title: Fluorescent DNA base replacements: Reporters and sensors for biological systems.
abstract: We describe the design, synthesis, and properties of nucleoside monomers in which the DNA base is replaced by fluorescent hydrocarbons and heterocycles, and the assembly of these monomers into DNA-like molecules in which the all bases are fluorescent. As monomers, such molecules have useful applications as reporters in the DNA context. The use of fluorescent DNA bases, rather than more traditional fluorophores tethered to the DNA strand, gives a more predictable location and orientation, and yields a more direct response to changes that occur within the helix. In addition to uses as monomers, such compounds can be assembled into polychromophoric oligomers ("oligodeoxyfluorosides" or ODFs). ODFs are water soluble, discrete molecules and are easily arranged into specific sequences by use of a DNA synthesizer. They have displayed a number of properties not readily available in commercial fluorophores, including large Stokes shifts, tunable excitation and emission wavelengths, and sensing responses to physical changes or molecular species in solution. We describe an approach to assembling and screening large sets of oligofluorosides for rapid identification of molecules with desirable properties. Such compounds show promise for applications in biochemistry, biology, environmental and materials applications.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305, USA.
authors.forename: James N
authors.initials: JN
authors.lastname: Wilson
authors.forename: Eric T
authors.initials: ET
authors.lastname: Kool
mesh_terms: D000249:Adenosine Monophosphate / Q000031:analogs & derivatives / Q000737:chemistry; D020029:Base Pairing; D001580:Benzopyrenes / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000138:chemical synthesis; D009243:NAD / Q000031:analogs & derivatives / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D010569:Perylene / Q000031:analogs & derivatives; D010770:Phosphotransferases / Q000378:metabolism; D011166:Porphyrins / Q000737:chemistry; D015265:Site-Specific DNA-Methyltransferase (Adenine-Specific) / Q000378:metabolism
chemical_list: D001580:Benzopyrenes; D003853:Deoxyribonucleosides; D005456:Fluorescent Dyes; D009838:Oligodeoxyribonucleotides; D011166:Porphyrins; D009243:NAD; C030368:etheno-AMP; C011038:nicotinamide 1,N(6)-ethenoadenine dinucleotide; D000249:Adenosine Monophosphate; D010569:Perylene; D004247:DNA; C059680:DNA modification methylase TaqI; D015265:Site-Specific DNA-Methyltransferase (Adenine-Specific); D010770:Phosphotransferases