Naphthalene-based environmentally sensitive fluorescent 8-substituted 2'-deoxyadenosines: application to DNA detection.
Azusa Suzuki, Naoya Takahashi, Yuji Okada, Isao Saito, Nobukatsu Nemoto, Yoshio Saito
Department of Chemical Biology and Applied Chemistry, School of Engineering, Nihon University, Koriyama, Fukushima 963-8642, Japan.
Bioorganic & medicinal chemistry letters 2013 Feb 1We synthesized various C8-naphthylethynylated 2'-deoxyadenosine derivatives and investigated their photophysical properties. Among them, cyano- and N,N-dimethylamino-substituted 8-naphthylethynylated 2'-deoxyadenosine derivatives ((cn)A and (dn)A) showed strong fluorescence with high quantum yields and a remarkable solvatofuorochromicity. In particular, fluorescence of N,N-dimethylamino-substituted (2,6dn)A was not quenched by neighboring guanines (Gs) when incorporated in DNA duplexes, in contrast to (cn)A. We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences. Copyright © 2012 Elsevier Ltd. All rights reserved.
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Azusa Suzuki, Naoya Takahashi, Yuji Okada, Isao Saito, Nobukatsu Nemoto, Yoshio Saito. Naphthalene-based environmentally sensitive fluorescent 8-substituted 2'-deoxyadenosines: application to DNA detection. Bioorganic & medicinal chemistry letters. 2013 Feb 1;23(3):886-92
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PMID: 23273411
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