Article

Enhancement of fluorescence quenching and exciplex formation in DNA major groove by double incorporation of modified fluorescent deoxyuridines.

Department of Chemical Biology and Applied Chemistry, School of Engineering, Nihon University, Koriyama, Fukushima 963-8642, Japan.
Bioorganic & medicinal chemistry letters (impact factor: 2.65). 04/2012; 22(12):4103-5. DOI:10.1016/j.bmcl.2012.04.067 pp.4103-5
Source: PubMed

ABSTRACT 5-(1-Naphthalenylethynyl)-2'-deoxyuridine ((N)U) and 5-[(4-cyano-1-naphthalenyl)ethynyl]-2'-deoxyuridine ((CN)U) were synthesized and incorporated into oligodeoxynucleotides. Fluorescence emissions of modified duplexes containing double (N)U were efficiently quenched depending upon the sequence pattern of the naphthalenes in DNA major groove, as compared to the duplex possessing single (N)U. When one of the naphthalene moieties has a cyano substituent, the exciplex emission from the chromophores in DNA major groove was observed at longer wavelength.

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Keywords

5-[(4-cyano-1-naphthalenyl)ethynyl]-2'-deoxyuridine
 
DNA major groove
 
exciplex emission
 
Fluorescence emissions
 
naphthalene moieties
 
sequence pattern
 
wavelength