Detection of hydrogen peroxide

1. A compound of formula

wherein

R 1 is boronic acid or a borate ester;

each R 4 , R 5 and R 7 is independently selected from H, halo, methyl, and trifluoromethyl; and

L 1 is a linker.

2. The compound of claim 1 , wherein

R 1 is —B(OR 6 ) 2 ; and

each R 6 is independently selected from H and C 1-4 alkyl.

3. The compound of claim 1 , wherein

R 1 is

and

each R 12 and R 13 is independently selected from H, C 1-4 alkyl, CF 3 , phenyl or substituted phenyl; or R 12 and R 13 together can be an alkyl ring having from 3-7 carbons or can be replaced by a fused 6-membered aromatic ring.

4. The compound of claim 1 , wherein

R 1 is

and

each R 14 , R 15 and R 16 is independently selected from H, C 1-4 alkyl, CF 3 , phenyl and substituted phenyl; or both R 15 together can form an alkyl ring having from 3-7 carbons; R 14 and R 15 together or R 15 and R 16 together can be an alkyl ring having from 3-7 carbon atoms or can be replaced by a 6-membered aromatic ring.

5. The compound of claim 1 ,

wherein

L 1 is

A is —C 6 (R 10 ) 4 —, —O—C 6 (R 10 ) 4 — or —(CR 11 ═CR 11 ) n — or —S—C 6 (R 10 ) 4 — or —NR′—C 6 (R 10 ) 4 or a direct bond;

R′ is H or C 1-4 alkyl;

each R 3 is independently halo, H, C 1-4 alkyl; C 1-4 hydroxyalkyl, or C 1-4 alkylcarboxylic acid;

each R 10 is independently H, halo, CH 3 , OCH 3 , or NO 2 ;

each R 11 is independently H or CH 3 ;

n is 1 or 2; and

X is a selected from —O—,

6. A method of detecting hydrogen peroxide in a cell comprising:

(a) contacting cells with a compound according to claim 1 ;

(b) adding a luciferase reaction mixture to the contacted cells; and

(c) measuring bioluminescence thereby detecting the presence of hydrogen peroxide in the cell.

7. The method of claim 6 , wherein the luciferase reaction mixture comprises D-cysteine.

8. The method of claim 6 , wherein the cells are treated with a test compound or test condition prior to contacting with a compound according to Formula (I)

wherein

R 1 is boronic acid or a borate ester;

each R 4 , R 5 and R 7 is independently selected from H, halo, methyl, and trifluoromethyl; and

L 1 is a linker.

9. The method of claim 8 , wherein the test condition comprises a change in temperature, oxygen tension or ionic strength or an osmotic change.

10. The method of claim 6 , wherein the cell is in a sample.

11. The method of claim 10 , wherein the sample is obtained from an animal.

12. A method of detecting hydrogen peroxide in a cell comprising:

(a) contacting cells with a compound according to claim 1 in a first reaction vessel to form an incubation mixture;

(b) transferring at least a portion of the incubation mixture to a second reaction vessel;

(c) adding a luciferase reaction mixture to the second reaction vessel; and

(d) measuring bioluminescence thereby detecting the presence of hydrogen peroxide in the cell.

13. The method of claim 12 , wherein the luciferase reaction mixture comprises D-cysteine.

14. The method of claims 12 , wherein the cells are treated with a test compound or test condition prior to contacting with a compound according to Formula (I)

wherein

R 1 is boronic acid or a borate ester;

each R 4 , R 5 and R 7 is independently selected from H, halo, methyl, and trifluoromethyl; and

L 1 is a linker.

15. The method of claim 14 , wherein the test condition comprises a change in temperature, oxygen tension or ionic strength or an osmotic change.

16. The method of claim 15 , wherein the cell is obtained from an animal.

17. A method of detecting hydrogen peroxide in a sample comprising:

(a) contacting a sample with a compound according to claim 1 to form a first mixture;

b) contacting at least a portion of the first mixture with a luciferase reaction mixture and D-cysteine and

c) measuring bioluminescence thereby detecting the presence of hydrogen peroxide in the sample.

18. The method of claim 17 , wherein the D-cysteine is part of the reaction mixture for a luciferase reaction mixture.

19. The method of claim 17 , wherein the sample is treated with a test compound or test condition prior to contacting with a compound according to Formula (I)

wherein

R 1 is boronic acid or a borate ester;

each R 4 , R 5 and R 7 is independently selected from H, halo, methyl, and trifluoromethyl; and

L 1 is a linker.

20. The method of claim 19 , wherein the test condition comprises a change in temperature, oxygen tension or ionic strength or an osmotic change.

21. The method of claim 17 , wherein the sample comprises a cell or cell medium.

22. The method of claim 21 , wherein the sample comprises a cell or physiological sample from an animal.

23. A method of determining the effect of a test compound or test condition on the presence or amount of hydrogen peroxide in a sample comprising:

a) treating a sample with a test compound or test condition,

b) contacting the sample from a) with a compound according to claim 1 ;

c) adding a luciferase reaction mixture to the sample;

d) measuring bioluminescence.

24. The method of claim 23 , wherein the sample comprises a cell or cell medium.

25. The method of claim 23 , wherein the sample comprises a cell or physiological sample from an animal.

26. The method of claim 23 , wherein the test condition comprises a change in temperature, oxygen tension, or ionic strength or an osmotic change.

27. A kit comprising a compound according to claim 1 .