Theoretical Study of the Inclusion Processes of Ibuprofen Enantiomers with Native and Modified β-CDs
Tóm tắt
PM3 calculations in vacuum were performedon the inclusion complexation ofβ-cyclodextrin (β-CD),heptakis-(2-O-methyl)-β-cyclodextrin(2-Me-β-CD) and heptakis-(6-O-methyl)-β-cyclodextrin(6-Me-β-CD) withibuprofen (IB) enantiomers. Inclusion processpathways are described and the most probablestructure of the 1:1 complex are sought througha potential energy scan. The energy differencesbetween the inclusion complexes and the hosts(native and modified CDs) by calculation show thatmodified CDs have much more interaction sites withIB and enhance van der Waals interaction andhydrophobic interaction between them, form morestable complexes than native CD does.Stabilization energies of S-IB complexes arehigher than that of R-IB complexes both for nativeand modified CDs.
Tài liệu tham khảo
citation_journal_title=Chem. Rev.; citation_author=J. Szjetli; citation_volume=98; citation_publication_date=1998; citation_pages=11743; citation_id=CR1
citation_inbook_title=Comprehensive Supramolecular Chemistry; citation_publication_date=1996; citation_pages=305; citation_id=CR2; citation_author=E. Fenyvesi; citation_author=L. Szente; citation_author=N.R. Russell; citation_author=M. McNammara; citation_publisher=Pergamon
citation_journal_title=Chem. Rev.; citation_author=K.A. Connors; citation_volume=97; citation_publication_date=1997; citation_pages=1325; citation_id=CR3
citation_journal_title=Tetrahedron; citation_author=I. Tabushi; citation_volume=40; citation_publication_date=1984; citation_pages=269; citation_id=CR4
citation_journal_title=J. Am. Chem. Soc.; citation_author=E.V. Akkaya, A.W. Czarnik; citation_volume=110; citation_publication_date=1988; citation_pages=8553; citation_id=CR5
citation_journal_title=Angew. Chem. Int. Ed. Engl.; citation_author=V. Schurig, H.-P. Nowotny; citation_volume=29; citation_publication_date=1990; citation_pages=939; citation_id=CR6
citation_title=Inclusion Compounds; citation_publication_date=1984; citation_id=CR7; citation_author=J.L. Atwood; citation_author=J.E.D. Davies; citation_author=D.D. MacNicol; citation_publisher=Academic Press
citation_journal_title=Water Res.; citation_author=T.A. Ternes; citation_volume=32; citation_publication_date=1998; citation_pages=3245; citation_id=CR8
citation_journal_title=Int. J. Pharm.; citation_author=P. Mura, G.P. Bettinetti, A. Manderioli, M.T. Faucci, G. Bramanti, M. Sorrenti; citation_volume=166; citation_publication_date=1998; citation_pages=189; citation_id=CR9
citation_journal_title=J. Phys. Chem.; citation_author=V.B. Luzhkow, C.A. Venanzi; citation_volume=99; citation_publication_date=1995; citation_pages=2312; citation_id=CR10
citation_journal_title=J. Chem. Soc., Faraday Trans.; citation_author=M. Stodeman, U. Berg, A. Svenssen; citation_volume=94; citation_publication_date=1998; citation_pages=1737; citation_id=CR11
citation_journal_title=J. Mol. Struct. (Theochem.); citation_author=B.S. Jursic, Z. Zdravkovski, A.D. French; citation_volume=366; citation_publication_date=1996; citation_pages=113; citation_id=CR12
citation_journal_title=J. Org. Chem.; citation_author=D. Salvatiorra, C. Jaime, A. Virgili, F. Sanchez-Ferrando; citation_volume=61; citation_publication_date=1996; citation_pages=9578; citation_id=CR13
citation_journal_title=J. Org. Chem.; citation_author=G. Fronza, A. Mele, E. Redenti, P. Ventura; citation_volume=61; citation_publication_date=1996; citation_pages=909; citation_id=CR14
citation_journal_title=Carbohydr. Res.; citation_author=M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue, R. Chujo; citation_volume=163; citation_publication_date=1987; citation_pages=1; citation_id=CR15
