Alpha cyano methine and polymethine dyes for the labeling of biological subtrates

Alpha-cyano-methine and alpha-cyano-polymethine dyes of the formulas:

• Wherein Z contains carbon, oxygen, nitrogen or sulfur and up to a total of 25 atoms and represents a group containing non-metallic atoms necessary to complete a heterocyclic or heterobicyclic ring with the atoms to which it is attached;
• and Z can also be substituted with one or more substituents selected from the group consisting of lower alkyl, nitro, halogen, carboxylic, sulfonic and amine groups;
• Q is an organic radical and is selected from the group consisting of ═CH—, ═CH—CH═CH—, ═CH—CH—CH—CH═CH—
• with Y being halogen, OH, SH, amino group, alkoxy which may be substituted, aryloxy, which may be substituted and arylthio group;
• R1 and R2 are independently selected from the group consisting of an alkyl group of up to 12 carbon atoms, with the proviso that at least one of the R1 and R2 groups has a substituent selected from the group consisting of —SO3H, —OSO3H, —OPO3H2,—COOH, halogen, SH, thioether group, NHSO3H, [COOH,]N═C═S, —NHNH2, maleimido group, succinate ester, amino group, and aralkyl group which may be substituted and heteroaralkyl group which may be substituted;
• R3 is hydrogen or cyano group;
• R4 is —OH, SH, —OPO3H2,—NH2, primary amino group and secondary amino group;
• M represents an aromatic or heteroaromatic group containing up to a total of 25 carbon atoms;
• and when M represents a heterocyclic group it can contain nitrogen, oxygen and sulfur and can also be substituted with one or more substituents selected from the group consisting of lower alkyl, nitro, halogen, carboxyl, sulfonic and phosphoric groups;
• with the proviso that in the formula containing M, Q can not represent ═CH—, X—is an anion consisting of an organic or inorganic group selected from the group consisting of Cl—, Br—, I—, CLO4—, SO4, CH2COO— and CH3CH2COO—.