Application using non-covalent bond between a cucurbituril derivative and a ligand

• US 20070092867A1
• Filed: 04/20/2006
• Published: 04/26/2007
• Est. Priority Date: 10/20/2005
• Status: Active Grant

• Current Assignee: Postech Academy-Industry Foundation, Postech Foundation
• Original Assignee: Postech Academy-Industry Foundation, Postech Foundation
• Inventors: Kim, Kimoon, Baek, Kangkyun, Selvapalam, Narayanan, Ko, Young, Kim, Jeeyeon, Park, Kyeng, Hwang, Iiha, Nagarajan, Erumaipatty
• Granted Patent: US 7,479,254 B2
• Time in Patent Office: Days
• US Class Current: 435/5
• CPC Class Codes: B01D 15/3804 Affinity chromatography
• CPC Class Codes: B01J 31/0249 Ureas (R2N-C(=O)-NR2)
• CPC Class Codes: B01J 31/0251 Guanidides (R2N-C(=NR)-NR2)
• CPC Class Codes: B01J 31/1658 immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
• CPC Class Codes: B82Y 15/00 Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07K 1/22 Affinity chromatography or related techniques based upon selective absorption processes

Abstract

Provided are a kit including a first component that is a compound of formula (1) below bound to a first material and a second component that is a ligand bound to a second material, wherein each of the first and second materials is independently selected from the group consisting of a solid phase, a biomolecule, an antioxidant, a chemical therapeutic agent, an anti-histaminic agent, a cucurbituril dendrimer, a cyclodextrin derivative, a crown ether derivative, a calixarene derivative, a cyclophane derivative, a cyclic peptide derivative, a metallic ion, a chromophore, a fluorescent material, a phosphor, a radioactive material, and a catalyst; and the ligand can non-covalently bind to the compound of formula (1); a method of separating and purifying a material bound to a ligand using the compound of formula (1) bound to a solid phase; a method of separating and purifying the compound of formula (1) or a material bound to the compound using a ligand bound to a solid phase; a sensor chip including a compound of formula (1) bound to a first material and a ligand bound to a second material; and a solid-catalyst complex including the compound of formula (1) bound to a first material and a ligand bound to a second material.

Claims

1. A kit comprising:

a first component that is a compound of formula (1) below bound to a first material; and

a second component that is a ligand bound to a second material,

wherein each of the first and second materials is independently selected from the group consisting of a solid phase, a biomolecule, an antioxidant, a chemical therapeutic agent, an anti-histaminic agent, a cucurbituril dendrimer, a cyclodextrin derivative, a crown ether derivative, a calixarene derivative, a cyclophane derivative, a cyclic peptide derivative, a metallic ion, a chromophore, a fluorescent material, a phosphor, a radioactive material, and a catalyst; and

the ligand can non-covalently bind to the compound of formula (1) below, has at least one amine group, and is selected from the group consisting of a C₁-C₂₀ alkyl group;

a C₂-C₂₀ alkenyl group;

a C₂-C₂₀ alkynyl group;

a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ aminoalkyl group;

a C₄-C₂₀ cycloalkyl group;

a C₄-C₇ heteroarylcyclo group;

a C₆-C₂₀ aryl group;

a C₅-C₂₀ heteroaryl group;

a C₁-C₂₀ alkylsilyl group;

a C₆-C₂₀ aryl group;

a C₅-C₂₀ heteroaryl group;

adamantane having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

ferrocene or metallocene having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

carborane having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

fullerene having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

cyclam or crown ether having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

an oxygen-protected amino acid having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

peptide having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

alkaloid having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

cisplatin having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

oligonucleotide having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group;

rhodamine having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group; and

a nanoparticle having a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group,

where n is an integer from 6 to 10;

X is O, S or NH;

each of A₁ and A₂ is independently H, OR, SR, or NHR, and A₁ and A₂ are not simultaneously H,

where R is selected from the group consisting of H;

a substituted or non-substituted C₁-C₃₀ alkyl group;

a substituted or non-substituted C₂-C₃₀ alkenyl group;

a substituted or non-substituted C₂-C₃₀ alkynyl group;

a substituted or non-substituted C₂-C₃₀ carbonylalkyl group;

a substituted or non-substituted C₁-C₃₀ thioalkyl group;

a substituted or non-substituted C₁-C₃₀ alkylthiol group;

a substituted or non-substituted C₁-C₃₀ hydroxyalkyl group;

a substituted or non-substituted C₁-C₃₀ alkylsilyl group;

a substituted or non-substituted C₁-C₃₀ aminoalkyl group;

a substituted or non-substituted C₁-C₃₀ aminoalkylthioalkyl group;

a substituted or non-substituted C₅-C₃₀ cycloalkyl group;

a substituted or non-substituted C₂-C₃₀ heterocycloalkyl group;

a substituted or non-substituted C₆-C₃₀ aryl group;

a substituted or non-substituted C₆-C₃₀ arylalkyl group;

a substituted or non-substituted C₄-C₃₀ heteroaryl group; and

a substituted or non-substituted C₄-C₃₀ heteroarylalkyl group.

