Fluorescent ozone sensor
View Patent ↗A selective, fluorescent “turn-on” probe and method for the detection of ozone in biological and atmospheric samples, wherein the method of detecting ozone in a sample comprises the steps of (1) contacting the sample with a fluorophore capable of undergoing allylic ether or allylic ester cleavage and (2) detecting fluorescence in the sample.
1. A method of detecting ozone in a sample comprising the steps of:
1) contacting the sample with a fluorophore capable of undergoing allylic ether or allylic ester cleavage, wherein the fluorophore is a compound having a formula
where X 1 and X 2 are each independently hydrogen, homoallyl group, or halogen;
Z is O, S, Se, or NR′, wherein R′ is a hydrogen or an homoallyl group;
n is an integer from 1 to 5;
each Y is independently hydrogen, or a functional group; and
R 1 , R 2 , and R 3 are independently either hydrogen atom, homoallyl, or aryl groups that may contain one or more further substitutions; and
2) detecting fluorescence in the sample.
2. The method of claim 1 , wherein the compound has a formula
3. The method of claim 1 , wherein Y is CH 2 OH.
4. The method of claim 3 , wherein at least one of X 1 and X 2 is Cl.
5. The method of claim 4 , wherein at least one of R1, R 2 , and R 3 is hydrogen.
6. The method of claim 1 , wherein the sample is a biological sample selected from the group consisting of cells, whole blood, plasma, serum, saliva, urine, sweat, tears, cerebrospinal fluid and solid tissue.
7. The method of claim 1 , wherein the sample is water or air.
8. The method according to claim 1 , further comprising the step of adding pyrrolidine as a catalyst.
9. The method according to claim 8 , wherein the step of adding pyrrolidine further comprises adding up to 1M of the pyrrolidine at 0-1M and about 1 nM to about 1M of aldehyde in a mixture of water-soluble organic solvents and buffer having pH 4-11.
10. The method according to claim 9 , wherein the ratio of pyrrolidine, aldehyde, and water-soluble organic solvents to buffer is about 0.1-80:99.9-20.
11. The method according to claim 9 , wherein the water-soluble organic solvents are selected from the group consisting of MeOH, EtOH, iPrOH, MeCN, 1,4-dioxane, THF, DMSO, and DMF.
12. A method of detecting ozone in a sample comprising the steps of:
1) contacting the sample with a fluorophore capable of undergoing allylic ether or allylic ester cleavage, wherein the fluorophore is a compound having a formula
where X is hydrogen, alkyl group, or halogen;
n is an integer from 1 to 2;
each Y is independently hydrogen, or a functional group; and
R 1 , R 2 , and R 3 are independently either hydrogen atom, alkyl, or aryl groups that may contain one or more further substitutions; and
2) detecting fluorescence in the sample.
13. The compound of claim 12 , wherein Y is CH 2 OH.
14. The compound of claim 13 , wherein at least one of X 1 or X 2 is Cl.
15. The compound of claim 14 , wherein at least one of R 1 , R 2 , and R 3 is hydrogen.
16. The method according to claim 12 , further comprising the step of adding pyrrolidine as a catalyst.
17. The method according to claim 16 , wherein the step of adding pyrrolidine further comprises adding up to 1M of the pyrrolidine at 0-1M and about 1 nM to about 1M of aldehyde in a mixture of water-soluble organic solvents and buffer having pH 4-11.
18. The method according to claim 17 , wherein the ratio of pyrrolidine, aldehyde, and water-soluble organic solvents to buffer is about 0.1-80:99.9-20.
19. The method according to claim 17 , wherein the water-soluble organic solvents are selected from the group consisting of MeOH, EtOH, iPrOH, MeCN, 1,4-dioxane, THF, DMSO, and DMF.
20. The method of claim 12 , wherein the sample is a biological sample selected from the group consisting of cells, whole blood, plasma, serum, saliva, urine, sweat, tears, cerebrospinal fluid and solid tissue.
