Chemiluminescent compositions, enhancing reagents for chemiluminescence and methods for the preparation and use thereof
View Patent ↗A enhancing reagent for enhancing chemiluminescence of 1,2-dioxetane compounds and a method for using the enhancing reagent to enhance chemiluminescence are provided, in which the enhancing reagent contains a multi-alkyl quaternary ammonium salt of Formula I. A chemiluminescent composition with a 1,2-dioxetane compound as a substrate and a kit thereof are further provided, which contain a 1,2-dioxetane compound and a multi-alkyl quaternary ammonium salt of Formula I.
1. A method for enhancing the chemiluminescence of 1,2-dioxetane compounds, the method comprising:
providing at least one aliphatic multi-alkyl quaternary ammonium salt having the structure of General Formula I:
wherein:
R 1 and R 2 are each independently selected from C 8-28 alkyl;
R 3 and R 4 are each independently selected from C 1-12 alkyl; or R 3 and R 4 are each independently selected from
wherein n is an integer selected from 5 to 10; and
X − is a negative ion; and
mixing the multi-alkyl quaternary ammonium salt with a 1,2-dioxetane compound.
2. The method of claim 1 , wherein R 1 and R 2 are identical alkyl, or R 1 , R 2 and R 3 are identical alkyl.
3. The method of claim 1 , wherein when R 3 is selected from C 1-8 alkyl, R 4 is selected from C 1-12 alkyl.
4. The method of claim 1 , wherein when R 3 is selected from C 1-8 alkyl, R 4 is selected from C 1-8 alkyl.
5. The method of claim 1 , wherein when R 3 and R 4 are selected from
n of R 3 and R 4 are identical integers.
6. The method of claim 1 , wherein X − is selected from halide ions, ClO 4 − , PF 6 − , CF 3 SO 3 − , BF 4 − , acetate, or p-toluene sulfonate anions.
7. The method of claim 1 , wherein the multi-alkyl quaternary ammonium salt compound is selected from at least one of: didodecyl dimethyl ammonium halide, dioctadecyl dimethyl ammonium halide, didodecyl polyoxyethylene ether ammonium halide, dioctadecyl polyoxyethylene ether ammonium halide, or a combination thereof.
8. The method of claim 1 , further comprising dissolving the multi-alkyl quaternary ammonium salt and the 1,2-dioxetane compound in water, wherein the concentration of the multi-alkyl quaternary ammonium salt is in a range of between about 0.1 g/L and about 10 g/L.
9. The method of claim 1 , further comprising dissolving the multi-alkyl quaternary ammonium salt and the 1,2-dioxetane compound in water, wherein the concentration of the multi-alkyl quaternary ammonium salt is in a range of between about 1 g/L and about 10 g/L.
10. The method of claim 1 , further comprising mixing the multi-alkyl quaternary ammonium salt and the 1,2-dioxetane compound with a fluorescent agent.
11. The method of claim 1 , further comprising mixing the multi-alkyl quaternary ammonium salt and the 1,2-dioxetane compound with at least one of: 2-amino-2-methyl-1-propanol or a magnesium ion or both.
12. A method for enhancing the chemiluminescence of 1,2-dioxetane compounds, the method comprising:
providing at least one multi-alkyl quaternary ammonium salt having the structure of General Formula I:
wherein:
R 1 and R 2 are each independently selected from C 8-28 alkyl;
R 3 and R 4 are each independently selected from C 1-12 alkyl; phenyl C 1-6 alkyl, wherein the phenyl is optionally substituted with one or more substituents selected from at least one of: halogen, hydroxyl, sulfhydryl, cyano, nitro, alkyl, alkoxy, haloalkyl, amino, alkylamino, or amido; or
wherein n is an integer selected from 5 to 10; and
X − is a negative ion;
mixing the multi-alkyl quaternary ammonium salt with a 1,2-dioxetane compound having the following structure:
wherein R 1 is selected from at least one of alkyl, aryl, aralkyl, alkaryl, heteroalkyl, heteroaryl, cycloalkyl, heterocycloalkyl, alkyloxyalkyl, alkyloxyaryl, alkyloxyhaloalkyl, alklalkenyl, alkylalkynyl, halogenated alkyl, alkyl alcohol, alkyl carbonitrile, alkyl amine, alkyl acid, halogenated alkyl alcohol, halogenated alkyl carbonitrile, halogenated alkyl amine, and halogenated alkyl acid;
X is hydrogen or a substituent on a phenyl ring;
Y is hydrogen, alkyl, acetoxyl, t-butyldimethylsilyl, a group capable of being cleaved by an enzyme, or a group capable of being cleaved by an antibody; and
Z is hydrogen or a substituent on an adamantane ring; and
dissolving the multi-alkyl quaternary ammonium salt and the 1,2-dioxetane compound in water, wherein the concentration of the multi-alkyl quaternary ammonium salt is in a range of between about 1 g/L to about 10 g/L.
13. The method of claim 12 , wherein the R 1 and R 2 of the multi-alkyl quaternary ammonium salt are identical alkyl, or the R 1 , R 2 and R 3 of the multi-alkyl quaternary ammonium salt are identical alkyl.
14. The method of claim 12 , wherein when the R 3 of the multi-alkyl quaternary ammonium salt is selected from C 1-8 alkyl, the R 4 of the multi-alkyl quaternary ammonium salt is selected from C 1-12 alkyl, or phenyl C 1-6 alkyl, wherein the phenyl is optionally substituted with one or more substituents selected from at least one of: halogen, hydroxyl, sulfhydryl, cyano, nitro, alkyl, alkoxy, haloalkyl, amino, or alkylamino.
15. The method of claim 12 , wherein when the R 3 of the multi-alkyl quaternary ammonium salt is selected from C 1-8 alkyl, the R 4 of the multi-alkyl quaternary ammonium salt is selected from C 1-8 alkyl or benzyl.
16. The method of claim 12 , wherein the multi-alkyl quaternary ammonium salt compound is selected from at least one of: didodecyl dimethyl ammonium halide, dioctadecyl dimethyl ammonium halide, dioctadecyl methyl benzyl ammonium halide, didodecyl polyoxyethylene ether ammonium halide, dioctadecyl polyoxyethylene ether ammonium halide, or a combination thereof.