Azaindole cyanine dyes, uses, and methods of preparation

A compound chosen from Formula (I) or Formula (II):

• wherein
• A is C or N;
• n is 0, 1, or 2;
• each of R1, R2, R3, and R4 is the same or different and is independently chosen from alkyl, heteroalkyl, sulfoalkyl group, alkyl with terminal -Su (succinimidyl/sulfosuccinimidyl) ester, heteroalkyl with terminal —SO3, and alkyl with terminal (Q)zC(O)OR*, and heteroalkyl with terminal (Q)zC(O)OR*,
• where Q is a 5 or 6 membered aryl or heteroaryl ring, z is 0, 1, 2, or 3, R* is chosen from —H, —(CH2)ySO3, and N-hydroxysuccinimide, and y is 1, 2, 3, 4, or 5;
• each of R5, R6, R11, and R12 is the same or different and is independently chosen from —SO3, -lower alkylene-QR13, -Q(CH2)zR13, -(Q′)y(R13)z, and -Q″(R13),
• where Q′ is chosen from thiophene, furan, and pyrrole rings, Q″ is a dithienothiophene, and R13 is chosen from —H, —SO3, —COOH;
• R7 is —H or SO3;
• R8 is chosen from —H, alkyl, and La-Z;
• or alternatively, R7 is SRr, and R8 is alkyl, wherein Rr is an alkylene that forms an unsaturated ring with R8;
• R9 is chosen from —H, alkyl, sulfoalkyl, La-Z, and La-X, on the condition that R8 and R9 are not both —H;
• and
• R10 is chosen from alkyl, sulfoalkyl, La-Z, and La-X,
• where La is selected from the group consisting of a divalent linear (—(CH2)o—, o=0 to 15), crossed, or cyclic alkane group that can be substituted by at least one atom selected from substituted nitrogen and/or sulfur;
• where L is selected from the group consisting of a divalent linear (—(CH2)o—, o=0 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;
• where Z is selected from the group consisting of H, CH3, alkyl, heteroalkyl, NH2, —COO−, —COOH, —COSH, CO—NH—NH2, —COF, —COCl, —COBr, —COI, —COO-Su (succinimidyl/sulfosuccinimidyl) ester, —COO-STP (4-sulfo-2,3,5,6-tetrafluorophenyl), —COO-TFP (2,3,5,6-tetrafluorophenyl), —COO-benzotriazole, —CO-benzotriazole, —CONR′—CO—CH2—I, —CONR′R″, —CONR′-biomolecule, —CONR′-L-COO—, —CONR′-L-COOH, —CONR′-L-COO-Su, —CONR′-L-COO-STP, —CONR′-L-COO-TFP, —CONR′-L-CONR″2, —CONR′-L-CO-biomolecule, —CONR′-L-CO—NH—NH2, —CONR′-L-OH, —CONR′-L-CHO, —CONR′-L-maleimide, and —CONR′-L-NH—CO—CH2—I;
• R′ and R″ is selected from the group consisting of H, alkyl group, and heteroalkyl group, and the biomolecule is a protein, antibody, nucleotide, oligonucleotide, biotin, or hapten;
• X is selected from the group consisting of —SH, —NH2, —NH—NH2, —F, —Cl, —Br, I, —NHS (hydroxysuccinimidyl/sulfosuccinimidyl) ester, —O-TFP (2,3,5,6-tetrafluorophenoxy), —O-STP (4-sulfo-2,3,5,6-tetrafluorophenoxy), —O-benzotriazole, -benzotriazole, —NR-L-OH, —NR-L-SH, —NR-L-NH2, —NR-L-NH—NH2, —NR-L-CO2H, —NR-L-CO—NHS, —NR-L-CO-STP, —NR-L-CO-TFP, —NR-L-CO-benzotriazole, —NR-L-CHO, —NR-L-maleimide, and —NR-L-NH—CO—CH2—I, where R is —H or an alkyl or heteroalkyl group;
• and
• with the proviso that the compound of Formula (II) cannot be chosen from: