Selective binding of bile salts by β-cyclodextrin derivatives with appended quinolyl arms  

作　　者：Sha-Sha Zhai Yong Chen Yu Liu 

机构地区：[1]Department of Chemistry,State Key Laboratory of Elemento-Organic Chemistry,Nankai University

出　　处：《Chinese Chemical Letters》2013年第6期442-446,共5页中国化学快报（英文版）

基　　金：973 Program(No.2011CB932502);NNSFC(Nos. 20932004,91027007 and 21272125);Program for New Century Excellent Talents in University(No.NCET-10-0500) for financial support

摘　　要：Two β-cyclodextrin derivatives bearing appended quinolyl and isoquinolyl arms,i.e.mono-（6-quinolyl- 6-deoxy）-β-cyclodextrin（1） and mono-（6-isoquinolyl-6-deoxy）-β-cyclodextrin（2） were synthesized in satisfactory yields and fully characterized.Their original conformations and binding behaviors toward four bile salt guests,that is,sodium cholate（CA）,sodium deoxycholate（DCA）,sodium glycocholate （GCA）,and sodium taurocholate（TCA）,were investigated by means of fluorescence,circular dichroism and 2D NMR spectroscopy.The study of solution structures revealed that both quinolyl and isoquinolyl arms were located outside the cyclodextrin cavity.The results obtained from the fluorescence titrations showed that the binding abilities of hosts 1 and 2 with selected bile salts varied in an order of DCA 〉 CA 〉 GCA.The selective binding of hosts toward bile salt guests was discussed from the viewpoints of induced-fit and multiple binding.Two β-cyclodextrin derivatives bearing appended quinolyl and isoquinolyl arms,i.e.mono-（6-quinolyl- 6-deoxy）-β-cyclodextrin（1） and mono-（6-isoquinolyl-6-deoxy）-β-cyclodextrin（2） were synthesized in satisfactory yields and fully characterized.Their original conformations and binding behaviors toward four bile salt guests,that is,sodium cholate（CA）,sodium deoxycholate（DCA）,sodium glycocholate （GCA）,and sodium taurocholate（TCA）,were investigated by means of fluorescence,circular dichroism and 2D NMR spectroscopy.The study of solution structures revealed that both quinolyl and isoquinolyl arms were located outside the cyclodextrin cavity.The results obtained from the fluorescence titrations showed that the binding abilities of hosts 1 and 2 with selected bile salts varied in an order of DCA 〉 CA 〉 GCA.The selective binding of hosts toward bile salt guests was discussed from the viewpoints of induced-fit and multiple binding.

关 键 词：Cyclodextrin derivatives Bile salts Molecular recognition 

分 类 号：O621.25[理学—有机化学]