Fluorescent compounds

Patent metadata

Field	Value
Publication number	US-11053222-B2
Application number	US-201916436512-A
Country	US
Kind code	B2
Filing date	Jun 10, 2019
Priority date	Dec 21, 2010
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

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 the same or different and is independently selected from the group consisting of an alkyl and sulfoalkyl group;
X is selected from the group consisting of —OH, —SH, —NH 2 , —NH—NH 2 , —F, —Cl, —Br, and —I,
Kat is one or more cations needed to balance the negative charge of the compound;
m is 0;
o is an integer from 0 to 12 inclusive; and
n is an integer from 1 to 3 inclusive.

2. A compound of general formula II

where:
each of R 1 , R 2 , R 5 , and R 6 is the same or different and is independently selected from the group consisting of an alkyl and sulfoalkyl group;
each of R 7 and R 8 is the same or different and is independently selected from either H or SO 3 ;
X is selected from the group consisting of —OH, —SH, —NH 2 , —NH—NH 2 , —F, —Cl, —Br, and —I;
Kat is one or more cations needed to balance the negative charge of the compound;
m is 0;
o is an integer from 0 to 12 inclusive; and
n is an integer from 1 to 3 inclusive.

3. The compound of claim 2 selected from the group consisting of

4. A compound of general formula IV

where:
each of R 1 , R 2 , R 5 , and R 6 is the same or different and is independently selected from an alkyl and sulfoalkyl group;
each of R 7 and R 8 is the same or different and is independently selected from H or SO 3 ;
X is selected from —OH, —SH, —NH 2 , —NH—NH 2 , —F, —Cl, —Br, and —I;
Kat is one or more cations needed to balance the negative charge of the compound;
m is 0;
o is an integer from 0 to 12 inclusive;
each of R 3 and R 4 is the same or different and is independently hydrogen, an aliphatic group, or a heteroaliphatic group; and
Y is selected from the group consisting of hydrogen, alkyl, sulfoalkyl, fluorine, chlorine, or bromine.

5. The compound of claim 2 conjugated to at least one biomolecule selected from 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, and inorganic polymeric carrier material.

6. A method of labelling at least one biomolecule, the method comprising combining a composition comprising at least one excipient and a compound of claim 2 in an effective concentration to at least one biomolecule under conditions sufficient for binding the compound to the biomolecule.

7. The method of claim 6 , wherein the at least one biomolecule is selected from 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, and inorganic polymeric carrier material.

8. A method of detecting at least one biomolecule, the method comprising combining a composition comprising at least one excipient and at least one compound of claim 2 in an effective concentration to the at least one biomolecule under conditions sufficient for binding the compound to the biomolecule, resulting in the at least one compound of claim 2 being bound to the at least one biomolecule; and detecting the biomolecule-bound compound.

9. The method of claim 8 , wherein the at least one biomolecule is selected from 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, and inorganic polymeric carrier material.

10. The method of claim 8 , 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.

11. The method of claim 8 , wherein the biomolecule is detected by in vivo imaging comprising combining 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.

12. A kit for performing an assay to detect at least one biomolecule in a sample, the kit comprising at least one compound of claim 2 and at least one excipient, and instructions for use to detect a biomolecule in a sample.

Assignees

• Pierce Biotechnology Inc
• Dyomics Gmbh

Inventors

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

Classifications

• C07D403/06 Primary

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

• C07D209/10

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