Fluorescent compounds

Patent metadata

Field	Value
Publication number	US-10351551-B2
Application number	US-201715817561-A
Country	US
Kind code	B2
Filing date	Nov 20, 2017
Priority date	Dec 21, 2010
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

Compounds used as labels with properties comparable to known fluorescent compounds. The compounds can be conjugated to proteins and nucleic acids for biological imaging and analysis. Synthesis of the compounds, formation and use of the conjugated compounds, and specific non-limiting examples of each are provided.

First claim

What is claimed is:

1. A compound of general formula I

where
each of R 1 and R 2 is sulfoalkyl;
X is selected from the group consisting of -NETS (hydroxysuccinimidyl), -O-TFP (2,3,5,6-tetrafluorophenoxy), -NR-L-maleimide and combinations thereof where R is —H or an aliphatic or heteroaliphatic group, and L is selected from the group consisting of a divalent linear, crossed, and cyclic alkyl group optionally substituted by at least one oxygen atom and/or sulfur atom;
Kat is one or more cations necessary to balance the negative charge of the compound;
m is 0; o is 3; and n is 1, 2 or 3,
conjugated to a biomolecule selected from at least one of a protein, antibody, enzyme, nucleoside triphosphate, oligonucleotide, biotin, hapten, cofactor, lectin, antibody binding protein, carotenoid, hormone, neurotransmitter, growth factor, toxin, biological cell, lipid, receptor binding drug, organic polymer carrier material, or inorganic polymeric carrier material.

2. A method of labeling at least one biomolecule, the method comprising providing a composition comprising at least one excipient and the compound of claim 1 in an effective concentration to bind to at least one biomolecule, resulting in the compound of claim 1 being bound to the at least one biomolecule.

3. The method of claim 2 wherein the biomolecule is selected from the group consisting of a protein, antibody, enzyme, nucleoside triphosphate, oligonucleotide, biotin, hapten, cofactor, lectin, antibody binding protein, carotenoid, hormone, neurotransmitter, growth factors, toxin, biological cell, lipid, receptor binding drug, fluorescent proteins, organic polymer carrier material, or inorganic polymeric carrier material.

4. A method of detecting at least one biomolecule, the method comprising providing a composition comprising at least one excipient and the compound of claim 1 in an effective concentration to bind to at least one biomolecule, resulting in the compound of claim 1 being bound to the at least one biomolecule, and detecting the biomolecule-bound compound.

5. The method of claim 4 wherein the biomolecule is selected from a protein, antibody, enzyme, nucleoside triphosphate, oligonucleotide, biotin, hapten, cofactor, lectin, antibody binding protein, carotenoid, hormone, neurotransmitter, growth factors, toxin, biological cell, lipid, receptor binding drug, fluorescent proteins, organic polymer carrier material, or inorganic polymeric carrier material.

6. The method of claim 4 wherein the at least one biomolecule is detected in an assay selected from fluorescence microscopy, flow cytometry, in vivo imaging, immunoassay, hybridization, chromatographic assay, electrophoretic assay, microwell plate based assay, fluorescence resonance energy transfer (FRET) system, high throughput screening, or microarray.

7. The method of claim 4 wherein when the biomolecule is detected by in vivo imaging, the method comprises providing the biomolecule-bound compound to at least one of a biological sample, tissue, or organism, and detecting the biomolecule within the at least one of a biological sample, tissue, or organism.

8. A kit for performing an assay to detect at least one biomolecule in a sample, the kit comprising the compound of claim 1 and at least one excipient, and instructions for use.

Assignees

• Pierce Biotechnology Inc
• Dyomics Gmbh

Inventors

• Hermanson Greg
• Czerney Peter T
• Desai Surbhi
• Wenzel Matthias S
• Dworecki Boguslawa
• Lehmann Frank G

Classifications

• C07D209/10

  with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring · CPC title

• C07D403/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title