# US 12,435,365 B2 · Luminescent lanthanide(III) chelates

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- Number: US 12,435,365 B2
- Document ID: US12435365B2
- Status: Granted
- Kind: B2
- Application number: 17/784,035
- Filed: 2020-11-03
- Published: 2023-01-26
- Granted: 2025-10-07
- Earliest claimed: 2019-12-09
- Assignees: Uniogen Oy
- Applicants: Uniogen Oy
- Inventors: Qi Wang
- Web page: https://patentgrep.com/patent/US12435365B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C12Q 1/6844: Nucleic acid amplification reactions
- C07F 5/003: {without C-Metal linkages}
- G01N 33/542: with steric inhibition or signal modification, e.g. fluorescent quenching
- G01N 33/54313: {the carrier being characterised by its particulate form}
- G01N 33/54346: {Nanoparticles}
- G01N 33/582: {with fluorescent label}
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms
- C09K 2211/182: of the rare earth metals, i.e. Sc, Y or lanthanide
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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

Disclosed are novel lanthanide(III) chelates including a pyridine 4-ethynylpyrazine subunit. These chelates have an excitation wavelength which allows excitation with UV LED.

## Claims

### Claim 1

A lanthanide (III) chelate comprising a 2-(pyridin-4-ylethynyl) pyrazine subunit.

### Claim 2 (depends on 1)

The lanthanide (III) chelate according to claim 1 comprising
a lanthanide ion Ln3+,
a chromophoric moiety comprising the 2-(pyridin-4-ylethynyl) pyrazine subunit, and
a chelating part comprising at least two carboxylic acid groups, phosphonic acid groups or esters, amides or salts of said acids, attached to the chromophoric moiety, either directly or via a cyclic or acyclic N-containing hydrocarbon chain.

### Claim 3 (depends on 1)

The lanthanide (III) chelate according to claim 1 comprising a reactive group A, tethered to the chromophoric moiety or to the chelating part either directly or via a linker L, said reactive group adapted to bind the chelate to a biomolecule or to a functional group of a solid support.

### Claim 4 (depends on 3)

The lanthanide (III) chelate according to claim 3 wherein the reactive group A is selected from a group consisting of isothiocyanato, bromoacetamido, iodoacetamido, maleimido, 4,6-dichloro-1,3,5-triazin-2-ylamino, pyridyldithio, thioester, aminooxy, azide, hydrazide, amino, alkynyl, a polymerizable group, and a carboxylic acid or acid halide or an active ester thereof.

### Claim 5 (depends on 3)

The lanthanide (III) chelate according to claim 3 wherein the linker L is formed from one to ten moieties, each moiety being selected from the group consisting of phenylene, alkyl containing 1-12 carbon atoms, alkylene containing 1-12 carbon atoms, ethynydiyl (—C≡C—), ethylenediyl (—C═C—), ether (—O—), thioether (—S—), amide (—CO—NH—, —CO—NR′—, —NH—CO— and —NR′—CO—), carbonyl (—CO—), ester (—COO— and —OOC—), disulfide (—SS—), sulfonamide (—SO2—NH—, —SO2—NR′—), sulfone (—SO2—), phosphate (—O—PO2—O—), diaza (—N═N—), and tertiary amine, wherein R′ represents an alkyl group containing less than 5 carbon atoms, or a secondary amine (—NH).

### Claim 6 (depends on 3)

The lanthanide (III) chelate according to claim 3 wherein the linker L is —NHCH2Ph, wherein—is the position of the chromophoric moiety.

### Claim 7 (depends on 1)

The lanthanide (III) chelate according to claim 1 selected from the group consisting of
wherein A is a reactive group selected from a group consisting of isothiocyanato, bromoacetamido, iodoacetamido, maleimido, 4,6-dichloro-1,3,5-triazin-2-ylamino, pyridyldithio, thioester, aminooxy, azide, hydrazide, amino, alkynyl, a polymerizable group, and a carboxylic acid or acid halide or an active ester thereof, and
L is a linker formed from one to ten moieties, each moiety being selected from the group consisting of phenylene, alkyl containing 1-12 carbon atoms, alkylene containing 1-12 carbon atoms, ethynydiyl (—C≡C—), ethylenediyl (—C═C—), ether (—O—), thioether (—S—), amide (—CO—NH—, —CO—NR′—, —NH—CO— and —NR′—CO—), carbonyl (—CO—), ester (—COO— and —OOC—), disulfide (—SS—), sulfonamide (—SO2—NH—, —SO2—NR′—), sulfone (SO2—), phosphate (—O—PO2—O—), diaza (—N═N—), and tertiary amine, wherein R′ represents an alkyl group containing less than 5 carbon atoms, or a secondary amine (—NH).

### Claim 8 (depends on 1)

The lanthanide (III) chelate according to claim 1, wherein the lanthanide ion Ln3+ is selected from europium, samarium, terbium or dysprosium.

### Claim 9 (depends on 1)

A biomolecule conjugated with a lanthanide (III) chelate according to claim 1.

### Claim 10 (depends on 8)

The biomolecule according to claim 8 selected from oligopeptide, oligonucleotide, DNA, RNA, modified oligo- or polynucleotide.

### Claim 11 (depends on 1)

A solid support conjugated with a lanthanide (III) chelate according to claim 1.

### Claim 12 (depends on 11)

The solid support according to claim 11 selected from nanoparticle or microparticle, a slide, a plate or a resin.

### Claim 13 (depends on 1)

A non-covalent conjugate of a nanoparticle and a lanthanide (III) chelate according to claim 1.

### Claim 14 (depends on 1)

A bioaffinity binding assay method wherein detection is based on time-resolved fluorescence derived from lanthanide (III) chelate according to claim 1.

### Claim 15 (depends on 1)

A bioaffinity assay method comprising applying the lanthanide (III) chelate according to claim 1 as a label.

### Claim 16 (depends on 1)

A time-resolved fluorescence resonance energy transfer assay method comprising applying the lanthanide (III) chelate according to claim 1 as a donor molecule.

### Claim 17 (depends on 3)

The lanthanide (III) chelate according to claim 3 wherein the reactive group A is selected from a group consisting of isothiocyanato, iodoacetamido, maleimido and 4,6-dichloro-1,3,5-triazin-2-ylamino.

### Claim 18 (depends on 7)

The lanthanide (III) chelate according to claim 7 selected from the group consisting of

### Claim 19 (depends on 7)

The lanthanide (III) chelate according to claim 7 is

### Claim 20 (depends on 1)

The lanthanide (III) chelate according to claim 1, wherein the lanthanide ion Ln3+ is selected from europium and samarium.