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