Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Synthesis and binding properties of carboxylphenyl-modified calix[4]arenes and cytochrome c

Language

English

Abstract

Two novel carboxylphenyl-modified calix[4]arenes, tetrakis-carboxylphenylcalix[4]arene (TCPC) and 1,3-bis-carboxylphenylcalix[4]arene (BCPC), as well as a corresponding analogue for comparison, tetrakis-phenylcalix[4]arene (TPC), have been synthesized by palladium-catalyzed Suzuki cross-coupling of arylboronic acid and tetrabromocalix[4]arene as a key step. The binding properties of these calix[4]arene derivatives with bovine heart cytochrome c (cyt c) in dimethylformamide (DMF) was investigated by fluorescence spectroscopy. The binding affinity in the order of TCPC > BCPC ≫ TPC reflects a clear dependence on the number of carboxyl ligating groups attached onto a receptor and suggests the electrostatic force may be the predominant factor driving the complexing process. The stable 1:1 complexes of TCPC and BCPC with cyt c were evidenced with the binding constants of 3.15 × 106 and 5.85 × 105 L mol-1, respectively. Due to a large overlap between the emission spectrum of TCPC and the absorption spectrum of cyt c, and a short interaction distance (estimated to be 5.6 nm) between them, the fluorescence quenching of TCPC upon complexation with cyt c is attributed to an efficient energy transfer. © 2009 Elsevier B.V. All rights reserved.

Keywords

Calix[4]arene carboxylphenyl derivatives, Cytochrome c, Fluorescence spectroscopy, Protein binding, Synthesis

Publication Date

2009

Source Publication Title

Talanta

Volume

79

Issue

1

Start Page

54

End Page

61

Publisher

Elsevier

DOI

10.1016/j.talanta.2009.03.007

ISSN (print)

00399140

ISSN (electronic)

18733573

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