NIR to SWIR fluorescent compounds for imaging and detection

A compound represented by the following structural formula:

• or a salt thereof, wherein:
• P1 and P2 are a benz[c,d]indole moiety;
• Q is a hydrogen, C1-C24 alkyl, aryl, heteroaryl, polyaryl, phenyl, thienyl, furanyl, pyridyl, pyridinium, halogen, substituted or unsubstituted S-alkyl, substituted or unsubstituted S-aryl, substituted or unsubstituted O-alkyl, substituted or unsubstituted O-aryl, substituted or unsubstituted N-alkyl, substituted or unsubstituted N-aryl, cyano, trifluoromethyl, azidoaryl, boronic acid, boronic ester, hydroxyl, alkoxy, aryloxy, alkylthio, arylthio, nitrogen, silicon, boron, carboxy, cyano, ester, amine, amide, amino acid, peptide or L,
• W is absent or a substituted or unsubstituted cyclic or polycyclic group containing aliphatic or aromatic carbon, nitrogen, oxygen, sulfur, or silicon forming a 4 to 9 membered ring;
• L is absent or is a linker moiety, optionally bearing a functional group or reactive group, such as selected from the group consisting of a carboxylate, carboxyalkyl, maleimide, succinimidyl ester, carboxamide, propargyl, azidoalkyl, alkyne, isothiocyanate, of —NH2 —OH, —SH, —SO3H, carboxyl, —COCl, —CONHNH2, acetoxymethyl esters, substituted and unsubstituted N-hydroxysuccinimidyl esters, substituted and unsubstituted N-hydroxysulfosuccinimido esters, nitro- or fluoro or phenol esters, azide, —COCH2I, phosphoramidite, phthalamido, acyl fluoride, acyl chloride, acyl azide, tyramide, cinnamamide, hydroxycinnamamide, aldehyde, ketone, phosphoramidite, isocyanate, isothiocyanate, sulfonyl chloride, maleimide and biotin;
• R is, independently for each occurrence, hydrogen, substituted or unsubstituted C1 to C24 alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C1 to C24 alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl, amide, amino acid, peptide or L, with the proviso that in at least one instance R in said compound comprises a sulfonate, aryl sulfonate, or C1 to C24 alkyl sulfonate;
• x and y are, independently for each occurrence, integers from 0 to 15;
• and
• wherein said compound comprises at least four sulfonates, alkyl sulfonates, arylsulfonates, taurines or a combination thereof, is water soluble, and absorbs and/or emits light between 950 nm and 1350 nm.

A compound of Formula III or Formula IV where:

• or a salt thereof, wherein:
• Q is a hydrogen, C1-C24 alkyl, aryl, heteroaryl, polyaryl, phenyl, thienyl, furanyl, pyridyl, pyridinium, halogen, substituted or unsubstituted S-alkyl, substituted or unsubstituted S-aryl, substituted or unsubstituted O-alkyl, substituted or unsubstituted O-aryl, substituted or unsubstituted N-alkyl, substituted or unsubstituted N-aryl, cyano, trifluoromethyl, azidoaryl, boronic acid, boronic ester, hydroxyl, alkoxy, aryloxy, alkylthio, arylthio, nitrogen, silicon, boron, carboxy, cyano, ester, amine, amide, amino acid, peptide or L;
• W is absent or a substituted or unsubstituted cyclic or polycyclic group containing aliphatic or aromatic carbon, nitrogen, oxygen, sulfur, or silicon forming a 4 to 9 membered ring;
• R1-R12 are, independently for each occurrence, hydrogen, substituted or unsubstituted C1 to C24 alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C1 to C24 alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl,amide, amino acid, peptide or L, with the proviso that in at least one instance R in said compound comprises a sulfonate, aryl sulfonate, or C1 to C24 alkyl sulfonate;
• L is absent or is a linker moiety, optionally bearing a functional group or reactive group, such as selected from the group consisting of a carboxylate, carboxyalkyl, maleimide, succinimidyl ester, carboxamide, propargyl, azidoalkyl, alkyne, isothiocyanate, of —NH2 —OH, —SH, —SO3H, carboxyl, —COCl, —CONHNH2, acetoxymethyl esters, substituted and unsubstituted N-hydroxysuccinimidyl esters, substituted and unsubstituted N-hydroxysulfosuccinimido esters, nitro- or fluoro or phenol esters, azide, —COCH2I, phosphoramidite, phthalamido, acyl fluoride, acyl chloride, acyl azide, tyramide, cinnamamide, hydroxycinnamamide, aldehyde, ketone, phosphoramidite, isocyanate, isothiocyanate, sulfonyl chloride, maleimide and biotin;
• and
• wherein said compound comprises at least four sulfonates, alkyl sulfonates, arylsulfonates, taurines or a combination thereof, is water soluble, and absorbs and/or emits light between 950 nm and 1350 nm.

