Hydrazinyl and aminooxy compounds and their methods of use

Patent metadata

Field	Value
Publication number	US-10793518-B2
Application number	US-201815894057-A
Country	US
Kind code	B2
Filing date	Feb 12, 2018
Priority date	Dec 3, 2014
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

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

3. The composition of claim 2 , further comprising a buffer solution.

4. The composition of claim 2 , 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.

5. 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 according to claim 1 ;
b) incubating the sample and the compound 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.

6. A method of detecting a glycan in a sample, the method comprising:
a) contacting the sample with a compound according to claim 1 ;
b) incubating the sample and the compound 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.

7. A method of labeling a glycan in a sample, the method comprising:
a) contacting the sample with a compound according to claim 1 ;
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.

8. A kit for labeling a glycan, wherein the kit comprises:
a) a compound according claim 1 ; and
b) instructions for labeling the glycan.

9. A kit for detecting an analyte in a sample, wherein the kit comprises:
a) a compound according to claim 1 ; and
b) instructions for detecting 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

• G01N33/582

  with fluorescent label · CPC title

• C07C2603/50

  Pyrenes; Hydrogenated pyrenes · 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

• 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

• 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