Highly efficient complexation of sanguinarine alkaloid by carboxylatopillar[6]arene: pKa shift, increased solubility and enhanced antibacterial activity

Chem Commun (Camb). 2017 Jun 29;53(53):7381-7384. doi: 10.1039/c7cc02799k.

Abstract

Encapsulation of a physiologically active substance, sanguinarine (SA), by a water soluble carboxylatopillar[6]arene (CP6A), is described. The efficient complexation by CP6A, giving a Ka value of (2.4 ± 0.3) × 105 M-1 in pH 7.4, served to increase the water solubility by 4.3-fold, cause a 2.02 shift in pKa, and enhance the antibacterial activity of SA.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Benzophenanthridines / chemistry
  • Benzophenanthridines / pharmacology*
  • Dose-Response Relationship, Drug
  • Hydrogen-Ion Concentration
  • Isoquinolines / chemistry
  • Isoquinolines / pharmacology*
  • Macrocyclic Compounds / chemistry
  • Macrocyclic Compounds / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Solubility
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Benzophenanthridines
  • Isoquinolines
  • Macrocyclic Compounds
  • carboxylatopillar(6)arene
  • sanguinarine