Back to results
US 11,453,783 B2Granted
Polymeric tandem dyes with linker groups
AssigneeSony Corporation
InventorsTracy Matray, Sharat Singh
Life of this patent
Estimating the term…
Abstract
Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I): or a stereoisomer, tautomer or salt thereof, wherein R1, R2, R3, R4, R5, L1, L2, L3, L4, M1, M2, m and n are as defined herein. Methods associated with preparation and use of such compounds is also provided.
Claims23
A compound having the following structure (I):
- or a stereoisomer, salt or tautomer thereof, wherein:
- M1 and M2 are, at each occurrence, independently a fluorescent or colored chromophore, provided that at least one of M1 and M2 is a FRET donor, and another one of M1 and M2 is a corresponding FRET acceptor, at least one of the FRET donor chromophores is positioned between two FRET acceptor chromophores, and at least one occurrence of M1 and M2 are different chromophores selected such that M1 and M2 form a FRET pair;
- L1 is, at each occurrence, independently an optional alkylene or heteroalkylene linker;
- 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 or heteroalkylene linker;
- R1 is, at each occurrence, independently H, alkyl or alkoxy;
- R2 and R3 are each independently H, OH, SH, alkyl, alkoxy, alkylether, heteroalkyl, —OP(═Ra)(Rdb)Rc, Q, or a protected form thereof, 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 reactive group, or protected form thereof, capable of forming a covalent bond with an analyte molecule, a targeting moiety, a solid support or a complementary reactive group Q;
- L′ is, at each occurrence, independently a linker comprising a covalent bond to Q, a linker comprising a covalent bond to a targeting moiety, a linker comprising a covalent bond to an analyte molecule, a linker comprising a covalent bond to a solid support, a linker comprising a covalent bond to a solid support residue, a linker comprising a covalent bond to a nucleoside or a linker comprising a covalent bond to a further compound of structure (I);
- m is, at each occurrence, independently an integer of zero or greater;
- and
- n is an integer of two or greater,
- provided that at least one occurrence of L4 is heteroalkylene or at least one occurrence of m is 0 when M1 and M2 are selected from fluorescein, pyrene and perylene chromophores.
16 more elements
A compound having the following structure (II):
- or a stereoisomer, salt or tautomer thereof, wherein:
- M1 and M2 are, at each occurrence, independently a fluorescent or colored chromophore, provided that at least one occurrence of M1 and M2 are different chromophores, at least one occurrence of M1 and M2 combine to form a FRET acceptor-donor pair, and the FRET donor chromophore in the FRET acceptor-donor pair is positioned between two FRET acceptor chromophores;
- L1 is at each occurrence, independently an optional alkylene or heteroalkylene linker;
- 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 or heteroalkylene linker;
- R1 is, at each occurrence, independently H, alkyl or alkoxy;
- R2 and R3 are each independently H, OH, SH, alkyl, alkoxy, alkylether, heteroalkyl, —OP(═Ra)(Rb)Rc, Q, or a protected form thereof, 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 reactive group, or protected form thereof, capable of forming a covalent bond with an analyte molecule, a targeting moiety, a solid support or a complementary reactive group Q′;
- L′ is, at each occurrence, independently a linker comprising a covalent bond to Q, a linker comprising a covalent bond to a targeting moiety, a linker comprising a covalent bond to an analyte molecule, a linker comprising a covalent bond to a solid support, a linker comprising a covalent bond to a solid support residue, a linker comprising a covalent bond to a nucleoside or a linker comprising a covalent bond to a further compound of structure (II);
- m is, at each occurrence, independently an integer of zero to two or greater than 6;
- and
- n is an integer of two or greater.
15 more elements
Dependencies are inferred from the claim text.