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Functionalized Tricyclic Cytosine Analogues Provide Nucleoside Fluorophores with Improved Photophysical Properties and a Range of Solvent Sensitivities.
- Source :
- Chemistry - A European Journal; Feb2014, Vol. 20 Issue 7, p2010-2015, 6p
- Publication Year :
- 2014
-
Abstract
- Tricyclic cytosines (tC and tC<superscript>O</superscript> 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<superscript>O</superscript> 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- CYTOSINE
BASE pairs
DNA
NUCLEIC acids
SOLVENTS
FLUOROPHORES
Subjects
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 20
- Issue :
- 7
- Database :
- Complementary Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 94232844
- Full Text :
- https://doi.org/10.1002/chem.201303410