# US 8,772,486 B2 · Iridium-based complexes for ECL

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- Number: US 8,772,486 B2
- Document ID: US8772486B2
- Status: Granted
- Kind: B2
- Application number: 13/961,381
- Filed: 2013-08-07
- Published: 2013-12-05
- Granted: 2014-07-08
- Earliest claimed: 2011-02-09
- Assignees: Roche Diagnostics Operations, Inc.
- Applicants: Roche Diagnostics Operations, Inc.
- Inventors: Robert Cysewski; Luisa de Cola; Jesus Miguel Fernandez Hernandez; Hans-Peter Josel; Eloisa Lopez-Calle; Toralf Zarnt
- Web page: https://patentgrep.com/patent/US8772486B2

## CPC

- G01N 33/53: Immunoassay; Biospecific binding assay; Materials therefor
- C07F 15/0033: {Iridium compounds}
- G01N 33/582: {with fluorescent label}
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

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

## Claims

### Claim 1

An iridium-based luminescent or electrochemiluminescent compound of Formula I
wherein R1-R12 is hydrogen, halide, cyano- or nitro-group, a hydrophilic group, or R19, wherein R19 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;
wherein R13-R16 is hydrogen, halide, cyano- or nitro-group, a hydrophilic group, -Q-Y, or R19, wherein R19 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;
wherein R17-R18 represents hydrogen, alkyl, aryl, substituted aryl and alkyl, heteroaromatic ring system, non-aromatic ring or ring system, imidazolium, cyclodextrin or Q-Y, 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, 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,
wherein X represents C or N;
wherein Y represents C or N;
wherein at least one of R13-R18 is -Q-Y; and
wherein Q represents a linker and Y is a functional group.

### Claim 2 (depends on 1)

The compound according to claim 1, 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.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 5)

The conjugate of claim 5, 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.

### Claim 7 (depends on 5)

The conjugate according to claim 5, wherein said affinity binding agent is a nucleic acid or an antibody.

### Claim 8 (depends on 5)

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 of claim 5 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.

### Claim 9 (depends on 8)

The method of claim 8, wherein the affinity binding agent of the conjugate 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.

### Claim 10 (depends on 8)

The method of claim 8, wherein the affinity binding agent of the conjugate is a nucleic acid or an antibody.