Document Detail

A ratiometric TICT-type dual fluorescent sensor for an amino acid.
MedLine Citation:
PMID:  20424794     Owner:  NLM     Status:  MEDLINE    
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.
Akitaka Ito; Shoji Ishizaka; Noboru Kitamura
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-04-21
Journal Detail:
Title:  Physical chemistry chemical physics : PCCP     Volume:  12     ISSN:  1463-9084     ISO Abbreviation:  Phys Chem Chem Phys     Publication Date:  2010 Jul 
Date Detail:
Created Date:  2010-06-17     Completed Date:  2010-09-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100888160     Medline TA:  Phys Chem Chem Phys     Country:  England    
Other Details:
Languages:  eng     Pagination:  6641-9     Citation Subset:  IM    
Department of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
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MeSH Terms
4-Aminobenzoic Acid / analogs & derivatives*,  chemical synthesis,  chemistry*
Amino Acids / chemistry*
Fluorescent Dyes / chemistry*
Nitriles / chemistry
Spectrometry, Fluorescence
Reg. No./Substance:
0/4-(n,n-dimethylamino)benzonitrile; 0/Amino Acids; 0/Fluorescent Dyes; 0/Nitriles; 150-13-0/4-Aminobenzoic Acid

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