# US 9,518,186 B2 · Luminescent lanthanide chelates with enhanced excitation properties

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- Number: US 9,518,186 B2
- Document ID: US9518186B2
- Status: Granted
- Kind: B2
- Application number: 13/723,505
- Filed: 2012-12-21
- Published: 2013-07-18
- Granted: 2016-12-13
- Earliest claimed: 2011-12-22
- Assignees: Radiometer Turku Oy
- Applicants: Radiometer Turku Oy
- Inventors: Niko Meltola; Harri Takalo; Henri Sund
- Web page: https://patentgrep.com/patent/US9518186B2

## CPC

- C09B 57/00: Other synthetic dyes of known constitution
- C07D 213/40: Acylated substituent nitrogen atom
- C09B 57/10: Metal complexes of organic compounds not being dyes in uncomplexed form
- C09K 11/06: containing organic luminescent materials
- G01N 33/582: {with fluorescent label}
- C09K 2211/182: of the rare earth metals, i.e. Sc, Y or lanthanide
- G01N 2458/40: Rare earth chelates
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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)

## Abstract

The present application discloses a luminescent lanthanide chelate comprising one or more chromophoric moieties of the formula (I) or of the formula (III) wherein R1, R2 and R2* each independently are selected from carbon-containing substituents forming a C—O bond with the neighbouring oxygen atom, R3 and R4 each represent a bond between the chromophoric moiety and other moieties of the chelate, and Ln3+ is a lanthanide ion, as well as the corresponding luminescence lanthanide chelating ligand. The application also discloses a detectable molecule comprising a biospecific binding reactant (such as an antibody) conjugated to the luminescent lanthanide chelate as well as a method of carrying out a biospecific binding assay, the use of such a detectable molecule in a specific bioaffinity based binding assay utilizing time-resolved fluorometric determination of a specific luminescence, and a solid support material conjugated with the luminescent lanthanide chelate.

## Claims

### Claim 1

A luminescent lanthanide chelate, wherein the luminescent lanthanide chelate has a structural formula selected from the group consisting of:
and
wherein the substituents R1, R2 and R2* are independently chosen from —CH2COOH and —CH2COO—.

### Claim 2 (depends on 1)

The luminescent lanthanide chelate according to claim 1, wherein the chelate further includes Na+ as a counter ion.

### Claim 3

A luminescent lanthanide chelate which is:

### Claim 4 (depends on 3)

The luminescent lanthanide chelate of claim 3 which is

### Claim 5 (depends on 3)

The luminescent lanthanide chelate of claim 3 which is

### Claim 6 (depends on 1)

A detectable molecule comprising a biospecific binding reactant conjugated to a luminescent lanthanide as defined in claim 1.

### Claim 7 (depends on 6)

The detectable molecule according to claim 6, wherein the biospecific binding reactant is an antibody, an antigen, a receptor ligand, a specific binding protein, a DNA probe, a RNA probe, an oligopeptide, an oligonucleotide, a modified oligonucleotide, a modified polynucleotide, a protein, an oligosaccharide, a polysaccharide, a phospholipid, a PNA, a steroid, a hapten, a drug, a receptor binding ligand, or lectine.

### Claim 8 (depends on 6)

The detectable molecule according to claim 6, wherein the biospecific binding reactant is an antibody.

### Claim 9 (depends on 1)

A method of carrying out a biospecific binding assay, comprising:
forming a biocomplex between an analyte and a biospecific binding reactant labeled with a luminescent lanthanide chelate according to claim 1;
exciting said biocomplex with radiation having an excitation wavelength, thereby forming an excited biocomplex; and
detecting emission radiation emitted from said excited biocomplex.

### Claim 10 (depends on 9)

The method according to claim 9, wherein the specific bioaffinity based binding assay is selected from the group consisting of a heterogeneous immunoassay, a homogenous immunoassay, a DNA hybridization assay, a receptor binding assay, an immunocytochemical or an immunohistochemical assay.

### Claim 11 (depends on 1)

A solid support material conjugated with a luminescent lanthanide chelate as defined in claim 1.