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Chemistry ; 20(7): 2010-5, 2014 Feb 10.
Artigo em Inglês | MEDLINE | ID: mdl-24311229

RESUMO

Tricyclic cytosines (tC and tC(O) frameworks) have emerged as a unique class of fluorescent nucleobase analogues that minimally perturb the structure of B-form DNA and that are not quenched in duplex nucleic acids. Systematic derivatization of these frameworks is a likely approach to improve on and diversify photophysical properties, but has not so far been examined. Synthetic methods were refined to improve on tolerance for electron-donating and electron-withdrawing groups, resulting in a series of eight new, fluorescent cytidine analogues. Photophysical studies show that substitution of the framework results in a pattern of effects largely consistent across tC and tC(O) and provides nucleoside fluorophores that are brighter than either parent. Moreover, a range of solvent sensitivities is observed, offering promise that this family of probes can be extended to new applications that require reporting on the local environment.


Assuntos
Citosina/análogos & derivados , Corantes Fluorescentes/química , Nucleosídeos/química , DNA de Forma B/análise , Conformação de Ácido Nucleico , Solventes/química
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