Cyanine dye labelling reagents with meso -substitution

Details Cyanine dye labelling reagents with meso -substitution Cyanine dye labelling reagents with meso -substitution

2007-02-06

2007-02-06

Ceperley, Mary E. (Department: 1641)

Chemistry: analytical and immunological testing

Involving producing or treating antigen or hapten

Producing labeled antigens

C435S006120, C435S007500, C435S188000, C436S501000, C530S391300, C530S391500, C548S156000, C548S219000, C548S455000

Reexamination Certificate

active

10394108

ABSTRACT:
Disclosed are cyanine dyes having meso-substituents in the polymethine chain linking the heterocyclic ring systems. The dyes are of formula (1):in which groups R3and R4are attached to the Z1ring structure and groups R5and R6are attached to the Z2ring structure, and n=1, 2 or 3; Z1and Z2independently represent the atoms necessary to complete one ring, or two fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; X and Y are the same or different and are selected from oxygen, sulphur, —CH═CH— and the group:at least one of groups R1, R2, R3, R4, R5, R6(and R8and R9if present) is the group -E-F where E is a spacer group and F is a target bonding group; one of groups R7is selected from —CN, —Cl, —F, —CF3and —C(O)R10wherein R10is selected from H, C1–C6alkyl and aryl. Preferred group R7is meso-substituted —CN, which confers an unexpected hypsochromic shift of approximately 40 nm in the emission spectrum, when compared with the corresponding unsubstituted analogue. The dyes are useful for labelling and detecting a variety of target molecules.

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