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Volumn 97, Issue 4, 2008, Pages 1484-1498

Complexation and chiral drug recognition of an amphiphilic phenothiazine derivative with β-cyclodextrin

Author keywords

Cyclodextrin; Drug delivery; Fluorescence; Molecular recognition; NMR spectroscopy

Indexed keywords

AMPHOPHILE; BETA CYCLODEXTRIN; MACROCYCLIC COMPOUND; PROMETHAZINE; BETA CYCLODEXTRIN DERIVATIVE;

EID: 43249083234     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21064     Document Type: Article
Times cited : (25)

References (44)
  • 1
    • 85031387709 scopus 로고    scopus 로고
    • Atwood JL, Davies JED, Macnicol DD, Vögtle FC. 1996. Comprehensive supramolecular chemistry (3: cyclodextrins). Tarritown: Pergamon.
    • Atwood JL, Davies JED, Macnicol DD, Vögtle FC. 1996. Comprehensive supramolecular chemistry (Vol. 3: cyclodextrins). Tarritown: Pergamon.
  • 2
    • 33645331847 scopus 로고    scopus 로고
    • Cyclodextrin rotaxanes and polyrotaxanes
    • Wenz G, Han BH, Muller A. 2006. Cyclodextrin rotaxanes and polyrotaxanes. Chem Rev 106:782-817.
    • (2006) Chem Rev , vol.106 , pp. 782-817
    • Wenz, G.1    Han, B.H.2    Muller, A.3
  • 4
    • 33750235246 scopus 로고    scopus 로고
    • Selective solvation of cyclodextrins by small molecules: An NOE study
    • Guerrero-Martínez A, Berger S, Tardajos G. 2006. Selective solvation of cyclodextrins by small molecules: An NOE study. ChemPhysChem 7:2074-2076.
    • (2006) ChemPhysChem , vol.7 , pp. 2074-2076
    • Guerrero-Martínez, A.1    Berger, S.2    Tardajos, G.3
  • 5
    • 0345179962 scopus 로고    scopus 로고
    • The stability of cyclodextrin complexes in solution
    • Connors KA. 1997. The stability of cyclodextrin complexes in solution. Chem Rev 97:1325-1358.
    • (1997) Chem Rev , vol.97 , pp. 1325-1358
    • Connors, K.A.1
  • 6
    • 33746907060 scopus 로고    scopus 로고
    • Inclusion complexes between beta-cyclodextrin and a gemini surfactant in aqueous solution: An NMR study
    • Guerrero-Martínez A, González-Gaitano G, Viñas MH, Tardajos G. 2006. Inclusion complexes between beta-cyclodextrin and a gemini surfactant in aqueous solution: An NMR study. J Phys Chem B 110:13819-13828.
    • (2006) J Phys Chem B , vol.110 , pp. 13819-13828
    • Guerrero-Martínez, A.1    González-Gaitano, G.2    Viñas, M.H.3    Tardajos, G.4
  • 8
    • 33746204093 scopus 로고    scopus 로고
    • Enzyme mechanisms, models, and mimics
    • Kirby AJ. 1996. Enzyme mechanisms, models, and mimics. Angew Chem, Int Ed Engl 35:707-724.
    • (1996) Angew Chem, Int Ed Engl , vol.35 , pp. 707-724
    • Kirby, A.J.1
  • 9
    • 0036172264 scopus 로고    scopus 로고
    • Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrins inclusion compounds
    • Fernandes CM, Vieira MT, Veiga FJB. 2002. Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrins inclusion compounds. Eur J Pharm Sci 15:79-88.
    • (2002) Eur J Pharm Sci , vol.15 , pp. 79-88
    • Fernandes, C.M.1    Vieira, M.T.2    Veiga, F.J.B.3
  • 10
    • 0034887576 scopus 로고    scopus 로고
    • Cyclodextrin complexes of salts of acidic drugs. Thermodynamic properties, structural features, and pharmaceutical applications
    • Redenti E, Szente L, Szejtli J. 2001. Cyclodextrin complexes of salts of acidic drugs. Thermodynamic properties, structural features, and pharmaceutical applications. J Pharm Sci 90:979-986.
    • (2001) J Pharm Sci , vol.90 , pp. 979-986
    • Redenti, E.1    Szente, L.2    Szejtli, J.3
  • 11
    • 0029819323 scopus 로고    scopus 로고
    • Loftsson T, Brewster ME. 1996. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85:1017-1025.
