Dyes
AssigneeMallinckrodt Inc.
InventorsSamuel Achilefu, Raghavan Rajagopalan, Richard B. Dorshow, Joseph E. Bugaj
Life of this patent
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Abstract
The sensitivity and specificity of the optical modality can be enhanced by the use of highly absorbing dyes as contrast agents. Novel cyanine dyes that absorb and emit light in the near infrared region of electromagnetic spectrum are disclosed. These dyes are useful for imaging, diagnosis and therapy of various diseased states. Particularly, the molecules of the invention are useful for optical diagnostic imaging and therapy, in endoscopic applications for the detection of tumors and other abnormalities, for localized therapy, for photoacoustic tumor imaging, detection and therapy, and for sonofluorescence tumor imaging, detection and therapy.
Claims16
A composition comprising a cyanine dye of the formula
- wherein a1 and b1 are independently from 0 to 5;
- W1 and X1 are independently selected from the group consisting of —C((CH2)zzOH)2, C((CH2)zzCO2H)2 and C ((CH2)zzNRppRpz)2;
- Rpp and Rpz are independently consisting of —(CH2)c—CO2H, —CH2—(CH2—O—CH2)d—CH2—CO2H, —(CH2)g—N(R14)—(CH2)h—CO2H and —(CH2)i—N(R15)—CH2—(CH2—O—CH2)j—CH2—CO2H;
- zz is independently from 1 to 5, Q1 is a single bond or is selected from the group consisting of —O—, —S—, —Se—, and —NR13;
- Y1 and Z1 are independently selected from the group consisting of —(CH2)c—CO2H, —CH2—(CH2—O—CH2)d—CH2—CO2H, —(CH2)e—NH2, —CH2—(CH2—O—CH2)f—CH2—NH2, —(CH2)g—N(R14)—(CH2)h—CO2H and —(CH2)i—N(R15)—CH2—(CH2—O—CH2)j—CH2—CO2H;
- R1 and R13to R15 are independently selected from the group consisting of—hydrogen, C1-C10 alkyl C1-C10 alkoxyl, —CH2(CH2—O—CH2)c—CH2—OH, —(CH2)d—CO2H, —CH2—(CH2—O—CH2)e—CH2—CO2H, —(CH2)f—NH2 and —CH2—(CH2—O—CH2)g—CH2—NH2;
- c, e, g, h, and i are independently from 1 to 10;
- d, f and j are independently from 1 to 100;
- and R2 to R9 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, amino, C1-C10 aminoalkyl, cyano, nitro and halogen;
- and a pharmaceutically acceptable carrier or excipient.
A method for performing a diagnostic or therapeutic procedure which comprises administering to an individual an effective amount of the composition of cyanine dye of formula
- wherein a1 and b1 are independently from 0 to 5;
- W1 and X1 are independently selected from the group consisting of —C((CH2)zzOH)21 C((CH2)zzCO2H)2 and C((CH2)zzNRppRpz)2;
- Rpp and Rpz are independently selected from the group consisting of —(CH2)c—CO2H, —CH2—(CH2—O—CH2)d—CH2—CO2H, —(CH2)g—N(R14)—(CH2)h—CO2H and —(CH2)i—N(R15)—CH2—(CH2—O—CH2)j—CH2—CO2H;
- zz is independently from 1 to 5;
- Q1 is a single bond or is selected from the group consisting of —O—, —S—, —Se— and —NR13;
- Y1 and Z1 are independently selected from the group consisting of —(CH2)c—CO2H, —CH2—(CH2—O—CH2)d—CH2—CO2H, —(CH2)e—NH2, —CH2—(CH2—O—CH2)f—CH2—NH2, —(CH2)g—N(R14)—(CH2)h—CO2H and —(CH2)i—N(R15)—CH2—(CH2—O—CH2)j—CH2—CO2H;
- R1 and R13 to R15 are independently selected from the group consisting of—hydrogen, C1-C10 alkyl, C1-C10 alkoxyl, —CH2(CH2—O—CH2)c—CH2—OH, —(CH2)d—CO2H, —CH2—(CH2—O—CH2)e—CH2—CO2H, —(CH2)f—NH2, and —CH2—(CH2—O—CH2)g—CH2—NH2;
- c, e, g, h, and i are independently from 1 to 10;
- d, f and j are independently from 1 to 100;
- and R2 to R9 are independently selected from the group consisting of hydrogen, C1-C10 alkyl, hydroxyl, C1-C10 alkoxyl, amino, C1-C10 aminoalkyl, cyano, nitro and halogen.
Dependencies are inferred from the claim text.