Synthesis and Fluorescence Properties of 1,1‐Dimethyl‐1,4‐Dihydrodibenzo[b,h][1,6]naphthyridinium Iodides: Turn‐on Type Detection of DNA

1,4‐Dihydrodibenzo[b,h][1,6]naphthyridines were synthesized by the reaction of 2‐acetylaminobenzaldehyde with acetophenones in the presence of NaOH. N‐Methylation of the dihydrodibenzonaphthyridines with MeI gave 1,1‐dimethylammonium iodides. These salts showed UV/Vis absorbance maxima at 235 and 41...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-12, Vol.2017 (46), p.6885-6888
Main Authors: Okuma, Kentaro, Oba, Akinori, Kuramoto, Risa, Iwashita, Hidefumi, Nagahora, Noriyoshi, Shioji, Kosei, Noguchi, Ryoma, Fukuda, Masatora
Format: Article
Language:English
Subjects:
Chemical synthesis
Deoxyribonucleic acid
DNA
DNA methylation
Fluorescence
Functional organic materials
Fused‐ring systems
Intercalations
Iodides
Maxima
Ribonucleic acid
RNA
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Summary:1,4‐Dihydrodibenzo[b,h][1,6]naphthyridines were synthesized by the reaction of 2‐acetylaminobenzaldehyde with acetophenones in the presence of NaOH. N‐Methylation of the dihydrodibenzonaphthyridines with MeI gave 1,1‐dimethylammonium iodides. These salts showed UV/Vis absorbance maxima at 235 and 418 nm and very weak fluorescence at 530 nm. The fluorescence intensities were enhanced 3–10 times upon treating these salts with double‐stranded DNA by intercalation, which enabled the detection of DNA/RNA by polyacrylamide gel electrophoresis (PAGE). The reaction of 2‐acetylaminobenzaldehyde with acetophenones under basic conditions gives dihydronaphthyridines in good yields. The reaction of dihydronaphthyridines with methyl iodide gives dimethylammonium iodides. Treatment of ammonium iodides with plasmid DNA produces bright fluorescence at 420 nm.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701277