Invertible amphiphilic molecular pockets made of cholic acid.
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.
Luo
Juntao
J
Département de Chimie, Université de Montréal, C. P. 6128, succursale Centre-Ville, Montréal, QC H3C 3J7, Canada.
Chen
Yilong
Y
Zhu
X X
XX
D002725:Chloroform; D019826:Cholic Acid / Q000737:chemistry*; D019281:Dimerization; D005453:Fluorescence; D005663:Furans; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011721:Pyrenes / Q000737:chemistry; D012996:Solutions; D012997:Solvents / Q000737:chemistry; D014508:Urea / Q000737:chemistry
D005663:Furans; D011721:Pyrenes; D012996:Solutions; D012997:Solvents; C018674:tetrahydrofuran; D002725:Chloroform; D014508:Urea; C030984:pyrene; D019826:Cholic Acid; D000432:Methanol