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 molecularly imprinted polymer intermediate, comprising: a crosslinked polymer made from monomers which are chemically bonded to each other, and a template having Formula (I):
wherein R 1 is selected from the group consisting of H, C 1-6 alkyl, substituted C 1-6 alkyl, and a halo substituted C 1-6 alkyl; R 2 is selected from the group consisting of 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 the group consisting of H, C 1-6 alkyl, and substituted C 1-6 alkyl; and R 3 is selected from the group consisting of 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, a C 4-7 cycloalkoxy ring, a hydroxy substituted C 4-7 cycloalkyl ring, or a carboxylic group substituted C 4-7 cycloalkyl; and R 3 is selected from the group consisting of H, C 1-6 alkoxy, and substituted C 1-6 alkyl,
wherein the crosslinked polymer defines a plurality of cavities, wherein at least one of the cavities comprises the template having Formula (I), and
wherein the at least one cavity is sized and/or shaped to allow an aflatoxin to be boundable therein when empty.
2. The molecularly imprinted polymer intermediate of claim 1 , wherein the template having Formula (I) is selected from the group consisting of 4-(chloromethyl)-5,7-dimethoxy coumarin, 5,7-dimethoxycyclo pentenon[2,3-c]coumarin, and any combination thereof.
3. The molecularly imprinted polymer intermediate of claim 1 , wherein the monomers are methacrylic acid, 2-vinylpyridine, 2-hydroxyethylmethacrylate, or any combination thereof.
4. The molecularly imprinted polymer intermediate of claim 1 , wherein the crosslinked polymer comprises a polymer network formed by monomers and a crosslinker.
5. The molecularly imprinted polymer intermediate of claim 1 , wherein the template having Formula (I) and the monomers are used in a molar ratio of from about 100:1 to about 1:100.
6. The molecularly imprinted polymer intermediate of claim 4 , wherein the monomers and the crosslinker are used in a molar ratio of from about 1:4.1 to about 1:10.
7. The molecularly imprinted polymer intermediate of claim 1 , wherein the at least one cavity has a capacity to form a complex with an aflatoxin to bind the aflatoxin therein.
8. The molecularly imprinted polymer intermediate of claim 1 , wherein the template having Formula (I) is an isolated compound that has a formula of:
9. The molecularly imprinted polymer intermediate of claim 1 , wherein R 1 is H; R 2 is selected from the group consisting of halo, CH 2 C(O)OR′, and CH(C(O)OR′) 2 , wherein R′ is selected from the group consisting of H or C 1-6 alkyl; and R 3 is a C 1-6 alkoxy group.
10. The molecularly imprinted polymer intermediate of claim 1 , wherein the at least one cavity has complementary shape and stereochemistry to the template having Formula (I) used to make the cavity.
11. The molecularly imprinted polymer intermediate of claim 1 , wherein the crosslinked polymer comprises a three-dimensional polymer network formed by 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, wherein the at least one cavity has a capacity to form a complex with an aflatoxin to bind the aflatoxin therein.
12. The molecularly imprinted polymer intermediate of claim 1 , wherein the template having Formula (I) is an isolated compound selected from the group consisting of:
and any combination thereof.