Improvement of antifungal activity of 10-undecyn-1-ol by inclusion complexation with cyclodextrin derivatives.
The inclusion complexation behavior between 10-undecyn-1-ol and cyclodextrin (CD) derivatives, namely, randomly methylated beta-CD (RM-beta-CD) and hydroxypropyl-beta-CD (HP-beta-CD), was studied in terms of solubility improvement, apparent stability constant, and the inclusion ratios of the resultant inclusion complexes. The aqueous solubility of 10-undecyn-1-ol was greatly improved through complexation with the CD derivatives. RM-beta-CD is comparatively more efficient in solubilizing 10-undecyn-1-ol with an apparent stability constant outstripping that of HP-beta-CD by about an order of magnitude. Comparative in vitro evaluations of the growth inhibition effects of inclusion complex solutions toward Rosellinia necatrix, a phytopathogenic fungus, were performed. In comparison with the positive control, appreciable improvements of the antifungal activity of 10-undecyn-1-ol through the addition of CD derivatives were observed visually. The improvement was evaluated in terms of area covered by the mycelia of Rosellinia necatrix and their growth rate. RM-beta-CD was proven to be more effective compared to HP-beta-CD with regard to the reduction of both fungal mycelium-covered area and growth rate constant, presumably owing to greater solubility enhancement by RM-beta-CD and thus the bioavailability of 10-undecyn-1-ol. Inclusion complexation of 10-undecyn-1-ol with CD derivatives suggests a potential means for production of an environmentally friendly 10-undecyn-1-ol-based fungicide to counteract R. necatrix.
Neoh
Tze Loon
TL
Department of Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori, 680-8552, Japan. neoh@bio.tottori-u.ac.jp
Tanimoto
Takahiro
T
Ikefuji
Shuichi
S
Yoshii
Hidefumi
H
Furuta
Takeshi
T
D003505:Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology; D004355:Drug Stability; D005233:Fatty Alcohols / Q000032:analysis*; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D012995:Solubility; D013329:Structure-Activity Relationship; D013098:Xylariales / Q000187:drug effects / Q000254:growth & development
C530289:10-undecyn-1-ol; D003505:Cyclodextrins; D005233:Fatty Alcohols; D005659:Fungicides, Industrial