Compounds for generating chemiluminescence with a peroxidase
AssigneeLumigen, Inc.
InventorsHashem Akhavan-Tafti, Renuka de Silva, Wenhua Xie
Life of this patent
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Abstract
Novel compounds comprising a C—C double bond substituted at one carbon with two sulfur atom-containing groups are disclosed. The compounds are useful in methods and compositions for generating chemiluminescence rapidly by reaction with a peroxidase enzyme and a peroxide. The chemiluminescence thus produced can be used as a detectable signal in assays for peroxidase enzymes or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.
Claims55
A compound of the formula:
- 35
- wherein R1 and R2 are independently selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups of 1-20 carbon atoms and can be joined together to form a ring, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and R3 is selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups.
A compound of the formula:
- 50
- wherein R1 and R2 are are joined together by a substituted alkylene or heteroalkylene chain to form a ring comprising from five to thirty atoms, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and R3 is selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups.
A compound of the formula:
- 53
- wherein R1 and R2 are are joined together by a ring comprising from five to thirty atoms fused to a second ring, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, R3 is selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups, and further comprising a group Z which confers water solubility.
A compound of the formula:
- 55
- wherein R1 and R2 are independently selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups of 1-20 carbon atoms and can each independently be joined to the nearest respective ring position R4 or R11 to close an additional ring and can be joined together to form a ring of 5 to 30 atoms, each of R4 to R6 and R8 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and the nitrogen atom is joined to close an additional 5-7 membered ring.
A compound of the formula:
- 56
- wherein at least one of the sulfur atoms is joined together to the nearest respective ring position R4 or R11 to form a ring of 5 to 7 atoms, and when only one of the sulfur atoms is so joined R1 is selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups of 1-20 carbon atoms, R3 is selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups and wherein each of R5 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms.
A method for producing chemiluminescence which comprises reacting a peroxidase enzyme with a peroxide and at least one compound of formula I to produce the chemiluminescence
- 57
- wherein R1 and R2 are are joined together by a substituted alkylene or heteroalkylene chain to form a ring comprising from five to thirty atoms, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and R3 is selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups.
A method for producing chemiluminescence which comprises reacting a peroxidase enzyme with a peroxide and at least one compound of formula I to produce the chemiluminescence
- 58
- wherein R1 and R2 are are joined together by a ring comprising from five to thirty atoms fused to a second ring, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, R3 is selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups, and further comprising a group Z which confers water solubility.
A method for producing chemiluminescence which comprises reacting a peroxidase enzyme with a peroxide and at least one compound of the formula:
- 60
- to produce the chemiluminescence wherein R1 and R2 are independently selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups of 1-20 carbon atoms and can each independently be joined to the nearest respective ring position R4 or R11 to close an additional ring and can be joined together to form a ring of 5 to 30 atoms, each of R4 to R6 and R8 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and the nitrogen atom is joined to close an additional 5-7 membered ring.
A method for producing chemiluminescence which comprises reacting a peroxidase enzyme with a peroxide and at least one compound of the formula:
- 61
- to produce the chemiluminescence wherein at least one of the sulfur atoms is joined together to the nearest respective ring position R4 or R11 to form a ring of 5 to 7 atoms, and each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms.
A compound of the formula:
- 65
- wherein R1 and R2 are independently selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups of 1-20 carbon atoms and can be joined together to form a ring-containing group, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and R3 is selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups.
A method for producing chemiluminescence which comprises reacting a peroxidase enzyme with a peroxide and at least one compound of the formula:
- 66
- to produce the chemiluminescence wherein R1 and R2 are independently selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups of 1-20 carbon atoms and can be joined together to form a ring-containing group, each of R4 to R11 is independently a substituent which can contain from 1 to 50 atoms selected from C, H, N, O, S, P, Si and halogen atoms, and R3 is selected from alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl groups.
Dependencies are inferred from the claim text.