Aflatoxin templates, molecularly imprinted polymers, and methods of making and using the same
Molecularly imprinted polymers (MIPs) are materials exhibiting molecular recognition of a target molecule. MIPs are synthesized in the presence of an aflatoxin template, a mimic to the targeted molecule, used as an imprint that is further washed away with suitable solvent after completion of the polymerization process, leaving a cavity in the polymer of the same stereochemistry, functionality and morphology to the template. When the MIP encounters an aflatoxin, the molecule is bound in the cavity with a receptor-like affinity.
1. A template composition comprising:
(a) an aflatoxin template having Formula (I):
wherein
R 1 is selected from H, C 1-6 alkyl, substituted C 1-6 alkyl, and a halo substituted C 1-6 alkyl;
R 2 is selected from halo, C 1-6 alkyl, substituted C 1-6 alkyl, a halo substituted C 1-6 alkyl, CH 2 C(O)OR′, and CH(C(O)OR′) 2 ; wherein R′ is selected from H, C 1-6 alkyl, and substituted C 1-6 alkyl; and
R 3 is selected from H, C 1-6 alkoxy, and substituted C 1-6 alkyl, or
wherein R 1 together with R 2 form a C 4-7 cycloalkyl ring, a halo substituted C 4-7 cycloalkyl ring, an oxo substituted C 4-7 cycloalkyl ring, C 4-7 cycloalkoxy ring, a hydroxy substituted C 4-7 cycloalkyl ring and a carboxylic group substituted C 4-7 cycloalkyl; and R 3 is selected from H, C 1-6 alkoxy, and substituted C 1-6 alkyl;
(b) monomers which are chemically-bondable to each other; and
(c) a carrier.
2. The composition of claim 1 , wherein the aflatoxin template and the monomers are present in a molar ratio of from about 100:1 to about 1:100.
3. The composition of claim 1 , wherein the monomers are methacrylic acid, 2-vinylpyridine, 2-hydroxyethylmethacrylate, or any combinations thereof.
4. The composition of claim 1 , further comprising crosslinker.
5. The composition of claim 4 , wherein the crosslinker is ethylene glycol dimethacrylate, divinylbenzene, trimethylolpropane trimethacrylate, or any combination thereof.
6. The composition of claim 4 , wherein the monomers and the crosslinker are present in a molar ratio of from about 1:4.1 to about 1:10.
7. The composition of claim 1 , wherein the carrier comprises a solvent.
8. The composition of claim 7 , wherein the solvent is selected from the group consisting of acetonitrile, toluene, cyclohexane, polyvinyl alcohol in water solution, and a mixture of two or more of acetonitrile, toluene, cyclohexane, polyvinyl alcohol in water solution, or any combination thereof.
9. The composition of claim 1 , wherein the aflatoxin template of Formula (I) is selected from the group consisting of 4-(2-chloroethyl)-5,7-dimethoxy coumarin, 5,7-dimethoxycyclo pentenon[2,3-c]coumarin, or any combination thereof.
10. A complex of a crosslinked polymer made from monomers which are chemically bonded to each other and an aflatoxin template having Formula (I):
wherein
R 1 is selected from H, C 1-6 alkyl, substituted C 1-6 alkyl, and a halo substituted C 1-6 alkyl;
R 2 is selected from halo, C 1-6 alkyl, substituted C 1-6 alkyl, a halo substituted C 1-6 alkyl, CH 2 C(O)OR′, and CH(C(O)OR′) 2 ; wherein R′ is selected from H, C 1-6 alkyl, and substituted C 1-6 alkyl; and
R 3 is selected from H, C 1-6 alkoxy, and substituted C 1-6 alkyl, or wherein R 1 together with R 2 form a C 4-7 cycloalkyl ring, a halo substituted C 4-7 cycloalkyl ring, an oxo substituted C 4-7 cycloalkyl ring, C 4-7 cycloalkoxy ring, a hydroxy substituted C 4-7 cycloalkyl ring and a carboxylic group substituted C 4-7 cycloalkyl; and R 3 is selected from H, C 1-6 alkoxy, and substituted C 1-6 alkyl,
wherein the aflatoxin template is removable from the crosslinked polymer to form a cavity sized and/or shaped to allow an aflatoxin to be boundable therein.
11. The complex of claim 10 , wherein the aflatoxin template and the monomers are used in a molar ratio of from about 100:1 to about 1:100.
12. The complex of claim 10 , wherein the crosslinked polymer comprises a polymer network formed by the monomers and a crosslinker, wherein the monomers and the crosslinker are used in a molar ratio of from about 1:4.1 to about 1:10.
13. The complex of claim 10 , wherein the aflatoxin template of Formula (I) is selected from the group consisting of 4-(2-chloroethyl)-5,7-dimethoxy coumarin, 5,7-dimethoxycyclo pentenon[2,3-c]coumarin, or any combination thereof.