NMR spectroscopic study of cyclodextrin inclusion complexes with A-007 prodrugs.
One- and two-dimensional NMR spectroscopy was used to demonstrate the formation of inclusion cyclodextrin complexes with several A-007 prodrugs. These complexes are comprised from the encapsulation of the two phenol moieties of the A-007 prodrugs within the cyclodextrin cavity. Considering the size of the two phenol moieties of the A-007 prodrugs compared to the sizes of alpha-, beta-, and gamma-cyclodextrin cavities, we observed complementary binding of the A-007 prodrug with only beta-cyclodextrin, which was also demonstrated spectroscopically. The beta-cyclodextrin inclusion complexes increased the prodrug solubility and modified the prodrug half-life in water. Therefore, beta-cyclodextrin inclusion complexes can be used as an essential form of A-007 prodrug delivery.
Sagiraju
Sarada
S
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, United States.
Jursic
Branko S
BS
D003505:Cyclodextrins / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011355:Prodrugs / Q000737:chemistry*; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization
C097674:4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone; D003505:Cyclodextrins; D006835:Hydrazones; D010636:Phenols; D011355:Prodrugs