title: Functionalized tricyclic cytosine analogues provide nucleoside fluorophores with improved photophysical properties and a range of solvent sensitivities.
abstract: 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.
authors: Department of Chemistry and Biochemistry, University of Denver, 2199 S. University Blvd., Denver, CO 80208 (USA).
authors: Brittney J
authors: BJ
authors: Rodgers
authors: Nada A
authors: NA
authors: Elsharif
authors: Nisha
authors: N
authors: Vashisht
authors: Macy M
authors: MM
authors: Mingus
authors: Mark A
authors: MA
authors: Mulvahill
authors: Gudrun
authors: G
authors: Stengel
authors: Robert D
authors: RD
authors: Kuchta
authors: Byron W
authors: BW
authors: Purse
mesh_terms: D003596:Cytosine / Q000031:analogs & derivatives*; D059371:DNA, B-Form / Q000032:analysis; D005456:Fluorescent Dyes / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D059371:DNA, B-Form; D005456:Fluorescent Dyes; D009705:Nucleosides; D012997:Solvents; D003596:Cytosine
keywords: DNA; RNA; fluorescent probes; nucleosides; structure-activity relationships