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US 2026/0276646 A1Published application
Coumarin-based crosslinking reagents
AssigneeVentana Medical Systems, Inc.
InventorsRui Hong, Mark Lefever, Eric May
Life of this patent
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Abstract
Disclosed herein are novel coumarin-based reagents, e.g. linkers, and conjugates including one or more of the disclosed coumarin-based reagents. In some embodiments, the presence of a coumarin moiety within the coumarin-based reagents enables detection of labels which are typically difficult to detect, e.g. certain haptens.
Claims20
A compound defined by the structure of any of Formulas (IA) or (IB):
- wherein
- a first of A or B is a moiety having Formula (VIIB),
- a second of A or B is a hapten selected from the group consisting of an oxazole, a pyrazole, a thiazole, a benzofurazan, a triterpene, a nitroaryl other than dinitrophenyl or trinitrophenyl, a rotenoid, a cyclolignan, and a benzodiazepine;
- L1 and L2 are each independently a bivalent linker selected from the group consisting of:
- —C(O)NH—(CH2CH2O)p—CH2CH2—NH—C(O)—;
- —C(O)NH—(CH2)q—NH—C(O)—;
- —C(O)O—(CH2CH2O)p—CH2CH2—NH—C(O)—;
- and —C(O)NH—(CH2CH2O)p—CH2CH2—O—C(O)—, wherein p is an integer from 2 to 12 and q is an integer from 2 to 10;
- R9 and R10 are independently a bond, a carbonyl group, an amide group, an imide group, an ester group, or a thione group;
- W has the structure of either of Formula (VC) or (VD):
- R2, R3, R4, R6, and R7 are each H;
- R5 is —CH2— or —C(O)—NH—;
- R1 is —O—, —O—CH2— or —NH—;
- each X is independently a bond —CH2—;
- Z is a bond, a —CH— group, a —CH—CH2— group or a —CH2—CH— group;
- m and n are 1.
13 more elements
A compound defined by the structure of any of Formulas (IA) or (IB):
- wherein
- a first of A or B is a moiety having Formula (VIIB),
- a second of A or B is a hapten selected from the group consisting of an oxazole, a pyrazole, a thiazole, a benzofurazan, a triterpene, a nitroaryl other than dinitrophenyl or trinitrophenyl, a rotenoid, a cyclolignan, and a benzodiazepine;
- L1 and L2 are linkers,
- wherein each L1 and/or L2 independently have Formula (VIC):
- wherein
- f is 0 or an integer ranging from 1 to 12;
- j is an integer ranging from 1 to 24;
- R9 and R10 are independently a bond, a carbonyl group, an amide group, an imide group, an ester group, or a thione group;
- W has the structure of either of Formula (VC) or (VD):
- R2, R3, R4, R6, and R7 are independently selected from H, a substituted or unsubstituted, straight chain or branched C1-C6 alkyl group;
- a substituted or unsubstituted, straight chain or branched C1-C6 alkoxy group;
- a substituted or unsubstituted, straight chain or branched C1-C6 heteroalkyl group;
- a trifluoromethyl group;
- a hydroxyl group;
- a sulfate group;
- a cyano group;
- a halogen;
- a phosphate group;
- a saccharide;
- a carboxylic acid group;
- a nitro group;
- —C(O)NRxRy;
- —S—Rx;
- —SO2;
- —SO2Cl;
- —SO3H;
- —SO4H;
- —SO2NRxRy;
- —N(H)—NRxRy;
- —NRxRy;
- and wherein Rx and Ry are independently H or a C1-C4 alkyl group
- R5 is a C1-C10 unsubstituted and unbranched alkylene group, —C(O)—O—;
- or —C(O)—N(H)—;
- R1 is a C1-C10 unsubstituted and unbranched alkylene group, —O—, —O—CH2—, —N(Rx)—;
- or —S—;
- and
- each X is independently a bond or an unsubstituted, straight chain or branched C1-C16 alkylene group;
- Z is a bond, a —CH— group, a —CH—CH2— group or a —CH2—CH— group;
- Rx is H or —CH3;
- and
- m and n are independently an integer ranging from 1 to 4.
39 more elements
A compound selected from the group consisting of:
- where Rv is an enzyme reactive moiety or a reactive functional group.
Dependencies are inferred from the claim text.