebatta A.A. Al-Nayeli (2002) J. Pharm. Biomed. Anal 28 217 Occurrence Handle10.1016/S0731-7085(01)00624-0 Occurrence Handle1:CAS:528:DC%2BD38XisFWns7s%3D

    Article  CAS  Google Scholar 

  6. C. Yañez R. Salazar L.J. Núñez-Vergara J.A. Squella (2004) J. Pharm. Biomed. Anal 35 51

    Google Scholar 

  7. P.M. Schmidt R.S. Brown J.H.T. Luong (1995) Chem. Eng. Sci 50 1867 Occurrence Handle1:CAS:528:DyaK2MXmsFeiuro%3D

    CAS  Google Scholar 

  8. A.C.S. Lino W. Loh (2000) J. Incl. Phenom. Macroc. Chem 36: 267

    Google Scholar 

  9. M.B.M. Azevedo J.B. Alderete A.C.S. Lino W. Loh A. Faljoni-Alario N. Durán (2000) J. Incl. Phenom. Macroc. Chem 37 67

    Google Scholar 

  10. K.S. Cameron L. Fielding (2001) J. Org. Chem 66 6891 Occurrence Handle10.1021/jo010081x Occurrence Handle1:CAS:528:DC%2BD3MXmvFGlt7g%3D

    Article  CAS  Google Scholar 

  11. R. Wimmer F.L. Aachmann K.L. Larsen S.B. Petersen (2002) Carbohydrate Res 337 841 Occurrence Handle10.1016/S0008-6215(02)00066-6 Occurrence Handle1:CAS:528:DC%2BD38XjtlKmtbY%3D

    Article  CAS  Google Scholar 

  12. C.M. Fernandes R.A. Carvalho S.P. Costa F.J.B. Veiga (2003) Eur. J. Pharm. Sci 18 285 Occurrence Handle1:CAS:528:DC%2BD3sXivFCqtb4%3D Occurrence Handle10.1016/S0928-0987(03)00025-3

    Article  CAS  Google Scholar 

  13. P. Franchi M. Lucarini E. Mezzina G.F. Pedulli (2004) J. Am. Chem. Soc 126 4343 Occurrence Handle10.1021/ja049713y Occurrence Handle1:CAS:528:DC%2BD2cXhvF2iurY%3D

    Article  CAS  Google Scholar 

  14. J.R. Grigera E.R. Caffarena S. Rosa (1998) Carbohydrate Res 310 253 Occurrence Handle10.1016/S0008-6215(98)00147-5 Occurrence Handle1:CAS:528:DyaK1cXntVSku7w%3D

    Article  CAS  Google Scholar 

  15. A.C.S. Lino Y. Takahata C. Jaime (2002) J. Mol. Struct. (THEOCHEM) 594 207 Occurrence Handle10.1016/S0166-1280(02)00393-7 Occurrence Handle1:CAS:528:DC%2BD38XnsF2kurk%3D

    Article  CAS  Google Scholar 

  16. M. Fermeglia M. Ferrone A. Lodi S. Pricl (2003) Carbohydrate Pol 53 15 Occurrence Handle1:CAS:528:DC%2BD3sXjsFCksbY%3D

    CAS  Google Scholar 

  17. N.J. Crane R.C. Mayrhofer T.A. Betts G.A. Baker (2002) J. Chem. Educ 79 1261 Occurrence Handle1:CAS:528:DC%2BD38XntlWiu7w%3D

    CAS  Google Scholar 

  18. B.D. Wagner N. Stojanovic G. Leclair C.K. Jankowski (2003) J. Incl. Phenom. Macroc. Chem 45 275 Occurrence Handle1:CAS:528:DC%2BD3sXltlKrtLc%3D Occurrence Handle10.1023/A:1024578819782

    Article  CAS  Google Scholar 

  19. C.L. Beildeck W.H. Steel R.A. Walker (2003) Langmuir 19 4933 Occurrence Handle10.1021/la0343122 Occurrence Handle1:CAS:528:DC%2BD3sXjs12rsrg%3D

    Article  CAS  Google Scholar 

  20. W.H. Steel R.A. Walker (2003) Nature 424 296 Occurrence Handle10.1038/nature01791 Occurrence Handle1:CAS:528:DC%2BD3sXlsVGjs7c%3D

