Hydrazinyl and aminooxy compounds and their methods of use

Patent metadata

Field	Value
Publication number	US-10246410-B2
Application number	US-201515529437-A
Country	US
Kind code	B2
Filing date	Dec 3, 2015
Priority date	Dec 3, 2014
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

The present disclosure is directed dye compounds containing a hydrazinyl substituent and optionally, one or more negatively charged groups, such as sulfonate, phosphate, phosphonate, and/or carboxylate groups and dye compounds containing an aminooxy substitutent. The compounds are useful in the detection of analytes containing aldehyde and ketone groups, including, for example, glycans.

First claim

We claim:

1. A compound selected from the group consisting of:

or a salt thereof.

2. The compound of claim 1 , wherein the salt comprises a potassium, sodium, ammonium, alkylammonium, tetralkylammonium, triethylammonium, tert-butylammonium, tetralkyl-phosphonium, tetraaryl-phosphonium, lithium or cesium ion.

3. A composition comprising:
(a) an analyte; and
(b) a compound according to claim 1 .

4. The composition of claim 3 , further comprising a buffer solution.

5. The composition of claim 4 , wherein the analyte is selected from the group consisting of: an amino acid, a peptide, a protein, a carbohydrate, a polysaccharide, a nucleoside, a nucleotide, an oligonucleotide, a nucleic acid polymer, a hapten, a psoralen, a drug, a hormone, a lipid, a lipid assembly, a synthetic polymer, a biotin-binding protein, a polymeric microparticle, a biological cell and a virus.

6. A method for determining the presence of an analyte of interest in a sample, wherein the method comprises:
a) contacting the sample with a compound of claim 1 ;
b) incubating the sample and the compound or composition for a sufficient amount of time to form a complex between the compound and analyte;
c) illuminating the complex with an appropriate wavelength to form an illuminated complex; and
d) detecting emissions from the illuminated complex, thereby determining the presence of the analyte.

7. A method for determining the presence of an analyte of interest in a sample, wherein the method comprises:
a) contacting the sample with a compound selected from the group consisting of:

or a salt thereof;
b) incubating the sample and the compound or composition for a sufficient amount of time to form a complex between the compound and analyte;
c) illuminating the complex with an appropriate wavelength to form an illuminated complex; and
d) detecting emissions from the illuminated complex, thereby determining the presence of the analyte.

8. The method of claim 7 , wherein the analyte and the compound are connected by a covalent bond.

9. The method of claim 8 , wherein the compound becomes fluorescent after formation of the complex.

10. The method of claim 9 , wherein the analyte is selected from the group consisting of: an amino acid, a peptide, a protein, a carbohydrate, a polysaccharide, a nucleoside, a nucleotide, an oligonucleotide, a nucleic acid polymer, a hapten, a psoralen, a drug, a hormone, a lipid, a lipid assembly, a synthetic polymer, a biotin-binding protein, a polymeric microparticle, a biological cell and a virus.

11. The method of claim 7 , wherein the sample comprises live cells, intracellular fluids, extracellular fluids, biological fluids, biological fermentation media, environmental sample, industrial samples, proteins, peptides, buffer solutions biological fluids or chemical reactors.

12. The method of claim 7 , wherein the sample comprises blood cells, immune cells, cultured cells, muscle tissue, neurons, extracellular vesicles; vascular tissue, blood fluids, saliva, urine; water, soil, waste water, sea water; pharmaceuticals, foodstuffs or beverages.

13. The method of claim 7 , wherein the sample is immobilized on a polymeric membrane, within a polymeric gel, on a microparticle, on a microarray, on a silicon chip, on a glass slide, on a microwell plate, and on a microfluidic chip.

14. A method of detecting a glycan in a sample, the method comprising:
a) contacting the sample with a compound according to claim 1 , or a composition according to claim 3 ;
b) incubating the sample and the compound or composition for a sufficient amount of time to form a complex between the compound and glycan;
c) illuminating the complex with an appropriate wavelength to form an illuminated complex; and
d) detecting emissions from the illuminated complex, thereby determining the presence of the glycan.

15. A method of detecting a glycan in a sample, the method comprising:
a) contacting the sample with a [a] compound selected from the group consisting of:

or a salt thereof;
b) incubating the sample and the compound or composition for a sufficient amount of time to form a complex between the compound and glycan;
c) illuminating the complex with an appropriate wavelength to form an illuminated complex; and
d) detecting emissions from the illuminated complex, thereby determining the presence of the glycan.

16. The method of claim 15 , wherein the salt comprises a potassium, sodium, ammonium, alkylammonium, tetralkylammonium, triethylammonium, tert-butylammonium, tetralkyl-phosphonium, tetraaryl-phosphonium, lithium or cesium ion.

17. A method of labeling a glycan in a sample, the method comprising:
a) contacting the sample with a compound according to claim 1 , or a composition according to claim 3 ;
b) incubating the sample and the compound for a sufficient amount of time to form a complex between the compound and the one or more glycans;
c) separating the sample using electrophoresis or chromatography, thereby determining the presence of the one or more glycans in the sample.

18. The method of claim 17 , wherein the separating step is performed using electrophoresis.

19. The method of claim 18 , wherein the electrophoresis is capillary electrophoresis.

20. The method of claim 9 , wherein the capillary electrophoresis is part of a glycan analysis system.

21. The method of claim 17 , wherein the separation step is performed using chromatography.

22. The method of claim 21 , wherein the chromatography is high-performance liquid chromatography (HPLC) or liquid chromatography-mass spectroscopy (LC-MS).

23. A kit for labeling a glycan, wherein the kit comprises:
a) a compound according to claim 1 ; and
b) instructions for labeling the glycan according to the method of claim 17 .

24. A kit for labeling a glycan, wherein the kit comprises:
a) a compound selected from the group consisting of:

or a salt thereof; and
b) instructions for labeling the glycan according to the method of claim 17 .

25. A kit for detecting an analyte in a sample, wherein the kit comprises:
a) a compound selected from the group consisting of:

or a salt thereof; and
b) instructions for detecting the analyte according to the method of claim 14 .

26. The kit of claim 25 , further comprising instructions for covalently bonding the compound to the analyte.

Assignees

• Life Technologies Corp

Inventors

• Zhou Wenjun
• Gee Kyle
• Tennico Yolanda
• Slade Peter
• Kang Hee Chol
• Khan Shaheer
• Evans Brian
• Stray James

Classifications

• C07D311/84

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9 · CPC title

• G01N33/582

  with fluorescent label · CPC title

• C07C309/47 Primary

  having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system · CPC title

• G01N2400/10

  Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters · CPC title

• C07C2603/50

  Pyrenes; Hydrogenated pyrenes · CPC title