Molecularly imprinted polymers selective for tobacco specific nitrosamines and methods of using same

• US 9,169,341 B2
• Filed: 10/20/2014
• Issued: 10/27/2015
• Est. Priority Date: 12/07/2006
• Status: Expired due to Fees

• Current Assignee: British American Tobacco (Investments) Limited (British American Tobacco PLC)
• Original Assignee: British American Tobacco (Investments) Limited (British American Tobacco PLC)
• Inventors: Rees, Anthony, Billing, Johan, Yilmaz, Ecevit
• Primary Examiner(s): CHEUNG, WILLIAM K
• Application Number:
  US14/518,074
• Publication Number:
  US 20150038648A1
• Time in Patent Office: 372 Days
• Field of Search: 525/279, 526/317.1, 526/319, 526/346
• US Class Current: 1/1
• CPC Class Codes: A24B 15/245 Nitrosamines
• CPC Class Codes: A24B 15/30 by organic substances A24B15/281 takes precedence
• CPC Class Codes: A24B 15/32 by acyclic compounds
• CPC Class Codes: A24D 3/14 of organic materials as additive 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: C08F 220/68 Esters
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/104 of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate

Abstract

A class of molecularly imprinted polymers that specifically recognizes and binds to TSNAs are useful, for example, in analysis and separation of TSNAs from biological fluids. Such 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 (TSNA), the polymer having been prepared using materials comprising:

a TSNA or a structural analogue thereof;

a neutral functional monomer; and

a hydrophobic cross-linker.

2. A polymer according to claim 1, wherein said structural analogue of a TSNA is an enamine analogue of a TSNA.

3. A polymer according to claim 1, wherein said structural analogue of a TSNA is an amide analogue of a TSNA.

4. A polymer according to claim 1, wherein said structural analogue of a TSNA is a sulfonamide analogue of a TSNA.

5. A polymer according to claim 1, wherein the polymer is selective for NNK.

6. A polymer according to claim 1, wherein the polymer is selective for NNA.

7. A polymer according to claim 1, wherein the polymer is selective for NNN.

8. A polymer according to claim 1, wherein the polymer is selective for NAB.

9. A polymer according to claim 1, wherein the polymer is selective for NAT.

10. A polymer according to claim 1, wherein the polymer is selective for NNAL.

11. A polymer according to claim 1, wherein the polymer is selective for iso-NNAL.

12. A polymer according to claim 1, wherein the polymer is selective for iso-NNAC.

13. A kit, comprising:

a molecularly imprinted polymer selective for at least one tobacco specific nitrosamine (TSNA), the polymer prepared using materials comprising;

a TSNA or a structural analogue thereof;

a neutral functional monomer; and

a hydrophobic cross-linker; and

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

14. A method of preparing a molecularly imprinted polymer selective for TSNAs, comprising:

co-polymerizing at least one neutral functional monomer and at least one hydrophobic cross-linker in the presence of at least one TSNA structural analogue in a polymerization medium containing at least one free radical initiator to produce a molecularly imprinted polymer bound to a TSNA structural analogue; and

removing the TSNA structural analogue from the molecularly imprinted polymer.

15. A molecularly imprinted polymer produced by the method of claim 14.