Solubilization of substituted indole compounds by beta-cyclodextrin in water.
The solubilization of four pairs of substituted indole compounds (SICs) by beta-cyclodextrin (beta-CD) in water was investigated. The results show that 1,2,3,4-tetrahydrocarbazole and N-methyl-1,2,3,4-tetrahydrocarbazole form 1:1 inclusion complexes with beta-CD, while the other six SICs form 1:2 inclusion complexes, respectively. To each pair of SICs with similar structures, the differences between their solubilization in beta-CD/water solutions has been explained by the difference of their contact area within the beta-CD cavity, the difference of their molecule polarity, or the presence of hydrogen bond between SIC molecule and beta-CD molecule.
Cao
J
J
Pollution Control and Resources Reuse National Key Laboratory, Department of Environmental Science and Engineering, Nanjing University, People's Republic of China. ecls@nju.edu.cn
Zhao
C
C
Huang
L
L
Ding
Y
Y
Wang
L
L
Han
S
S
D002227:Carbazoles / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D012995:Solubility / Q000187:drug effects; D014867:Water / Q000737:chemistry*; D047392:beta-Cyclodextrins
D002227:Carbazoles; D003505:Cyclodextrins; D007211:Indoles; C409926:N-methyl-1,2,3,4-tetrahydrocarbazole; D047392:beta-Cyclodextrins; D014867:Water; C409925:1,2,3,4-tetrahydrocarbazole; C031215:betadex