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US RE49,362 E1Granted
Dye compounds and the use of their labelled conjugates
AssigneeIllumina Cambridge Limited
InventorsColin Barnes, Nikolai Nikolaevich Romanov
Life of this patent
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Abstract
Novel rhodamine dye compounds, labelled conjugates comprising the dyes are described, together with methods for their use. The dyes and labelled conjugates are useful as molecular probes in a variety of applications, such as in assays involving staining of cells, protein binding, and analysis of nucleic acids, such as hybridization assays and nucleic acid sequencing.
Claims73
A compound of the Formula (I):
- wherein
- X is SO3−,
- M+ is a common counter ion,
- k and m are independently integers from 1 to 6,
- n is 3,
- R1, R4, R5, R6, R8 and R9 are all H,
- R2 and R3 are independently H or CH3,
- Z is carboxy-, carboxamido- or a substituted carboxamido group,
- a is 1 and
- R7 is OH.
7 more elements
A compound of the Formula (I):
- wherein
- X is SO3H or SO3−,
- M+ is a common counter ion,
- k, n, m are independently integers from 1 to 6,
- R1 is linked to R2 via a chain of CH2 groups to form a ring, or
- R4 is linked to R3 via a chain of CH2 groups to form a ring,
- R5 and R6 are independently H, alkyl or substituted alkyl group, halogen, hydroxy- or alkoy group,
- R8 is H, halogen, hydroxy- or alkoxy group, alkyl or substituted alkyl group or together with R1 is a carbon or heterosubstituted carbon chain forming a ring,
- R9 is H, halogen, hydroxy- or alkoxy group, alkyl or substituted alkyl group or together with R4 is a carbon or heterosubstituted carbon chain forming a ring,
- R7 is NR11R12 where R11 is H, alkyl or a substituted alkyl, and R12 is a substituted alkyl,
- Z is halogen, amino or substituted amino, hydroxyl- hydroxy-, alkoxy-, carboxy-, carboxamido- or a substituted carboxamido group, SO3H or SO3−, and
- a is 0 to 4, wherein if a is 0, R7 is NR11R12 where R11 and R12 are independently H, alkyl or a substituted alkyl.
9 more elements
A compound of the Formula (I):
- wherein
- X is SO3−,
- M+ is a common counter ion,
- k is an integer from 1 to 6,
- n=3,
- m=3 and
- R1 is H or an alkyl or substituted alkyl group (CH2)mSO3−,
- R2, R3, R5, R6, R8 and R9 are all H,
- R4 is H, or an alkyl or substituted alkyl group (CH2)mSO3−,
- R7 is OHor is joined to form aliphatic or aromatic cyclic or substituted aliphatic-, aromatic- or heterocyclic rings,
- Z is halogen, amino or substituted amino, hydroxyl- hydroxy-, alkoxy-, carboxy-, carboxamido- or a substituted carboxamido group, SO3H or SO3− and
- a is 0.
9 more elements
A method of synthesizing a compound of the Formula (I):
- wherein
- X is SO3H or SO3−,
- M+ is a common counter ion,
- k, n, m are independently integers from 1 to 6,
- R1 is H or an alkyl or substituted alkyl group,
- R2 is H, alkyl or substituted alkyl group, halogen, carboxy, carboxamide, hydroxy- or alkoxy group,
- or R2 together with R1 or R5 is a carbon or heterosubstituted chain forming a ring,
- R3 is H, alkyl or substituted alkyl group, halogen, carboxy, carboxamide, hydroxy- or alkoxy group
- R4 is H, or an alkyl or substituted alkyl group,
- or R3 together with R4 or R6 is a carbon or heterosubstituted chain forming a ring,
- R5 and R6 are independently H, alkyl or substituted alkyl group, halogen, hydroxy- or alkoxy group,
- R8 is H, halogen, hydroxy- or alkoxy group, alkyl or substituted alkyl group or together with R1 is a carbon or heterosubstituted carbon chain forming a ring,
- R9 is H, halogen, hydroxy- or alkoxy group, alkyl or substituted alkyl group or together with R4 is a carbon or heterosubstituted carbon chain forming a ring,
- R7 is OH, OR10 where R10 is alkyl or substituted alkyl, or NR11R12 where R11 and R12 are independently H, alkyl or a substituted alkyl, or is joined to form aliphatic or aromatic cyclic or substituted aliphatic-, aromatic- or heterocyclic rings,
- Z is halogen, amino or substituted amino, hydroxyl- hydroxy-, alkoxy-, carboxy-, carboxamido- or a substituted carboxamido group, SO3H or SO331 SO3− and
- a is 0 to 4, wherein if a is 0, R7 is NR11R12 where R11 and R12 are independently H, alkyl or a substituted alkyl,
- comprising the steps of:
- (a) providing the following starting materials
- (b) further providing substituted or unsubstituted phthalic anhydride derivatives, and
- (c) allowing a condensation reaction to occur, thereby obtaining the compound.
17 more elements
Dependencies are inferred from the claim text.