    • Loftsson T, Brewster ME. 1996. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85:1017-1025.
  • 12
    • 0032119526 scopus 로고    scopus 로고
    • Cyclodextrin drug carrier systems
    • Uekama K, Hirayama F, Irie T. 1998. Cyclodextrin drug carrier systems. Chem Rev 98:2045-2076.
    • (1998) Chem Rev , vol.98 , pp. 2045-2076
    • Uekama, K.1    Hirayama, F.2    Irie, T.3
  • 13
    • 0343262203 scopus 로고
    • Phenothiazine drugs structure-activity relationships explained by a conformation that mimics dopamine
    • Feinberg AP, Snyder SH. 1975. Phenothiazine drugs structure-activity relationships explained by a conformation that mimics dopamine. Proc Natl Acad Sci USA 1899-1903.
    • (1975) Proc Natl Acad Sci USA , pp. 1899-1903
    • Feinberg, A.P.1    Snyder, S.H.2
  • 15
    • 0029852699 scopus 로고    scopus 로고
    • Rajewski RA, Stella VJ. 1996. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci 85:1142-1169.
    • Rajewski RA, Stella VJ. 1996. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci 85:1142-1169.
  • 16
    • 0033621920 scopus 로고    scopus 로고
    • Effect of cyclodextrin complexation on aqueous solubility and photostability of phenothiazine
    • Lutka A. 2000. Effect of cyclodextrin complexation on aqueous solubility and photostability of phenothiazine. Pharmazie 55:120-123.
    • (2000) Pharmazie , vol.55 , pp. 120-123
    • Lutka, A.1
  • 18
    • 0021018448 scopus 로고
    • Reduction in the local tissue toxicity of chlorpromazine by beta-cyclodextrin complexation
    • Irie T, Kuwahara S, Otagiri M, Uekama K, Iwamasa T. 1983. Reduction in the local tissue toxicity of chlorpromazine by beta-cyclodextrin complexation. J Pharm Dyn 6:790-792.
    • (1983) J Pharm Dyn , vol.6 , pp. 790-792
    • Irie, T.1    Kuwahara, S.2    Otagiri, M.3    Uekama, K.4    Iwamasa, T.5
  • 19
    • 1942436116 scopus 로고    scopus 로고
    • Destruction of perfluoroalkyl surfactant aggregates by beta-cyclodextrin
    • Nicolle GM, Merbach AE. 2004. Destruction of perfluoroalkyl surfactant aggregates by beta-cyclodextrin. Chem Commun 854-855.
    • (2004) Chem Commun , pp. 854-855
    • Nicolle, G.M.1    Merbach, A.E.2
  • 20
    • 0035964760 scopus 로고    scopus 로고
    • Enantioseparation of phenothiazines in capillary zone electrophoresis using cyclodextrins as chiral selectors
    • Lin CE, Chen KH. 2001. Enantioseparation of phenothiazines in capillary zone electrophoresis using cyclodextrins as chiral selectors. J Chromatogr, A 930:155-163.
    • (2001) J Chromatogr, A , vol.930 , pp. 155-163
    • Lin, C.E.1    Chen, K.H.2
  • 21
    • 0035847239 scopus 로고    scopus 로고
    • Enantioseparations in capillary electromigration techniques: Recent developments and future trends
    • Chankvetadze B, Blaschke G. 2001. Enantioseparations in capillary electromigration techniques: Recent developments and future trends. J Chromatogr, A 906:309-363.
    • (2001) J Chromatogr, A , vol.906 , pp. 309-363
    • Chankvetadze, B.1    Blaschke, G.2
  • 23
    • 33746883556 scopus 로고    scopus 로고
    • Effect of cyclodextrin nanocavity confinement on the photorelaxation of the cardiotonic drug milrinone
    • El-Kemary M, Organero JA, Santos L, Douhal A. 2006. Effect of cyclodextrin nanocavity confinement on the photorelaxation of the cardiotonic drug milrinone. J Phys Chem B 110:14128-14134.
    • (2006) J Phys Chem B , vol.110 , pp. 14128-14134
    • El-Kemary, M.1    Organero, J.A.2    Santos, L.3    Douhal, A.4
  • 24
    • 0000835931 scopus 로고    scopus 로고
    • NMR studies of cyclodextrins and cyclodextrin complexes
    • Schneider J-J, Hacket F, Rüdiger V. 1998. NMR studies of cyclodextrins and cyclodextrin complexes. Chem Rev 98:1755-1785.
