Dipyridamole/β-cyclodextrin complexation: Effect of buffer species, thermodynamics, and guest-host interactions probed by 1H-NMR and molecular modeling studies

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 64, Issue 3-4, 2009, Pages 305-315

  Al Omari, Mahmoud M ^a   El Barghouthi, Musa I ^b   Zughul, Mohammad B ^c   Davies, J Eric D ^d   Badwan, Adnan A ^a  

^a JORDANIAN PHARMACEUTICAL MANUFACTURING COMPANY   (Jordan)

^b HASHEMITE UNIVERSITY   (Jordan)

^c UNIVERSITY OF JORDAN   (Jordan)

^d LANCASTER UNIVERSITY   (United Kingdom)

Author keywords

Cyclodextrin; 1H NMR; Complex characterization; Dipyridamole; Hydrophobic effect; Molecular modeling; Thermodynamic

Indexed keywords

EID: 70349667283     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9569-y     Document Type: Article

References (20)

1. AHFS drug information: Dipyridamole monograph. www.ashp.Org/mngrphs/ahfs/a382830.htm.
2. Drug bank: Dipyridamole monograph. http://www.drugbank.ca/drugs/DB00975.
3. Khalil, A., Belal, F., Al-Badr, A.A.: Dipyridamole comprehensive profile. In: Brittain, H.G. (ed.) Profiles of Drug Substances, Excipients, and Related Methodology, vol. 31, pp. 215-280. Elsevier Academic Press Inc., CA/USA (2005).
4. Stella, V.J., Rajewski, R.A.: Cyclodextrins: their future in drug formulation and delivery. Pharm. Res 14, 556-567 (1997). doi:10.1023/A:1012136608249.
5. del Valle, E.M.M.: Cyclodextrins and their uses: a review. Process Biochem 39, 1033-1046 (2004). doi:10.1016/S0032-9592(03)00258-9.
6. Loftsson, T., Duchêne, D.: Cyclodextrins and their therapeutic applications. Int. J. Pharm. 329, 1-11 (2007). doi:10.1016/j.ijpharm.2006.10.044.
7. Torri, G., Naggi, A., Fregnan, G.B., Trebbi, A.: Dipyridamole-β-cyclodextrin complex: preparation and characterization. Pharmazie 45, 193-195 (1990).
8. 1H-NMR and molecular modeling studies. J. Pharm. Biomed. Anal 41, 857-865 (2006). doi:10.1016/j.jpba.2006.01.055.
9. Al Omari, M.M., Zughul, M.B., Davies, J.E.D., Badwan, A.A.: Effect of buffer species on the complexation of basic drug terfenadine with β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem 58, 227-235 (2007). doi:10.1007/s10847-006-9147-5.
10. Higuchi, T., Connors, K.A.: In: Reilley, C.N. (ed.) Advances in Analytical Chemistry Instrumentation, pp. 117-212. Wiley-Interscience, New York (1965).
11. 2 type phase solubility diagrams, complex formation and chemical speciation of soluble species. J. Incl. Phenom. Macrocycl. Chem 31, 243-264 (1998). doi:10.1023/A:1007965424219.
12. Al Omari, M.M., Zughul, M.B., Davies, J.E.D., Badwan, A.A.: Effect of buffer species on the inclusion complexation of acidic drug celecoxib with cyclodextrin in solution. J. Incl. Phenom. Macrocycl. Chem 55, 247-254 (2006). doi:10.1007/s10847-005-9041-6.
13. Taraszewska, J., Migut, K., Kozbiat, M.: Complexation of flutamide by native and modified cyclodextrins. J. Phys. Org. Chem 16, 121-126 (2003). doi:10.1002/poc.582.
14. Avdeef, A., Bendels, S., Tsinman, O., Tsinman, K., Kansy, M.: Solubility-excipient classification gradient maps. Pharm. Res 24, 530-545 (2007). doi:10.1007/s11095-006-9169-0.
15. 1H-NMR and molecular modeling studies. J. Incl. Phenom. Macrocycl. Chem 57, 511-517 (2007). doi:10.1007/s10847-006-9242-7.
16. Al Omari, M.M., El-Barghouthi, M.I., Zughul, M.B., Davies, J.E.D., Badwan, A.A.: Comparative study of the inclusion complexation of pizotifen and ketotifen with native and modified cyclodextrins. J. Solut. Chem 37, 249-264 (2008). doi:10.1007/s10953-007-9234-2.
17. Al Omari, M.M., Zughul, M.B., Davies, J.E.D., Badwan, A.A.: Astemizole/cyclodextrin inclusion complexes: phase solubility, physicochemical characterization and molecular modeling studies. J. Solut. Chem 37, 875-893 (2008). doi:10.1007/s10953-008-9277-z.
18. Ventura, C.A., Giannone, I., Paolino, D., Pistara, V., Corsaro, A., Puglisi, G.: Preparation of celecoxib-dimethy-β-cyclodextrin inclusion complex: characterization and in vitro permeation study. Eur. J. Med. Chem 40, 624-631 (2005). doi:10.1016/j.ejmech.2005.03.001.
19. Saichek, R.E., Reddy, K.R.: Electrokinetically enhanced remediation of hydrophobic organic compounds in soils: a review. Crit. Rev. Environ. Sci. Technol 35, 115-192 (2005). doi:10.1080/10643380590900237.
20. Connors, K.A.: The stability of cyclodextrin complexes in solution. Chem. Rev 97, 1325-1358 (1997). doi:10.1021/cr960371r.