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US 2025/0051577 A1Published application
Sulforhodamine phosphoramidite dyes
AssigneeCepheid
InventorsKevin P. LUND, Dmitri SERGUEEV, Maher N. QABAR, Alexander GALL
Life of this patent
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Abstract
Automated oligonucleotide synthesis-compatible sulforhodamine dye phosphoramidite compounds and labeled polynucleotides incorporating these dyes are provided.
Claims15
A compound represented by Formula (III):
- or a stereoisomer, tautomer, or salt thereof, wherein:
- R2 is H, halogen or SO2NH2;
- R3 is halogen or H;
- R4, R7, R8, and R11 when taken alone are independently H, halogen, or optionally substituted C1-C6 alkyl,
- R5, R6, R9, and R10 when taken alone are independently H or optionally substituted C1-C6 alkyl;
- R4 and R5 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R4 and R5 are attached;
- R6 and R7 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R6 and R7 are attached;
- R8 and R9 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R8 and R9 are attached;
- R10 and R11 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R10 and R11 are attached;
- R5 and R6, when taken together with the nitrogen atom to which R5 and R6 are attached, form a 5-membered or a 6-membered unsaturated ring;
- R9 and R10, when taken together with the nitrogen atom to which R9 and R10 are attached, form a 5-membered or a 6-membered unsaturated ring;
- n is an integer from 1 to 9;
- Y is:
- wherein:
- Q is a hydroxyl protecting group;
- and
- R12 and R13 are independently optionally substituted C1-C6 alkyl.
14 more elements
A labeled polynucleotide comprising a compound of formula IV:
- or a stereoisomer, tautomer, or salt thereof, wherein:
- R2 is halogen or SO2NH2;
- R3 is H or halogen;
- R4, R7, R8, and R11 when taken alone are independently H, halogen, or optionally substituted C1-C6 alkyl,
- R5, R6, R9 and R10 when taken alone are independently H or optionally substituted C1-C6 alkyl;
- R4 and R5 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R6 and R7 are attached;
- R6 and R7 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R6 and R7 are attached;
- R8 and R9 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R8 and R9 are attached;
- R10 and R11 when taken together are an optionally substituted C2-C3 alkylene chain connecting the atoms to which R10 and R11 are attached;
- R5 and R6, when taken together with the nitrogen atom to which R5 and R6 are attached, form a 5-membered or a 6-membered unsaturated ring;
- R9 and R10, when taken together with the nitrogen atom to which R9 and R10 are attached, form a 5-membered or a 6-membered unsaturated ring;
- n is an integer from 1 to 9;
- Y is:
- wherein:
- the wavy line is the point of attachment to Formula III;
- R12 and R13 are independently optionally substituted C1-C6 alkyl;
- W is H or L4-O—Z2;
- L3, L4, and L5 are independently an optionally substituted C2-C10 alkylene or optionally substituted C2-C30 heteroalkylene;
- Z is CH, N, NHC(O)N, or OC(O)N;
- Z1 is a nucleotide or oligonucleotide;
- and
- Z2 is a nucleotide, oligonucleotide, or H.
19 more elements
A compound represented by Formula VI:
- or a stereoisomer, tautomer, or salt thereof, wherein:
- R1 is L1-X;
- R2, R3, R4, and R5 are independently H, halogen, C1-C6 alkyl, or SO2NH2;
- R6 and R9 are independently H or optionally substituted C1-C6 alkyl;
- R7, R8, R10, R11, R14, and R15 are independently H or optionally substituted C1-C6 alkyl;
- L1 is an optionally substituted C2-C10 alkylene or optionally substituted C2-C20 heteroalkylene;
- X is —O—P(OCH2CH2CN)NR12R13 or:
- wherein
- L3 and L4 are independently an optionally substituted C2-C10 alkylene or optionally substituted C2-C30 heteroalkylene;
- Q is a hydroxyl protecting group;
- Z is CH, N, NHC(O)N, or OC(O)N;
- and
- R12 and R13 are independently optionally substituted C1-C6 alkyl.
10 more elements
Dependencies are inferred from the claim text.