Labeling Reagents and Methods of Their Use
AssigneeLife Technologies Corporation
InventorsEvan ANTOULINAKIS, Kyle GEE, Aleksey RUKAVISHNIKOV
Life of this patent
Estimating the term…
Abstract
The present disclosure is directed to a reactive ester agent capable of conjugating a reporter molecule to a carrier molecule or solid support. The reactive ester agent has the general formula: wherein the variables are described throughout the application.
Claims56
A compound of Formula IA or a tautomer or salt thereof:
- wherein,
- L is a linker;
- R1 is a halogen;
- R2 is a halogen;
- R3 comprises a water solubilizing group;
- and
- Ra is a reporter molecule.
A compound of Formula II or a tautomer or salt thereof:
- wherein,
- L is a linker;
- R1 is a halogen;
- R2 is a halogen;
- R3 is a water solubilizing group;
- R6, R7 and R9 are each independently selected from the group consisting of H, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, acylamino, acyloxy, amino, substituted amino, aminocarbonyl, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyl, aminosulfonyloxy, aminosulfonylamino, amidino, carboxyl, carboxyl ester, (carboxyl ester)amino, (carboxyl ester)oxy, cyano, halo, hydroxy, nitro, SO3−, sulfonyl, substituted sulfonyl, sulfonyloxy, thioacyl, thiol, alkylthio, substituted alkylthio, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl;
- and
- n is 0, 1, or 2.
A compound of Formula III or a tautomer or salt thereof:
- wherein,
- Y is —CR14═(CR15—CR16═)m;
- m is 0, 1, 2, or 3;
- R10 and R11 are each independently selected from the group consisting of H, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, acylamino, acyloxy, amino, substituted amino, aminocarbonyl, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyl, aminosulfonyloxy, aminosulfonylamino, amidino, carboxyl, carboxyl ester, (carboxyl ester)amino, (carboxyl ester)oxy, cyano, halo, hydroxy, nitro, SO3−, sulfonyl, substituted sulfonyl, sulfonyloxy, thioacyl, thiol, alkylthio, substituted alkylthio, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl;
- R12 and R13 are each independently H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl;
- R18 is methyl;
- and
- wherein one of R13 or R18 is:
- L is a linker;
- R1 is a halogen;
- R2 is a halogen;
- and
- R3 is a water solubilizing group.
A compound selected from the group consisting of:
A compound having the following structure or a tautomer or salt thereof:
- wherein,
- R1 is a halogen;
- R2 is a halogen;
- and
- R3 is a water solubilizing group.
A method of making a compound of Formula I comprising:
- contacting a carrier molecule or a solid support comprising a nucleophile with a compound of Formula IA or a tautomer or salt thereof:
- wherein,
- L is a linker;
- R1 is a halogen;
- R2 is a halogen;
- R3 comprises a water solubilizing group;
- and
- Ra is a reporter molecule;
- forming a compound of Formula I or a tautomer or salt thereof:
- wherein
- L is the linker;
- Ra is the reporter molecule;
- and
- Rb is the carrier molecule or solid support comprising a nucleophile (X).
A method of labeling a carrier molecule or solid support comprising:
- contacting the carrier molecule or solid support with a compound of Formula IA or a tautomer or salt thereof:
- wherein,
- L is a linker;
- R1 is a halogen;
- R2 is a halogen;
- R3 comprises a water solubilizing group;
- Ra is a reporter molecule;
- and
- the carrier molecule or solid support comprises a nucleophile;
- and
- forming a labeled carrier molecule or solid support.
A method of making a compound of Formula IA or a tautomer or salt thereof comprising:
- contacting a compound of Formula IB or a tautomer or salt thereof:
- with a compound of Formula IC or a tautomer or salt thereof:
- and forming the compound of Formula IA or a tautomer or salt thereof:
- wherein,
- R1 is a halogen;
- R2 is a halogen;
- R3 comprises a water solubilizing group;
- L is a linker;
- and
- Ra is a reporter molecule.
A kit for forming a conjugate with a carrier molecule or solid support and a labeling reagent, wherein the kit comprises:
- a) a labeling reagent according to Formula IA or a tautomer or salt thereof:
- wherein,
- L is a linker;
- R1 is a halogen;
- R2 is a halogen;
- R3 comprises a water solubilizing group;
- and
- Ra is a reporter molecule;
- b) instructions for forming a conjugate with the carrier molecule or solids support.
Dependencies are inferred from the claim text.