Organotellurium compounds, compositions and methods of use thereof

Patent metadata

Field	Value
Publication number	US-10222380-B2
Application number	US-201515505197-A
Country	US
Kind code	B2
Filing date	Aug 20, 2015
Priority date	Aug 20, 2014
Publication date	Mar 5, 2019
Grant date	Mar 5, 2019

Abstract

A compound of formula (I) as described herein and methods and uses thereof as probes in the mass tagging of biosensors or biologically active materials for use in mass cytometry analysis of tissue samples such as in the detection, labelling and quantification of oxygen-deprived cells by using, for example, tellurophene-tagged 2-nitroimidazole.

First claim

The invention claimed is:

1. A kit capable of mass detection assay, the kit comprising:
a plurality of organotellurophene compounds of the below formula;

 wherein
A is a naturally occurring isotope of Te;
R 1 is selected from H, unsubstituted or substituted C 1 -C 20 alkyl, unsubstituted or substituted C 3 -C 20 cycloalkyl, unsubstituted or substituted aryl and an electron withdrawing group;
L is C 1-20 alkylene, unsubstituted or substituted with one or more substituents, and/or optionally interrupted with one or more heteromoieties independently selected from O, S, NR 7 , and/or optionally interrupted with one or more of C(O) and C(S);
R 7 is independently selected from H, protecting group (PG) and C 1-6 alkyl;
Z is an enzyme substrate selected from oxidoreductase substrates, xanthine substrates, P450 substrates, glycosyl hydrolase substrates, lipase substrates, phosphatase substrates, kinase substrates, and protease substrates; an affinity agent selected from antibodies or binding fragment thereof, aptamer, avidin reagent, nucleic acid and lectin, or a thiol reactive functional group; and/or a salt and/or solvate thereof; and

wherein each compound comprises a distinct tellurium isotope.

2. The kit of claim 1 , wherein one or more of the plurality of compounds comprise the enzyme substrate.

3. The kit of claim 2 , wherein the enzyme substrate is an oxidoreductase substrate.

4. The kit of claim 1 , wherein one or more of the plurality of compounds comprise the affinity reagent.

5. The kit of claim 4 , wherein the affinity reagent is an antibody.

6. The kit of claim 1 , wherein one or more of the plurality of compounds comprises the thiol reactive functional group.

7. The kit of claim 1 , wherein one or more of the plurality of compounds comprises a tellurophene heterocycle.

8. The kit of claim 1 , wherein the plurality of compounds are packaged as barcoding reagents.

9. The kit of claim 1 , wherein the thiol reactive functional group is maleimide.

10. The kit of claim 9 , wherein one or more of the plurality of compounds are of the below formula:

11. The kit of claim 3 , wherein the oxidoreductase substrate is 2-nitroimidazole.

Assignees

• Governing Council Univ Toronto
• Univ Health Network

Inventors

• Nitz Mark
• Edgar Landon J
• Wouters Bradley G
• Hedley David
• Willis Lisa M
• Lumba Matthew A
• Park Hanuel
• Vellanki Ravi N

Classifications

• C07D345/00

  Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms · CPC title

• G01N33/58 Primary

  involving labelled substances (G01N33/53 takes precedence) · CPC title

• G01N33/569

  for microorganisms, e.g. protozoa, bacteria, viruses · CPC title

• G01N2458/15

  Non-radioactive isotope labels, e.g. for detection by mass spectrometry · CPC title

• C07D421/06 Primary

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