Biomaterial Database

Energy-transfer-based wavelength-shifting DNA probes with "clickable" cyanine dyes. 2013

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.

The insertion of cyanine dye azides as energy donor dyes via postsynthetic "click"-type cycloaddition chemistry with e.g. a new thiazole orange azide combined with thiazole red yields dual emitting DNA probes with good fluorescence readout properties.

UI	MeSH Term	Description	Entries
D011804	Quinolines
D002232	Carbocyanines	Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	Carbocyanine
D004735	Energy Transfer	The transfer of energy of a given form among different scales of motion. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed). It includes the transfer of kinetic energy and the transfer of chemical energy. The transfer of chemical energy from one molecule to another depends on proximity of molecules so it is often used as in techniques to measure distance such as the use of FORSTER RESONANCE ENERGY TRANSFER.	Transfer, Energy
D005456	Fluorescent Dyes	Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.	Flourescent Agent,Fluorescent Dye,Fluorescent Probe,Fluorescent Probes,Fluorochrome,Fluorochromes,Fluorogenic Substrates,Fluorescence Agents,Fluorescent Agents,Fluorogenic Substrate,Agents, Fluorescence,Agents, Fluorescent,Dyes, Fluorescent,Probes, Fluorescent,Substrates, Fluorogenic
D013056	Spectrophotometry, Ultraviolet	Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Ultraviolet Spectrophotometry
D015342	DNA Probes	Species- or subspecies-specific DNA (including COMPLEMENTARY DNA; conserved genes, whole chromosomes, or whole genomes) used in hybridization studies in order to identify microorganisms, to measure DNA-DNA homologies, to group subspecies, etc. The DNA probe hybridizes with a specific mRNA, if present. Conventional techniques used for testing for the hybridization product include dot blot assays, Southern blot assays, and DNA:RNA hybrid-specific antibody tests. Conventional labels for the DNA probe include the radioisotope labels 32P and 125I and the chemical label biotin. The use of DNA probes provides a specific, sensitive, rapid, and inexpensive replacement for cell culture techniques for diagnosing infections.	Chromosomal Probes,DNA Hybridization Probe,DNA Probe,Gene Probes, DNA,Conserved Gene Probes,DNA Hybridization Probes,Whole Chromosomal Probes,Whole Genomic DNA Probes,Chromosomal Probes, Whole,DNA Gene Probes,Gene Probes, Conserved,Hybridization Probe, DNA,Hybridization Probes, DNA,Probe, DNA,Probe, DNA Hybridization,Probes, Chromosomal,Probes, Conserved Gene,Probes, DNA,Probes, DNA Gene,Probes, DNA Hybridization,Probes, Whole Chromosomal
D052160	Benzothiazoles	Compounds with a benzene ring fused to a thiazole ring.
D057930	Click Chemistry	Organic chemistry methodology that mimics the modular nature of various biosynthetic processes. It uses highly reliable and selective reactions designed to "click" i.e., rapidly join small modular units together in high yield, without offensive byproducts. In combination with COMBINATORIAL CHEMISTRY TECHNIQUES, it is used for the synthesis of new compounds and combinatorial libraries.	Click Chemical Reactions,Click Chemical Techniques,Chemical Reaction, Click,Chemical Reactions, Click,Chemical Technique, Click,Chemical Techniques, Click,Chemistries, Click,Chemistry, Click,Click Chemical Reaction,Click Chemical Technique,Click Chemistries,Reaction, Click Chemical,Reactions, Click Chemical,Technique, Click Chemical,Techniques, Click Chemical
D061565	Cycloaddition Reaction	Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products.	Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction

Related Publications

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes.

July 2016, Journal of visualized experiments : JoVE,

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Synthesis of Wavelength-Shifting Fluorescent DNA and RNA with Two Photostable Cyanine-Styryl Dyes as the Base Surrogate Pair.

August 2017, ChemistryOpen,

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

The role of duplex stability for wavelength-shifting fluorescent DNA probes: energy transfer vs. exciton interactions in DNA "traffic lights".

August 2014, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology,

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Development of a wavelength-shifting fluorescent module for the adenosine aptamer using photostable cyanine dyes.

April 2015, ChemistryOpen,

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Fluorescent tandem phycobiliprotein conjugates. Emission wavelength shifting by energy transfer.

September 1983, Biophysical journal,

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Cyanine dyes with high absorption cross section as donor chromophores in energy transfer primers.

December 1996, Analytical biochemistry,

Carolin Holzhauser, and Moritz M Rubner, and Hans-Achim Wagenknecht

Cell-resistant wavelength-shifting molecular beacons made of L-DNA and a clickable L-configured uridine.

May 2024, Organic & biomolecular chemistry,