New luminescent dyes - of cyanine, merocyanine or styryl type, contg. sulpho gps., useful for labelling components in aq. media

摘要

(A) Luminescent dyes of formula (I)-(III) are new; where X and Y = O, S or CMe2; m = 1-4; at least one of R1-R7 contains a NCS, NCO, mono- or dichlorotriazinyl; mono- or dihalopyridyl, mono- or dihalodiazinyl, maleimido, aziridinyl, halosulphonyl, halocarbonyl, succinimidyloxycarbonyl, sulphosuccinimidyloxycarbonyl, imido ester, hydrazino, azidonitrophenyl, N3, 3-(2-pyridyldithio)propionamido, COCHO or CHO gp.; at least one of R8 and R9 contains a sulpho gp., opt. in salt form, bonded to an aromatic ring; apart from the above characteristics, R1-R9 are not specifically defined; the significance of the dotted lines is not defined, but in subsidiary claims the left-hand dotted line represents an o-phenylene or 1, 2-naphthylene gp. in (I)-(III) and the right-hand dotted line represents an o-phenylene or 1, 2-naphthylene gp. in (I) and completes and 2-Z-hexahydro-4, 6-dioxo-5-pyrimidylidene gp. in (II), where Z = O or S. (B) New prods. are prepd. by reacting a component contg. an amine, CHO, SH or OH gp. with a water-soluble sulphoindolenin- or naphthosulphoindolenin-based polymethine dye contg. at least one substit. covalently reactive with the amine, CHO, SH or OH gp. The individual dye mols. on the reaction prod. have a mean molar extinction coefft. of at least 50,000 l/mol-cm and a mean quantum efficiency of at least 2% and have absorption and emission maxima in the 400-850 nm range in aq. media. USE/ADVANTAGE - The process may be used to label proteins, nucleic acids, drugs, toxins, cells, particles, plastics or glass surfaces, polymer membranes, etc., for use in assay or flow cytometry systems. The SO3H gps. increase the water-solubility of the dyes and reduce luminescence quenching due to dye/dye interactions.