Carboxamide-substituted xanthene dyes

1. A carboxamide-substituted dye of the formula (I)

in which:

R 1 and R 10 are hydrogen,

R 2 and R 9 are independently hydrogen or halogen,

R 5 and R 6 are independently hydrogen, SO 3 X, or SO 2 NH—(CH 2 ) n —SO 3 X, and n=2-5,

R 3 , R 4 , R 7 , and R 8 are independently H or C 1 -C 5 alkyl, where each alkyl is optionally further substituted with halogen or SO 3 X, or

R 3 in combination with R 2 form a 5- or 6-membered saturated or unsaturated ring that is optionally substituted with a C 1 -C 5 alkyl, where each alkyl is optionally further substituted with SO 3 X, or

R 8 in combination with R 9 form a 5- or 6-membered saturated ring that is optionally substituted with a C 1 -C 5 alkyl, where each alkyl is optionally further substituted with SO 3 X,

X is H or a counterion,

R 11 and R 12 are polyethylene glycol,

R 13 is N-hydroxysuccinimidyl, p-nitrophenyl, pentafluorophenyl, N-hydroxybenzotriazolyl ester, maleimido, alpha-haloacetamido, pyridyldisulfides, carbodiimide, carbonyl, diazirine, hydrazide, hydroxymethyl phosphine, imidoester, NHS-ester, PFP-ester, psoralen, pyridyl disulfide, vinyl sulfone, terminal alkyne, azide, trans-cyclooctene, or a biomolecule selected from the group consisting of a nucleic acid, a nucleotide, a protein, an amino acid, a carbohydrate monomer, or a polysaccharide, and

R 14 is hydrogen.

2. The compound according to claim 1 , wherein R 13 is a biomolecule selected from the group consisting of a protein and a nucleotide.

3. A carboxamide-substituted dye of the formula:

in which:

R 1 , R 2 , R 9 and R 10 are independently hydrogen or halogen,

R 5 and R 6 are independently hydrogen, SO 3 X, or SO 2 NH—(CH 2 ) n —SO 3 X, where X is H or a counterion, and n=2-5,

R 3 , R 4 , R 7 , and R 8 are independently H or C 1 -C 5 alkyl, where each alkyl is optionally further substituted with halogen or SO 3 X, where X is H or a counterion,

R 11 is C 1 -C 18 alkyl or a branched or cyclic saturated or unsaturated hydrocarbon group having up to 300 carbon atoms, any one of which is optionally interrupted by O or N atoms, optionally further substituted with F, Cl, Br, I, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester, SO 3 X, or PO 3 X, where X is H or a counterion,

R 12 is a N-hydroxysuccinimidyl, p-nitrophenyl, pentafluorophenyl, N-hydroxybenzotriazolyl ester, maleimido, alpha-haloacetamido, pyridyldisulfides, carbodiimide, carbonyl, diazirine, hydrazide, hydroxymethyl phosphine, imidoester, NHS-ester, PFP-ester, psoralen, pyridyl disulfide, vinyl sulfone, terminal alkyne, azide, trans-cyclooctene, or a biomolecule selected from the group consisting of a nucleic acid, a nucleotide, a protein, an amino acid, a carbohydrate monomer, or a polysaccharide, and

R 13 is hydrogen or halogen.

4. The compound according to claim 3 , wherein R 11 is polyethylene glycol.

5. A carboxamide-substituted dye of the formula:

in which:

R 1 , R 2 , R 3 , R 6 , R 7 , and R 8 are independently hydrogen, or C 1 -C 5 alkyl, where each alkyl is optionally further substituted with halogen or SO 3 X, where X is H or a counterion,

R 9 and R 10 are independently hydrogen, SO 3 X, or SO 2 NH—(CH 2 ) n —SO 3 X, where X is H or a counterion, and n=2-5,

R 4 and R 5 are independently hydrogen, CH 3 , or SO 3 X, where X is H or counterion,

R 11 is C 1 -C 18 alkyl or a branched or cyclic saturated or unsaturated hydrocarbon group having up to 300 carbon atoms, any one of which is optionally interrupted by 0 or N atoms, optionally further substituted with F, Cl, Br, I, a carboxylic acid, a salt of carboxylic acid, or a carboxylic acid ester, SO 3 X, or PO 3 X, where X is H or a counterion,

R 12 is a N-hydroxysuccinimidyl, p-nitrophenyl, pentafluorophenyl, N-hydroxybenzotriazolyl ester, maleimido, alpha-haloacetamido, pyridyldisulfides, carbodiimide, carbonyl, diazirine, hydrazide, hydroxymethyl phosphine, imidoester, NHS-ester, PFP-ester, psoralen, pyridyl disulfide, vinyl sulfone, terminal alkyne, azide, trans-cyclooctene, or a biomolecule selected from the group consisting of a nucleic acid, a nucleotide, a protein, an amino acid, a carbohydrate monomer, or a polysaccharide, and

R 13 is hydrogen or halogen.

6. The compound according to claim 5 , wherein R 11 is polyethylene glycol.