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Functionalized Tricyclic Cytosine Analogues Provide Nucleoside Fluorophores with Improved Photophysical Properties and a Range of Solvent Sensitivities
Author(s) -
Rodgers Brittney J.,
Elsharif Nada A.,
Vashisht Nisha,
Mingus Macy M.,
Mulvahill Mark A.,
Stengel Gudrun,
Kuchta Robert D.,
Purse Byron W.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303410
Subject(s) - nucleobase , derivatization , tricyclic , cytidine , nucleoside , fluorescence , nucleic acid , combinatorial chemistry , dna , cytosine , chemistry , solvent , stereochemistry , organic chemistry , biochemistry , enzyme , physics , high performance liquid chromatography , quantum mechanics
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.