Fluorescent DNA base replacements: Reporters and sensors for biological systems

James N Wilson, Eric T. Kool

Research output: Contribution to journalArticle

218 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4265-4274
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number23
DOIs
StatePublished - Nov 20 2006
Externally publishedYes

Fingerprint

Biological systems
deoxyribonucleic acid
DNA
sensors
Sensors
monomers
Monomers
Molecules
Fluorophores
molecules
synthesizers
biochemistry
Biochemistry
nucleosides
Hydrocarbons
assembling
biology
Nucleosides
oligomers
Oligomers

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

Cite this

Fluorescent DNA base replacements : Reporters and sensors for biological systems. / Wilson, James N; Kool, Eric T.

In: Organic and Biomolecular Chemistry, Vol. 4, No. 23, 20.11.2006, p. 4265-4274.

Research output: Contribution to journalArticle

@article{1b1e844c30014b6faf6bcd5aac687288,
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.",
author = "Wilson, {James N} and Kool, {Eric T.}",
year = "2006",
month = "11",
day = "20",
doi = "10.1039/b612284c",
language = "English",
volume = "4",
pages = "4265--4274",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "23",

}

TY - JOUR

T1 - Fluorescent DNA base replacements

T2 - Reporters and sensors for biological systems

AU - Wilson, James N

AU - Kool, Eric T.

PY - 2006/11/20

Y1 - 2006/11/20

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33751016032&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33751016032&partnerID=8YFLogxK

U2 - 10.1039/b612284c

DO - 10.1039/b612284c

M3 - Article

C2 - 17102869

AN - SCOPUS:33751016032

VL - 4

SP - 4265

EP - 4274

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 23

ER -