Citation: Sha-Sha Zhai, Yong Chen, Yu Liu. Selective binding of bile salts by β-cyclodextrin derivatives with appended quinolyl arms[J]. Chinese Chemical Letters, ;2013, 24(6): 442-446. shu

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

1.
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Yu Liu,
Received Date: 28 February 2013
Available Online: 26 March 2013

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.
- Cyclodextrin derivatives,
- Bile salts,
- Molecular recognition
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沈阳化工大学材料科学与工程学院沈阳 110142