Effect of hydroxypropyl-beta-cyclodextrin on the solubility of an antibacterial isoxazolyl-naphthoquinone.
The complexation of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (I) with a highly soluble cyclodextrin, hydroxypropyl-beta-cyclodextrin (HP-beta-CD) was studied in aqueous media by solubility methods. I is an antibacterial and trypanocidal agent that is undergoing preclinical testing. Unfortunately, I exhibits low water solubility, and it is therefore difficult to prepare the solutions for biological tests. I inclusion took place with 1:1 stoichiometry. The stability constants of the I complexes calculated from the slope and the intercept of the phase solubility diagrams are larger in the less ionized form, whereas greater overall solubility is obtained in basic media.
Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Argentina.
M S
MS
Linares
M M
MM
de Bertorello
M R
MR
Longhi
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D000890:Anti-Infective Agents / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D005079:Excipients / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D007555:Isoxazoles / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D012995:Solubility; D014344:Trypanocidal Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins
D000890:Anti-Infective Agents; D003505:Cyclodextrins; D005079:Excipients; D007555:Isoxazoles; D009284:Naphthols; D014344:Trypanocidal Agents; D047392:beta-Cyclodextrins; D014867:Water; D000073738:2-Hydroxypropyl-beta-cyclodextrin; C070800:2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone imine