Spectrophotometric study of fluorescence sensing and selective binding of biochemical substrates by 2,2'-bridged bis(beta-cyclodextrin) and its water-soluble fullerene conjugate.
A bis(beta-cyclodextrin)-fullerene conjugate (3) linked at the secondary hydroxyl side was prepared in a good yield from its precursor N,N'-bis(2-(2-aminoethylamino)ethyl)malonamide-bridged bis(beta-cyclodextrin) (2). Spectrophotomeric studies on the conformation and the inclusion complexation behavior of 3 with a variety of organic and biochemical substrates by means of UV-vis, FT-IR, NMR, fluorescence, and circular dichroism spectroscopy showed that the bis(beta-cyclodextrin)-fullerene conjugate displayed an intramolecular capsule-type conformation in aqueous solution. Because of the multiple binding of bis(beta-cyclodextrin) with substrates, 2 can act as an efficient fluorescence sensor for biochemical substrates, while its fullerene conjugate 3 displays a capability of cleaving DNA under visible-light irradiation.
Liu
Yu
Y
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China. yuliu@public.tpt.tj.cn
Liang
Peng
P
Chen
Yong
Y
Zhao
Yan-Li
YL
Ding
Fei
F
Yu
Ao
A
D001593:Benzyl Compounds / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D012995:Solubility; D013050:Spectrometry, Fluorescence; D014867:Water / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D001593:Benzyl Compounds; D037741:Fullerenes; D008314:Malonates; C511016:N,N'-bis(2-((2-hydroxybenzylidine)amino)ethyl)malonamide; D047392:beta-Cyclodextrins; D014867:Water