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US 8,785,637 B2Granted
Carboxamide-substituted dyes for analytical applications
AssigneeATTO-TEC GmbH
InventorsJutta Arden-Jacob, Karl-Heinz Drexhage, Monika Hamers-Schneider, Norbert Kemnitzer, Alexander Zilles
Life of this patent
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Abstract
The present invention relates to carboxamide-substituted dyes, the production and use of such dyes as labeling groups in analytics.
Claims28
A carboxamide-substituted dye of the formula (I)
- in which
- Y=sulfur, selenium, a direct linkage or is NRc;
- R1, R3, R4 are independently hydrogen, halogen, —O⊖, a hydroxyl group, thiol group, amino group, ammonium group, sulfo group, phospho group, nitro group, carbonyl group, carboxyl group, a carboxylic acid group, a nitrile group, isonitrile group, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon group having up to 40 carbon atoms;
- Rc independently is as defined for R1, R3, R4;
- in which
- R7, R8, R9 independently are hydrogen or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon group having up to 40 carbon atoms;
- or
- R1 together with R2 is
- in which
- R10, R11, R13 are as defined for R1, R3, R4;
- in which
- R16, R17, R18 are as defined for R7, R8, R9;
- R5, R6, independently are a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon moiety having up to 40 carbon atoms;
- Cyc1 is selected from aromatic, heteroaromatic, quinoidal and cycloaliphatic rings;
- Cyc2 is selected from aromatic, heteroaromatic, quinoidal and cycloaliphatic rings;
- each of said moieties in the dye of the formula (I) being able to form a ring system with one or more neighboring moieties;
- and
- X being one or more mono- or multivalent anions, when required for balancing the charge.
15 more elements
A method of detecting an analyte using carboxamide-substituted dye comprising the steps of providing one or more compounds of the general formula (I)
- wherein
- Y=sulfur, selenium, a direct linkage or is NRc;
- R1, R3, R4 are independently hydrogen, halogen, —O⊖, a hydroxyl group, thiol group, amino group, ammonium group, sulfa group, phospho group, nitro group, carbonyl group, carboxyl group, a carboxylic acid derivative, a nitrile group, isonitrile group, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon group having up to 40 carbon atoms;
- Rc independently are as defined for R1, R3, R4;
- in which
- R7, R8, R9 independently are hydrogen or a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon group having up to 40 carbon atoms;
- or
- R1 together with R2 is
- in which
- R10, R11, R13 are as defined for R1, R3, R4;
- in which
- R16, R17, R18 are as defined for R7, R8, R9;
- R5, R6, independently are a straight-chain, branched or cyclic saturated or unsaturated hydrocarbon moiety having up to 40 carbon atoms;
- Cyc1 is an organic moiety which comprises a ring system selected from aromatic, heteroaromatic, quinoidal and cycloaliphatic rings;
- Cyc2 is an organic moiety which comprises a ring system selected from aromatic, heteroaromatic, quinoidal and cycloaliphatic rings;
- each of said moieties in the dye of the formula (I) forming a ring system with one or more neighboring moieties;
- and X being one or more mono- or multivalent anions, when required for balancing the charge;
- coupling the carboxamide-substituted dye to the analyte to be detected;
- and
- then determining at least one of the qualitative and quantitative presence of the analyte.
17 more elements
Dependencies are inferred from the claim text.