Sulfonamide Derivatives of Xanthene Compounds

A biocompatible dye composition comprising at least one excipient and a compound selected from at least one of formula I or formula II

• resulting in a biocompatible dye composition, wherein
• R1 and R2 are the same or different and are independently selected from the group consisting of —H, —C1-C18-alkyl or -ω-sulfoalkyl;
• X and Y are the same or different and are independently selected from the group consisting of —O−, —OH, —SH, —NH—NH2, —F, —Cl, —Br, —I, —O-Su (succinimidyl/sulfosuccinimidyl), —O-STP (4-sulfo-2,3,5,6-tetrafluorophenyl), —O-TFP (2,3,5,6-tetrafluorophenyl), —O-benzotriazole, -benzotriazole, —NR—CO—CH2—I, —NR2, —NR-biomolecule, —NR-L-COO−, —NR-L-COOH, —NR-L-COO-Su, —NR-L-COO-STP, —NR-L-COO-TFP, —NR-L-CONR2, —NR-L-CO-biomolecule, —NR-L-CO—NH—NH2, —NR-L-OH, —NR-L-O-phosphoramidite, —NR-L-CHO, —NR-L-maleimid, or —NR-L-NH—CO—CH2—I;
• where R is equal to R1 and R2 and L is selected from the group consisting of a divalent linear (—(CH2)o—, o=1 to 15), crossed, or cyclic alkane group that can be substituted by at least one atom selected from the group consisting of oxygen, substituted nitrogen, and/or sulfur, and the biomolecule is a protein, antibody, nucleotide, oligonucleotide, biotin, or hapten;
• Z is —O− or OH;
• U is —O−, —OH or NH-L-SO2Z;
• Kat is Li, Na, K, ammonium (mono-, di- or trialkyl) or another cation;
• An is F, Cl, Br, I, BF4, ClO4, CH3CO2, CF3CO2 or another anion;
• m is an integer from 1-6 necessary to compensate the negative or positive charge from the dye moiety in formula I or formula II;
• and
• n is an integer from 0-12.

A method of labelling at least one biomolecule, the method comprising

• providing a composition comprising at least one excipient and a compound of at least one of formula I or formula II
• in an effective concentration to a biomolecule under conditions sufficient for conjugating the compound to the biomolecule, and
• detecting the biomolecule-bound conjugate, wherein
• R1 and R2 are the same or different and are independently selected from the group consisting of —H, —C1-C18-alkyl or -ω-sulfoalkyl;
• X and Y are the same or different and are independently selected from the group consisting of —O−, —OH, —SH, —NH—NH2, —F, —Cl, —Br, —I, —O-Su (succinimidyl/sulfosuccinimidyl), —O-STP (4-sulfo-2,3,5,6-tetrafluorophenyl), —O-TFP (2,3,5,6-tetrafluorophenyl), —O-benzotriazole, -benzotriazole, —NR—CO—CH2—I, —NR2, —NR-biomolecule, —NR-L-COO−, —NR-L-COOH, —NR-L-COO-Su, —NR-L-COO-STP, —NR-L-COO-TFP, —NR-L-CONR2, —NR-L-CO-biomolecule, —NR-L-CO—NH—NH2, —NR-L-OH, —NR-L-O-phosphoramidite, —NR-L-CHO, —NR-L-maleimid, or —NR-L-NH—CO—CH2—I;
• where R is equal to R1 and R2 and L is selected from the group consisting of a divalent linear (—(CH2)o—, o=1 to 15), crossed, or cyclic alkane group that can be substituted by at least one atom selected from the group consisting of oxygen, substituted nitrogen, and/or sulfur, and the biomolecule is a protein, antibody, nucleotide, oligonucleotide, biotin, or hapten;
• Z is —O− or OH;
• U is —O−, —OH or NH-L-SO2Z;
• Kat is Li, Na, K, ammonium (mono-, di- or trialkyl) or another cation;
• An is F, Cl, Br, I, BF4, CO4, CH3CO2, CF3CO2 or another anion;
• m is an integer from 1-6 necessary to compensate the negative or positive charge from the dye moiety in formula I or formula II;
• and
• n is an integer from 0-12