Compounds for determining the presence of hydrogen sulfide and methods of use

Patent metadata

Field	Value
Publication number	US-9664696-B1
Application number	US-201414292378-A
Country	US
Kind code	B1
Filing date	May 30, 2014
Priority date	May 30, 2013
Publication date	May 30, 2017
Grant date	May 30, 2017

Abstract

Disclosed herein are embodiments of H 2 S-reactive compounds, or compositions thereof, which can be used to determine the presence of H 2 S, and in some embodiments quantify H 2 S. Also disclosed herein are methods of using the H 2 S-reactive compounds. The methods can use colorimetric, chemiluminescent, or bioluminescent testing methods to determine the presence of and/or amount of H 2 S in a sample.

First claim

We claim:

1. A method, comprising:
providing an H 2 S-reactive compound, or a composition thereof, represented by the structure of Formula 1

wherein R 1 is selected from an azide, fluoro, bromo, iodo, mesylate, besylate, tosylate, triflate, ether, or thioether;
R 2 is selected from nitro, haloalkyl, cyano, sulfonate, carboxyl, ester, aldehyde, ketone, or N(R 5 ) 3 + wherein each R 5 independently is selected from hydrogen, alkyl, aryl, alkenyl, alkynyl, or combinations thereof;
each R 3 independently is a 5- or 6-membered heteroaryl group or a 5- or 6-membered heterocyclyl;
at least one of B, C, D, or E is carbon bound to R 1 and the remaining of B, C, D, and E independently are CH, CR 2 , or nitrogen;
n is 0, 1, 2, or 3;
m is 0, 1, or 2;
ring A is selected from

wherein R 6 is a heterocyclyl or a heteroaryl; and
wherein the H 2 S-reactive compound is other than 4-azido-7-nitrobenzo[c][1,2,5]oxadiazole and 2-(6-((4-boronobenzyl)oxy)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid;
exposing a sample to the H 2 S-reactive compound, or composition thereof; and
analyzing the sample for a reaction product obtained from reaction between the H 2 S-reactive compound and H 2 S to determine whether H 2 S is present.

2. The method of claim 1 , wherein R 1 is an azide.

3. The method of claim 1 , wherein R 1 is an ether having a formula

wherein each R 4 independently is selected from halogen, alkoxy, nitro, haloalkyl, cyano, sulfonate, carboxyl, ester, aldehyde, ketone, amine, hydroxyl, amide, alkyl, alkenyl, alkynyl, or aryl; and m can be 0, 1, 2, 3, 4, or 5.

4. The method of claim 1 , wherein R 1 is a thioether having a formula

wherein each R 4 independently is selected from independently can be selected from halogen, alkoxy, nitro, haloalkyl, cyano, sulfonate, carboxyl, ester, aldehyde, ketone, amine, hydroxyl, amide, alkyl, alkenyl, alkynyl, or aryl; and m can be 0, 1, 2, 3, 4, or 5.

5. The method of claim 1 , wherein the sample is a biological sample selected from a cell, tissue, or bodily fluid.

6. The method of claim 1 , wherein the sample is an environmental sample selected from a water sample, a soil sample, a gas sample, a plant sample, or an air sample.

7. The method of claim 1 , wherein analyzing the sample comprises visually detecting a color change produced by a reaction product obtained from reaction between the H 2 S-reactive compound and H 2 S.

8. The method of claim 7 , wherein the reaction product has an absorbance ranging from 450 nm to 600 nm.

9. The method of claim 1 , further comprising exposing the sample to an oxidant, a transition metal cation, a luciferase enzyme, a peroxidase enzyme, an enhancer, a base, or any combination thereof, in any order.

10. The method of claim 9 , wherein analyzing comprises visually detecting chemiluminescence or bioluminescence produced by the compound.

11. The method of claim 10 , wherein the chemiluminescence or bioluminescence emits at a wavelength ranging from 400 nm to 600 nm.

12. The method of claim 1 , wherein the providing an H 2 S-reactive compound, or a composition thereof, comprises providing a colorimetric compound precursor, or a composition thereof, having a formula

wherein R 4 is selected from H, F, OMe, or NO 2 ;
wherein the exposing the sample to the H 2 S-reactive compound, or composition thereof comprises exposing a biological or environmental sample to the colorimetric compound precursor, or composition thereof; and
wherein the analyzing the sample comprises analyzing the biological or environmental sample for a color change produced by a reaction product obtained from reaction between the colorimetric compound precursor and H 2 S.

13. The method of claim 1 , wherein the providing an H 2 S-reactive compound, or a composition thereof, comprises providing a chemiluminescent compound precursor, or a composition thereof, having a formula

wherein the exposing the sample to the H 2 S-reactive compound, or composition thereof comprises exposing the sample to the chemiluminescent compound precursor, or composition thereof, a peroxidase enzyme, a transition metal cation, an oxidant, an enhancer, a base, or combination thereof, in any order; and
wherein the analyzing the sample comprises analyzing the biological or environmental sample for chemiluminescence produced by a reaction product obtained from the chemiluminescent compound precursor.

14. The method of claim 1 , wherein the providing an H 2 S-reactive compound, or a composition thereof, comprises providing a bioluminescent compound precursor, or a composition thereof, having a formula

wherein the exposing the sample to the H 2 S-reactive compound, or composition thereof comprises exposing a biological sample to the bioluminescent compound precursor, or composition thereof and exposing the bioluminescent compound precursor, or composition thereof, to a luciferase enzyme; and
wherein the analyzing the sample comprises analyzing the biological sample for bioluminescence produced by a reaction product obtained from the bioluminescent compound precursor.

15. The method of claim 1 , wherein the H 2 S-reactive compound is selected from

or combinations thereof.

16. The method of claim 1 , wherein the sample is an environmental sample.

Assignees

• Univ Oregon

Inventors

• Pluth Michael D
• Bailey T Spencer
• Montoya Leticia A
• Pearce Taylor F

Classifications

• C07D277/68

  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 2 · CPC title

• G01N33/84 Primary

  involving inorganic compounds or pH · CPC title

• C07D271/12

  condensed with carbocyclic rings or ring systems · CPC title

• C07D237/32

  with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring · CPC title

• G01N31/22

  using chemical indicators (G01N31/02 takes precedence) · CPC title