| Guest-responsive fluorescence variations of gamma-cyclodextrins labeled with hetero-functionalized pyrene and tosyl moieties. | |
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MedLine Citation:
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PMID: 11874110 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Regioselectively hetero-labeled hosts, 6A-pyrenebutylate-6X-tosyl-modified gamma-cyclodextrins (X = B or H, C or G, D or F, and E for gamma-1, gamma-2, gamma-3, and gamma-4, respectively), were synthesized in order to investigate their chemo-sensor properties for applications to organic compounds, such as bile acids and terpenes. The hosts (gamma-1, gamma-2, gamma-3, and gamma-4) exhibit pure monomer fluorescence. The guest-induced fluorescence emissions of these hosts were suppressed in the presence of guests. The extent of fluorescence variations of these hosts with guests was recognized as a manifestation of the sensing ability of the hosts. A sensing parameter (deltaI/I0, where I and I0 are the fluorescence intensities in the presence and absence of a guest and deltaI = I0-I) was used to describe the sensing ability of these hosts. Host gamma-analogs were able to detect progesterone, ursodeoxycholic acid, chenodeoxycholic acid, and (-)-borneol with high sensitivity. The behaviors of the appended moieties of these hosts during the formation of host-guest complexes were studied using induced circular dichroism (ICD) spectra, fluorescence spectra and the MM2-energy-minimized structure. The host gamma-analogs exhibited different ICD spectra patterns before and after the addition of ursodeoxycholic acid. The guest-induced variations of ICD and the fluorescence spectra and MM2-minimized structures suggest that the pyrene and tosyl moieties move by altering the spatial relationship between them, in which the pyrene moiety works as a hydrophobic cap and the tosyl moiety is speculated to act as a spacer. |
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Authors:
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Akira Makabe; Kentaro Kinoshita; Miyuki Narita; Fumio Hamada |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry Volume: 18 ISSN: 0910-6340 ISO Abbreviation: Anal Sci Publication Date: 2002 Feb |
Date Detail:
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Created Date: 2002-03-04 Completed Date: 2002-04-05 Revised Date: 2003-11-03 |
Medline Journal Info:
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Nlm Unique ID: 8511078 Medline TA: Anal Sci Country: Japan |
Other Details:
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Languages: eng Pagination: 119-24 Citation Subset: - |
Affiliation:
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Department of Materials-process Engineering and Applied Chemistryfor Environments, Faculty of Engineering and Resource Science, Akita University, Tegata, Japan. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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