2. The kit of claim 1, wherein one of the first and second materials is a biomolecule, and the other is a chromophore, a fluorescent material, or a phosphor.

3. The kit of claim 1, wherein the solid phase is a solid support selected from the group consisting of a polymer, a resin, a magnetic material, a silicagel, a polymer- or gold-coated silicagel, a zirconium oxide, a monolithic polymer, a polymer-coated magnetic particle, a gold thin film, a silver thin film, glass, an ITO-coated glass, silicon, a metal electrode, a nanorod, a nanotube, a nanowire, curdlan gum, cellulose, a nylon film, sepharose, and sephadex.

4. The kit of claim 3, wherein the solid phase is polystyrene resin or polymer-coated silicagel.

5. The kit of claim 1, wherein the biomolecule is selected from the group consisting of an enzyme, a nucleic acid, a protein, an amino acid, an antibody, an antigen, an inhibitor, a vitamin, a cofactor, a fatty acid, a cell, a cell membrane, a substrate, a substrate analogue, a suppressor, a coenzyme, a virus, lectin, a polysaccharide, a glucoprotein, a receptor, histone, ATP, ADP, a hormone, a receptor, and glutathione.

6. The kit of claim 5, wherein the enzyme is selected from the group consisting of cellulase, hemicellulase, peroxidase, protease, amylase, xylanase, lipase, esterase, cutinase, pectinase, keratinase, reductase, oxidase, phenoloxidase, lipoxigenase, ligninase, pullulanase, arabinosidase, hyaluronidase, and a combination thereof.

7. The kit of claim 1, wherein the catalyst is a Grobbs catalyst, a radical initiator, or a combination thereof.

8. The kit of claim 1, wherein, in said formula (1), each of A₁ and A₂ is independently H, OR, SR, or NHR where R is a substituted or non-substituted C₂-C₃₀ alkenyl group.

9. The kit of claim 1, wherein, in said formula (1), n is 7, and X is O.

10. The kit of claim 1, wherein the ligand is adamantane, ferrocene, or metallocene that have at least one amine group and a substituted or non-substituted C₁-C₂₀ alkyl group, C₆-C₂₀ aryl group or C₅-C₂₀ heteroaryl group.

11. The kit of claim 10, wherein the amine group is a primary amine, a secondary amine, or a hydrogenated amine.

12. The kit of claim 10, wherein the ligand is adamantanamine or ferrocene methylamine.

13. A method of separating and purifying a material bound to a ligand, the material being selected from the group consisting of a solid support or a biomolecule, an antioxidant, a chemical therapeutic agent, an anti-histaminic agent, a cucurbituril dendrimer, a cyclodextrin derivative, a crown ether derivative, a calixarene derivative, a cyclophane derivative, a cyclic peptide derivative, a metallic ion, a chromophore, a fluorescent material, a phosphor, a radioactive material, and a catalyst, the method comprising:

(a) preparing an affinity chromatography column filled with a compound of formula (1) below bound to a solid phase as a stationary phase;

(b) supplying a mixture containing the material bound to a ligand into the affinity chromatography column;

(c) washing the affinity chromatography column with a washing solution; and

(d) loading a mobile phase solvent into the affinity chromatography column to separate and purify the material bound to the ligand,

where n, X, A₁, and A₂ are the same as defined in claim 1.

14. The method of claim 13, further comprising binding the compound of said formula (1) to the solid phase before operation (a).

15. The method of claim 13, further comprising binding the ligand and the material between operations (a) and (b).

16. The method of claim 13, wherein the mobile phase solvent is selected from the group consisting of methanol, trifluoracetic acid, triethylamine, methylene chloride, chloroform, dimethylformamide, dimethyl sulfoxide, toluene, acetonitrile, xylene, chlorobenzine, tetrahydrofurane, diethylether, ethanol, diglycol ether, silicon, supercritical carbon dioxide, ionic liquids, N-methylpyrrolidine, pyridine, water, ammonium hydroxide, and dioxane.