    • (1998) Chem Rev , vol.98 , pp. 1755-1785
    • Schneider, J.-J.1    Hacket, F.2    Rüdiger, V.3
  • 27
    • 0000611486 scopus 로고
    • A quantitative study of the effect of solvent on the electronic absorption and fluorescence spectra of substituted phenothiazines: Evaluation of their ground and excited singlet state dipole moments
    • Párkányi C, Boniface C, Aaron JJ, Maafi M. 1993. A quantitative study of the effect of solvent on the electronic absorption and fluorescence spectra of substituted phenothiazines: Evaluation of their ground and excited singlet state dipole moments. Spectrochim Acta, Part A 49:1715-1725.
    • (1993) Spectrochim Acta, Part A , vol.49 , pp. 1715-1725
    • Párkányi, C.1    Boniface, C.2    Aaron, J.J.3    Maafi, M.4
  • 28
    • 0000817164 scopus 로고
    • 2-Laser photochemistry of phenothiazine in solution: Ionization and bond-cleavage from upper states
    • Smith GA, McGimpsey WG. 1994. 2-Laser photochemistry of phenothiazine in solution: Ionization and bond-cleavage from upper states. J Phys Chem 98:2923-2929.
    • (1994) J Phys Chem , vol.98 , pp. 2923-2929
    • Smith, G.A.1    McGimpsey, W.G.2
  • 29
    • 0029557162 scopus 로고
    • Mechanism and solvent dependence for photoionization of promazine and chlorpromazine
    • García C, Smith GA, McGimpsey WG, Kochevar IE, Redmond RW. 1995. Mechanism and solvent dependence for photoionization of promazine and chlorpromazine. J Am Chem Soc 117:10841-10878.
    • (1995) J Am Chem Soc , vol.117 , pp. 10841-10878
    • García, C.1    Smith, G.A.2    McGimpsey, W.G.3    Kochevar, I.E.4    Redmond, R.W.5
  • 30
    • 0031100903 scopus 로고    scopus 로고
    • Picosecond flash photolysis studies on phenothiazine in organic and micellar solution
    • Gosh HN, Sarpre AV, Palit DK, Mittal JP. 1997. Picosecond flash photolysis studies on phenothiazine in organic and micellar solution. J Phys Chem B 101:2315-2320.
    • (1997) J Phys Chem B , vol.101 , pp. 2315-2320
    • Gosh, H.N.1    Sarpre, A.V.2    Palit, D.K.3    Mittal, J.P.4
  • 31
    • 0000590273 scopus 로고    scopus 로고
    • Steady-state and time-resolved studies on photoinduced interaction of phenothiazine and 10-methyl-phenothiazine with chloroalkanes
    • Nath S, Pal H, Palit DK, Sapre AV, Mittal JP. 1998. Steady-state and time-resolved studies on photoinduced interaction of phenothiazine and 10-methyl-phenothiazine with chloroalkanes. J Phys Chem A 102:5822-5830.
    • (1998) J Phys Chem A , vol.102 , pp. 5822-5830
    • Nath, S.1    Pal, H.2    Palit, D.K.3    Sapre, A.V.4    Mittal, J.P.5
  • 32
    • 0000060559 scopus 로고
    • Simultaneous analysis of multiple fluorescence decay curves: A global approach
    • Knutson JR, Beechem JM, Brand L. 1983. Simultaneous analysis of multiple fluorescence decay curves: A global approach. Chem Phys Lett 102: 501-507.
    • (1983) Chem Phys Lett , vol.102 , pp. 501-507
    • Knutson, J.R.1    Beechem, J.M.2    Brand, L.3
  • 33
    • 0010713847 scopus 로고    scopus 로고
    • Determination of stoi-chiometry and equilibrium constants of complexes of tyrosine with cyclodextrins by time-resolved fluorescence spectroscopy and global analysis of fluorescence decays
    • Wiczk W, Mrozek J, Szabelsky M, Karolczak J, Guzow K, Malicka J. 2001. Determination of stoi-chiometry and equilibrium constants of complexes of tyrosine with cyclodextrins by time-resolved fluorescence spectroscopy and global analysis of fluorescence decays. Chem Phys Lett 341:161-167.
    • (2001) Chem Phys Lett , vol.341 , pp. 161-167
    • Wiczk, W.1    Mrozek, J.2    Szabelsky, M.3    Karolczak, J.4    Guzow, K.5    Malicka, J.6
  • 35
