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US 2017/0285040 A1Published application
Ca ix - nir dyes and their uses
AssigneeOn Target Laboratories, LLC
InventorsSumith A. Kularatne, Pravin Gagare, Ananda Kumar
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Abstract
The present disclosure relates to compounds that are useful as near-infrared fluorescence probes, wherein the compounds include i) a ligand that binds to the active site of carbonic anhydrase, ii) a dye molecule, and iii) a linker molecule that comprises an amino acid, amide, ureido, or polyethylene glycol derivative thereof. The disclosure further describes methods and compositions for making and using the compounds, methods incorporating the compounds, and kits incorporating the compounds.
Claims56
A compound having the formula:
- B-W-X-Y-Z
- wherein B is a CA IX-targeted molecule;
- W is an extended hydrophobic residue;
- X is a hydrophobic spacer;
- Y is an amino acid spacer;
- and
- Z is a NIR dye.
4 more elements
A compound having the structural formula:
- or a pharmaceutically acceptable salt thereof, or isotopes thereof, wherein:
- R19 represents a hydrogen or SO3H;
- R20 represents a hydrogen, CH3, C3H6SO3−, C3H6SO3H or C4H8SO3−, or C4H8SO3H or C3H6N+(CH3)3;
- R21 represents a carbon, optionally one or more sharing bonds,
- R22 represents a carbon with optionally one or more sharing bonds;
- R23 represents nitrogen, oxygen, or sulfur or no atom (direct C—C bond between aromatic ring and vinyl ring);
- R24 is optional and when present represents aromatic substitution group to enhance the spectral properties such as increase brightness and stability of the vinyl ether bridge;
- R25 is optional and when present
- represents linkers with aromatic amino acids such as Phe, Trp, His or derivative thereof, cationic amino acids such Arg, Lys, or derivative thereof, anionic amino acids such as Asp, Glu or derivative of them, unnatural amino acids of aromatic/cationic/anionic acids or derivative thereof;
- R26 is optional and when present represents a linear carbon chain, or polyethylene glycol linker, cationic linker, or derivative thereof;
- R27 optional and when present represents hydrophobic moiety such as Phe, Val, Leu, Ile, Trp, His, Arg, Lys, Asp, Glu, or derivative thereof;
- R28 represents hydrophobic linker;
- and
- R29 is optional and when present represents aromatic substitution group to enhance the binding affinity, stability, hydrophobicity of the molecule such as F, NO2, or thereof, R30 optional and when present represents hydrophobic moiety such as Phe, Val, Leu, Ile, Trp, His, or derivative thereof or cyclic moiety such as cyclohexyl, cyclooctyl, or derivative thereof.
11 more elements
Dependencies are inferred from the claim text.