Molecularly imprinted polymers selective for nitrosamines and method of preparing the same

• US 8,807,142 B2
• Filed: 11/21/2006
• Issued: 08/19/2014
• Est. Priority Date: 05/24/2004
• Status: Expired due to Fees

• Current Assignee: British American Tobacco Limited (British American Tobacco PLC)
• Original Assignee: British American Tobacco Limited (British American Tobacco PLC)
• Inventors: Bhattacharyya, Sumita, Rees, Anthony, Sellergren, Brje, Widstrand, Christine, McAdam, Kevin
• Primary Examiner(s): Crispino, Richard
• Assistant Examiner(s): NGUYEN, PHU HOANG
• Application Number:
  US11/604,003
• Publication Number:
  US 20070186940A1
• Time in Patent Office: 2,828 Days
• Field of Search: None
• 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 comprises reactive sites configured to bind selectively to a tobacco-specific nitrosamine but lacking the nitrosamine moiety imprinted structure;

wherein the polymer reactive sites comprise imprints corresponding to one of 4-(methylpropenyl-amino)-1-pyridin-3-yl-butan-1-ol and pyridine carbinol; and

wherein said molecularly imprinted polymer does not retain nicotine.

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 imprinted structure comprises a stereo-chemical configuration corresponding to an isosteric analogue of a nicotine-derived nitrosamine.

4. The molecularly imprinted polymer according to claim 1, wherein the polymer reactive sites comprise imprints corresponding to a compound which includes a substructure of the tobacco-specific nitrosamine.

5. A kit, comprising:

a molecularly imprinted polymer according to claim 1; and

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

6. The molecularly imprinted polymer according to claim 1, selective for the nicotine-derived nitrosamine NNAL.

7. The molecularly imprinted polymer according to claim 1, wherein the polymer reactive sites comprise imprints corresponding to an enamine analogue of a nicotine-derived nitrosamine.

8. The molecularly imprinted polymer according to claim 1, wherein the polymer reactive sites comprise imprints corresponding to a sulfonamide analogue of a nicotine-derived nitrosamine.

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

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

removing the isosteric analogue of a tobacco specific nitrosamine from the molecularly imprinted polymer; and

wherein the analogue is selected from the group consisting of 4-(methylpropenyl-amino)-1-pyridin-2-yl-butan-1-ol (4 MPAPB) and pyridine carbinol.

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

11. The method according to claim 9, wherein the functional monomer is selected from a group consisting of methacrylic acid (MAA), TFMAA, vinylbenzoic acid, and itaconic acid.

12. The method according to claim 9, where the crosslinker is selected from a group consisting of ethylene glycol dimethacrylate (EDMA), trimethylopropane trimethacrylate (TRIM), and pentaerythriol tetraacrylate.

13. A molecularly imprinted polymer comprising engineered reactive sites targeted at a tobacco specific nitrosamine

wherein said sites selectively bind said tobacco specific nitrosamine;

wherein said molecularly imprinted polymer does not retain nicotine; and

wherein prior to exposure to said tobacco specific nitrosamine said molecularly imprinted polymer is substantially free of detectable traces of said tobacco specific nitrosamine.

14. The molecularly imprinted polymer according to claim 13 wherein said tobacco specific nitrosamine is selected from the group consisting of NNK, 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone;

NNN, N-Nitrosnornicotine;

NAB, N-nitrosoanabasine;

NAT, N-nitrosoanatabine;

iso-NNAL, 4-(Methylnitrosamino)-4-(3-pyridyl)-1-butanol.