Organotellurium compounds, compositions and methods of use thereof

Patent metadata

Field	Value
Publication number	US-10816552-B2
Application number	US-201916245328-A
Country	US
Kind code	B2
Filing date	Jan 11, 2019
Priority date	Aug 20, 2014
Publication date	Oct 27, 2020
Grant date	Oct 27, 2020

Abstract

A compound of formula (I):

as described herein and methods and uses thereof as for mass tagging a biosensor or biologically active material.

First claim

The invention claimed is:

1. A compound of formula (II):

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; and
Z is a biologically active material and/or a salt and/or solvate thereof, wherein the biologically active material is selected from polypeptide, nucleic acid, peptidic nucleic acid, oligosaccharide, polysaccharide lipopolysaccharide, hormone, pharmacologically active substance, steroid, vitamin, amino acid and sugar, preferably wherein the biologically active material is selected from an affinity reagent selected from an antibody or binding fragment thereof, aptamer, avidin reagent, nucleic acid or lectin.

2. The compound of claim 1 ,
wherein R 1 is an electron withdrawing group selected from selected from C(O)R 2 , C(R 3 ) 3 , C≡N, and NO 2 , wherein
R 2 is selected from H and C 1-6 alkyl; and
R 3 is halo;
wherein the substituents on R 1 are independently selected from one or more of halo, C1-6 alkyl and C 1-6 alkoxy;
wherein the substituents on L are independently selected from halo, C 1-6 alkyl, C 1-6 alkoxy, C(O)R 4 and NR 5 R 6 , wherein R 4 is selected from H and C 1-6 alkyl and R 5 and R 6 are independently selected from H, PG, C(O)C 1-20 alkyl and C(O)OC 1-20 alkyl;
wherein R 1 is selected from H, unsubstituted or substituted C 1-10 alkyl, unsubstituted or substituted C 3 -C 10 cycloalkyl, unsubstituted or substituted phenyl and an electron withdrawing group selected from C(O)R 2 and C(R 3 ) 3 ;
the substituents on R 1 are independently selected from one or more of halo and C 1-3 alkyl;
R 2 is selected from H and C 1-6 alkyl; and
R 3 is F, Cl, Br, and I, preferably wherein R 1 is selected from H and C(R 3 ) 3 wherein R 3 is F, optionally wherein R 1 is H;
wherein L is a C 1-25 alkylene, unsubstituted or substituted with one or more substituents independently selected from C 1-3 alkyl, C(O)R 4 and NR 5 R 6 , and/or optionally interrupted with one or more heteromoieties independently selected from O and NR 7 , and/or optionally interrupted with C(O);
R 4 is selected from H and C 1-2 alkyl;
R 5 and R 6 are independently selected from H, PG, C(O)C 1-6 alkyl and C(O)OC 1-6 alkyl; and
R7 is independently selected from H and PG.

3. The compound of claim 1 , wherein
L is a C 1-25 alkylene, unsubstituted or substituted with one or more substituents independently selected from NR 5 R 6 , and/or optionally interrupted with one or more heteromoieties independently selected from 0 and NR 7 , and/or optionally interrupted with C(O);
R 5 and R 6 are independently selected from H, PG, and C(O)OC 1-4 alkyl; and
R 7 is H.

4. The compound of claim 1 , wherein the compound is compatible with biological systems.

5. The compound of claim 4 , wherein the compound is non-toxic.

6. The compound of claim 1 , wherein the biologically active material is an amino acid.

7. The compound of claim 6 , wherein the amino acid is phenylalanine or an analog thereof.

8. The compound of claim 6 , wherein the compound is incorporated into a biomolecule target analyte.

9. The compound of claim 6 , wherein the compound is for incorporation into a biomolecule target analyte.

10. The compound of claim 9 , wherein the biomolecule target analyte is a protein.

11. The compound of claim 1 , wherein the biologically active material is a nucleic acid.

12. The compound of claim 1 , wherein the biologically active material is an antibody or binding fragment thereof.

13. A kit comprising a compound of formula (II):

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; and
Z is a biologically active material and/or a salt and/or solvate thereof, wherein the biologically active material is selected from polypeptide, nucleic acid, peptidic nucleic acid, oligosaccharide, polysaccharide lipopolysaccharide, hormone, pharmacologically active substance, steroid, vitamin, amino acid and sugar, preferably wherein the biologically active material is selected from an affinity reagent selected from an antibody or binding fragment thereof, aptamer, avidin reagent, nucleic acid or lectin.

Assignees

• Governing Council Univ Toronto
• Univ Health Network

Inventors

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

Classifications

• C07D421/06 Primary

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

• G01N33/569

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

• C07D345/00

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

• G01N2458/15

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

• G01N2560/00

  Chemical aspects of mass spectrometric analysis of biological material · CPC title