Solubilization of substituted indole compounds by beta-cyclodextrin in water

Chemosphere. 2000 Jun;40(12):1411-6. doi: 10.1016/s0045-6535(99)00321-5.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemistry*
  • Cyclodextrins / chemistry*
  • Cyclodextrins / pharmacology
  • Dose-Response Relationship, Drug
  • Hydrogen Bonding
  • Indoles / chemistry*
  • Molecular Structure
  • Solubility / drug effects
  • Water / chemistry*
  • beta-Cyclodextrins*

Substances

  • Carbazoles
  • Cyclodextrins
  • Indoles
  • N-methyl-1,2,3,4-tetrahydrocarbazole
  • beta-Cyclodextrins
  • Water
  • 1,2,3,4-tetrahydrocarbazole
  • betadex