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Volumn 353, Issue 1-2, 2008, Pages 160-169

Supramolecular complex of fluoxetine with β-cyclodextrin: An experimental and theoretical study

Author keywords

Cyclodextrin; Computational methods; Fluoxetine; Inclusion compound; Isothermal Titration Calorimetry; Supramolecular complex

Indexed keywords

BETA CYCLODEXTRIN; FLUOXETINE;

EID: 40349106142     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.11.050     Document Type: Article
Times cited : (66)

References (52)
  • 1
    • 19444379194 scopus 로고    scopus 로고
    • Complexation of fluoxetine hydrochloride with [beta]-cyclodextrin. A proton magnetic resonance study in aqueous solution. Il
    • Ali S.M., Asmat F., Maheshwari A., and Koketsu M. Complexation of fluoxetine hydrochloride with [beta]-cyclodextrin. A proton magnetic resonance study in aqueous solution. Il. Farmaco 60 (2005) 445-449
    • (2005) Farmaco , vol.60 , pp. 445-449
    • Ali, S.M.1    Asmat, F.2    Maheshwari, A.3    Koketsu, M.4
  • 3
    • 84961981991 scopus 로고    scopus 로고
    • A new definition of cavities for the computation of solvation free energies by the polarizable continuum model
    • Barone V., Cossi M., and Tomasi J. A new definition of cavities for the computation of solvation free energies by the polarizable continuum model. J. Chem. Phys. 107 (1997) 3210-3221
    • (1997) J. Chem. Phys. , vol.107 , pp. 3210-3221
    • Barone, V.1    Cossi, M.2    Tomasi, J.3
  • 4
    • 5144229966 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax A., and Davis D.G. Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 63 (1969) 207-213
    • (1969) J. Magn. Reson. , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 5
    • 4243553426 scopus 로고
    • Density-functional exchange-energy approximation with correct asymptotic-behavior
    • Becke A.D. Density-functional exchange-energy approximation with correct asymptotic-behavior. Phys. Rev. A 38 (1988) 3098-3100
    • (1988) Phys. Rev. A , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 6
    • 0037163017 scopus 로고    scopus 로고
    • Cyclodextrin enhanced spectrofluorimetric determination of fluoxetine in pharmaceuticals and biological fluids
    • Berzas J.J., Alanon A., and Lazaro J.A. Cyclodextrin enhanced spectrofluorimetric determination of fluoxetine in pharmaceuticals and biological fluids. Talanta 58 (2002) 301-309
    • (2002) Talanta , vol.58 , pp. 301-309
    • Berzas, J.J.1    Alanon, A.2    Lazaro, J.A.3
  • 7
    • 34047272332 scopus 로고    scopus 로고
    • Theoretical study of structure and properties of a molecular reactor based on the urea-linked β-cyclodextrin dimer
    • Blenke C., Silva V.J.D., Junqueira G.M.A., De Almeida W.B., and Dos Santos H.F. Theoretical study of structure and properties of a molecular reactor based on the urea-linked β-cyclodextrin dimer. J. Mol. Struc.: Theochem. 809 (2007) 95-102
    • (2007) J. Mol. Struc.: Theochem. , vol.809 , pp. 95-102
    • Blenke, C.1    Silva, V.J.D.2    Junqueira, G.M.A.3    De Almeida, W.B.4    Dos Santos, H.F.5
  • 8
    • 17444428907 scopus 로고    scopus 로고
    • Structural analysis of cyclodextrins: a comparative study of classical and quantummechanical methods
    • Britto M., Nascimento Jr. C.S., and Dos Santos H.F. Structural analysis of cyclodextrins: a comparative study of classical and quantummechanical methods. Quim. Nova 27 (2004) 882-888
    • (2004) Quim. Nova , vol.27 , pp. 882-888
    • Britto, M.1    Nascimento Jr., C.S.2    Dos Santos, H.F.3
  • 10
    • 32844466577 scopus 로고    scopus 로고
    • Burden of phase-specific sexual dysfunction with SSRIs
    • Claytona A., Kellera A., and Mcgarvey E.L. Burden of phase-specific sexual dysfunction with SSRIs. J. Affect. Disorders 91 (2006) 27-32
    • (2006) J. Affect. Disorders , vol.91 , pp. 27-32
    • Claytona, A.1    Kellera, A.2    Mcgarvey, E.L.3
  • 11
    • 33847062914 scopus 로고    scopus 로고
