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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE (Open Access)

The synthesis and application of a colour-switch β-arylethenesulfonyl fluoride fluorescent probe in the detection of serum albumin

Marie-Claire Giel A , Tze Cin Owyong A B and Yuning Hong https://orcid.org/0000-0002-8085-1651 A A *
+ Author Affiliations
- Author Affiliations

A Department of Biochemistry and Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Vic. 3086, Australia.

B School of Chemistry, The University of Melbourne, Parkville, Vic. 3010, Australia.

* Correspondence to: y.hong@latrobe.edu.au

Handling Editor: Curt Wentrup

Australian Journal of Chemistry 75(11) 877-883 https://doi.org/10.1071/CH22165
Submitted: 27 July 2022  Accepted: 26 September 2022   Published: 22 November 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

Proteins play a pivotal role in regulating important physiological processes and serve as important biomarkers for many diseases. Herein, we present a new strategy for bovine serum albumin (BSA) detection using a novel colour-switch fluorescent probe CPV-ESF ((E)-2-(4-((Z)-1-cyano-2-(4-(diethylamino)phenyl)vinyl)phenyl)ethene-1-sulfonyl fluoride). CPV-ESF reacts with nucleophilic amino acids of BSA via 1,4-Michael addition click chemistry to create a covalently linked CPV-ESF:BSA complex, which can be easily detected by a fluorescence colour-switch response. The sensing mechanism, sensitivity and selectivity of CPV-ESF for BSA detection as well as its application for cell imaging have been investigated.

Keywords: 1,4-Michael addition chemistry, aggregation-induced emission, BSA, click chemistry, fluorescence probe, protein detection.


References

[1]  Z Lv, J Liu, W Bai, S Yang, A Chen, A simple and sensitive label-free fluorescent approach for protein detection based on a perylene probe and aptamer. Biosens Bioelectron 2015, 64, 530.
         | A simple and sensitive label-free fluorescent approach for protein detection based on a perylene probe and aptamer.Crossref | GoogleScholarGoogle Scholar |

[2]  A Jahanban-Esfahlan, A Ostadrahimi, R Jahanban-Esfahlan, L Roufegarinejad, M Tabibiazar, R Amarowicz, Recent developments in the detection of bovine serum albumin. Int J Biol Macromol 2019, 138, 602.
         | Recent developments in the detection of bovine serum albumin.Crossref | GoogleScholarGoogle Scholar |

[3]  Q Hu, B Yao, TC Owyong, S Prashanth, C Wang, X Zhang, WWH Wong, Y Tang, Y Hong, Detection of urinary albumin using a ‘turn-on’ fluorescent probe with aggregation-induced emission characteristics. Chem Asian J 2021, 16, 1245.
         | Detection of urinary albumin using a ‘turn-on’ fluorescent probe with aggregation-induced emission characteristics.Crossref | GoogleScholarGoogle Scholar |

[4]  B Yao, M-C Giel, Y Hong, Detection of kidney disease biomarkers based on fluorescence technology. Mater Chem Front 2021, 5, 2124.
         | Detection of kidney disease biomarkers based on fluorescence technology.Crossref | GoogleScholarGoogle Scholar |

[5]  E Babu, P Muthu Mareeswaran, S Singaravadivel, J Bhuvaneswari, S Rajagopal, A selective, long-lived deep-red emissive ruthenium(ii) polypyridine complexes for the detection of BSA. Spectrochim Acta A Mol Biomol Spectrosc 2014, 130, 553.
         | A selective, long-lived deep-red emissive ruthenium(ii) polypyridine complexes for the detection of BSA.Crossref | GoogleScholarGoogle Scholar |

[6]  LA MacManus-Spencer, ML Tse, PC Hebert, HN Bischel, RG Luthy, Binding of perfluorocarboxylates to serum albumin: a comparison of analytical methods. Anal Chem 2010, 82, 974.
         | Binding of perfluorocarboxylates to serum albumin: a comparison of analytical methods.Crossref | GoogleScholarGoogle Scholar |

[7]  LL Zhang, FF Ma, YF Kuang, S Cheng, YF Long, QG Xiao, Highly sensitive detection of bovine serum albumin based on the aggregation of triangular silver nanoplates. Spectrochim Acta A Mol Biomol Spectrosc 2016, 154, 98.
         | Highly sensitive detection of bovine serum albumin based on the aggregation of triangular silver nanoplates.Crossref | GoogleScholarGoogle Scholar |

[8]  D Zhao, Q Zhang, Y Zhang, Y Liu, Z Pei, Z Yuan, S Sang, Sandwich-type surface stress biosensor based on self-assembled gold nanoparticles in PDMS film for BSA Detection. ACS Biomater Sci Eng 2019, 5, 6274.
         | Sandwich-type surface stress biosensor based on self-assembled gold nanoparticles in PDMS film for BSA Detection.Crossref | GoogleScholarGoogle Scholar |