    Article  CAS  Google Scholar 

  21. X. Zhang W.H. Steel R.A. Walker (2003) J.Phys.Chem 107 3829 Occurrence Handle1:CAS:528:DC%2BD3sXisVaktbg%3D

    CAS  Google Scholar 

  22. M.C. Rezende P. Campodonico E. Abuin J. Kossanyi (2001) Spectrochim. Acta A 57 1183 Occurrence Handle1:STN:280:DC%2BD38%2FhsVOgtg%3D%3D

    CAS  Google Scholar 

  23. P. Flores M.C. Rezende L. Villarroel J. Guerrero (2004) Spectrochim. Acta A 60 1637

    Google Scholar 

  24. B.R. Brooks R.E. Bruccoleri B.D. Olafson D.J. States S. Swaminahan M.J. Karplus (1983) J.Comp.Chem 4 187 Occurrence Handle1:CAS:528:DyaL3sXit1aiu7w%3D

    CAS  Google Scholar 

  25. L. Lawtrakul H. Viernstein P. Wolschann (2003) Int. J. Pharm 256 33 Occurrence Handle10.1016/S0378-5173(03)00060-7 Occurrence Handle1:CAS:528:DC%2BD3sXivVGjsbw%3D

    Article  CAS  Google Scholar 

  26. InsightII User Guide, Accelrys, San Diego, USA (1998)

  27. G.M. Morris D.S. Goodsell R.S. Halliday R. Huey W.E. Hart R.K. Belew A.J. Olson (1998) J. Comp. Chem 19 1639 Occurrence Handle1:CAS:528:DyaK1cXntFemur4%3D

    CAS  Google Scholar 

  28. W.L. Jorgensen J. Chandraskhar J.D. Madura R.W. Impey M.L. Klein (1983) J. Chem. Phys 79 926 Occurrence Handle10.1063/1.445869 Occurrence Handle1:CAS:528:DyaL3sXksF2htL4%3D

    Article  CAS  Google Scholar 

  29. X. Sanchez-Ruiz M. Ramos C. Jaime (1998) J. Mol. Struct 442 93 Occurrence Handle1:CAS:528:DyaK1cXhvFKnurw%3D

    CAS  Google Scholar 

  30. J. M. Kohler Hohla R. Sollner H.J. Eberle (1998) Supramol. Sci 5 101

    Google Scholar 

  31. J. Srinivasan T.E. Cheatham P. Cieplak P.A. Kollman D.A. Case (1998) J. Am. Chem. Soc 120 9401 Occurrence Handle1:CAS:528:DyaK1cXlsVyqtLo%3D

    CAS  Google Scholar 

  32. J. Marelius T. Hansson J. Åqvist (1998) Int. J. Quantum Chem 69 77 Occurrence Handle10.1002/(SICI)1097-461X(1998)69:1<77::AID-QUA10>3.0.CO;2-2 Occurrence Handle1:CAS:528:DyaK1cXktVektrw%3D

    Article  CAS  Google Scholar 

  33. M.M.H. Lipzig Particlevan A.M. ter Laak A. Jongejan N.P.E. Vermeulen M. Wamelink D. Geerke J.H.N. Meerman (2004) J. Med. Chem 47 1018

    Google Scholar 

  34. M. Almlöf B.O. Brandsdal J. Åqvist (2004) J. Comp. Chem 25 1242

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Facultad de Química y Biología, Universidad de Santiago, Casilla 40, Correo 33, Santiago, Chile

    Francisco Jara, Carolina Mascayano, Marcos Caroli Rezende, Cristian Tirapegui & Alejandro Urzua

Authors
  1. Francisco Jara
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Carolina Mascayano
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marcos Caroli Rezende
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Cristian Tirapegui
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alejandro Urzua
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marcos Caroli Rezende.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jara, F., Mascayano, C., Rezende, M.C. et al. A Spectral and Molecular Dynamics Simulation Study of β-Cyclodextrin Inclusion Complexes with Solvatochromic Dyes Derived from Barbituric Acid. J Incl Phenom Macrocycl Chem 54, 95–99 (2006). https://doi.org/10.1007/s10847-005-4806-5

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-005-4806-5

Key words

Search

Navigation