    • 13444267752 scopus 로고    scopus 로고
    • NMR spectroscopy of micelles and related systems
    • Furo I. 2005. NMR spectroscopy of micelles and related systems. J Mol Liq 117:117-137.
    • (2005) J Mol Liq , vol.117 , pp. 117-137
    • Furo, I.1
  • 36
    • 1942466466 scopus 로고    scopus 로고
    • Self-association of cromolyn sodium in aqueous solution characterized by nuclear magnetic resonance spectroscopy
    • Ding X, Stringfellow TC, Robinson JR. 2004. Self-association of cromolyn sodium in aqueous solution characterized by nuclear magnetic resonance spectroscopy. J Pharm Sci 93:1351-1358.
    • (2004) J Pharm Sci , vol.93 , pp. 1351-1358
    • Ding, X.1    Stringfellow, T.C.2    Robinson, J.R.3
  • 37
    • 0035127716 scopus 로고    scopus 로고
    • Thermodynamic properties of some antidepressant drugs in acqueous solution
    • Taboada P, Attwood D, Ruso JM, Garcia M, Mosquera V. 2001. Thermodynamic properties of some antidepressant drugs in acqueous solution. Langmuir 17:173-177.
    • (2001) Langmuir , vol.17 , pp. 173-177
    • Taboada, P.1    Attwood, D.2    Ruso, J.M.3    Garcia, M.4    Mosquera, V.5
  • 38
    • 0001042655 scopus 로고
    • Self-association of amphiphilic phenothiazine drugs in aqueous solutions of low ionic-strength
    • Attwood D, Mosquera V, Rey C, Vasquez E. 1991. Self-association of amphiphilic phenothiazine drugs in aqueous solutions of low ionic-strength. J Chem Soc Faraday Trans 87:2971-2973.
    • (1991) J Chem Soc Faraday Trans , vol.87 , pp. 2971-2973
    • Attwood, D.1    Mosquera, V.2    Rey, C.3    Vasquez, E.4
  • 39
    • 0035815012 scopus 로고    scopus 로고
    • Thermodynamic and spectroscopic study of a molecular rotaxane containing a bolaform surfactant and beta-cyclodextrin
    • González-Gaitano G, Guerrero-Martínez A, Ortega F, Tardajos G. 2001. Thermodynamic and spectroscopic study of a molecular rotaxane containing a bolaform surfactant and beta-cyclodextrin. Langmuir 17:1392-1398.
    • (2001) Langmuir , vol.17 , pp. 1392-1398
    • González-Gaitano, G.1    Guerrero-Martínez, A.2    Ortega, F.3    Tardajos, G.4
  • 40
    • 10644222011 scopus 로고    scopus 로고
    • Structural characterization and enantioseparation of the chiral compound praziquantel
    • Liu Y, Wang X, Wang JK, Ching CB. 2004. Structural characterization and enantioseparation of the chiral compound praziquantel. J Pharm Sci 93:3039-3046.
    • (2004) J Pharm Sci , vol.93 , pp. 3039-3046
    • Liu, Y.1    Wang, X.2    Wang, J.K.3    Ching, C.B.4
  • 41
    • 0034801426 scopus 로고    scopus 로고
    • Murrastifoline-F: First total synthesis, atropo-enantiomer resolution, and stereoanalysis of an axially chiral N,C-coupled biaryl alkaloid
    • Bringmann G, Tasler S, Endress H, Kraus J, Messer K, Wohlfarth M, Lobin W. 2001. Murrastifoline-F: First total synthesis, atropo-enantiomer resolution, and stereoanalysis of an axially chiral N,C-coupled biaryl alkaloid. J Am Chem Soc 123:2703-2711.
    • (2001) J Am Chem Soc , vol.123 , pp. 2703-2711
    • Bringmann, G.1    Tasler, S.2    Endress, H.3    Kraus, J.4    Messer, K.5    Wohlfarth, M.6    Lobin, W.7
  • 43
    • 29444441601 scopus 로고    scopus 로고
    • Self-diffusion NMR studies of the host-guest interaction between beta-cyclodextrin and alkyltri-methylammonium bromide surfactants
    • Cabaleiro-Lago C, Nilsson M, Söderman O. 2005. Self-diffusion NMR studies of the host-guest interaction between beta-cyclodextrin and alkyltri-methylammonium bromide surfactants. Langmuir 21:11637-11644.
    • (2005) Langmuir , vol.21 , pp. 11637-11644
    • Cabaleiro-Lago, C.1    Nilsson, M.2    Söderman, O.3


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