A 5,7-Dimethoxyflavone/Hydroxypropyl-beta-Cyclodextrin Inclusion Complex with Anti-Butyrylcholinesterase Activity. Songngam, S., Sukwattanasinitt, M., Siralertmukul, K., & Sawasdee, P. AAPS PHARMSCITECH, 15(5):1189-1196, OCT, 2014. doi abstract bibtex This study aimed to improve the water solubility of 5,7-dimethoxyflavone (5,7-DMF) isolated from Kaempferia parviflora by complexation with 2-hydroxypropyl-beta-cyclodextrin (HP beta-CD). The phase solubility profile of 5,7-DMF in the presence of HP beta-CD was classified as A(L)-type and indicated a 1:1 mole ratio. Differential scanning colorimetry, X-ray diffraction, NMR and SEM analyses supported the formation of a 5,7-DMF/HP beta-CD inclusion complex involving the A ring of 5,7-DMF inside the HP beta-CD cavity. This is the first example of CD inclusion with the A ring of non-hydroxyl flavones. The stability and binding constants of the complexes were determined using the phase solubility and UV-vis absorption spectroscopy, respectively. The water solubility of 5,7-DMF was increased 361.8-fold by complexation with HP beta-CD and overcame the precipitation problem observed in aqueous buffers, such as during in vitro anti-butyrylcholinesterase activity assays. The 1:1 mole ratio of the 5,7-DMF/HP beta-CD complex showed a 2.7-fold higher butyrylcholinesterase inhibitory activity (in terms of the IC50 value) compared to the non-complexed compound.
@article{ ISI:000342489200016,
Author = {Songngam, Supachai and Sukwattanasinitt, Mongkol and Siralertmukul,
Krisana and Sawasdee, Pattara},
Title = {{A 5,7-Dimethoxyflavone/Hydroxypropyl-beta-Cyclodextrin Inclusion Complex
with Anti-Butyrylcholinesterase Activity}},
Journal = {{AAPS PHARMSCITECH}},
Year = {{2014}},
Volume = {{15}},
Number = {{5}},
Pages = {{1189-1196}},
Month = {{OCT}},
Abstract = {{This study aimed to improve the water solubility of 5,7-dimethoxyflavone
(5,7-DMF) isolated from Kaempferia parviflora by complexation with
2-hydroxypropyl-beta-cyclodextrin (HP beta-CD). The phase solubility
profile of 5,7-DMF in the presence of HP beta-CD was classified as
A(L)-type and indicated a 1:1 mole ratio. Differential scanning
colorimetry, X-ray diffraction, NMR and SEM analyses supported the
formation of a 5,7-DMF/HP beta-CD inclusion complex involving the A ring
of 5,7-DMF inside the HP beta-CD cavity. This is the first example of CD
inclusion with the A ring of non-hydroxyl flavones. The stability and
binding constants of the complexes were determined using the phase
solubility and UV-vis absorption spectroscopy, respectively. The water
solubility of 5,7-DMF was increased 361.8-fold by complexation with HP
beta-CD and overcame the precipitation problem observed in aqueous
buffers, such as during in vitro anti-butyrylcholinesterase activity
assays. The 1:1 mole ratio of the 5,7-DMF/HP beta-CD complex showed a
2.7-fold higher butyrylcholinesterase inhibitory activity (in terms of
the IC50 value) compared to the non-complexed compound.}},
DOI = {{10.1208/s12249-014-0157-0}},
ISSN = {{1530-9932}},
ResearcherID-Numbers = {{Sukwattanasinitt, Mongkol/E-8912-2010}},
Unique-ID = {{ISI:000342489200016}},
}
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