Cyclodextrin complexes: Chiral recognition and complexation behaviour

Current Drug Discovery Technologies

Volumn 4, Issue 4, 2007, Pages 282-294

  Bikádi, Zsolt ^a   Iványi, Róbert ^b   Szente, Lajos ^b   Ilisz, István ^c   Hazaia, Eszter ^a  

^a Virtua Drug Ltd   (Hungary)

^b CycloLab Cyclodextrin Research & Development Laboratory Ltd   (Hungary)

^c INSTITUTE OF BIOCHEMISTRY   (Hungary)

Author keywords

Me tryptophan; Alpha cyclodextrin; Amino acids; Capillary electrophoresis; Complexation; Molecular docking; Molecular dynamics

Indexed keywords

ALPHA CYCLODEXTRIN; AMINO ACID; BETA METHYLTRYPTOPHAN; CYCLODEXTRIN DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CALCULATION; CAPILLARY ELECTROPHORESIS; COMPARATIVE STUDY; COMPLEX FORMATION; COMPUTER MODEL; CORRELATION ANALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; ENERGY; ERROR; EXPERIMENTAL STUDY; GEOMETRY; HOST; HYPOTHESIS; MODEL; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; PREDICTION; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SIMULATION; STRENGTH;

AMINO ACIDS; CARBOHYDRATE CONFORMATION; CHEMISTRY, PHYSICAL; COMPUTER SIMULATION; CYCLODEXTRINS; ELECTROPHORESIS, CAPILLARY; ENERGY TRANSFER; MODELS, CHEMICAL; MODELS, MOLECULAR; STEREOISOMERISM; TRYPTOPHAN;

EID: 37549047660     PISSN: 15701638     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016307783220549     Document Type: Article

References (63)