A compound of any of the following formulae:

• or a salt thereof, wherein:
• Q is a hydrogen, C1-C24 alkyl, aryl, heteroaryl, polyaryl, phenyl, thienyl, furanyl, pyridyl, pyridinium, halogen, substituted or unsubstituted S-alkyl, substituted or unsubstituted S-aryl, substituted or unsubstituted O-alkyl, substituted or unsubstituted O-aryl, substituted or unsubstituted N-alkyl, substituted or unsubstituted N-aryl, cyano, trifluoromethyl, azidoaryl, boronic acid, boronic ester, hydroxyl, alkoxy, aryloxy, alkylthio, arylthio, nitrogen, silicon, boron, carboxy, cyano, ester, amine, amide, amino acid, peptide or L,
• W is absent or a substituted or unsubstituted cyclic or polycyclic group containing aliphatic or aromatic carbon, nitrogen, oxygen, sulfur, or silicon forming a 4 to 9 membered ring;
• R1-R10 are, independently for each occurrence, hydrogen, substituted or unsubstituted C1 to C24 alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C1 to C24 alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl, amide, amino acid, peptide or L, wherein at least four of R1-R8 are sulfonates, alkyl sulfonates, arylsulfonates or taurine;
• L is absent or is a linker moiety, optionally bearing a functional group or reactive group selected from the group consisting of a carboxylate, carboxyalkyl, maleimide, succinimidyl ester, carboxamide, propargyl, azidoalkyl, alkyne, isothiocyanate, of —NH2 —OH, —SH, —SO3H, carboxyl, —COCl, —CONHNH2, acetoxymethyl esters, substituted and unsubstituted N-hydroxysuccinimidyl esters, substituted and unsubstituted N-hydroxysulfosuccinimido esters, nitro- or fluoro or phenol esters, azide, —COCH2I, phosphoramidite, phthalamido, acyl fluoride, acyl chloride, acyl azide, tyramide, cinnamamide, hydroxycinnamamide, aldehyde, ketone, phosphoramidite, isocyanate, isothiocyanate, sulfonyl chloride, maleimide and biotin.

A compound represented by the following formula:

• or a salt thereof, wherein:
• Q is a hydrogen, C1-C24 alkyl, aryl, heteroaryl, polyaryl, phenyl, thienyl, furanyl, pyridyl, pyridinium, halogen, substituted or unsubstituted S-alkyl, substituted or unsubstituted S-aryl, substituted or unsubstituted O-alkyl, substituted or unsubstituted O-aryl, substituted or unsubstituted N-alkyl, substituted or unsubstituted N-aryl, cyano, trifluoromethyl, azidoaryl, boronic acid, boronic ester, hydroxyl, alkoxy, aryloxy, alkylthio, arylthio, nitrogen, silicon, boron, carboxy, cyano, ester, amine, amide, amino acid, peptide or L,
• W is absent or a substituted or unsubstituted cyclic or polycyclic group containing aliphatic or aromatic carbon, nitrogen, oxygen, sulfur, or silicon forming a 4 to 9 membered ring;
• R1-R12 are, independently for each occurrence, hydrogen, substituted or unsubstituted C1 to C24 alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C1 to C24 alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl, amide, amino acid, peptide or L, wherein at least four of R1-R8 are sulfonates, alkyl sulfonates, arylsulfonates or taurine;
• L is absent or is a linker moiety, optionally bearing a functional group or reactive group selected from the group consisting of a carboxylate, carboxyalkyl, maleimide, succinimidyl ester, carboxamide, propargyl, azidoalkyl, alkyne, isothiocyanate, of —NH2 —OH, —SH, —SO3H, carboxyl, —COCl, —CONHNH2, acetoxymethyl esters, substituted and unsubstituted N-hydroxysuccinimidyl esters, substituted and unsubstituted N-hydroxysulfosuccinimido esters, nitro- or fluoro or phenol esters, azide, —COCH2I, phosphoramidite, phthalamido, acyl fluoride, acyl chloride, acyl azide, tyramide, cinnamamide, hydroxycinnamamide, aldehyde, ketone, phosphoramidite, isocyanate, isothiocyanate, sulfonyl chloride, maleimide and biotin.