Host–Guest Sensory System of Dansyl-Modifled β-Cyclodextrin for Detecting Steroidal Compounds by Dansyl Fluorescence

Ueno, Akihiko; Minato, Shingo; Suzuki, I.; Fukushima, Mitsuru; Ohkubo, Masahiro; Osa, Tetsuo; Hamada, Fumio; Murai, Koichi

doi:10.1246/cl.1990.605

Cited by 102 publications

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“…10 In this system, these hosts exhibited higher sensitive and selective molecular recognition ability for ursodeoxycholic acid, chenodeoxycholic acid and (-)-borneol compared to monoand di-dansyl-modified β-and γ -analogs, which were reported previously. [11][12][13][14] As a further extension of our work, we investigated the fluorescence spectral changes of the titled hosts, fluorescent hetero-modified cyclodextrins, concerning the accommodation of endocrine-disrupting chemicals. In this paper, we wish to describe the fluorescent-sensing abilities of these host compounds for environmental hormones.…”

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confidence: 99%

Fluorescent Molecular Recognition for Endocrine-Disrupting Chemicals and Their Analogs by Fluorescent Hetero-Modified Cyclodextrins

2000

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The detection of endocrine-disrupting chemicals required high technology, such as an analysis by GC/MS, which is very costly, and the analytical results require many days to obtain. [1][2][3][4][5][6][7][8] However, it is urgent to quickly and conveniently confirm the existence of endocrine-disrupting chemicals in rivers and lakes. In a previous paper, we discussed the first example of fluorescent molecular sensing for endocrine-disrupting chemicals and dioxin analogs by homo fluorescent β-and γ -cyclodextrins, which were modified with bis fluorescent-active units such as dansyl or anthranilate. 9 In the present study, endocrine-disrupting chemicals, including p-nonylphenol and bisphenol A, and a dioxin analog, such as 2,4,6-trichlorophenol, were conveniently and directly detected by these fluorescent cyclodexstrins with high sensitivity and selectivity; pattern recognition of endocrinedisrupting chemicals would be expected to be possible. Furthermore, it was obvious that bis anthranilate-modified β-cyclodextrins can detect 10 -6 M of p-nonylphenol. We have previously discussed the synthesis of regioselectively fluorescent hetero-substituted cyclodextrins, which are 6 A -dansyl-6 X -tosylmodified β-cyclodextrins (X=B or G, C or F, and D or E) and 6 A -dansyl-6 X -tosyl-modified γ -analogs (X=B or H, C or G, D or F, and E), and examined of their fluorescent molecular-sensing abilities for organic compounds, such as bile acids and terpenes. 10 In this system, these hosts exhibited higher sensitive and selective molecular recognition ability for ursodeoxycholic acid, chenodeoxycholic acid and (-)-borneol compared to monoand di-dansyl-modified β-and γ -analogs, which were reported previously. [11][12][13][14] As a further extension of our work, we investigated the fluorescence spectral changes of the titled hosts, fluorescent hetero-modified cyclodextrins, concerning the accommodation of endocrine-disrupting chemicals. In this paper, we wish to describe the fluorescent-sensing abilities of these host compounds for environmental hormones. These hetero-modified hosts detect bisphenol A and 2,4,6-trichlorophenol with high sensitivity and selectivity. ExperimentalPreparations of β-1, β-2, β-3, γ -1, γ -2, γ -3, and γ -4The host compounds (β -1, β-2, β-3, γ -1, γ -2, γ -3, and γ -4) were prepared according to previously reported procedures. 10 MeasurementsThe fluorescence spectra were measured at 25˚C with a Perkin Elmer LS 40B fluorescence spectrometer. In fluorescence measurements, the excitation wavelength of the fluorescence spectra was 340 nm and the excitation and emission slits were 10 nm. An ethylene glycol aqueous solution (10 vol.%) was used as the solvent for hosts for spectroscopic measurements, because their solubility in pure water is poor. Five microliters of guest species (500, 50 and 5 mM) in dimethyl sulfoxide (DMSO) or MeOH were injected into a 10 vol.% ethylene glycol aqueous solution of the host (2.5 mL) to make a sample solution with a host concentration of 1×10 -6 M and guest concentrations of 0.0...

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Fluorescent Molecular Recognition for Endocrine-Disrupting Chemicals and Their Analogs by Fluorescent Hetero-Modified Cyclodextrins

2000

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“…1,2 CyDs, which are water soluble and cyclically composed of only D-glucopyranose units connected by α-1,4-likages, are basically spectroscopically inert. However, CyDs can be converted spectroscopically to active compounds by a modification with lumophore, such as naphthalene, 3 anthranilic acid, 4,5 fluorescamine, 6 terphenyl, 7 or dansyl 8,9 units. These lumophore-modified CyDs in an aqueous solution have shown guest-responsive fluorescence variations caused by environmental changes of the polarity around at the appended moiety when host-guest complexation has occurred.…”

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confidence: 99%

“…Therefore, these fluorescent CyDs have been used as sensors or indicators of molecules in aqueous solution. For at least four years we have reported on fluorescent molecular systems of homo-substituted β-and γ-CyDs bearing anthranilic acid 10 or dansyl moieties, 11,12 in which these CyDs showed a higher sensing ability for bile acid than mono-substituted CyDs, 4,5,8,9 exhibiting two homo moieties having the same functions, such as a hydrophobic cap or a spacer. Furthermore, we have discussed fluorescent molecular recognition of hetero-modified β-and γ-CyDs having dansyl and tosyl groups or pyrene and cyanobenzene groups.…”

Section: Introductionmentioning

confidence: 99%

Guest-Responsive Fluorescence Variations of γ-Cyclodextrins Labeled with Hetero-Functionalized Pyrene and Tosyl Moieties

et al. 2002

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“…CyDs have been studied as an enzyme model and molecular receptor, because they can include various organic compounds into their hydrophobic cavity. 1,2 For the last decade, we have contributed to report chemo-sensory systems based on fluorescent CyDs modified with naphthalene, 3 anthracene, 4 anthranilate, [5][6][7][8][9] fluorescamine, 10 terphenyl, 11 and dansyl, [12][13][14][15] in which these fluorescent CyDs detect biologically important bile acids such as lithocholic acid, chenodoxycholic acid and ursodeoxycholic acids with high sensing ability.…”

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confidence: 99%

Fluorescent Molecular Sensory System Based on Bis Pyrene-Modified γ-Cyclodextrin Dimer for Steroids and Endocrine Disruptors

et al. 2001

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Host–Guest Sensory System of Dansyl-Modifled β-Cyclodextrin for Detecting Steroidal Compounds by Dansyl Fluorescence

Abstract: Dansyl-modifled β-cyclodextrin decreases its fluorescence intensity upon guest binding, and this phenomenon was used to detect steroidal compounds. This system exhibited remarkable molecular recognition, showing high sensitivities for ursodeoxycholic acid and chenodeoxycholic acid.

Cited by 102 publications

References 6 publications

Fluorescent Molecular Recognition for Endocrine-Disrupting Chemicals and Their Analogs by Fluorescent Hetero-Modified Cyclodextrins

Fluorescent Molecular Recognition for Endocrine-Disrupting Chemicals and Their Analogs by Fluorescent Hetero-Modified Cyclodextrins

Guest-Responsive Fluorescence Variations of γ-Cyclodextrins Labeled with Hetero-Functionalized Pyrene and Tosyl Moieties

Fluorescent Molecular Sensory System Based on Bis Pyrene-Modified γ-Cyclodextrin Dimer for Steroids and Endocrine Disruptors

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