citation_journal_title=Bull. Chem. Soc. Jpn.; citation_author=M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue, R. Chujo; citation_volume=62; citation_publication_date=1989; citation_pages=2067; citation_id=CR16
citation_journal_title=J. Org. Chem.; citation_author=F. Perez, C. Jaime, X. Sanchez-Ruiz; citation_volume=60; citation_publication_date=1995; citation_pages=3840; citation_id=CR17
citation_journal_title=J. Colloid. Interface Sci.; citation_author=J. Madrid, J. Pozuelo, F. Mendicuti, W.L. Mattice; citation_volume=193; citation_publication_date=1997; citation_pages=112; citation_id=CR18
citation_journal_title=J. Phys. Chem. B; citation_author=J. Madrid, F. Mendicuti, W.L. Mattice; citation_volume=102; citation_publication_date=1998; citation_pages=2037; citation_id=CR19
citation_journal_title=J. Mol. Struct. (Theochem.); citation_author=E. Cervelloa, C. Jaime; citation_volume=428; citation_publication_date=1998; citation_pages=195; citation_id=CR20
citation_journal_title=J. Mol. Struct. (Theochem.); citation_author=X. Sanchez-Ruiz, M. Ramos, C. Jaime; citation_volume=442; citation_publication_date=1998; citation_pages=93; citation_id=CR21
citation_journal_title=J. Am. Chem. Soc.; citation_author=R. Coner, M.A. Peterson; citation_volume=63; citation_publication_date=1997; citation_pages=732; citation_id=CR22
citation_journal_title=J. Org. Chem.; citation_author=H. Dodziuk, A. Ejchart, O. Lukin, M.O. Vysotsky; citation_volume=64; citation_publication_date=1999; citation_pages=1503; citation_id=CR23
citation_journal_title=Chem. Rev.; citation_author=K.B. Lipkowitz; citation_volume=98; citation_publication_date=1998; citation_pages=1829; citation_id=CR24
citation_journal_title=J. Incl. Phenom. Macrocycle. Chem.; citation_author=L. Liu, X.-S. Li, T.-W. Mu, Q.-X. Guo, Y.C. Liu; citation_volume=38; citation_publication_date=2000; citation_pages=199; citation_id=CR25
citation_journal_title=Starch/staerke.; citation_author=S. Immel, W.F. Lichtenthaler; citation_volume=48; citation_publication_date=1996; citation_pages=255; citation_id=CR26
citation_journal_title=J. Mol. Struct. (Theochem.); citation_author=P. Jiang, H.-W. Sun, R. X. Shen, J. Shi, C.M. Lai; citation_volume=528; citation_publication_date=2000; citation_pages=211; citation_id=CR27
citation_journal_title=Carbohydr. Res.; citation_author=K. Takeo, H. Mitoh, K. Uemura; citation_volume=187; citation_publication_date=1989; citation_pages=203; citation_id=CR28
citation_journal_title=Monatsh. Chem.; citation_author=X.-S. Li, L. Liu, T.-W. Mu, Q.-X. Guo; citation_volume=131; citation_publication_date=2000; citation_pages=849; citation_id=CR29
citation_journal_title=J. Am. Chem. Soc.; citation_author=C. Betzek, W. Saenger, B.E. Hingerty, G.M. Brown; citation_volume=106; citation_publication_date=1984; citation_pages=7545; citation_id=CR30
citation_journal_title=Carbohydr. Res.; citation_author=M. Kitagawa, H. Hoshi, M. Sakurai, Y. Inoue, R. Chujo; citation_volume=198; citation_publication_date=1987; citation_pages=C1; citation_id=CR31
citation_journal_title=J. Incl. Phenom. Macrocycle. Chem.; citation_author=L. Liu, Q.-X. Guo; citation_volume=42; citation_publication_date=2002; citation_pages=1; citation_id=CR32
citation_journal_title=J. Pharm. Sci.; citation_author=A.R. Green, J.K. Guillory; citation_volume=78; citation_publication_date=1989; citation_pages=427; citation_id=CR33
citation_journal_title=Anal. Chem.; citation_author=T.J. Ward; citation_volume=72; citation_publication_date=2000; citation_pages=4521; citation_id=CR34