1. Szejtli J.: Chemistry, Physical and Biological Properties of Cyclodextrins. In: Comprehensive Supramolecular Chemistry (CDs). J. Szejtli, T. Osa (Eds.), Pergamon, Oxford, (1996).
2. Harata K.: Structure of cyclodextrin inclusion complexes. Trends Phys. Chem. 1, 45-57, (1990).
3. Nasongkla N., Wiedmann A.F., Bruening A., Beman M., Ray D., Bornmann W.G., Boothman D.A., Gao, J.M.: Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes. Pharm. Res. 20, 1626-1633, (2003).
4. Loftsson T., Brewster M.E.: Pharmaceutical applications of cyclodextrins .1. Drug solubilization and stabilization. J. Pharm. Sci. 85, 1017-1025, (1996).
5. Rajewski R.A., Stella V.J.: Pharmaceutical applications of cyclodextrins .2. In vivo drug delivery. J. Pharm. Sci. 85, 1142-1169, (1996).
6. Faucci M.T., Melani F., Mura P.: Computer-aided molecular modeling techniques for predicting the stability of drug-cyclodextrin inclusion complexes in aqueous solutions. Chem. Phys. Lett. 358, 383-390, (2002).
7. Connors K.A.: Prediction of binding constants of alpha-cyclodextrin complexes. J. Pharm. Sci. 85, 796-802, (1996).
8. Connors K.A.: The stability of cyclodextrin complexes in solution. Chem. Rev. 97, 1325-1357, (1997).
9. Davies D.M., Savage J.R.: Cyclodextrin complexes of substituted perbenzoic and benzoic-acids and their conjugate bases - free-energy relationships show the interaction of polar and steric factors. J. Chem. Soc. Perkin Trans. 2, 1525-1530, (1994).
10. Huang, M.J., Watts J.D., Bodor N.: Theoretical studies of inclusion complexes of beta-cyclodextrin with methylated benzoic acids. Int. J. Quantum Chem. 64, 711-719, (1997).
11. Liu L., Guo Q. X.: The driving forces in the inclusion complexation of cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 42, 1-14, (2002).
12. Bikadi Z., Kurdi R., Balogh S., Szeman J., Hazai E.: Aggregation of cyclodextrins as an important factor to determine their complexation behavior. Chem. Biodivers. 3, 1266-78, (2006).
13. Leclercq L., Bricout H., Tilloy S., Monflier E.: Biphasic aqueous organometallic catalysis promoted by cyclodextrins: Can surface tension measurements explain the efficiency of chemically modified cyclodextrins? J. Colloid Interface Sci. 307, 481-487, (2007).
14. Cramer F., Dietsche W.: Occlusion compounds. XV. Resolution of racemates with cyclodextrins. Chem. Ber. 92, 378-384, (1959).
15. Kano K.: Mechanisms for chiral recognition by cyclodextrins. J. Phys. Org. Chem. 10, 286-291, (1997).
16. Kitae T., Nakayama T., Kano K.: Chiral recognition of alpha-amino acids by charged cyclodextrins through cooperative effects of Coulomb interaction and inclusion. J. Chem. Soc. Perkin Trans. 2, 207-212, (1998).
17. Leffingwell J. C.: Chirality & Bioactivity I. Pharmacol. Leffingwell Rep. 3, 1-27, (2003).
18. Yanagida, A., Shoji A., Shibusawa Y., Shindo H., Tagashira M., Ikeda M., Ito Y.: Analytical separation of tea catechins and food-related polyphenols by high-speed counter-current chromatography. J. Chromatogr. A. 1112, 195-201, (2006).
19. Kodama S., Yamamoto A., Matsunaga A., Yanai H.: Direct enantioseparation of catechin and epicatechin in tea drinks by 6-O-alpha-D-glucosyl-beta-cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis 25, 2892-2898, (2004).
20. Chankvetadze B.: Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins. Chem. Soc. Rev. 33, 337-47, (2004).
21. Hutt L. D., Glavin D. P., Bada J. L., Mathies R. A.: Microfabricated capillary electrophoresis amino acid chirality analyzer for extraterrestrial exploration. Anal. Chem. 71, 4000-4006, (1999).
22. Dalgliesh C. E.: The optical resolution of aromatic amino-acids on paper chromatograms. J. Chem. Soc. 137, 3940-3942, (1952).
23. Prelog V., Helmchen G.: Basic Principles of The Cip-System And Proposals For A Revision. Angew. Chem. Int. Ed. Engl. 21, 567-583 (1982).
24. Dodziuk H., Mirowicz M.: A Proposal For A Modification of The Cahn, Ingold And Prelog Classification of Chirality. Tetrahedron-Asymmetry 1, 171-186 (1990).
