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US 8,273,875 B2Granted
High performance luminescent compounds
AssigneesUniversity of Notre Dame du Lac, Molecular Targeting Technologies, Inc.
InventorsBradley Smith, Arunkumar Easwaran
Life of this patent
Estimating the term…
Abstract
Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to novel near-infrared dyes that are photostable and resistant to quenching. The dyes belong to a novel family of squaraine rotaxanes, and they are particularly well-suited for use in biological applications. Also disclosed are methods of synthesizing the dyes and methods of using the dyes.
Claims19
A compound having the formula:
- or a pharmaceutically acceptable salt thereof, wherein:
- R1, R2, and R3 are each independently alkyl, phenyl, polyethylene glycol, alkyl-phosphonate, alkyl-sulfonate, methylene-triazole-alkyl-sulfonate, methylene-triazole-alkyl-phosphonate, methylene-triazole-methylene-dimethylammonium-alkyl-sulfonate, or methylene-dimethylammonium-alkyl-phosphonate;
- X=alkyl, phenyl, alkyl-carboxylic acid, alkyl ester, alkyl hydroxysuccinimde ester, alkyl maleimide, alkyl isothiocyanate, alkyl azide, alky alkyne, alkyl haloacetamido, aryl ester, aryl hydroxysuccinimde ester, aryl maleimide, aryl isothiocyanate, aryl azide, aryl alkyne, or aryl haloacetamido;
- Y1 and Y2 are each independently H, alkoxy-triazole-methylene-sulfonate, alkoxy-triazole-methylene-dimethylammonium-alkyl-sulfonate, alkoxy-triazole-methylene-phosphonate, alkoxy-triazole-methylene-dimethylammonium-alkyl-phosphonate, triazole-methylene-sulfonate, triazole-methylene-phosphonate;
- triazole-methylene-dimethylammonium-alkyl-sulfonate, triazole-methylene-methylene-dimethylammonium-alkyl-phosphonate, alkyl, phenyl, alkyl-carboxylic acid, alkyl ester, alkyl hydroxysuccinimde ester, alkyl maleimide, alkyl isothiocyanate, alkyl azide, alky alkyne, alkyl haloacetamido, aryl ester, aryl hydroxysuccinimde ester, aryl maleimide, aryl isothiocyanate, aryl azide, aryl alkyne, or aryl haloacetam;
- Z1 and Z2 are each independently CH or N;
- and
- W1, W2, W3, and W4 are each independently H or OH, at least one of W1, W2, W3, and W4 being OH.
5 more elements
A compound having the formula:
- or a pharmaceutically acceptable salt thereof, wherein:
- R1, R2, and R3 are each independently alkyl, phenyl, polyethylene glycol, alkyl-phosphonate, alkyl-sulfonate, methylene-triazole-alkyl-sulfonate, methylene-triazole-alkyl-phosphonate, methylene-triazole-methylene-dimethylammonium-alkyl-sulfonate, or methylene-dimethylammonium-alkyl-phosphonate;
- X=alkyl, phenyl, alkyl-carboxylic acid, alkyl ester, alkyl hydroxysuccinimde ester, alkyl maleimide, alkyl isothiocyanate, alkyl azide, alky alkyne, alkyl haloacetamido, aryl ester, aryl hydroxysuccinimde ester, aryl maleimide, aryl isothiocyanate, aryl azide, aryl alkyne, or aryl haloacetamido;
- Y1 and Y2 are each independently H, alkoxy-triazole-methylene-sulfonate, alkoxy-triazole-methylene-dimethylammonium-alkyl-sulfonate, alkoxy-triazole-methylene-phosphonate, alkoxy-triazole-methylene-dimethylammonium-alkyl-phosphonate, triazole-methylene-sulfonate, triazole-methylene-phosphonate;
- triazole-methylene-dimethylammonium-alkyl-sulfonate, triazole-methylene-methylene-dimethylammonium-alkyl-phosphonate, alkyl, phenyl, alkyl-carboxylic acid, alkyl ester, alkyl hydroxysuccinimde ester, alkyl maleimide, alkyl isothiocyanate, alkyl azide, alkyl alkyne, alkyl haloacetamido, aryl ester, aryl hydroxysuccinimde ester, aryl maleimide, aryl isothiocyanate, aryl azide, aryl alkyne, or aryl haloacetamido;
- and
- W1, W2, W3, and W4 are each independently H or OH, at least one of W1, W2, W3, and W4 being OH.
4 more elements
A compound having the formula:
- or a pharmaceutically acceptable salt thereof, wherein:
- R1, R2, and R3 are each independently alkyl, phenyl, polyethylene glycol, alkyl-phosphonate, alkyl-sulfonate, methylene-triazole-alkyl-sulfonate, or methylene-triazole-alkyl-phosphonate, methylene-triazole-methylene-dimethylammonium-alkyl-sulfonate, or methylene-dimethylammonium-alkyl-phosphonate;
- X=alkyl, phenyl, alkyl-carboxylic acid, alkyl ester, alkyl hydroxysuccinimde ester, alkyl maleimide, alkyl isothiocyanate, alkyl azide, alky alkyne, alkyl haloacetamido, aryl ester, aryl hydroxysuccinimde ester, aryl maleimide, aryl isothiocyanate, aryl azide, aryl alkyne, or aryl haloacetamido;
- Y1 and Y2 are each independently H, alkoxy-triazole-methylene-sulfonate, alkoxy-triazole-methylene-dimethylammonium-alkyl-sulfonate, alkoxy-triazole-methylene-phosphonate, alkoxy-triazole-methylene-dimethylammonium-alkyl-phosphonate, triazole-methylene-sulfonate, triazole-methylene-phosphonate;
- triazole-methylene-dimethylammonium-alkyl-sulfonate, triazole-methylene-methylene-dimethylammonium-alkyl-phosphoriate, alkyl, phenyl, alkyl-carboxylic acid, alkyl ester, alkyl hydroxysuccinimde ester, alkyl maleimide, alkyl isothiocyanate, alkyl azide, alky alkyne, alkyl haloacetamido, aryl ester, aryl hydroxysuccinimde ester, aryl maleimide, aryl isothiocyanate, aryl azide, aryl alkyne, or aryl haloacetamido;
- and
- W1, W2, W3, and W4 are each independently H or OH.
4 more elements
Dependencies are inferred from the claim text.