2-substituted benzothiazolyl-3-substituted phenyl-5-substituted sulfonated phenyl-2H-tetrazolium salt, reagent for biological component concentration measurement containing said salt, and biological component concentration measurement method using said salt

Patent metadata

Field	Value
Publication number	US-10851094-B2
Application number	US-201916255535-A
Country	US
Kind code	B2
Filing date	Jan 23, 2019
Priority date	Sep 14, 2016
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

A 2-substituted benzothiazolyl-3-substituted phenyl-5-substituted sulfonated phenyl-2H-tetrazolium salt represented by the following Formula (1):

wherein, R 1 can be a hydrogen atom, a hydroxyl group, a methoxy group, and an ethoxy group; R 2 can be a nitro group, —OR 4 , and a carboxyl group; R 3 is a hydrogen atom, a methyl group, or an ethyl group, while at least one is a methyl group or an ethyl group; R 4 is a methyl group or an ethyl group; m is 1 or 2; n is an integer from 0 to 2; p is 0 or 1; n+p is 1 or greater; q is 1 or 2; when q is 2, the OR 3 's are disposed adjacently to each other and may form a ring; and X is a hydrogen atom or an alkali metal atom.

First claim

What is claimed is:

1. A 2-substituted benzothiazolyl-3-substituted phenyl-5-substituted sulfonated phenyl-2H-tetrazolium salt represented by the following Formula (1):

wherein in Formula (1), R 1 represents any one selected from the group consisting of a hydrogen atom, a hydroxyl group, a methoxy group, and an ethoxy group; R 2 represents any one selected from the group consisting of a nitro group, —OR 4 , and a carboxyl group; R 3 represents a hydrogen atom, a methyl group, or an ethyl group, while at least one is a methyl group or an ethyl group; R 4 represents a methyl group or an ethyl group; m represents the number of sulfo groups (—SO 3 − ) bonded to the phenyl group at the 5-position of the tetrazole skeleton, and is 1 or 2; n represents the number of R 2 bonded to the phenyl group at the 3-position of the tetrazole skeleton, and is an integer from 0 to 2; p represents the number of sulfo groups (—SO 3 − ) bonded to the phenyl group at the 3-position of the tetrazole skeleton, and is 0 or 1; n+p is 1 or greater; q is 1 or 2; when q is 2, the OR 3 's are disposed adjacently to each other and may be bonded to each other and forma ring; and X represents a hydrogen atom or an alkali metal atom.

2. The tetrazolium salt of claim 1 , wherein in Formula (1), m is 2.

3. The tetrazolium salt of claim 1 , wherein in Formula (1), p is 1, or p is 0, with at least one R 2 is a carboxyl group.

4. The tetrazolium salt of claim 1 , wherein in Formula (1), the phenyl group at the 5-position of the tetrazole skeleton is a phenyl group having a sulfo group (—SO 3 − ) at the 2-position or the 4-position.

5. The tetrazolium salt of claim 1 , wherein in Formula (1), at least one —OR 3 of the substituted benzothiazolyl group existing at the 2-position of the tetrazole skeleton is bonded to the 6-position of the benzothiazolyl group.

6. The tetrazolium salt of claim 1 , wherein in Formula (1), n is 1 or 2, and at least one R 2 is an —OR 4 group.

7. The tetrazolium salt of claim 6 , wherein the —OR 4 group is a methoxy group.

8. The tetrazolium salt of claim 1 , wherein in Formula (1), p is 1, and the phenyl group at the 3-position of the tetrazole skeleton is a phenyl group having a sulfo group (—SO 3 − ) existing at the 3-position or the 5-position.

9. The tetrazolium salt of claim 1 , wherein in Formula (1), the phenyl group existing at the 3-position of the tetrazole skeleton is a 4-methoxy-3-sulfophenyl group, a 2-methoxy-5-sulfophenyl group, a 3-carboxy-4-methoxyphenyl group, or a 4-methoxy-5-sulfophenyl group.

10. A reagent for biological component concentration measurement, the reagent comprising the tetrazolium salt of claim 1 .

11. The reagent for biological component concentration measurement of claim 10 , the reagent further comprising a transition metal compound.

12. The reagent for biological component concentration measurement of claim 11 , wherein the transition metal compound is a nickel compound.

13. The reagent for biological component concentration measurement of claim 10 , wherein the reagent is used for the measurement of the concentration of glucose, cholesterol, neutral lipids, nicotinamide adenine dinucleotide phosphate (NADPH), nicotinamide adenine dinucleotide (NADH), or uric acid in blood or a body fluid.

14. A method for measuring a concentration of a biological component, the method comprising:
adding the 2-substituted benzothiazolyl-3-substituted phenyl-5-substituted sulfonated phenyl-2H-tetrazolium salt of claim 1 , an oxidoreductase, and a transition metal compound to a biological sample;
measuring the quantity of color development; and
quantitatively determining the concentration of a biological component in the biological sample based on the quantity of color development.

15. The method of claim 14 , wherein the biological component in the biological sample is glucose, cholesterol, neutral lipids, nicotinamide adenine dinucleotide phosphate (NADPH), nicotinamide adenine dinucleotide (NADH), or uric acid in blood or a body fluid.

16. A blood sugar level measuring reagent, comprising a 2-substituted benzothiazolyl-3-substituted phenyl-5-substituted sulfonated phenyl-2H-tetrazolium salt, GDH-FAD, and a transition metal ion.

17. A method for measuring blood sugar level, the method comprising adding a reagent of a 2-substituted benzothiazolyl-3-substituted phenyl-5-substituted sulfonated phenyl-2H-tetrazolium salt, GDH-FAD, and a transition metal ion to a sample.

Assignees

• Terumo Corp

Inventors

• Sato Hiroya

Classifications

• C12Q1/60

  involving cholesterol · CPC title

• C12Q1/54

  involving glucose or galactose · CPC title

• C12Q1/62

  involving uric acid · CPC title

• C12Q1/32

  involving dehydrogenase · CPC title

• G01N33/66

  involving blood sugars, e.g. galactose · CPC title