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

Wen Ting An, Yong Jiao, Xiao Hua Sun, Xiao Ling Zhang, Chuan Dong, Shao Min Shuang*, Ping Fang Xia, Ricky M S WONG

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

9 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)54-61
Number of pages8
Issue number1
Publication statusPublished - 30 Jun 2009

Scopus Subject Areas

  • Analytical Chemistry

User-Defined Keywords

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


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