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

doi:10.1016/j.talanta.2009.03.007

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

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	54-61
Number of pages	8
Journal	Talanta
Volume	79
Issue number	1
DOIs	https://doi.org/10.1016/j.talanta.2009.03.007
Publication status	Published - 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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10.1016/j.talanta.2009.03.007

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@article{b843f4af18ca4b7fa13007acc943c2c0,

title = "Synthesis and binding properties of carboxylphenyl-modified calix[4]arenes and cytochrome c",

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.",

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

author = "An, {Wen Ting} and Yong Jiao and Sun, {Xiao Hua} and Zhang, {Xiao Ling} and Chuan Dong and Shuang, {Shao Min} and Xia, {Ping Fang} and WONG, {Ricky M S}",

note = "Funding Information: This work was supported by the Natural Science Foundation of China (No.90813018), the Youth Foundation of Shanxi Province (No. 2006021009), and Hong Kong Baptist University, Faculty Research Grant (FRG/08-09/II-16). Helpful suggestions by anonymous referees are also gratefully acknowledged. ",

year = "2009",

month = jun,

day = "30",

doi = "10.1016/j.talanta.2009.03.007",

language = "English",

volume = "79",

pages = "54--61",

journal = "Talanta",

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TY - JOUR

T1 - Synthesis and binding properties of carboxylphenyl-modified calix[4]arenes and cytochrome c

AU - An, Wen Ting

AU - Jiao, Yong

AU - Sun, Xiao Hua

AU - Zhang, Xiao Ling

AU - Dong, Chuan

AU - Shuang, Shao Min

AU - Xia, Ping Fang

AU - WONG, Ricky M S

N1 - Funding Information: This work was supported by the Natural Science Foundation of China (No.90813018), the Youth Foundation of Shanxi Province (No. 2006021009), and Hong Kong Baptist University, Faculty Research Grant (FRG/08-09/II-16). Helpful suggestions by anonymous referees are also gratefully acknowledged.

PY - 2009/6/30

Y1 - 2009/6/30

N2 - 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.

AB - 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.

KW - Calix[4]arene carboxylphenyl derivatives

KW - Cytochrome c

KW - Fluorescence spectroscopy

KW - Protein binding

KW - Synthesis

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U2 - 10.1016/j.talanta.2009.03.007

DO - 10.1016/j.talanta.2009.03.007

M3 - Journal article

C2 - 19376343

AN - SCOPUS:64649101751

SN - 0039-9140

VL - 79

SP - 54

EP - 61

JO - Talanta

JF - Talanta

IS - 1

ER -

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

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