Molecularly imprinted polymers selective for nitrosamines and methods of using the same

• US 20070186940A1
• Filed: 11/21/2006
• Published: 08/16/2007
• Est. Priority Date: 05/24/2004
• Status: Active Grant

• Current Assignee: British American Tobacco Limited (British American Tobacco PLC)
• Original Assignee: British American Tobacco Limited (British American Tobacco PLC)
• Inventors: Sellergren, Borje, Rees, Anthony, Widstrand, Christine, McAdam, Kevin, Bhattacharyya, Sumita
• Granted Patent: US 8,807,142 B2
• Time in Patent Office: Days
• US Class Current: 131/334
• CPC Class Codes: A24B 15/24 by extraction; Tobacco extracts
• CPC Class Codes: A24B 15/245 Nitrosamines
• CPC Class Codes: A24D 3/02 Manufacture of tobacco smoke filters manufacture of paper or cellulosic materials for filters D21
• CPC Class Codes: A24D 3/067 characterised by functional properties
• CPC Class Codes: A24D 3/08 of organic materials as carrier or major constituent of ion exchange materials A24D3/12
• CPC Class Codes: B01D 15/3852 using imprinted phases or molecular recognition; using imprinted phases
• CPC Class Codes: B01J 20/268 Polymers created by use of a template, e.g. molecularly imprinted polymers
• CPC Class Codes: G01N 33/0098 Plants or trees wood G01N33/46

Abstract

A class of molecularly imprinted polymers that specifically recognizes and binds to nitrosamines members of which class are useful, for example, in analysis and separation of nitrosamines from biological fluids. Such molecularly imprinted polymers are also useful in methods of treating and manufacturing tobacco products and materials.

Claims

1. A molecularly imprinted polymer selective for at least one tobacco-specific nitrosamine, wherein said molecularly imprinted polymer is prepared using a tobacco-specific nitrosamine template or an isosteric analogue thereof.

2. The molecularly imprinted polymer according to claim 1, wherein said at least one tobacco-specific nitrosamine is derived from nicotine, nornicotine, anabasine or anatabine.

3. The molecularly imprinted polymer according to claim 1, wherein the polymer is prepared using an isosteric analog of a nicotine nitrosamine as the template.

4. The molecularly imprinted polymer according to claim 1, wherein the polymer is prepared using 4-(methylpropenyl-amino)-1-pyridin-3-yl-butan-1-ol as the template.

5. The molecularly imprinted polymer according to claim 1, wherein the polymer is prepared using pyridine carbinol as the template.

6. The molecularly imprinted polymer according to claim 1, wherein the polymer is prepared using a compound which includes a substructure of the tobacco-specific nitrosamine.

7. A kit, comprising:

a molecularly imprinted polymer selective for at least one tobacco-specific nitrosamine, wherein the polymer is prepared using a tobacco-specific nitrosamine template or an isosteric analogue thereof; and

instructions for using the polymer to perform at least one of detecting, quantifying, and separating nitrosamines in a sample.

8. A method of preparing a molecularly imprinted polymer, comprising:

co-polymerizing at least one functional monomer and at least one cross-linker in the presence of at least one tobacco-specific nitrosamine template or an isosteric analogue thereof in a polymerization medium containing at least one free radical initiator to produce the molecularly imprinted polymer bound to the tobacco-specific nitrosamine template or the isosteric analogue thereof; and

removing the template or the isosteric analogue thereof from the molecularly imprinted polymer.

9. The method according to claim 8, wherein the functional monomer exhibits acidic functionality.

10. The method according to claim 8, wherein the functional monomer is selected from a group consisting of methacrylic acid (MAA), TFMAA, vinylbenzoic acid, and itaconic acid.

11. The method according to claim 8, where the crosslinker is selected from a group consisting of ethylene glycol dimethacrylate (EDMA), trimethylopropane trimethacrylate (TRIM), and pentraerythritol tetraacrylate.

12. The method according to claim 8, wherein the analogue is selected from the group consisting of 4-(Methylpropenyl-amino)-1-pyridin-3-yl-butan-1-ol (4MPAPB) and pyridine carbinol.

13. A method of preparing a molecularly imprinted polymer comprising:

co-polymerizing a polymerization mixture and at least one tobacco-specific nitrosamine template or an isosteric analogue thereof in a homogeneous reaction medium; and

recovering suspended particles from the reaction medium.

14. A method of preparing a molecularly imprinted polymer comprising:

co-polymerizing a polymerization mixture and at least one tobacco-specific nitrosamine template or an isosteric analogue thereof in a heterogeneous reaction medium; and

recovering polymerized material from the heterogeneous reaction medium.

15. A method of determining if a sample of a tobacco product contains nitrosamines, comprising:

reacting the sample with a molecularly imprinted polymer under conditions that would allow binding of nitrosamines present in the sample to the molecularly imprinted polymer; and

evaluating whether the molecularly imprinted polymer has bound to any nitrosamines, wherein an evaluation resulting in observation of molecularly imprinted polymer bound to nitrosamines indicates that the sample contains nitrosamines.

16. A method of quantifying the amount of nitrosamines in a sample of a tobacco product, comprising:

reacting the sample with a molecularly imprinted polymer under conditions that would allow binding of nitrosamines present in the sample to the molecularly imprinted polymer; and

measuring the amount of nitrosamines bound to the molecularly imprinted polymer.

17. A method of treating a tobacco product to reduce the level of a targeted component therein comprising treating the tobacco product with a molecularly imprinted polymer.

18. The method according to claim 17, wherein the tobacco product is produced by thermal decomposition of a material containing tobacco, a tobacco substitute or a mixture thereof.

19. The method according to claim 18, wherein the tobacco product is produced by heating to a temperature below its combustion temperature.

20. The method according to claim 18, wherein the tobacco product is produced by combustion of the tobacco product.

21. The method according to claim 17, wherein the tobacco product is produced by contacting a material containing tobacco, a tobacco substitute or a mixture thereof with a solvent.

22. A method of manufacturing a tobacco material, comprising the steps of:

extracting nitrosamines from a material containing tobacco, a tobacco substitute or a mixture thereof by contacting said material with a solvent to produce an extract;

contacting the extract containing nitosamine with a molecularly imprinted polymer to reduce the level of nitorsamines in the extract.

23. A smoking article comprising:

a smoking material; and

a molecularly imprinted polymer found in thermal decomposition products of the smoking material.

24. The smoking article according to claim 23, wherein the molecularly imprinted polymer is selective for at least one volatile nitrosamine found in the vapor phase of thermal decomposition products of the smoking material.

25. A smoke filter comprising a molecularly imprinted polymer selective for at least one tobacco-specific nitrosamine.

26. The smoke filter according to claim 25, wherein the molecularly imprinted polymer is selective for at least one volatile nitrosamine found in the vapor phase of thermal decomposition products of tobacco or a tobacco substitute.