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US 12,006,438 B2Granted
Polymeric dyes with linker groups comprising deoxyribose
AssigneeSony Group Corporation
InventorsSharat Singh, Tracy Matray, Michael Vanbrunt, John McCutcheon
Life of this patent
Estimating the term…
Abstract
Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I): (I) or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, R4, R5, L1a, L1b, L2, L3, L4, L5, L6, L7, M1, M2, q, w, m and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.
Claims25
A compound having the following structure (Ia):
- or a stereoisomer, salt or tautomer thereof, wherein:
- M1 is, at each occurrence, independently a moiety comprising a chromophore;
- L1a is, at each occurrence, independently a heteroarylene linker;
- L1b L2 and L3 are, at each occurrence, independently optional alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linkers;
- L4 is, at each occurrence, independently an alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linker;
- R1 and R2 are each independently H, OH, SH, alkyl, alkoxy, alkylether, heteroalkyl, —OP(═Ra)(Rb)Rc, Q, or L′;
- R4 is, at each occurrence, independently OH, SH, O−, S−, ORd or SRd;
- R5 is, at each occurrence, independently oxo, thioxo or absent;
- Ra is O or S;
- Rb is OH, SH, O−, S−, ORd or SRd;
- Rc is OH, SH, O−, S−, ORd, OL′, SRd, alkyl, alkoxy, heteroalkyl, heteroalkoxy, alkylether, alkoxyalkylether, phosphate, thiophosphate, phosphoalkyl, thiophosphoalkyl, phosphoalkylether or thiophosphoalkylether;
- Rd is a counter ion;
- 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;
- L′, at each occurrence, independently comprises an alkylene or heteroalkylene linker covalently bonded to:
- Q, a targeting moiety selected from an antibody and a cell surface receptor antagonist, an amino acid or polymer thereof, an enzyme, a receptor, a receptor ligand, a glycoprotein, an aptamer and a prion, an analyte molecule selected from a nucleic acid or polymer thereof, a solid support selected from a polymeric bead and a non-polymeric bead, or a nucleoside;
- m is, at each occurrence, an integer of one or greater;
- and
- n is an integer of one or greater.
15 more elements
A compound having one of the following structures:
- wherein:
- F″ is
- wherein R is H or a direct bond.
A compound having the following structure (IIa):
- or a stereoisomer, salt or tautomer thereof, wherein:
- G1 is, at each occurrence, independently a moiety comprising an aldehyde, oxime, hydrazone, alkyne, amine, azide, acylazide, acylhalide, nitrile, nitrone, sulfhydryl, disulfide, sulfonyl halide, isothiocyanate, imidoester, activated ester, ketone, α,β-unsaturated carbonyl, alkene, maleimide, α-haloimide, epoxide, aziridine, tetrazine, tetrazole, phosphine, biotin or thiirane functional group;
- L1a is, at each occurrence, independently a heteroarylene linker;
- L1b′, L2 and L3 are, at each occurrence, independently optional alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linkers;
- L4 is, at each occurrence, independently an alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linker;
- R1 and R2 are each independently H, OH, SH, alkyl, alkoxy, alkylether, heteroalkyl, —OP(═Ra)(Rb)Rc, Q, or L′;
- R3 is, at each occurrence, independently H, alkyl or alkoxy;
- R4 is, at each occurrence, independently OH, SH, O—, S—, ORd or SRd;
- R5 is, at each occurrence, independently oxo, thioxo or absent;
- Ra is O or S;
- Rb is OH, SH, O—, S—,ORd or SRd;
- Rc is OH, SH, O—, S—, ORd, OL′, SRd, alkyl, alkoxy, heteroalkyl, heteroalkoxy, alkylether, alkoxyalkylether, phosphate, thiophosphate, phosphoalkyl, thiophosphoalkyl, phosphoalkylether or thiophosphoalkylether;
- Rd is a counter ion;
- 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;
- L′, at each occurrence, independently comprises an alkylene or heteroalkylene linker covalently bonded to:
- Q, a targeting moiety selected from an antibody and a cell surface receptor antagonist, an amino acid or polymer thereof, an enzyme, a receptor, a receptor ligand, a glycoprotein, an aptamer and a prion, an analyte molecule selected from a nucleic acid or polymer thereof, a solid support selected from a polymeric bead and a non-polymeric bead, or a nucleoside;
- m is, at each occurrence, an integer of one or greater;
- and
- n is an integer of one or greater.
16 more elements
A compound of structure (III) having one of the following structures:
- wherein DMT is dimethoxytrityl.
Dependencies are inferred from the claim text.