Fluorescence and electrochemical detection of pyrimidine/purine transversion by a ferrocenyl aminonaphthyridine derivative.
A novel hydrogen bond-forming ligand for pyrimidine/purine transversion, which contains both a fluorescent naphthyridine moiety and a ferrocenyl group as an electrochemical indicator, is described. Hydrogen bond-mediated recognition for a target nucleobase at an abasic site in a DNA duplex is confirmed by both fluorescence and electrochemical measurements. The analysis by fluorescence titration reveals that the ligand shows significant fluorescent quenching upon formation of a 1 : 1 complex with the target nucleobase opposite the abasic site, and the selectivity is in the order of cytosine > thymine > adenine, guanine, reflecting the stability of the hydrogen bond formation.
Morita
Kotaro
K
Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan.
Sato
Yusuke
Y
Seino
Takehiro
T
Nishizawa
Seiichi
S
Teramae
Norio
N
D004247:DNA / Q000737:chemistry*; D004563:Electrochemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D005453:Fluorescence; D006860:Hydrogen Bonding; D007202:Indicators and Reagents / Q000737:chemistry; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry*; D017354:Point Mutation; D011687:Purines / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D005296:Ferrous Compounds; D007202:Indicators and Reagents; D008024:Ligands; D009287:Naphthyridines; D011687:Purines; D011743:Pyrimidines; C527565:ferrocenyl aminonaphthyridine; D004247:DNA; C030986:pyrimidine; C030985:purine