17. The method of claim 13, wherein the washing solution is selected from the group consisting of methanol, trifluoracetic acid, triethylamine, methylene chloride, chloroform, dimethylformamide, dimethyl sulfoxide, toluene, acetonitrile, xylene, chlorobenzine, tetrahydrofurane, diethylether, ethanol, diglycol ether, silicon, supercritical carbon dioxide, ionic liquids, N-methylpyrrolidine, pyridine, water, ammonium hydroxide, and dioxane.

18. A method of separating and purifying a compound of formula (1) below or a material bound to the compound, the material being selected from the group consisting of a solid support or a biomolecule, an antioxidant, a chemical therapeutic agent, an anti-histaminic agent, a cucurbituril dendrimer, a cyclodextrin derivative, a crown ether derivative, a calixarene derivative, a cyclophane derivative, a cyclic peptide derivative, a metallic ion, a chromophore, a fluorescent material, a phosphor, a radioactive material, and a catalyst, the method comprising:

(a) preparing an affinity chromatography column filled with a solid phase bound to a ligand as a stationary phase;

(b) supplying a mixture containing the compound of formula (1) below or the material bound to the compound into the affinity chromatography column;

(c) washing the affinity chromatography column with a washing solution; and

(d) loading a mobile phase solvent into the affinity chromatography column to separate and purify the compound of formula (1) below or the material bound to the ligand,

where n, X, A₁, and A₂ are the same as defined in claim 1.

19. The method of claim 18, further comprising binding the ligand to the solid phase before operation (a).

20. The method of claim 18, further comprising binding the compound of said formula (1) and the material between operations (a) and (b).

21. The method of claim 18, wherein the mobile phase solvent is selected from the group consisting of methanol, trifluoracetic acid, triethylamine, methylene chloride, chloroform, dimethylformamide, dimethyl sulfoxide, toluene, acetonitrile, xylene, chlorobenzine, tetrahydrofurane, diethylether, ethanol, diglycol ether, silicon, supercritical carbon dioxide, ionic liquids, N-methylpyrrolidine, pyridine, water, ammonium hydroxide, and dioxane.

22. The method of claim 18, wherein the washing solution is selected from the group consisting of methanol, trifluoracetic acid, triethylamine, methylene chloride, chloroform, dimethylformamide, dimethyl sulfoxide, toluene, acetonitrile, xylene, chlorobenzine, tetrahydrofurane, diethylether, ethanol, diglycol ether, silicon, supercritical carbon dioxide, ionic liquids, N-methylpyrrolidine, pyridine, water, ammonium hydroxide, and dioxane.

23. A sensor chip comprising a compound of formula (1) below bound to a first material and a ligand bound to a second material, wherein one of the first and second materials is a solid phase, and the other is selected from the group consisting of an enzyme including histidine, cystein, or tryptophane, a substrate, a substrate analogue, a suppressor, a coenzyme, an antibody, an antigen, a virus, cell lectin, a polysaccharide, a glucoprotein, a cell surface receptor, a nucleic acid, a complementary base sequence, histone, a nucleic acid polymerase, a nucleic acid binding protein, ATP, ADP, a hormone, a vitamine, a receptor, a carrier protein, glutathione, a GST fusion protein, a metallic ion, a polyHIS fusion protein, a natural protein, and a combination thereof,

24. The sensor chip of claim 23, wherein the solid phase is a gold thin film, a silver thin film, or an ITO-coated glass.

25. A solid-catalyst complex comprising a compound of formula (1) below bound to a first material and a ligand bound to a second material, wherein one of the first and second materials is a solid phase, and the other is a catalyst,

26. The solid-catalyst complex of claim 25, wherein the solid phase is selected from the group consisting of a polymer, a resin, a magnetic material, a silicagel, a polymer- or gold-coated silicagel, a zirconium oxide, a monolithic polymer, a polymer-coated magnetic particle, a gold thin film, a silver thin film, glass, an ITO-coated glass, silicon, a metal electrode, a nanorod, a nanotube, a nanowire, curdlan gum, cellulose, a nylon film, sepharose, and sephadex.

27. The solid-catalyst complex of claim 26, wherein the solid phase is polystyrene resin or polymer-coated silicagel.

28. The solid-catalyst complex of claim 25, wherein the catalyst is a Grubbs catalyst, a radical initiator, or a combination thereof.

29. The solid-catalyst complex of claim 25, wherein the catalyst is selected from the group consisting of cellulase, hemicellulase, peroxidase, protease, amylase, xylanase, lipase, esterase, cutinase, pectinase, keratinase, reductase, oxidase, phenoloxidase, lipoxigenase, ligninase, pullulanase, arabinosidase, hyaluronidase, and a combination thereof.