Document Detail

Construction of helical J-aggregates self-assembled from a thymidylic acid appended anthracene dye and DNA as a template.
MedLine Citation:
PMID:  19206120     Owner:  NLM     Status:  MEDLINE    
The thymidylic acid appended anthracene dye 2,6-bis[5-(3'-thymidylic acid)pentyloxy]anthracene (1) was synthesized, and the self-assembly of 1 and the binary self-assembly of 1 with a complementary single-stranded 20-meric oligodeoxyadenylic acid (dA(20)) were performed in 0.1 x TE buffer solution (i.e., 1.0 x 10(-3) M Tris-HCl, 1.0 x 10(-4) M ethylenediaminetriacetic acid (EDTA)). The characteristic J-band, small Stokes shift (6 nm), Cotton effect, and helical nanofibers 5.1 nm in diameter are observed in UV/Vis, fluorescence, and circular dichroism (CD) spectroscopies and atomic force microscopy (AFM) measurements for the binary self-assembly of 1 and dA(20) in aqueous solution. These observations revealed that the helical J-aggregates, in which the short-axis transition dipoles of the anthracene moieties are aligned in a head-to-tail fashion, are formed from the binary self-assembly of 1 and dA(20). The UV/Vis absorption and CD band of the anthracene L(a) region were found to be strongly dependent on temperature and showed cooperative changes for the binary self-assembly of 1 and dA(20). The self-assembly of the single-component 1 produced right- and left-handed helical nanofibers with diameters ranging from 4.0 to 10 nm. In contrast, for the binary self-assembly, the UV/Vis and fluorescence spectra showed no J-band and the Stokes shift was at approximately 107 nm for the single-component 1 in aqueous solution. In addition, the binary self-assembly of 1 and noncomplementary single-stranded 20-meric oligothymidylic acid (dT(20)) showed a small J-band and the J-band disappeared at 50 degrees C upon heating. On the basis of these observations, we concluded that thymine-adenine base-pair formation induced supramolecular helical J-aggregates in the binary self-assembly of 1 and dA(20) in aqueous solutions.
Rika Iwaura; Mayumi Ohnishi-Kameyama; Tomohiko Iizawa
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  15     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2009  
Date Detail:
Created Date:  2009-03-31     Completed Date:  2009-05-07     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  3729-35     Citation Subset:  IM    
National Food Research Institute, National Agriculture and Food Research Organization, 2-1-12 Kannondai, Tsukuba, Ibaraki, 305-8642, Japan.
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MeSH Terms
Anthracenes / chemistry*
Circular Dichroism
DNA / chemistry*
Microscopy, Atomic Force
Molecular Structure
Thymidine Monophosphate / chemistry*
Reg. No./Substance:
0/Anthracenes; 0/Solutions; 120-12-7/anthracene; 365-07-1/Thymidine Monophosphate; 7732-18-5/Water; 9007-49-2/DNA

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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