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Synthesis of Organoselenium‐Modified β ‐Cyclodextrins Possessing a 1,2‐Benzisoselenazol‐3(2 H )‐one Moiety and Their Enzyme‐Mimic Study
Author(s) -
Liu Yu,
Li Bin,
Li Li,
Zhang HengYi
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200201)85:1<9::aid-hlca9>3.0.co;2-h
Subject(s) - chemistry , moiety , pyrogallol , circular dichroism , superoxide dismutase , yield (engineering) , bifunctional , proton nmr , peroxidase , glutathione peroxidase , stereochemistry , enzyme , organic chemistry , medicinal chemistry , nuclear chemistry , catalysis , materials science , metallurgy
Six novel H 2 O‐soluble β ‐cyclodextrin derivatives containing a 1,2‐benzisoselenazol‐3(2 H )‐one moiety were synthesized by a convenient method in 25–60% yield and characterized by MS, elemental analysis, IR, 1 H‐NMR, and UV/VIS spectroscopy. The conformations of these β ‐cyclodextrin derivatives 1 – 6 were analyzed by circular dichroism and fluorescence‐lifetime experiments. The superoxide dismutase (SOD) activities of 1 – 6 were determined by auto‐oxidation of pyrogallol at 25.0° in buffer solution (pH 8.2), giving relatively high SOD activities of up to 121–330 U/mg. Also, the glutathione peroxidase (GPX) activities of hosts 1 – 6 , determined by the method of Wilson at 37° in buffer solution (pH 7.0), show good GPX activities in the range of 0.34–0.86 U/μmol. The mimicking results of the bifunctional artificial enzyme models 1 – 6 were globally compared with regard to their structural and conformational difference.