Claims
- 1. A chemiluminescent compound of the formula: ##STR62## wherein Z.sup.1 and Z.sup.2 are independently selected from O, S and NR.sup.12, R.sup.12 is selected from alkyl, aryl, alkylsulfonyl and arylsulfonyl groups, R.sup.1 is a group containing from 1 to about 50 non-hydrogen atoms which is removable by an acid and R.sup.2 and R.sup.3 are organic groups containing from 1 to 50 non-hydrogen atoms selected from C, N, O, S, P and halogen atoms, R.sup.4 -R.sup.11 are independently selected from hydrogen and substituents which do not interfere with the generation of chemiluminescence, L is a linking group selected from a bond, divalent groups and polyvalent groups, and RG is a reactive group selected from carboxyl, carboxyl ester, acid anhydride, acid chloride, acyl azide, aldehyde, chloroformate, amine, hydroxyl, hydrazine, isocyanate, isothiocyanate, sulfonyl chloride, SO.sub.2 CH.sub.2 CF.sub.3, tosyl, maleimide, N-hydroxy-succinimide ester, aziridine, imine, disulfide ##STR63## wherein X is selected from chlorine bromine and iodine.
- 2. The compound of claim 1 wherein the groups Z.sup.1 and R.sup.1 are combined to form a phosphate group OPO(OR')(OR"), R' and R" are independently selected from alkyl groups, substituted alkyl groups and alkali metal ions and the compound has the formula ##STR64##
- 3. The compound of claim 2 wherein R' and R" are each a 2-cyanoethyl group.
- 4. The compound of claim 2 wherein R' and R" are each alkali metal ions.
- 5. The compound of claim 1 wherein Z.sup.2 is O or S, and R.sup.2 is selected from phenyl and substituted phenyl groups.
- 6. The compound of claim 5 wherein each of the groups R.sup.4 -R.sup.11 is a hydrogen, R.sup.3 is methyl, Z.sup.1 and R.sup.1 are combined to form a phosphate group --OPO.sub.3 M.sub.2, and each M is an alkali metal ion and the compound has the formula
- 7. The compound of claim 1 wherein the groups Z.sup.2 and R.sup.2 --L--RG are combined to form a phosphate group OPO(OR') (O--L--RG), R' is independently selected from alkyl groups, substituted alkyl groups, hydrogen and alkali metal ions and the compound has the formula:
- 8. The compound of claim 7 wherein Z.sup.1 is S and R.sup.1 is phenyl.
- 9. The compound of claim 1 wherein L is a divalent group containing from 1 to 30 non-hydrogen atoms selected from C, N, O, P and S atoms.
- 10. The compound of claim 1 wherein the reactive group RG is selected from OH, NH.sub.2, COOH, SO.sub.2 CH.sub.2 CF.sub.3, N-hydroxysuccinimide ester and maleimide groups.
- 11. A chemiluminescent labeled compound comprising a conjugate of a compound to be detected and a compound of the formula wherein Z.sup.1 and Z.sup.2 are independently selected from O, S and NR.sup.12, R.sup.12 is selected from alkyl, aryl, alkylsulfonyl and arylsulfonyl groups, R.sup.1 is a group containing from 1 to about 50 non-hydrogen atoms which is removable by an acid and R.sup.2 and R.sup.3 are organic groups containing from 1 to 50 non-hydrogen atoms selected from C, N, O, S, P and halogen atoms, R.sup.4 -R.sup.11 are independently selected from hydrogen and substituents which do not interfere with the generation of chemiluminescence, L is a linking group selected from a bond, divalent groups and polyvalent groups, and RG is a reactive group and the compound to be detected is an analyte or a specific binding pair member.
- 12. The chemiluminescent labeled compound of claim 11 wherein the groups Z.sup.1 and R.sup.1 are combined to form a phosphate group OPO(OR')(OR"), and R' and R" are independently selected from alkyl groups, substituted alkyl groups and alkali metal ions.
- 13. The chemiluminescent labeled compound of claim 12 wherein R' and R" are each a 2-cyanoethyl group.
- 14. The chemiluminescent labeled compound of claim 12 wherein R' and R" are each alkali metal ions.
- 15. The chemiluminescent labeled compound of claim 11 wherein Z.sup.2 is O or S, and R.sup.2 is selected from phenyl and substituted phenyl groups.
- 16. The chemiluminescent labeled compound of claim 15 wherein each of the groups R.sup.4 -R.sup.11 is a hydrogen, R.sup.3 is methyl, Z.sup.1 and R.sup.1 are combined to form a phosphate group--OPO.sub.3 M.sub.2, and each M is an alkali metal ion.
- 17. The chemiluminescent labeled compound of claim 11 wherein the groups Z.sup.2 and R.sup.2 --L--RG are combined to form a phosphate group OPO (OR') (O--L--RG), and R' is independently selected from alkyl groups, substituted alkyl groups, hydrogen and alkali metal ions.
- 18. The chemiluminescent labeled compound of claim 17 wherein Z.sup.1 is S and R.sup.1 is phenyl.
- 19. The chemiluminescent labeled compound of claim 11 wherein L is a divalent group containing from 1 to 30 non-hydrogen atoms selected from C, N, O, P and S atoms.
- 20. The chemiluminescent labeled compound of claim 11 wherein the reactive group is selected from OH, NH.sub.2, COOH, SO.sub.2 CH.sub.2 CF.sub.3, N-hydroxy-succinimide ester and maleimide groups.
- 21. The chemiluminescent labeled compound of claim 11 wherein the the compound to be detected is the analyte and is selected from drugs, hormones, pesticides, pesticide metabolites, DNA, RNA, oligonucleotides, antibodies, and antigens.
- 22. The chemiluminescent labeled compound of claim 11 wherein the compound to be detected is the specific binding partner and is selected from antigens, antibodies, haptens, oligo-nucleotides, polynucleotides, avidin, streptavidin, hormones, receptors, lectins, carbohydrates, IgG, protein A, and nucleic acid binding proteins.
CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of applicants' co-pending U.S. application Ser. No. 08/927,381 filed on Sep. 12, 1997.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5772926 |
Akhavan-Tafti |
Jun 1998 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
927381 |
Sep 1997 |
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