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US 12,577,403 B2Granted
Ultra bright dimeric or polymeric dyes
AssigneeSony Group Corporation
InventorsTracy Matray, Sharat Singh, Michael VanBrunt
Life of this patent
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Abstract
Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (II): or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, R4, R5, L1, L2, L3, L4, M, m and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.
Claims8
A method, comprising:
- labeling an analyte molecule, including:
- (a) admixing an intermediary compound with a compound of formula M-L1b-G′, wherein the intermediary compound has the following structure (II), or a stereoisomer, salt or tautomer thereof:
- wherein:
- L1a, L2 and L3 are, at each occurrence, independently an optional alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, heteroalkynylene or heteroatomic linker;
- L4 is, at each occurrence, independently an alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linker;
- R1 is, at each occurrence, independently H, alkyl or alkoxy;
- R2 and R3 are each independently H, OH, SH, alkyl, alkoxy, alkylether, —OP(═Ra)(Rb)Rc, Q, a linker comprising a covalent bond to Q, a linker comprising a covalent bond to a solid support or a linker comprising a covalent bond to a further compound of structure (II), wherein:
- Ra is O or S;
- Rb is OH, SH, O−, S−, ORd or SRd;
- Rc is OH, SH, O−, S−, ORd, SRd, alkyl, alkoxy, alkylether, alkoxyalkylether, phosphate, thiophosphate, phosphoalkyl, thiophosphoalkyl, phosphoalkylether or thiophosphoalkylether;
- and Rd is a counter ion, and wherein at least R2 or R3 is Q or a linker comprising a covalent bond to Q;
- R4 is, at each occurrence, independently OH, SH, O−, S−, ORd or SRd;
- R5 is, at each occurrence, independently oxo, thioxo or absent;
- Q is, at each occurrence, independently a moiety comprising a sulfhydryl, disulfide, activated ester, isothiocyanate, azide, alkyne, alkene, diene, dienophile, acid halide, sulfonyl halide, phosphine, α-haloamide, biotin, amino or maleimide functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester;
- m is, at each occurrence, independently an integer of zero or greater, wherein at least one occurrence of m is an integer of one or greater;
- and
- n is an integer of one or greater, and
- wherein admixing includes forming at least one covalent bond by reaction of G and G′;
- and
- (b) reacting the product of step (a) with the analyte molecule, including forming a conjugate of the product of step (a) and the analyte molecule, the analyte molecule being covalently attached to an end of the product of step (a);
- wherein:
- G is a moiety including an aldehyde, oxime, hydrazone, alkyne, amine, azide, acylazide, acylhalide, nitrile, nitrone, sulfhydryl, disulfide, sulfonyl halide, isothiocyanate, activated ester, ketone, α, β-unsaturated carbonyl, alkene, maleimide, α-haloimide, epoxide, aziridine, tetrazine, tetrazole, phosphine, biotin, or thiirane functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester;
- M is, at each occurrence, independently a moiety comprising two or more carbon-carbon double bonds and at least one degree of conjugation and at least one occurrence of M is a moiety comprising a carbocyclic or a heterocyclic;
- L1b is an optional alkylene or heteroalkylene linker;
- and
- G′ is a reactive group complementary to G.
23 more elements
Dependencies are inferred from the claim text.