Imprinted polymers prepared with stoichiometric template-monomer complexes:: Efficient binding of ampicillin from aqueous solutions

被引:99
作者
Lübke, C [1 ]
Lübke, M [1 ]
Whitcombe, MJ [1 ]
Vulfson, EN [1 ]
机构
[1] Inst Food Res, Norwich NR4 7UA, Norfolk, England
关键词
D O I
10.1021/ma000467u
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Two new functional monomers for molecular imprinting, 5-(4"'-vinyl)benzyloxy-1,3-bis[2'(3 ",3 ",4 ",4 "-tetramethyl-2 ",5 "-dioxaborolanyl)phenylcarbomoyl]benzene (3) and 2-(4-vinylphenyloxy)-3,5,6-trichlorobenzoquinone (4), designed to interact with carboxylate and amino groups, respectively, were synthesized. NMR titrations confirmed the interactions of 3 with tertabutylammonium acetate and ampicillin carboxylate in d(6)-DMSO and of 4 with the free amino group of ampicillin in the same solvent. Polymers mere prepared, using DMSO or THF as porogen, imprinted with ampicillin carboxylate using 3 and 4 present in the polymerization mixture in only stoichiometric amounts. The polymer made in DMSO was shown to bind ampicillin from aqueous buffer at pH 8.0 with two populations of binding sites, the first characterized by K-d = (3.0 +/- 0.3) x 10(-5) mol/L at a capacity of 5.8 +/- 0.3 mu mol/g and the second by K-d = (9.6 +/- 1.1) x 10(-4) mol/L and 48 +/- 3.4 mu mol/g.
引用
收藏
页码:5098 / 5105
页数:8
相关论文
共 87 条
[1]   Imprinted polymers as protecting groups for regioselective modification of polyfunctional substrates [J].
Alexander, C ;
Smith, CR ;
Whitcombe, MJ ;
Vulfson, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6640-6651
[2]   Application of molecular imprinting to the development of aqueous buffer and organic solvent based radioligand binding assays for (S)-propranolol [J].
Andersson, LI .
ANALYTICAL CHEMISTRY, 1996, 68 (01) :111-117
[3]   MIMICS OF THE BINDING-SITES OF OPIOID RECEPTORS OBTAINED BY MOLECULAR IMPRINTING OF ENKEPHALIN AND MORPHINE [J].
ANDERSSON, LI ;
MULLER, R ;
VLATAKIS, G ;
MOSBACH, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (11) :4788-4792
[4]   FORMATION OF BIMOLECULAR AND TERMOLECULAR COMPLEXES OF TETRAHALO-PARA-BENZOQUINONES WITH A VARIETY OF NONAROMATIC DONORS [J].
ANDREWS, LJ ;
KEEFER, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2163-2166
[5]  
BARTSCH RA, 1998, ACS S SER, V703
[6]   DESIGNED CATALYSTS - A SYNTHETIC NETWORK POLYMER THAT CATALYZES THE DEHYDROFLUORINATION OF 4-FLUORO-4-(P-NITROPHENYL)BUTAN-2-ONE [J].
BEACH, JV ;
SHEA, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) :379-380
[7]   Recognition in molecularly imprinted polymer alpha(2)-adrenoreceptor mimics [J].
Berglund, J ;
Nicholls, IA ;
Lindbladh, C ;
Mosbach, K .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (18) :2237-2242
[8]   MOLECULAR-COMPLEX FORMATION BETWEEN BRIDGEHEAD AMINES AND QUINONES [J].
CAMPBELL, MJM ;
DEMETRIOU, B ;
JONES, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (07) :917-921
[9]   A glucose-sensing polymer [J].
Chen, GH ;
Guan, ZB ;
Chen, CT ;
Fu, LT ;
Sundaresan, V ;
Arnold, FH .
NATURE BIOTECHNOLOGY, 1997, 15 (04) :354-357
[10]   Self-assembling capsules [J].
Conn, MM ;
Rebek, J .
CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668