Formation of natamycin:cyclodextrin inclusion complexes and their characterization.
Natamycin is a broad spectrum antimycotic with very low water solubility, which is used to extend the shelf life of shredded cheese products. beta-Cyclodextrin (beta-CD), hydroxypropyl beta-cyclodextrin (HP beta-CD), and gamma-cyclodextrin (gamma-CD) were found to form inclusion complexes with natamycin in aqueous solution. The increase in solubility of natamycin with added beta-CD was observed to be linear (type A(L) phase solubility diagram). The 1:1 stability constant of natamycin:beta-CD complex was estimated from its phase solubility diagram to be 1010 M(-1). The phase solubility diagrams of both gamma-CD and HP beta-CD exhibited negative deviation from linearity (type A(N) diagram) and, therefore, did not allow the estimation of binding constants. The water solubility of natamycin was increased 16-fold, 73-fold, and 152-fold with beta-CD, gamma-CD, and HP beta-CD, respectively. The natamycin:CD inclusion complexes resulted in in vitro antifungal activity nearly equivalent to that of natamycin in its free state.
Koontz
John L
JL
Department of Food Science and Technology, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA.
Marcy
Joseph E
JE
D000935:Antifungal Agents / Q000737:chemistry*; D002611:Cheese; D003505:Cyclodextrins / Q000737:chemistry*; D005519:Food Preservation; D006358:Hot Temperature; D010866:Natamycin / Q000737:chemistry*; D012995:Solubility; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D014867:Water; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins
D000935:Antifungal Agents; D003505:Cyclodextrins; D012996:Solutions; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins; D014867:Water; D010866:Natamycin; C031215:betadex; C023792:gamma-cyclodextrin