Document Detail

Exploiting the nitrilotriacetic acid moiety for biolabeling with ultrastable perylene dyes.
MedLine Citation:
PMID:  18376823     Owner:  NLM     Status:  MEDLINE    
Fluorescent probes are essential for the exploration of protein function, detection of molecular interactions, and conformational changes. The nitrilotriacetic acid derivatives of different chromophores were successfully used for site-selective noncovalent fluorescence labeling of histidine-tagged proteins. All of them, however, suffer from the same drawback--loss of the fluorescence upon binding of the nickel ions. Herein we present the solution and solid phase synthesis of water-soluble perylene(dicarboximide) functionalized with a nitrilotriacetic acid moiety (PDI-NTA). The photophysical properties of PDI-NTA revealed an exceptional photostability and fluorescence quantum yield that remained unchanged upon addition of nickel ions. The F1 complex of F0F1-ATP synthase from Escherichia coli, containing three hexahistidine tags, was labeled and the suitability for site-specific labeling of the new chromophore demonstrated using fluorescence correlation spectroscopy.
Kalina Peneva; Gueorgui Mihov; Andreas Herrmann; Nawid Zarrabi; Michael Börsch; Thomas M Duncan; Klaus Müllen
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Publication Detail:
Type:  Journal Article     Date:  2008-04-01
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  130     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2008 Apr 
Date Detail:
Created Date:  2008-04-18     Completed Date:  2008-07-11     Revised Date:  2008-12-15    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5398-9     Citation Subset:  IM    
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
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MeSH Terms
Adenosine Triphosphatases / metabolism
Binding Sites
Escherichia coli / enzymology
Fluorescence Resonance Energy Transfer
Fluorescent Dyes / chemical synthesis*
Nickel / chemistry
Nitrilotriacetic Acid / chemistry*
Perylene / analogs & derivatives,  chemical synthesis*
Water / chemistry
Reg. No./Substance:
0/Fluorescent Dyes; 139-13-9/Nitrilotriacetic Acid; 198-55-0/Perylene; 7440-02-0/Nickel; 7732-18-5/Water; EC 3.6.1.-/Adenosine Triphosphatases

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