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

• US 7,479,254 B2
• Filed: 04/20/2006
• Issued: 01/20/2009
• 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: Hwang, Iiha, Kim, Kimoon, Baek, Kangkyun, Park, Kyeng Min, Selvapalam, Narayanan, Ko, Young Ho, Nagarajan, Erumaipatty R., Kim, Jeeyeon
• Primary Examiner(s): Riley; Jezia
• Application Number:
  US11/407,143
• Publication Number:
  US 20070092867A1
• Time in Patent Office: 1,006 Days
• Field of Search: 422/61, 422/68.1, 424/486, 424/489, 424/278.1, 424/280, 435/6, 435/7.1, 435/7.2
• US Class Current: 422/400
• 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,

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.