New iridium-based complexes for ecl

Patent metadata

Field	Value
Publication number	US-2016145281-A1
Application number	US-201514867074-A
Country	US
Kind code	A1
Filing date	Sep 28, 2015
Priority date	Feb 9, 2011
Publication date	May 26, 2016
Grant date	—

Abstract

Novel iridium-based Ir(III) luminescent complexes, conjugates comprising these complexes as a label and their application, for example in the electrochemiluminescence based detection of an analyte.

First claim

What is claimed is:

1 . An iridium-based chemiluminescent compound of Formula I

wherein R1-R16 is hydrogen, halide, cyano- or nitro-group, amino, alkylamino, substituted alkylamino, arylamino, substituted arylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylic acid ester, carbamoyl, hydroxy, substituated or unsubstituated alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, alkylsulfonyl, arylsulfonyl, sulfo, sulfino, sulfeno, sulfonamide, sulfoxide, sulfodioxide, phosphonate, phosphinate or R17, wherein R17 is aryl, substituted aryl, alkyl, substituted alkyl branched alkyl, substituted branched alkyl, arylalkyl, substituted arylalkyl, alkylaryl, substituted alkylaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, wherein the substituent is selected from hydrogen, halide, cyano- or nitro-group, a hydrophilic group, like amino, alkylamino, substituted alkylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylic acid ester, carbamoyl, hydroxy, substituted or unsubstituated alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, alkylsulfonyl, arylsulfonyl, sulfo, sulfino, sulfeno, sulfonamide, sulfoxide, sulfodioxide, phosphonate, phosphinate or,
wherein within R1-R12 and/or within R13-R16, respectively, two adjacent Rs can form an aromatic ring or a substituted aromatic ring, wherein the substituent is selected from hydrogen, halide, cyano- or nitro-group, a hydrophilic group, like amino, alkylamino, substituted alkylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylic acid ester, carbamoyl, hydroxy, substituted or unsubstituted alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, alkylsulfonyl, arylsulfonyl, sulfo, sulfino, sulfeno, sulfonamide, sulfoxide, sulfodioxide, phosphonate, phosphinate or,
wherein within R1-R12 or/and within R13-R16, respectively, two adjacent Rs can form an aliphatic ring or a substituted aliphatic ring, wherein the substituent is selected from hydrogen, halide, cyano- or nitro-group, a hydrophilic group, like amino, alkylamino, substituted alkylamino, alkylammonium, substituted alkylammonium, carboxy, carboxylic acid ester, carbamoyl, hydroxy, substituted or unsubstituted alkyloxy, substituted or unsubstituted aryloxy, sulfanyl, alkylsulfonyl, arylsulfonyl, sulfo, sulfino, sulfeno, sulfonamide, sulfoxide, sulfodioxide, phosphonate, phosphinate and
wherein at least one of R13-R16 is -Q-Y, wherein Q represents a linker and Y is a functional group and wherein the linker Q is a straight or branched saturated, unsaturated, unsubstituted or substituted C1-C20 alkyl chain, or a 1 to 20 atom chain with a backbone consisting of carbon atoms and one or more heteroatoms selected from O, N and S.

2 . The compound according to claim 1 , wherein the linker Q is a saturated C1-C12 alkyl chain or a 1 to 12 atom chain with a backbone consisting of carbon atoms and one or more heteroatoms selected from O, N and S.

3 . The compound according to claim 1 , wherein the functional group Y is selected from the group consisting of carboxylic acid, N-hydroxysuccinimide ester, amino group, halogen, sulfhydryl, maleimido, alkynyl, azide and phosphoramidite.

4 . A conjugate comprising a compound according to claim 1 and covalently bound thereto an affinity binding agent.

5 . The conjugate of claim 4 , wherein the affinity binding agent is selected from the group consisting of antigen and antibody, biotin or biotin analogue and avidin or streptavidin, sugar and lectin, nucleic acid or nucleic acid analogue and complementary nucleic acid and receptor and ligand.

6 . The conjugate according to claim 4 , wherein said affinity binding agent is a nucleic acid or an antibody.

7 . A method for measuring an analyte by an in vitro method, the method comprising the steps of:
a) providing a sample suspected or known to comprise the analyte; b) contacting said sample with a conjugate according to claim 4 under conditions appropriate for formation of an analyte conjugate complex; and c) measuring the complex formed in step (b) and thereby obtaining a measure of the analyte.

8 . The method of claim 7 , wherein said step of contacting is performed in an aqueous solution.

9 . The method of claim 7 , wherein the affinity binding agent is selected from the group consisting of antigen and antibody, biotin or biotin analogue and avidin or streptavidin, sugar and lectin, nucleic acid or nucleic acid analogue and complementary nucleic acid and receptor and ligand.

10 . The method of claim 7 , wherein the affinity binding agent of the conjugate is a nucleic acid or an antibody.

Assignees

• Roche Diagnostics Operations

Inventors

• Cysewski Robert
• De Cola Luisa
• Fernandez Hernandez Jesus Miguel
• Josel Hans-Peter
• Lopez-Calle Eloisa
• Zarnt Toralf

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• G01N2458/30

  Electrochemically active labels · CPC title

• G01N21/76

  Chemiluminescence; Bioluminescence · CPC title

• G01N33/582

  with fluorescent label · CPC title

• C01G55/002

  Compounds containing ruthenium, rhodium, palladium, osmium, iridium or platinum, with or without oxygen or hydrogen, and containing two or more other elements (C01G55/007 takes precedence) · CPC title