    • Spontaneous association of hydrophobized dextran and poly-[beta]-cyclodextrin into nanoassemblies: formation and interaction with a hydrophobic drug
    • Daoud-Mahammed S., Ringard-Lefebvre C., Razzouq N., Rosilio V., Gillet B., Couvreur P., Amiel C., and Gref R. Spontaneous association of hydrophobized dextran and poly-[beta]-cyclodextrin into nanoassemblies: formation and interaction with a hydrophobic drug. J. Colloid Interface Sci. 307 (2007) 83-93
    • (2007) J. Colloid Interface Sci. , vol.307 , pp. 83-93
    • Daoud-Mahammed, S.1    Ringard-Lefebvre, C.2    Razzouq, N.3    Rosilio, V.4    Gillet, B.5    Couvreur, P.6    Amiel, C.7    Gref, R.8
  • 15
    • 36849115659 scopus 로고
    • Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules
    • Ditchfield R., Hehre W.J., and Pople J.A. Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules. J. Chem. Phys. 54 (1971) 724-728
    • (1971) J. Chem. Phys. , vol.54 , pp. 724-728
    • Ditchfield, R.1    Hehre, W.J.2    Pople, J.A.3
  • 16
    • 0001391872 scopus 로고
    • Spectroscopic studies on [beta]-cyclodextrin
    • Egyed O. Spectroscopic studies on [beta]-cyclodextrin. Vib. Spectrosc. 1 (1990) 225-227
    • (1990) Vib. Spectrosc. , vol.1 , pp. 225-227
    • Egyed, O.1
  • 17
    • 40349109072 scopus 로고    scopus 로고
    • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y.
    • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., 2004. Gaussian 2003, Revision C.02. Wallingford, CT.
  • 18
    • 33847031647 scopus 로고    scopus 로고
    • Formation of colloidal suspension of hydrophobic compounds with an amphiphilic self-assembling peptide
    • Fung S.Y., Yang H., and Chen P. Formation of colloidal suspension of hydrophobic compounds with an amphiphilic self-assembling peptide. Colloid Surf. B 55 (2007) 200-211
    • (2007) Colloid Surf. B , vol.55 , pp. 200-211
    • Fung, S.Y.1    Yang, H.2    Chen, P.3
  • 19
    • 33746474818 scopus 로고    scopus 로고
    • Polyionic hydrocolloids for the intestinal delivery of protein drugs: alginate and chitosan-a review
    • George M., and Abraham T.E. Polyionic hydrocolloids for the intestinal delivery of protein drugs: alginate and chitosan-a review. J. Control. Release 114 (2006) 1-14
    • (2006) J. Control. Release , vol.114 , pp. 1-14
    • George, M.1    Abraham, T.E.2
  • 20
    • 40349104028 scopus 로고    scopus 로고
    • Gil, V.M.S., Geraldes, C.F., 1987. Ressonância Magnética Nuclear. Fundamentos, Métodos e Aplicações, Portugal, Fundação Calouste Gulbenkian.
    • Gil, V.M.S., Geraldes, C.F., 1987. Ressonância Magnética Nuclear. Fundamentos, Métodos e Aplicações, Portugal, Fundação Calouste Gulbenkian.
  • 21
    • 0001354595 scopus 로고    scopus 로고
    • Industrial applications of cyclodextrins
    • Hedges A.R. Industrial applications of cyclodextrins. Chem. Rev. 98 (1998) 2035-2044
    • (1998) Chem. Rev. , vol.98 , pp. 2035-2044
    • Hedges, A.R.1
  • 22
    • 0037384041 scopus 로고    scopus 로고
    • Pharmacokinetics of fluoxetine and norfluoxetine in pregnancy and lactation
    • Heikkinen T., Ekblad U., Palo P., and Laine K. Pharmacokinetics of fluoxetine and norfluoxetine in pregnancy and lactation. Clin. Pharmacol. Ther. 73 (2002) 330-337
    • (2002) Clin. Pharmacol. Ther. , vol.73 , pp. 330-337
    • Heikkinen, T.1    Ekblad, U.2    Palo, P.3    Laine, K.4
  • 23
    • 0344110152 scopus 로고    scopus 로고
    • Pharmacokinetics of selective serotonin reuptake inhibitors
    • Hiemke C., and Härtter S. Pharmacokinetics of selective serotonin reuptake inhibitors. Pharmacol. Therapeut. 85 (2000) 11-28
    • (2000) Pharmacol. Therapeut. , vol.85 , pp. 11-28
    • Hiemke, C.1    Härtter, S.2
  • 24
    • 0033104290 scopus 로고    scopus 로고
    • Cyclodextrin-based controlled drug release system
    • Hirayama F., and Ukeama K. Cyclodextrin-based controlled drug release system. Adv. Drug Deliv. Rev. 36 (1999) 125-141
    • (1999) Adv. Drug Deliv. Rev. , vol.36 , pp. 125-141
    • Hirayama, F.1    Ukeama, K.2
