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US 2015/0307774 A1Published application
Chelates, chelating agents, conjugates derived thereof and their use
AssigneeQi WANG
InventorQi Wang
Life of this patent
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Abstract
This invention relates to a group of novel stable and luminescent lanthanide(III) chelates and chelating agents. This invention further relates to a detectable molecule comprising the lanthanide chelate and the use of the molecule in a method of carrying out a biospecific binding assay. Suggested figure:
Claims15
A chelate comprising a lanthanide(III) ion selected from europium, terbium, samarium and dysprosium and a chelating ligand of formula (I)
- wherein
- X is an aromatic unit,
- L is a linker formed from one to ten moieties, each moiety being selected from the group consisting of phenylene, 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, and L replacing a hydrogen anywhere in the parent compound, or not present,
- A is a reactive group selected from isothiocyanate, bromoacetamido, iodoacetamido, maleimido, 4,6-dichloro-1,3,5-triazin-2-ylamino, pyridyldithio, thioester, aminooxy, azide, hydrazide, amino, alkyne, a methacroyl group, carboxylic acid, acid halide, and an active ester,
- wherein A′ is cleaving group selected from Cl, (CH3)2SO, H2O, and NO3 wherein—is the position of the linker L and
- wherein—is the position of linker L,
- and A replacing a hydrogen of the aromatic unit X when the linker L is not present, and
- Ra is selected from —CH2COO− and —(CH2)nN(CH2COO−)2, wherein n is 2 or 3, and
- Rb is −(CH2)mN(CH2COO−)2, wherein m is 2 or 3, and
- Rc is selected from CH2COO−, and —(CH2)1N(CH2COO−)2, wherein 1 is 2 or 3.
7 more elements
A chelating agent of formula II
- wherein X is an aromatic unit,
- L is a linker formed from one to ten moieties, each moiety being selected from the group consisting of phenylene, 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, and L replacing a hydrogen anywhere in the parent compound 2,
- A is a reactive group selected from the group consisting of carboxylic acid or its salt, acid halide, carboxylic acid ester, an amino acid residue —CH(NHR1)R2where R1 is a transient protecting group and R2 is a carboxylic acid or its salt, carboxylic acid halide or an active ester and a group of
- —Z1—O—PZ2—O—R3
- wherein
- one or two of the oxygen atoms optionally is replaced by sulfur,
- Z2 is chloro or NR4R5,
- R3 is a protecting group,
- R4 and R5 are alkyl groups including 1-8 carbons,
- Z1 is absent or is a radical of a purine base or a pyrimidine base wherein the base is connected to the oxygen atom via either
- a) a hydrocarbon chain, which is substituted with a protected hydroxymethyl group, or
- b) a furan ring or pyrane ring,
- Rd is selected from —CH2COOR″ and —(CH2)nN(CH2COOR″)2, wherein n is 2 or 3,
- Rb is —(CH2)mN(CH2COOR″)2, wherein m is 2 or 3, and
- Rc is selected from CH2COOR″, and —(CH2)1N(CH2COOR″)2, wherein 1 is 2 or 3 and wherein R″ is a protecting group.
12 more elements
(canceled)
A biomolecule obtained by synthesis on a solid phase by introduction of a chelating agent of formula II
- wherein X is an aromatic unit,
- L is a linker formed from one to ten moieties, each moiety being selected from the group consisting of phenylene, alkylene containing 1-12 carbon atoms, ethynydiyl (—O≡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, and L replacing a hydrogen anywhere in the parent compound 2,
- A is a reactive group selected from the group consisting of carboxylic acid ester, an amino acid residue —CH(NHR1)R2 where R1 is a transient protecting group and R2 is a carboxylic acid or its salt, carboxylic acid halide or an active ester and a group of
- —Z1—O—PZ2—O—R3
- wherein
- one or two of the oxygen atoms optionally is replaced by sulfur,
- Z2 is chloro or NR4R5,
- R3 is a protecting group,
- R4 and R5 are alkyl groups including 1-8 carbons,
- Z1 is absent or is a radical of a purine base or a pyrimidine base wherein the base is connected to the oxygen atom via either
- a) a hydrocarbon chain, which is substituted with a protected hydroxymethyl group, or
- b) a furan ring or pyrane ring,
- Rd is selected from —CH2COOR″ and —(CH2)nN(CH2COOR″)2, wherein n is 2 or 3,
- Rb is —(CH2)mN(CH2COOR″)2, wherein m is 2 or 3, and
- Rc is selected from CH2COOR″, and —(CH2)1N(CH2COOR″)2, wherein 1 is 2 or 3 and
- wherein R″ is a protecting group into the biomolecule structure followed by deprotection and introduction of a lanthanide ion.
13 more elements
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Dependencies are inferred from the claim text.