ArticleBioconjugate chemistry2012
Fluorescence quenchers for hydrazone and oxime orthogonal bioconjugation.
Article in Bioconjugate chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 39 citations in OpenAlex.
- Molecular Engineering ofMolecules (Basel, Switzerland) · 2023Article
- Discovery of Potent and Selective Inhibitors against Protein-Derived Electrophilic Cofactors.Journal of the American Chemical Society · 2022Article
- Chemistry of Peptide-Oligonucleotide Conjugates: A Review.Molecules (Basel, Switzerland) · 2021Review
- Borylated oximes: versatile building blocks for organic synthesis.Chemical communications (Cambridge, England) · 2017Article
- Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.Chemical reviews · 2017Review
- Erythromycin Modification That Improves Its Acidic Stability while Optimizing It for Local Drug Delivery.Antibiotics (Basel, Switzerland) · 2017Article
- Selective Chemical Labeling of Natural T Modifications in DNA.Journal of the American Chemical Society · 2015Article
- A genetically encoded aldehyde for rapid protein labelling.Chemical communications (Cambridge, England) · 2014Article
- Synthesis of Hydrophilic Aminooxy Linkers and Multivalent Cores for Chemoselective Aldehyde/Ketone Conjugation.Tetrahedron letters · 2014Article
- Thioamide quenching of fluorescent probes through photoinduced electron transfer: mechanistic studies and applications.Journal of the American Chemical Society · 2013Article
- Fast hydrazone reactants: electronic and acid/base effects strongly influence rate at biological pH.Journal of the American Chemical Society · 2013Article
- Water-soluble organocatalysts for hydrazone and oxime formation.The Journal of organic chemistry · 2013Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
We describe the synthesis and properties of new fluorescence quenchers containing aldehyde, hydrazine, and aminooxy groups, allowing convenient bioconjugation as oximes or hydrazones. Conjugation to oligonucleotides proceeded in high yield with aniline as catalyst. Kinetics studies of conjugation show that, under optimal conditions, a hydrazine or aminooxy quencher can react with aldehyde-modified DNA to form a stable hydrazone or oxime adduct in as little as five minutes. The resulting quencher-containing DNAs were assessed for their ability to quench the emission of fluorescein in labeled complements and compared to the commercially available dabcyl and Black Hole Quencher 2 (BHQ2), which were conjugated as phosphoramidites. Results show that the new quenchers possess slightly different absorbance properties compared to dabcyl and are as efficient as the commercial quenchers in quenching fluorescein emission. Hydrazone-based quenchers were further successfully incorporated into molecular beacons and shown to give high signal to background ratios in single nucleotide polymorphism detection in vitro. Finally, aminooxy and hydrazine quenchers were applied to quenching of an aldehyde-containing fluorophore associated with living cells, demonstrating cellular quenching within one hour.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.