Invertible Amphiphilic Molecular Pockets Made of Cholic Acid

被引:34
作者
Luo, Juntao [1 ]
Chen, Yilong [1 ]
Zhu, X. X. [1 ]
机构
[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
UMBRELLA-ASSISTED TRANSPORT; ONE-POT SYNTHESIS; INCLUSION COMPLEXES; BETA-CYCLODEXTRIN; ION CHANNELS; DENDRITIC POLY(AMIDE-UREA)S; CURTIUS REARRANGEMENT; PHOSPHOLIPID-BILAYERS; REVERSED MICELLES; DERIVATIVES;
D O I
10.1021/la9013703
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A trimer of cholic acid was prepared via a simple isocyanate linkage. Fluorescence and UV-vis spectroscopic studies showed that the same cholane trimer can form either a hydrophobic cavity in aqueous solutions or a hydrophilic cavity in an apolar solvent using pyrene and a derivative of pyrene as probes. The dynamic inversion of the cavities was demonstrated for the first time by a simple change of the polarity of the solvent media by adjusting from an aqueous buffer to tetrahydrofuran and vice versa. The NMR study of a dimer model compound of cholic acid indicated a restricted conformation exist in the solvent mixture of chloroform and methanol.
引用
收藏
页码:10913 / 10917
页数:5
相关论文
共 36 条
[1]  
Bhattacharya S, 2006, MOLECULAR GELS: MATERIALS WITH SELF-ASSEMBLED FIBRILLAR NETWORKS, P613, DOI 10.1007/1-4020-3689-2_18
[2]   Fluorescence study of inclusion complexes between star-shaped cholic acid derivatives and polycyclic aromatic fluorescent probes and the size effects of host and guest molecules [J].
Chen, Yilong ;
Luo, Juntao ;
Zhu, X. X. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (11) :3402-3409
[3]   Temperature dependence of the inclusion-dissociation behavior of the inclusion complexes between cationic substituted 3H-indoles and β-cyclodextrin -: Design of a novel type of semi-rotaxane [J].
Chen, YL ;
Xu, TK ;
Shen, XH ;
Gao, HC .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 173 (01) :42-50
[4]  
DELAPENA AM, 1991, J PHYS CHEM-US, V95, P3330
[5]  
DELAPENA AM, 1991, J AM CHEM SOC, V113, P1572
[6]   Introduction: Molecular recognition [J].
Gellman, SH .
CHEMICAL REVIEWS, 1997, 97 (05) :1231-1232
[7]   Artificial ion channels showing rectified current behavior [J].
Goto, C ;
Yamamura, M ;
Satake, A ;
Kobuke, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) :12152-12159
[8]   Molecular umbrella-assisted transport of an oligonucleotide across cholesterol-rich phospholipid bilayers [J].
Janout, V ;
Jing, BW ;
Regen, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15862-15870
[9]   Molecular umbrella-assisted transport of thiolated AMP and ATP across phospholipid bilayers [J].
Janout, V ;
Jing, BW ;
Regen, SL .
BIOCONJUGATE CHEMISTRY, 2002, 13 (02) :351-356
[10]   Molecular umbrella-assisted transport of glutathione across a phospholipid membrane [J].
Janout, V ;
Zhang, LH ;
Staina, IV ;
Di Giorgio, C ;
Regen, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) :5401-5406