  • 25
    • 0033105151 scopus 로고    scopus 로고
    • Cyclodextrins in peptide and protein delivery
    • Irie T., and Ukeama K. Cyclodextrins in peptide and protein delivery. Adv. Drug Deliv. Rev. 36 (1999) 101-123
    • (1999) Adv. Drug Deliv. Rev. , vol.36 , pp. 101-123
    • Irie, T.1    Ukeama, K.2
  • 27
    • 58149323927 scopus 로고
    • Investigation of cyclodextrin inclusion compounds using FT-IR and Raman spectroscopy
    • Lamcharfi E., Kunesch G., Meyer C., and Robert B. Investigation of cyclodextrin inclusion compounds using FT-IR and Raman spectroscopy. Spectrochim. Acta A 51 (1995) 1861-1870
    • (1995) Spectrochim. Acta A , vol.51 , pp. 1861-1870
    • Lamcharfi, E.1    Kunesch, G.2    Meyer, C.3    Robert, B.4
  • 28
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37 (1988) 785
    • (1988) Phys. Rev. B , vol.37 , pp. 785
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 29
    • 49049134955 scopus 로고
    • Crystal and molecular-structure of cyclohepta-amylose dodecahydrate
    • Lindner K., and Saenger W. Crystal and molecular-structure of cyclohepta-amylose dodecahydrate. Carbohydr. Res. 99 (1982) 103-115
    • (1982) Carbohydr. Res. , vol.99 , pp. 103-115
    • Lindner, K.1    Saenger, W.2
  • 30
    • 12344333404 scopus 로고    scopus 로고
    • Use of quantum chemical methods to study cyclodextrin chemistry
    • Liu L., and Guo Q.X. Use of quantum chemical methods to study cyclodextrin chemistry. J. Incl. Phenom. Macro. Chem. 50 (2004) 95-103
    • (2004) J. Incl. Phenom. Macro. Chem. , vol.50 , pp. 95-103
    • Liu, L.1    Guo, Q.X.2
  • 31
    • 33845573098 scopus 로고    scopus 로고
    • Cyclodextrins and their pharmaceutical applications
    • Loftsson T., and Duchene D. Cyclodextrins and their pharmaceutical applications. Int. J. Pharm. 329 (2007) 1-11
    • (2007) Int. J. Pharm. , vol.329 , pp. 1-11
    • Loftsson, T.1    Duchene, D.2
  • 33
    • 9644262342 scopus 로고    scopus 로고
    • Solid-state characterization and dissolution properties of Naproxen-Arginine-Hydroxypropyl-[beta]-cyclodextrin ternary system
    • Mura P., Bettinetti G.P., Cirri M., Maestrelli F., Sorrenti M., and Catenacci L. Solid-state characterization and dissolution properties of Naproxen-Arginine-Hydroxypropyl-[beta]-cyclodextrin ternary system. Eur. J. Pharm. Biopharm. 59 (2005) 99-106
    • (2005) Eur. J. Pharm. Biopharm. , vol.59 , pp. 99-106
    • Mura, P.1    Bettinetti, G.P.2    Cirri, M.3    Maestrelli, F.4    Sorrenti, M.5    Catenacci, L.6
  • 35
    • 7444222326 scopus 로고    scopus 로고
    • Theoretical study of the formation of the alpha-cyclodextrin hexahydrate
    • Nascimento Jr. C.S., Dos Santos H.F., and De Almeida W.B. Theoretical study of the formation of the alpha-cyclodextrin hexahydrate. Chem. Phys. Lett. 397 (2004) 422-428
    • (2004) Chem. Phys. Lett. , vol.397 , pp. 422-428
    • Nascimento Jr., C.S.1    Dos Santos, H.F.2    De Almeida, W.B.3
  • 36
    • 0026951903 scopus 로고
    • Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions
    • Piotto M., Saudek V., and Sklenár V. Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions. J. Biom. NMR 2 (1992) 661-665
    • (1992) J. Biom. NMR , vol.2 , pp. 661-665
    • Piotto, M.1    Saudek, V.2    Sklenár, V.3
  • 38
    • 17444420664 scopus 로고    scopus 로고
    • Cyclodextrin complexes of valdecoxib: properties and anti-inflammatory activity in rat
    • Rajendrakumar K., Madhusudan S., and Pralhad T. Cyclodextrin complexes of valdecoxib: properties and anti-inflammatory activity in rat. Eur. J. Pharm. Biopharm. 60 (2005) 39-46
    • (2005) Eur. J. Pharm. Biopharm. , vol.60 , pp. 39-46
    • Rajendrakumar, K.1    Madhusudan, S.2    Pralhad, T.3
  • 39
    • 4243778369 scopus 로고    scopus 로고
    • Complexation thermodynamics of cyclodextrins
    • Rekharsky M.V., and Inoue Y. Complexation thermodynamics of cyclodextrins. Chem. Rev. 98 (1998) 1875-1918
    • (1998) Chem. Rev. , vol.98 , pp. 1875-1918
