Recognition of caffeine in aqueous solutions

被引：44

作者：

Fiammengo, R ^{[1
]}

Crego-Calama, M ^{[1
]}

Timmerman, P ^{[1
]}

Reinhoudt, DN ^{[1
]}

机构：

[1] Univ Twente, Lab Supramol Chem & Technol, MESA Res Inst, NL-7500 AE Enschede, Netherlands

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 03期

关键词：

caffeine; noncovalent interactions; porphyrinoids; sensors; water chemistry;

D O I：

10.1002/chem.200390088

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Binding of caffeine in aqueous solutions has been achieved for the first time by using water-soluble, tetracationic peptide-porphyrin conjugates Zn-1 as the receptor molecules. The association constant for caffeine with receptor Zn-1 is in some cases as high as 6000 m(-1), only 5-6 times lower than the highest binding constant reported for an artificial caffeine receptor in low polarity aprotic solvents. The binding mechanism has been studied by a combination of experimental techniques such as UV-visible and NMR spectroscopy and microcalorimetry. Recognition of caffeine involves both stacking with the porphyrin ring and metal coordination. Subtle variations of the receptor structure affect the complexation. Receptors Zn-1 have also been investigated for the recognition of molecules structurally related to caffeine, for example, 1-methylimidazole. Selectivity towards oxopurine derivatives (caffeine and theophylline) have been found.

引用

页码：784 / 792

页数：9

共 52 条

[1] INTERACTIONS OF TETRAKIS(-MU-CARBOXYLATO)DIRHODIUM(II), AN ANTI-TUMOR AGENT, WITH NUCLEIC-ACID BASES - X-RAY CRYSTAL-STRUCTURES OF [RH2(ACETATO)4(THEOPHYLLINE)2] AND [RH2(ACETATO)4(CAFFEINE)2] [J].

AOKI, K ;

YAMAZAKI, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (04) :186-188

[2] Binding of caffeine by a synthetic co-receptor [J].

Ballester, P ;

Barceló, MA ;

Costa, A ;

Deyà, PM ;

Morey, J ;

Orell, M ;

Hunter, CA .

TETRAHEDRON LETTERS, 2000, 41 (20) :3849-3853

[3]

Carter SR, 2002, ADV MATER, V14, P667, DOI 10.1002/1521-4095(20020503)14:9<667::AID-ADMA667>3.0.CO

[4]

2-3

[5] The self-association of the black tea polyphenol theaflavin and its complexation with caffeine [J].

Charlton, AJ ;

Davis, AL ;

Jones, DP ;

Lewis, JR ;

Davies, AP ;

Haslam, E ;

Williamson, MP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (02) :317-322

[6]

Connors K. A., 1987, BINDING CONSTANTS ME, P141

[7] TRIPHENYLMETHYLPHOSPHONIUM TRICHLORO(CAFFEINE)PLATINUM(II), [P(C6H5)3(CH3)][PTCL3(CAFFEINE)], STRUCTURE AND ANTI-CANCER ACTIVITY [J].

CRAMER, RE ;

HO, DM ;

VANDOORNE, W ;

IBERS, JA ;

NORTON, T ;

KASHIWAGI, M .

INORGANIC CHEMISTRY, 1981, 20 (08) :2457-2461

[8] Aggregation and axial ligand exchange behavior of water-soluble pyrrole-beta brominated porphyrins [J].

DSouza, F ;

Deviprasad, GR ;

Zandler, ME .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (20) :3699-3703

[9] Non-covalent synthesis of calix[4]arene-capped porphyrins in polar solvents via ionic interactions [J].

Fiammengo, R ;

Timmerman, P ;

Huskens, J ;

Versluis, K ;

Heck, AJR ;

Reinhoudt, DN .

TETRAHEDRON, 2002, 58 (04) :757-764

[10] Detection of small organic analytes by fluorescing molecular switches [J].

Frauendorf, C ;

Jäschke, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (10) :2521-2524

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