US11344632B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11344632-B2 |
| Application number | US-201916408495-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 10, 2019 |
| Priority date | Jan 28, 2010 |
| Publication date | May 31, 2022 |
| Grant date | May 31, 2022 |
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The present invention aims at providing a novel indocyanine compound solving problems of conventionally used indocyanine green, such as solubility in water or physiological saline, a synthesis method and a purification method thereof, and a diagnostic composition including the novel indocyanine compound. Further, provided are a method for evaluating biokinetics of the novel indocyanine compound and a device for measuring biokinetics, and a method and a device for visualizing circulation of fluid such as blood in a living body, which utilize the diagnostic composition. Also, found are a novel indocyanine compound in which a hydrophobic moiety in a near-infrared fluorescent indocyanine molecule is included in a cavity of a cyclic sugar chain cyclodextrin to cover the hydrophobic moiety in the indocyanine molecule with the glucose, and a synthesis method and a purification method thereof. Furthermore, found are a method for fluorescence-imaging an organ other than liver by intravenous administration, a method for evaluating biokinetics of the novel indocyanine compound, a device for measuring biokinetics, and a method and a device for visualizing circulation of fluid such as blood in a living body, utilizing the diagnostic composition including the novel indocyanine compound.
Opening claim text (preview).
The invention claimed is: 1. An aqueous solution comprising a cyclodextrin-bonded indocyanine compound, which is an isomerization equilibrium compound represented by chemical formulas 15 and 16, or chemical formulas 19 and 20: wherein the aqueous solution has a lower adsorption than a corresponding non-cyclodextrin bonded indocyanine compound as measured by at least one of a cellulose fiber model test, a meat model test, and a protein model test. 2. The aqueous solution of claim 1 , wherein the cyclodextrin-bonded indocyanine compound is the isomerization equilibrium compound represented by the chemical formulas 15 and 16. 3. The aqueous solution of claim 1 , wherein the cyclodextrin-bonded indocyanine compound is the isomerization equilibrium compound represented by the chemical formulas 19 and 20. 4. The aqueous solution of claim 1 , wherein the corresponding non-cyclodextrin bonded indocyanine compound is indocyanine green, and the adsorption of the aqueous solution is compared with an aqueous solution of indocyanine green. 5. The aqueous solution of claim 1 , wherein the adsorption is measured by the cellulose fiber model test which comprises applying the aqueous solution of the cyclodextrin-bonded indocyanine compound to the cellulose fiber model, washing with water for 5 seconds after 3 minutes, and comparing the degree of washout with that obtained when the cellulose fiber model test is performed with indocyanine green. 6. The solution of claim 1 , wherein the adsorption is measured by the meat model test which comprises applying the aqueous solution of the cyclodextrin-bonded indocyanine compound to pork loin meat, washing with water for 10 seconds after 3 minutes, and comparing the degree of washout with that obtained when the meat model test is performed with indocyanine green. 7. The aqueous solution of claim 1 , wherein the adsorption is measured by the protein model test which comprises applying the aqueous solution of the cyclodextrin-bonded indocyanine compound to chicken breast meat, washing with water for 10 seconds after 3 minutes, and comparing the degree of washout with that obtained when the protein model test is performed with indocyanine green. 8. A cyclodextrin-bonded indocyanine compound represented by chemical formula 15, 16, 19 or 20: wherein a degree of adsorption of the cyclodextrin-bonded indocyanine compound to a target is such that an aqueous solution of the cyclodextrin-bonded indocyanine compound is washable by water as shown by at least one of a cellulose fiber model test, a meat model test, and a protein model test. 9. The cyclodextrin-bonded indocyanine compound of claim 8 , wherein the cellulose fiber model test includes applying a 1 mM aqueous solution (0.05 mL) including the cyclodextrin-bonded indocyanine compound to a cellulose fiber model, and washing with running water (tap water, 1 L/minute) for 5 seconds after 3 minutes, the meat model test includes using a commercially available pork loin meat as a meat model of a living body, making a depression part with a diameter of 5 mm on the pork loin meat, and applying a 1 mM aqueous solution (0.05 mL) including the cyclodextrin-bonded indocyanine compound to the depression part, washing with running water (tap water, 1 L/minute) for 10 seconds after 3 minutes, and the protein model test includes using a commercially available chicken breast meat as a protein model of a living body, making a depression part with a diameter of 5 mm on the chicken breast meat, applying a 1 mM aqueous solution (0.05 mL) including the cyclodextrin-bonded indocyanine compound to the depression part on the chicken breast meat, and washing with running water (tap water, 1 L/minute) for 10 seconds after 3 minutes. 10. A composition comprising a cyclodextrin-bonded indocyanine compound, which is an isomerization equilibrium compound represented by chemical formulas 15 and 16, or chemical formulas 19 and 20: wherein the composition is formulated such that adsorption to a target is lower than that of indocyanine green, and the adsorption is measured by at least one of a cellulose fiber model test, a meat model test, and a protein model test. 11. The composition of claim 10 , wherein the adsorption is measured by the cellulose fiber model test which includes applying an aqueous solution of the cyclodextrin-bonded indocyanine compound to the cellulose fiber model, washing with water for 5 seconds after 3 minutes, and comparing the degree of washout with that obtained when the cellulose fiber model test is performed with indocyanine green. 12. The composition of claim 10 , wherein the adsorption is measured by the meat model test which includes applying an aqueous solution of the cyclodextrin-bonded indocyanine compound to pork loin meat, washing with water for 10 seconds after 3 minutes, and comparing the degree of washout with that obtained when the meat model test is performed with indocyanine green. 13. The composition of claim 10 , wherein the adsorption is measured by the protein model test which includes applying an aqueous solution of the cyclodextrin-bonded indocyanine compound to chicken breast meat, washing with water for 10 seconds after 3 minutes, and comparing the degree of washout with that obtained when the protein model test is performed with indocyanine green. 14. The composition of claim 10 , wherein the cellulose fiber model test includes applying a 1 mM aqueous solution (0.05 mL) including each of the cyclodextrin-bonded indocyanine compounds of the chemical formulas 16 and 20 and indocyanine green to a cellulose fiber model, and washing with running water (tap water, 1 L/minute) for 5 seconds after 3 minutes, the meat model test includes using a commercially available pork loin meat as a meat model of a living body, making a depression part with a diameter of 5 mm on the pork loin meat, and applying a 1 mM aqueous solution (0.05 mL) including each of the cyclodextrin-bonded indocyanine compounds of the chemical formulae 16 and 20 and indocyanine green to the depression part, washing with running water (tap water, 1 L/minute) for 10 seconds after 3 minutes, and the protein model test includes using a commercially available chicken breast meat as a protein model of a living body, making a depression part with a diameter of 5 mm on the chicken breast meat, applying a 1 mM aqueous solution (0.05 mL) including each of the cyclodextrin-bonded indocyanine compounds of the chemical formulae 16 and 20 and Indocyanine Green to the depression part on the chicken breast meat, and washing with running water (tap water, 1 L/minute) for 10 seconds after 3 minutes.
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