Degradable cationic surfactants and use thereof in enhancing chemiluminescence

Patent metadata

Field	Value
Publication number	US-10073039-B2
Application number	US-201414891262-A
Country	US
Kind code	B2
Filing date	May 13, 2014
Priority date	May 14, 2013
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to methods of enhancing chemiluminescence from a chemiluminescent label comprising contacting a chemiluminescent label with an acid in the presence of a degradable cationic surfactant and hydrogen peroxide followed by the addition of a base. Related kits containing such degradable cationic surfactant are also provided. The degradable cationic surfactant can compress light emission time of the chemiluminescent label to an extent that is comparable to or shorter than conventional surfactants. The degradable cationic surfactant can also increase chemiluminescence of the chemiluminescent label, providing increased light emission output that is comparable to conventional surfactants.

First claim

The invention claimed is:

1. A method of enhancing chemiluminescence from a chemiluminescent label, comprising contacting a chemiluminescent label with an acid and hydrogen peroxide in the presence of a degradable cationic surfactant having formula I:

wherein:
X is nitrogen or phosphorus;
R 1 , R 2 and R 3 are each independently selected from hydrogen and an alkyl, alkenyl, alkynyl, cycloalkyl or aralkyl group optionally having one or more heteroatoms;
R 4 and R 5 are each independently selected from an alkyl, alkenyl, alkynyl, cycloalkyl or aralkyl group optionally having one or more heteroatoms;
Y is a cleavable linkage selected from the group consisting of a carbonate linkage, an amide linkage, an ester linkage and any combination thereof; and
A − is an anionic counterion to X + ,

wherein said chemiluminescent label is an acridinium dimethylphenyl ester, an acridinium sulfonamide, or a derivative or conjugate thereof.

2. The method of claim 1 , wherein said surfactant provides a compressed emission time of said chemiluminescent label shorter than that of cetyltrimethylammonium chloride.

3. The method of claim 2 , wherein said compressed emission time is about 20% shorter than that of cetyltrimethylammonium chloride.

4. The method of claim 2 , wherein said compressed emission time is about 30% shorter than that of cetyltrimethylammonium chloride.

5. The method of claim 2 , wherein said compressed emission time is about 50% shorter than that of cetyltrimethylammonium chloride.

6. The method of claim 1 , wherein said surfactant is as effective as cetyltrimethylammonium chloride in enhancing total light yield of the chemiluminescent label.

7. The method of claim 1 , wherein the chemiluminescence of said chemiluminescent label is increased, thereby providing an increased light emission relative to a standard light emission without surfactants.

8. The method of claim 7 , wherein said increased light emission is at least about 2.5 fold enhancement compared to the standard light emission without surfactants.

9. The method of claim 7 , wherein said enhancement is at least about 70% that of cetyltrimethylammonium chloride.

10. The method of claim 7 , wherein said enhancement is at least about 80% that of cetyltrimethylammonium chloride.

11. The method of claim 7 , wherein said enhancement is at least about 90% that of cetyltrimethylammonium chloride.

12. The method of claim 7 , wherein said surfactant is at least as effective as cetyltrimethylammonium chloride in compressing emission time of the chemiluminescent label.

13. The method of claim 1 , wherein R 1 , R 2 and R 3 are each independently a C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-10 cycloalkyl or C 4-10 aralkyl group optionally having one or more heteroatoms.

14. The method of claim 1 , wherein R 4 is a C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 3-20 cycloalkyl or C 4-20 aralkyl group optionally having one or more heteroatoms.

15. The method of claim 1 , wherein R 5 is a C 1-30 alkyl, C 2-30 alkenyl, C 2-30 alkynyl, C 3-30 cycloalkyl or C 4-30 aralkyl group optionally having one or more heteroatoms.

16. The method of claim 1 , wherein Y is degradable under hydrolytic conditions.

17. The method of claim 1 , wherein A − is chloride, bromide, iodide, sulfate, sulfonate or hydroxide ion.

18. The method of claim 1 , wherein said surfactant is compound 1 or 2 or a mixture thereof:

19. The method according to claim 1 , wherein R 1 -R 3 are each independently alkyl optionally having one or more heteroatoms.

20. The method according to claim 1 wherein R 4 and R 5 are independently selected from alkyl, cycloalkyl, or aralkyl optionally having one or more heteroatoms.

Assignees

• Siemens Healthcare Diagnostics Inc
• Siemens Healthcare Diagnostics Inc

Inventors

• Natrajan Anand
• Wen David

Classifications

• C12Q1/66 Primary

  involving luciferase · CPC title

• G01N21/76 Primary

  Chemiluminescence; Bioluminescence · CPC title

• G01N33/582

  with fluorescent label · CPC title