25. Camilleri P., Edwards A. J., Rzepa H. S., Green S. M.: Aryl Group Pi-Facial Electrostatic Asymmetry As A Contributing Factor To Chiral Resolution On Beta-Cyclodextrin Hplc Phases. J. Chem. Soc. Chem. Commun. 1122-1124, (1992).
26. Ahn S., Ramirez J., Grigorean G., Lebrilla C. B.: Chiral recognition in gas-phase cyclodextrin: Amino acid complexes - Is the three point interaction still valid in the gas phase? J. Am. Soc. Mass Spectrom. 12, 278-287, (2001).
27. Armstrong D. W., Yang X. F., Han S. M., Menges R. A.: direct liquid-chromatographic separation of racemates with an alpha-cyclodextrin bonded phase. Anal. Chem. 59, 2594-2596, (1987).
28. Asztemborska M., Nowakowski R., Sybilska D.: Separation ability and stoichiometry of cyclodextrin complexes. J. Chromatogr. A. 902, 381-387, (2000).
29. Dodziuk H., Sitkowski J., Stefaniak L., Jurczak J., Sybilska D.: c-13 nmr differentiation of diastereoisomeric complexes of cis-decalin with beta-cyclodextrin. J. Chem. Soc. Chem. Commun. 207-208, (1992).
30. Dodziuk H., Sitkowski J., Stefaniak L., Sybilska D.: Structure of cyclodextrins and their complexes .7. Unusual NMR manifestations of chiral recognition of (1R,5R)- and (1S,5S)-alpha-pinenes by alpha-cyclodextrin in different solvents. Polish J. Chem. 70, 1361-1364, (1996).
31. Chankvetadze B., Burjanadze N., Pintore G., Bergenthal D., Bergander K., Muhlenbrock C., Breitkreuz J., Blaschke G.: Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV spectrometry, electrospray ionization mass spectrometry and X-ray crystallography. J. Chromatogr. A. 875, 471-484, (2000).
32. Grandeury A., Condamine E., Hilfert L., Gouhier G., Petit S., Coquerel G.: Chiral discrimination in host-guest supramolecular complexes. Understanding enantioselectivity and solid solution behaviors by using spectroscopic methods and chemical sensors. J. Phys. Chem. B 111, 7017-7026, (2007).
33. Chankvetadze B., Burjanadze N., Maynard D. M., Bergander K., Bergenthal D., Blaschke G.: Comparative enantioseparations with native beta-cyclodextrin and heptakis-(2-O-methyl-3,6-di-O-sulfo)-beta-cyclodextrin in capillary electrophoresis. Electrophoresis 23, 3027-3034, (2002).
34. Amato M. E., Djedaini F., Pappalardo G. C., Perly B., Scarlata G.: molecular modeling of beta-cyclodextrin complexes with nootropic drugs. J. Pharm. Sci. 81, 1157-1161 (1992).
35. Lipkowitz K. B.: Applications of computational chemistry to the study of cyclodextrins. Chem. Rev. 98, 1829-1873, (1998).
36. Piel G., Dive G., Evrard B., Van Hees T., de Hassonville S. H., Delattre L.: Molecular modeling study of beta- and gamma-cyclodextrin complexes with miconazole. Eur. J. Pharm. Sci. 13, 271-279, (2001).
37. Knegtel R. M., Strokopytov B., Penninga D., Faber O. G., Rozeboom H. J., Kalk K. H., Dijkhuizen L., Dijkstra B. W.: Crystallographic studies of the interaction of cyclodextrin glycosyltransferase from Bacillus circulans strain 251 with natural substrates and products. J. Biol. Chem. 270, 29256-64, (1995).
38. Goodsell D. S., Morris G. M., Olson A. J.: Automated docking of flexible ligands: Applications of AutoDock. J. Mol. Recognit. 9, 1-5, (1996).
39. Solis F. J., Wets R. J. B.: Minimization By Random Search Techniques. Math. Oper. Res. 6, 19-30, (1981).
40. Van der Spoel D., Lindahl E., Hess B., Groenhof G., Mark A. E., Berendsen H. J. C.: GROMACS: Fast, flexible, and free. J. Comput. Chem. 26, 1701-1718, (2005).
41. Schuttelkopf A. W., van Aalten D. M. F.: PRODRG: a tool for high-throughput crystallography of protein-ligand complexes. Acta. Crystallogr. D Biol. Cryst. 60, 1355-1363, (2004).
42. Rundlett K. L., Armstrong D. W.: Examination of the origin, variation, and proper use of expressions for the estimation of association constants by capillary electrophoresis. J. Chromatogr. A. 721, 173-186, (1996).
