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US 2010/0136567 A1Published application
Cyanine dyes
AssigneeBiosearch Technologies, Inc.
InventorsTim Carter, Mark Reddington
Life of this patent
Estimating the term…
Abstract
The invention provides a novel class of cyanine dyes that are functionalized with a linker moiety that facilitates their conjugation to other species. Also provided are conjugates of the dyes, methods of using the dyes and their conjugates and kits including the dyes and their conjugates.
Claims32
A cyanine dye having the formula:
- wherein
- R1 is a member selected from substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl groups and does not comprise a carboxylic acid ester moiety;
- R2 is a member selected from substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl with the proviso that R2 comprises a group that is a member selected from oxygen-containing reactive functional groups, solid supports and carrier molecules
- wherein said oxygen-containing reactive functional group is a member selected from hydroxyl and activated derivatives thereof, and phosphoramidite;
- R3 is a member selected from H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl, and R2 and R3, together with the nitrogen to which they are attached, are optionally joined to form a ring which is substituted or unsubstituted 5-7-membered heterocycloalkyl;
- each of L is C(R17)
- wherein each R17 is a member independently selected from H, halide, substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl, and wherein two adjacent R17 groups may join to form a ring;
- n is an integer from 1 to 4;
- R4, R5, R6, R7, R8, R9, R10, and R11 are members independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, halogen, H, NO2, CN, Z1R19, NR20R21, and C(Z2)R22
- wherein
- Z1 is a member selected from O and S;
- Z2 is a member selected from O, S and NH;
- R19 and R20 are members independently selected from H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl;
- R21 is a member selected from H, substituted or unsubstituted alkyl and) substituted or unsubstituted heteroalkyl and C(Z3)R22
- wherein
- Z3 is a member selected from O, S and NH;
- R22 is a member selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl and OR23, and NR24R25,
- wherein
- R23 is a member selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and C(O)R26
- wherein
- R26 is a member selected from substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl;
- R24 and R25 are members independently selected from H, substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl;
- or R20 and R21, together with the nitrogen to which they are attached, are members selected from —NHNH2, —N═C═S and N═C═O;
- R12 is a member selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
- and
- R13, R14, R15 and R16 are members independently selected from H, substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl.
23 more elements
(canceled)
A cyanine dye having the formula:
- wherein
- R1 is a member selected from substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl groups and does not comprise a carboxylic acid ester moiety;
- R2 is a member selected from substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl with the proviso that R2 comprises a group that is a member selected from oxygen-containing reactive functional groups, solid supports and carrier molecules;
- R3 is a member selected from H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl, and R2 and R3, together with the nitrogen to which they are attached, are optionally joined to form a ring which is substituted or unsubstituted 5-7-membered heterocycloalkyl;
- -(L=L)n-L=has a structure which is a member selected from:
- wherein
- Z4 is H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heterocycloalkyl;
- R4, R5, R6, R7, R8, R9, R10, and R11 are members independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, halogen, H, NO7, CN, Z1R19, NR20R21, and C(Z2)R22
- wherein
- Z1 is a member selected from O and S;
- Z2 is a member selected from O, S and NH;
- R19 and R20 are members independently selected from H, substituted or unsubstituted alkyl, and substituted or unsubstituted heteroalkyl;
- R21 is a member selected from H, substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl and C(Z3)R22
- wherein
- Z3 is a member selected from O, S and NH;
- R22 is a member selected from substituted or unsubstituted substituted or unsubstituted heteroalkyl and OR23, and NR24R25,
- wherein
- R23 is a member selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and C(O)R26
- wherein
- R26 is a member selected from substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl;
- R24 and R25 are members independently selected from H., substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl;
- or R20 and R21, together with the nitrogen to which they are attached, are members selected from —NHNH2, —N═C═S and N═C═O;
- R12 is a member selected from substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
- and
- R13, R14, R15 and R16 are members independently selected from H, substituted or unsubstituted alkyl and substituted or unsubstituted heteroalkyl.
22 more elements
(canceled)
Dependencies are inferred from the claim text.