21. The method of claim 12 , wherein the sample is water or air.
22. A method of detecting ozone in a sample comprising the steps of:
1) contacting the sample with a fluorophore capable of undergoing allylic ether or allylic ester cleavage, wherein the fluorophore is a compound having a formula:
where each X is independently hydrogen, alkyl group, or halogen;
n is an integer from 1 to 2;
each Y is independently hydrogen, or a functional group; and
R 1 , R 2 , and R 3 are independently either hydrogen atom, alkyl, or aryl groups that may contain one or more further substitutions; and
2) detecting fluorescence in the sample.
23. The compound of claim 22 , wherein Y is CH 2 OH.
24. The compound of claim 23 , wherein at least one of X 1 or X 2 is Cl.
25. The compound of claim 24 , wherein at least one of R 1 , R 2 , and R 3 is hydrogen.
26. The method according to claim 22 , further comprising the step of adding pyrrolidine as a catalyst.
27. The method according to claim 26 , wherein the step of adding pyrrolidine further comprises adding up to 1M of the pyrrolidine at 0-1M and about 1 nM to about 1M of aldehyde in a mixture of water-soluble organic solvents and buffer having pH 4-11.
28. The method according to claim 27 , wherein the ratio of pyrrolidine, aldehyde, and water-soluble organic solvents to buffer is about 0.1-80:99.9-20.
29. The method according to claim 27 , wherein the water-soluble organic solvents are selected from the group consisting of MeOH, EtOH, iPrOH, MeCN, 1,4-dioxane, THF, DMSO, and DMF.
30. The method of claim 22 , wherein the sample is a biological sample selected from the group consisting of cells, whole blood, plasma, serum, saliva, urine, sweat, tears, cerebrospinal fluid and solid tissue.
31. The method of claim 22 , wherein the sample is water or air.
32. A method of detecting ozone in a sample comprising the steps of:
a) providing a non-fluorescent fluorophore in a mixture water-soluble organic solvents and buffer to form the sample, wherein the non-fluorescent fluorophore has a formula
b) exposing the sample to ozone;
c) incubating the sample at a predetermined temperature for a predetermined time; and
d) measuring the fluorescence of the sample for the detection of ozone in human cells.
33. The method according to claim 32 , further comprising the step of adding pyrrolidine as a catalyst.
34. A method of detecting ozone in a sample comprising the steps of:
a) providing a non-fluorescent fluorophore in a mixture water-soluble organic solvents and buffer to form the sample, wherein the non-fluorescent fluorophore has a formula
b) exposing the sample to ozone;
c) incubating the sample at a predetermined temperature for a predetermined time; and
d) measuring the fluorescence of the sample for the detection of ozone in air samples.
35. The method according to claim 34 , further comprising the step of adding pyrrolidine as a catalyst.
36. A method of detecting ozone in an indoor air sample comprising the steps of:
a) providing an adsorbent paper having a non-fluorescent fluorophore being disposed on a portion of the adsorbent paper, wherein the non-fluorescent fluorophore has a formula
b) exposing the sample to ozone for a predetermined time;
c) placing the samples into a scintillation vial and eluting the dyes before fluorescence and absorbance measurement; and
d) measuring the fluorescence and absorbance of the sample.
37. The method according to claim 36 , further comprising the step of adding pyrrolidine as a catalyst to the adsorbent paper.
38. A method of detecting ozone in a sample comprising the steps of:
a) providing a non-fluorescent fluorophore in a mixture water-soluble organic solvents and buffer to form the sample, wherein the non-fluorescent fluorophore has a formula
b) exposing the sample to ozone;
c) incubating the sample at a predetermined temperature for a predetermined time; and
d) measuring the fluorescence of the sample for the detection of ozone in air samples.
39. The method according to claim 38 , further comprising the step of adding pyrrolidine as a catalyst.