| A ratiometric TICT-type dual fluorescent sensor for an amino acid. | |
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MedLine Citation:
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PMID: 20424794 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A novel ratiometric fluorescent sensor 1 having the 4-(N,N-dimethylamino)benzoate (DMAB) group as a twisted intramolecular charge transfer (TICT) dual fluorescence site and the guanidinium group as a binding site for an amino acid at the 12- and 3-positions of cholic acid, respectively, was designed and synthesized. The sensor 1 showed characteristic dual fluorescence and it was shown that the guanidinium group in the proximity of the DMAB group influenced largely the TICT formation process in 1. Liquid/liquid extraction experiments demonstrated that the intensity ratio of the TICT fluorescence to the locally-excited (LE) fluorescence (I(TICT)/I(LE)) observed from the organic layer decreased with an increase in the concentration of N-acetyl-d-phenylalanine (AcPhe) in the water phase. Such fluorescence titration experiments afforded the apparent binding constant between 1 and AcPhe to be 7.0 x 10(5) M(-1). Temperature dependence of the fluorescence spectrum of 1 in the absence and presence of AcPhe indicated that the primary origin of the change in the I(TICT)/I(LE) value upon recognition of the amino acid was the increase in the activation energy of the TICT formation process in 1. |
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Authors:
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Akitaka Ito; Shoji Ishizaka; Noboru Kitamura |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-04-21 |
Journal Detail:
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Title: Physical chemistry chemical physics : PCCP Volume: 12 ISSN: 1463-9084 ISO Abbreviation: Phys Chem Chem Phys Publication Date: 2010 Jul |
Date Detail:
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Created Date: 2010-06-17 Completed Date: 2010-09-14 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100888160 Medline TA: Phys Chem Chem Phys Country: England |
Other Details:
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Languages: eng Pagination: 6641-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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4-Aminobenzoic Acid
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analogs & derivatives*,
chemical synthesis,
chemistry* Amino Acids / chemistry* Fluorescent Dyes / chemistry* Kinetics Nitriles / chemistry Spectrometry, Fluorescence |
| Chemical | |
Reg. No./Substance:
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0/4-(n,n-dimethylamino)benzonitrile; 0/Amino Acids; 0/Fluorescent Dyes; 0/Nitriles; 150-13-0/4-Aminobenzoic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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