Fluorogen-peptide conjugates with tunable aggregation-induced emission characteristics for bioprobe design

Ruoyu Zhang; Youyong Yuan; Jing Liang; Ryan T.K. Kwok; Qing Zhu; Guangxue Feng; Junlong Geng; Ben Zhong Tang; Bin Liu

doi:10.1021/am5036048

Fluorogen-peptide conjugates with tunable aggregation-induced emission characteristics for bioprobe design

Ruoyu Zhang, Youyong Yuan, Jing Liang, Ryan T.K. Kwok, Qing Zhu, Guangxue Feng, Junlong Geng, Ben Zhong Tang, Bin Liu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

Fluorogens with aggregation-induced emission (AIE) characteristics are attracting intense research interest, and an AIE-peptide conjugate strategy has been reported for developing turn-on probes based on hydrophilic peptide ligands. To build a model also suitable for hydrophobic ligands, we propose to fine-tune the AIE characteristics for probe design. In this work, an iconic AIE fluorogen tetraphenylethene (TPE) was designed to conjugate with peptide fragments containing different numbers of aspartic acid (D) units. Relationships between the numbers of D and the hydrophilicity, optical properties, and aggregate sizes and the AIE characteristics of TPE-peptide conjugates were investigated carefully. Five carboxyl groups were found to be the threshold to "turn off" the fluorescence of TPE. As a proof-of-concept, TPE-SS-D₅ containing a cleavable disulfide bond was synthesized for thiol turn-on detection. The validated tunable AIE characteristic offers new opportunities to design fluorescence turn-on probes based on hydrophobic recognition elements and AIE fluorogens.

Original language	English
Pages (from-to)	14302-14310
Number of pages	9
Journal	ACS applied materials & interfaces
Volume	6
Issue number	16
DOIs	https://doi.org/10.1021/am5036048
Publication status	Published - 27 Aug 2014
Externally published	Yes

Keywords

aggregation-induced emission
fluorescent probes
light-up probe
tetraphenylethene
thiol detection

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10.1021/am5036048

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abstract = "Fluorogens with aggregation-induced emission (AIE) characteristics are attracting intense research interest, and an AIE-peptide conjugate strategy has been reported for developing turn-on probes based on hydrophilic peptide ligands. To build a model also suitable for hydrophobic ligands, we propose to fine-tune the AIE characteristics for probe design. In this work, an iconic AIE fluorogen tetraphenylethene (TPE) was designed to conjugate with peptide fragments containing different numbers of aspartic acid (D) units. Relationships between the numbers of D and the hydrophilicity, optical properties, and aggregate sizes and the AIE characteristics of TPE-peptide conjugates were investigated carefully. Five carboxyl groups were found to be the threshold to {"}turn off{"} the fluorescence of TPE. As a proof-of-concept, TPE-SS-D5 containing a cleavable disulfide bond was synthesized for thiol turn-on detection. The validated tunable AIE characteristic offers new opportunities to design fluorescence turn-on probes based on hydrophobic recognition elements and AIE fluorogens.",

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author = "Ruoyu Zhang and Youyong Yuan and Jing Liang and Kwok, {Ryan T.K.} and Qing Zhu and Guangxue Feng and Junlong Geng and Tang, {Ben Zhong} and Bin Liu",

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AU - Zhang, Ruoyu

AU - Yuan, Youyong

AU - Liang, Jing

AU - Kwok, Ryan T.K.

AU - Zhu, Qing

AU - Feng, Guangxue

AU - Geng, Junlong

AU - Tang, Ben Zhong

AU - Liu, Bin

PY - 2014/8/27

Y1 - 2014/8/27

N2 - Fluorogens with aggregation-induced emission (AIE) characteristics are attracting intense research interest, and an AIE-peptide conjugate strategy has been reported for developing turn-on probes based on hydrophilic peptide ligands. To build a model also suitable for hydrophobic ligands, we propose to fine-tune the AIE characteristics for probe design. In this work, an iconic AIE fluorogen tetraphenylethene (TPE) was designed to conjugate with peptide fragments containing different numbers of aspartic acid (D) units. Relationships between the numbers of D and the hydrophilicity, optical properties, and aggregate sizes and the AIE characteristics of TPE-peptide conjugates were investigated carefully. Five carboxyl groups were found to be the threshold to "turn off" the fluorescence of TPE. As a proof-of-concept, TPE-SS-D5 containing a cleavable disulfide bond was synthesized for thiol turn-on detection. The validated tunable AIE characteristic offers new opportunities to design fluorescence turn-on probes based on hydrophobic recognition elements and AIE fluorogens.

AB - Fluorogens with aggregation-induced emission (AIE) characteristics are attracting intense research interest, and an AIE-peptide conjugate strategy has been reported for developing turn-on probes based on hydrophilic peptide ligands. To build a model also suitable for hydrophobic ligands, we propose to fine-tune the AIE characteristics for probe design. In this work, an iconic AIE fluorogen tetraphenylethene (TPE) was designed to conjugate with peptide fragments containing different numbers of aspartic acid (D) units. Relationships between the numbers of D and the hydrophilicity, optical properties, and aggregate sizes and the AIE characteristics of TPE-peptide conjugates were investigated carefully. Five carboxyl groups were found to be the threshold to "turn off" the fluorescence of TPE. As a proof-of-concept, TPE-SS-D5 containing a cleavable disulfide bond was synthesized for thiol turn-on detection. The validated tunable AIE characteristic offers new opportunities to design fluorescence turn-on probes based on hydrophobic recognition elements and AIE fluorogens.

KW - aggregation-induced emission

KW - fluorescent probes

KW - light-up probe

KW - tetraphenylethene

KW - thiol detection

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ER -

Fluorogen-peptide conjugates with tunable aggregation-induced emission characteristics for bioprobe design

Abstract

Keywords

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