    • Rekharsky, M.V.1    Inoue, Y.2
  • 40
    • 40349098989 scopus 로고
    • 3-Dimensional structure and absolute-configurations of fluoxetine-(F), a selective serotonin uptake inhibitor
    • Robertson D.W., Krushinski J.H., and Wong D.T. 3-Dimensional structure and absolute-configurations of fluoxetine-(F), a selective serotonin uptake inhibitor. FASEB J. 2 (1988) A1405-A11405
    • (1988) FASEB J. , vol.2
    • Robertson, D.W.1    Krushinski, J.H.2    Wong, D.T.3
  • 41
    • 33750008879 scopus 로고    scopus 로고
    • Cyclodextrin-insulin complex encapsulated polymethacrylic acid based nanoparticles for oral insulin delivery
    • Sajeesh S., and Sharma C.P. Cyclodextrin-insulin complex encapsulated polymethacrylic acid based nanoparticles for oral insulin delivery. Inter. J. Pharm. 325 (2006) 147-154
    • (2006) Inter. J. Pharm. , vol.325 , pp. 147-154
    • Sajeesh, S.1    Sharma, C.P.2
  • 42
    • 0000835931 scopus 로고    scopus 로고
    • NMR studies of cyclodextrins and cyclodextrin complexes
    • Schneider H.J., Hacket F., Rudiger V., and Ikeda H. NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98 (1998) 1755-1786
    • (1998) Chem. Rev. , vol.98 , pp. 1755-1786
    • Schneider, H.J.1    Hacket, F.2    Rudiger, V.3    Ikeda, H.4
  • 43
    • 14044255378 scopus 로고    scopus 로고
    • Study on structure and characterization of inclusion complex of gossypol/beta cyclodextrin
    • Shen Y.-L., Yang S.-H., Wu L.-M., and Ma X.-Y. Study on structure and characterization of inclusion complex of gossypol/beta cyclodextrin. Spectrochim. Acta A 61 (2005) 1025-1028
    • (2005) Spectrochim. Acta A , vol.61 , pp. 1025-1028
    • Shen, Y.-L.1    Yang, S.-H.2    Wu, L.-M.3    Ma, X.-Y.4
  • 46
    • 84988073214 scopus 로고
    • Optimization of parameters for semiempirical methods. 2. Applications
    • Stewart J.J.P. Optimization of parameters for semiempirical methods. 2. Applications. J. Comput. Chem. 10 (1989) 221-264
    • (1989) J. Comput. Chem. , vol.10 , pp. 221-264
    • Stewart, J.J.P.1
  • 47
    • 33746468534 scopus 로고    scopus 로고
    • Buccal bioadhesive drug delivery-a promising option for orally less efficient drugs
    • Sudhakar Y., Kuotsu K., and Bandyopadhyay A.K. Buccal bioadhesive drug delivery-a promising option for orally less efficient drugs. J. Control. Release 114 (2006) 15-40
    • (2006) J. Control. Release , vol.114 , pp. 15-40
    • Sudhakar, Y.1    Kuotsu, K.2    Bandyopadhyay, A.K.3
  • 48
    • 33646819673 scopus 로고    scopus 로고
    • 1H NMR studies on host-guest interaction of paeonol and two of its isomers with [beta]-cyclodextrin
    • 1H NMR studies on host-guest interaction of paeonol and two of its isomers with [beta]-cyclodextrin. Int. J. Pharm. 316 (2006) 7-13
    • (2006) Int. J. Pharm. , vol.316 , pp. 7-13
    • Sun, D.-Z.1    Li, L.2    Qiu, X.-M.3    Liu, F.4    Yin, B.-L.5
  • 49
    • 0346461917 scopus 로고    scopus 로고
    • Introduction and general overview of cyclodextrin chemistry
    • Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998) 1743-1754
    • (1998) Chem. Rev. , vol.98 , pp. 1743-1754
    • Szejtli, J.1
  • 50
    • 0345293146 scopus 로고    scopus 로고
    • On the value of c: Can low affinity systems be studied by Isothermal Titration Calorimetry?
    • Turnbull W.B., and Daranas A.H. On the value of c: Can low affinity systems be studied by Isothermal Titration Calorimetry?. J. Am. Chem. Soc. 125 (2003) 14859-14866
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14859-14866
    • Turnbull, W.B.1    Daranas, A.H.2
  • 52
    • 0032737401 scopus 로고    scopus 로고
    • A review of recent applications of cyclodextrins for drug discovery
    • Zhang M.-Q., and Rees D.C. A review of recent applications of cyclodextrins for drug discovery. Expert Opin. Ther. Pat. 9 (1999) 1697-1717
    • (1999) Expert Opin. Ther. Pat. , vol.9 , pp. 1697-1717
    • Zhang, M.-Q.1    Rees, D.C.2


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