Indocyanine dyes
AssigneeMallinckrodt Inc.
InventorsSamuel Achilefu, Raghavan Rajagopalan, Richard B. Dorshow, Joseph E. Bugaj
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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 indocyanine 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 indocyanine dyes of the general formula
- wherein a2 and b2 are independently 0 to 5;
- W2 and X2 are independently selected from the group consisting of C((CH2zzOH)2, C((CH2)zzCO2H)2, C((CH2)zzNRppRpz)2;
- and zz is from 1 to 5;
- 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;
- Q2 is bond or is selected from the group consisting of —O—, —S—, —Se—, and NR13;
- Y2 and Z2 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;
- R13-R16 are independently selected from the group consisting of -hydrogen, C1-C10 alkyl, C1-C10 alkoxyl, —(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 1 to 10;
- d, f and j are independently 1 to 100;
- and R17 to R28 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 of performing a diagnostic or therapeutic procedure which comprises administering to an individual an effective amount of the composition of indocyanine dyes of the formula
- wherein a2 and b2 are independently 0 to 5;
- W2 and x2 are independently selected from the group consisting of C((CH2)zzOH)2, C((CH2)zzCO2H)2 and C((CH2)zzNRppRpz)2;
- zz is from 1 to 5;
- 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;
- Q2 is a single bond or is selected from the group consisting of —O—, —S—, —Se—, and NR13;
- Y2 and Z2 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;
- R16 and R13 to R15 are independently selected from the group consisting of -hydrogen, C1-C10 alkyl, C1-C10 alkoxyl, —(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 1 to 10;
- d, f and j are independently 1 to 100;
- and R17 to R28 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.