Inclusion behavior of oxybutynin with hydroxypropyl-β-cyclodextrin

Pan-liang Zhang , Chun-yue Pan , Ke-wen Tang , Hong-jian Li

Journal of Central South University ›› 2011, Vol. 18 ›› Issue (6) : 1897 -1901.

PDF
Journal of Central South University ›› 2011, Vol. 18 ›› Issue (6) : 1897 -1901. DOI: 10.1007/s11771-011-0920-2
Article

Inclusion behavior of oxybutynin with hydroxypropyl-β-cyclodextrin

Author information +
History +
PDF

Abstract

Inclusion behavior of oxybutynin (OBN) with hydroxypropyl-β-cyclodextrin (HP-β-CD) was investigated by ultraviolet absorption spectrum and fluorescence spectrum. A reliable determination of the complex stoichiometry was provided by the continuous variation technique. Alcohol was added to further investigate the mechanism of the inclusion behavior. Thermodynamic constants ΔG, ΔH and ΔS for inclusion interaction of OBN and HP-β-CD were determined. The results show that host-guest complex with molar ratio of 1:1 is formed, and inclusion stability constant between OBN and HP-β-CD is 54.9 L/mol determined by ultraviolet spectrum and 11.1 L/mol determined by fluorescence spectrum. OBN has weak binding ability with HP-β-CD in aqueous solution (stability constant <102 L/mol) and addition of alcohol leads to a decrease of stability constant, which indicates that the hydrophobic force contributes to the inclusion process. ΔG, ΔH and ΔS are all less than zero, which indicates that the inclusion process is a spontaneous and exothermic process.

Keywords

oxybutynin / β-cyclodextrin derivatives / inclusion interaction / ultraviolet spectrum / fluorescence spectrum

Cite this article

Download citation ▾
Pan-liang Zhang, Chun-yue Pan, Ke-wen Tang, Hong-jian Li. Inclusion behavior of oxybutynin with hydroxypropyl-β-cyclodextrin. Journal of Central South University, 2011, 18(6): 1897-1901 DOI:10.1007/s11771-011-0920-2

登录浏览全文

4963

注册一个新账户 忘记密码

References

[1]

MohantyJ., BhasikuttanA. C., NauW. M., PalH.. Host-guest complexation of neutral red with macrocyclic host molecules: Contrasting pKa shifts and binding affinities for cucurbit[7]uril and β-cyclodextrin [J]. Journal of Physical Chemistry B, 2006, 110(10): 5132-5138

[2]

JordheimL. P., DegobertG., DiabR., PeyrotteS., PerigaudC., DumontetC., FessiH.. Inclusion complexes of a nucleotide analogue with hydroxypropyl-beta-cyclodextrin [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2009, 63(1/2): 11-16

[3]

RekharskyM. V., InoueY. I.. Complexation thermodynamics of cyclodextrins [J]. Chemical Reviews, 1998, 98(5): 1875-1918

[4]

ShanmugamM., RameshD., NagalakshmiV., KavithaR., RajamohanR., StalinT.. Host-guest interaction of l-tyrosine with-cyclodextrin [J]. Spectrochim Acta Part A, 2008, 71(1): 125-132

[5]

LiJ.-x., ZhaoC., ChaoJ.-bin.. Investigation on the inclusion behavior of norfloxacin with 2-methyl-β-cyclodextrin [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2008, 62(3/4): 325-331

[6]

CrupiV., FicarraR., GuardoM., MajolinoD., StancanelliR., VenutiV.. UV-vis and FTIR-ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins [J]. Journal of Pharmaceutical and Biomedical Analysis, 2007, 44(1): 110-117

[7]

LiuY., LiX.-y., ZhangH.-y., LiC.-j., DingFei.. Cyclodextrin-driven movement of cucurbit[7]uril [J]. Journal of Organic Chemistry, 2007, 72(10): 3640-3645

[8]

ZhouS.-s., OuyangJ., BaeyensW., ZhaoH.-c., YangY.-ping.. Chiral separation of four fluoroquinolone compounds using capillary electrophoresis with hydroxypropyl-β-cyclodextrin as chiral selector [J]. Journal Chromatography A, 2006, 1130(2): 296-301

[9]

AmeyiborE., StewartJ. T.. Enantiomeric HPLC Separation of Selected Chiral Drugs Using Native and Derivatized β-Cyclodextrins as Chiral Mobile Phase Additives [J]. Journal of Liquid Chromatography & Related Technologies, 1997, 20(6): 855-869

[10]

PolyakoveN. E., LeshinaT. V., HandE. O., PetrenkoA., KispertL. D.. β-Ionone cyclodextrins inclusion complexes: 1H-NMR study and photolysis [J]. Journal of Photochemistry and Photobiology A: Chemistry, 2004, 161(2/3): 261-267

[11]

Al-MarzouqilA. H., ShehattaI., JobelB., DowaidarA.. Phase solubility and inclusion complex of itraconazole with β-cyclodextrin using supercritical carbon dioxide [J]. Journal of Pharmaceutical Sciences, 2006, 95(2): 292-304

[12]

RecueroV., FerreroM., Gotor-FernandezV., BrievaR., GotorV.. Enzymatic resolution of hindered cyanohydrins, key precursors of muscarinic receptor antagonists [J]. Tetrahedron: Asymmetry, 2007, 18(8): 994-1002

[13]

GuoN., GaoX.-x., XuG.-f., GuoX.-jie.. High performance liquid chromatographic separation of oxybutynin enantiomers using chiral mobile phase additive [J]. Chinese Journal of Chromatography, 2008, 26(2): 259-261

[14]

ParkK., KimK. H., JungS., LimH., HongC., KangJ.. Enantioselective stabilization of inclusion complexes of metoprolol in carboxymethylated β-cyclodextrin [J]. Journal of Pharmaceutical and Biomedical Analysis, 2002, 27(3/4): 569-576

[15]

CalabroM. L., TommasiniS., DonatoP., RaneriD., StancanelliR., FicarraP., FicarraR., CostaC., CataniaS., RustichelliC., GamberiniG.. Effects of α- and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones [J]. Journal of Pharmaceutical and Biomedical Analysis, 2004, 35(2): 365-377

[16]

BettinettiG. P., MuraP., LiguoriA., BramantiG., GiordanoF.. Solubilization and interaction of naproxen with cyclodextrins in aqueous solution and in the solid state [J]. Farmaco Prat, 1988, 43(11): 331-343

AI Summary AI Mindmap
PDF

71

Accesses

0

Citation

Detail

Sections
Recommended

AI思维导图

/