43. Smith V. K., Ndou T. T., Warner I. M.: spectroscopic study of the interaction of catechin with alpha-cyclodextrin, beta-cyclodextrin, and gamma-cyclodextrin. J. Phys. Chem. 98, 8627-8631, (1994).
44. Liu L., Li X. S., Song K. S., Guo Q. X.: PM3 studies on the complexation of alpha-cyclodextrin with benzaldehyde and acetophenone. J. Mol. Struc. Theochem 531, 127-134, (2000).
45. Liu L., Guo Q. X.: Use of quantum chemical methods to study cyclodextrin chemistry. J. Incl. Phenom. Macrocycl. Chem. 50, 95-103, (2004).
46. Yan C. L., Li X. H., Xiu Z. L., Hao C.: A quantum-mechanical study on the complexation of beta-cyclodextrin with quercetin. J. Mol. Struc. Theochem 764, 95-100, (2006).
47. Steiner T., Saenger W.: Geometry of C-H...O hydrogen-bonds in carbohydrate crystal-structures - analysis of neutron-diffraction data. J. Amer. Chem. Soc. 114, 10146-10154, (1992).
48. Lipkowitz K. B., Stoehr C. M.: Detailed experimental and theoretical analysis of chiral discrimination: Enantioselective binding of R/S methyl mandelate by beta-cyclodextrin. Chirality 8, 341-350, (1996).
49. Dodziuk H., Ejchart A., Lukin O., Vysotsky M. O.: H-1 and C-13 NMR and molecular dynamics study of chiral recognition of camphor enantiomers by alpha-cyclodextrin. J. Org. Chem. 64, 1503-1507, (1999).
50. Kim H., Jeong K., Lee S., Jung S. H.: Molecular Modeling of the chiral recognition of propranolol enantiomers by a beta-cyclodextrin. Bull. Kor. Chem. Soc. 24, 95-98, (2003).
51. Sun M., Liu X. H., Yan L. S., Luo G., Zhao Y. F.: Molecular recognition between 4aS/R-galanthamine diastereoisomers and alpha-cyclodextrin. J. Mol. Model. 9, 419-422, (2003).
52. Kano K., Nishiyabu R.: General mechanism for chiral recognition by native and modified cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 44, 355-359, (2002).
53. Castronuovo G., Elia V., Fessas D., Giordano A., Velleca F.: thermodynamics of the interaction of cyclodextrins with aromatic and alpha, omega-amino acids in aqueous-solutions - a calorimetric study at 25-Degrees-C. Carbohyd. Res. 272, 31-39, (1995).
54. Cheng Y., Hercules D. M.: Measurement of chiral complexes of cyclodextrins and amino acids by electrospray ionization time-of-flight mass spectrometry. J. Mass Spectrom. 36, 834-836, (2001).
55. Kahle C., Holzgrabe U.: Determination of binding constants of cyclodextrin inclusion complexes with amino acids and dipeptides by potentiometric titration. Chirality 16, 509-515, (2004).
56. Cooper A., Macnicol D. D.: chiral host-guest complexes - interaction of alpha-cyclodextrin with optically-active benzene-derivatives. J. Chem. Soc. Perkin Trans. 2, 760-763, (1978).
57. Dodziuk H.: Cyclodextrins and their complexes. Wiley-VCH Verlag GmbH & Co., Weinheim, (2006).
58. Pirkle W. H., Pochapsky T. C.: considerations of chiral recognition relevant to the liquid-chromatographic separation of enantiomers. Chem. Rev. 89, 347-362, (1989).
59. Dupuy, N., Barbry D., Bria M., Marquis S., Vrielynck L., Kister J.: H-1 NMR study of inclusion compounds of phenylurea derivatives in beta-cyclodextrin. Spectrochim. Acta A Mol. Biomol Spectrosc. 61, 1051-1057, (2005).
60. Fernandes C. M., Carvalho R. A., da Costa S. P., Veiga F. J. B.: Multimodal molecular encapsulation of nicardipine hydrochloride by beta-cyclodextrin, hydroxypropyl-beta-cyclodextrin and triacetyl-beta- cyclodextrin in solution. Structural studies by H-1 NMR and ROESY experiments. Eur. J. Pharm. Sci.18, 285-296, (2003).
61. Inoue Y., Okuda T., Miyata Y.: side-chain conformational-changes of some amino-acids and dipeptides having aromatic side-chains induced by complexation with cycloamyloses. J. Am. Chem. Soc. 103, 7393-7394, (1981).
62. Monti, S., Kohler G., Grabner G.: photophysics and photochemistry of methylated phenols in beta-cyclodextrin inclusion complexes. J. Phys. Chem. 97, 13011-13016, (1993).
63. Nishijo J., Tsuchitani M.: Interaction of L-tryptophan with alpha-cyclodextrin: Studies with calorimetry and proton nuclear magnetic resonance spectroscopy. J. Pharm. Sci. 90, 134-140, (2001).