[9]  T-Y Lin, C-H Hu, T-C Chou, Determination of albumin concentration by MIP-QCM sensor. Biosens Bioelectron 2004, 20, 75.
         | Determination of albumin concentration by MIP-QCM sensor.Crossref | GoogleScholarGoogle Scholar |

[10]  M-Y Wu, J-K Leung, L Liu, C Kam, KYK Chan, RA Li, S Feng, S Chen, A small-molecule AIE chromosome periphery probe for cytogenetic studies. Angew Chem Int Ed 2020, 59, 10327.
         | A small-molecule AIE chromosome periphery probe for cytogenetic studies.Crossref | GoogleScholarGoogle Scholar |

[11]  H Kobayashi, M Ogawa, R Alford, PL Choyke, Y Urano, New strategies for fluorescent probe design in medical diagnostic imaging. Chem Rev 2010, 110, 2620.
         | New strategies for fluorescent probe design in medical diagnostic imaging.Crossref | GoogleScholarGoogle Scholar |

[12]  LD Lavis, RT Raines, Bright ideas for chemical biology. ACS Chem Biol 2008, 3, 142.
         | Bright ideas for chemical biology.Crossref | GoogleScholarGoogle Scholar |

[13]  H Li, H Kim, J Han, V-N Nguyen, X Peng, J Yoon, Activity-based smart AIEgens for detection, bioimaging, and therapeutics: recent progress and outlook. Aggregate 2021, 2, 1.
         | Activity-based smart AIEgens for detection, bioimaging, and therapeutics: recent progress and outlook.Crossref | GoogleScholarGoogle Scholar |

[14]  M Kamiya, H Kobayashi, Y Hama, Y Koyama, M Bernardo, T Nagano, PL Choyke, Y Urano, An enzymatically activated fluorescence probe for targeted tumor imaging. J Am Chem Soc 2007, 129, 3918.
         | An enzymatically activated fluorescence probe for targeted tumor imaging.Crossref | GoogleScholarGoogle Scholar |

[15]  J Mei, H Tian, Most recent advances on enzyme‐activatable optical probes for bioimaging. Aggregate 2021, 2, 1.
         | Most recent advances on enzyme‐activatable optical probes for bioimaging.Crossref | GoogleScholarGoogle Scholar |

[16]  W Pham, Y Choi, R Weissleder, C-H Tung, Developing a peptide-based near-infrared molecular probe for protease sensing. Bioconjugate Chem 2004, 15, 1403.
         | Developing a peptide-based near-infrared molecular probe for protease sensing.Crossref | GoogleScholarGoogle Scholar |

[17]  K Mizusawa, Y Ishida, Y Takaoka, M Miyagawa, S Tsukiji, I Hamachi, Disassembly-driven turn-on fluorescent nanoprobes for selective protein detection. J Am Chem Soc 2010, 132, 7291.
         | Disassembly-driven turn-on fluorescent nanoprobes for selective protein detection.Crossref | GoogleScholarGoogle Scholar |

[18]  Y Hong, C Feng, Y Yu, J Liu, JWY Lam, KQ Luo, BZ Tang, Quantitation, visualization, and monitoring of conformational transitions of human serum albumin by a tetraphenylethene derivative with aggregation-induced emission characteristics. Anal Chem 2010, 82, 7035.
         | Quantitation, visualization, and monitoring of conformational transitions of human serum albumin by a tetraphenylethene derivative with aggregation-induced emission characteristics.Crossref | GoogleScholarGoogle Scholar |

[19]  S Thurley, L Röglin, O Seitz, Hairpin peptide beacon: dual-labeled PNA-peptide-hybrids for protein detection. J Am Chem Soc 2007, 129, 12693.
         | Hairpin peptide beacon: dual-labeled PNA-peptide-hybrids for protein detection.Crossref | GoogleScholarGoogle Scholar |

[20]  SM Borisov, OS Wolfbeis, Optical biosensors. Chem Rev 2008, 108, 423.
         | Optical biosensors.Crossref | GoogleScholarGoogle Scholar |

[21]  Y Hong, JWY Lam, BZ Tang, Aggregation-induced emission. Chem Soc Rev 2011, 40, 5361.
         | Aggregation-induced emission.Crossref | GoogleScholarGoogle Scholar |

[22]  RF Chen, JR Knutson, Mechanism of fluorescence concentration quenching of carboxyfluorescein in liposomes: energy transfer to non-fluorescent dimers. Anal Biochem 1988, 172, 61.
         | Mechanism of fluorescence concentration quenching of carboxyfluorescein in liposomes: energy transfer to non-fluorescent dimers.Crossref | GoogleScholarGoogle Scholar |

[23]  HN Kim, MH Lee, HJ Kim, JS Kim, J Yoon, A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. Chem Soc Rev 2008, 37, 1465.
         | A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions.Crossref | GoogleScholarGoogle Scholar |

[24]  L-J Fan, WE Jones Jr, A highly selective and sensitive inorganic/organic hybrid polymer fluorescence ‘turn-on’ chemosensory system for iron cations. J Am Chem Soc 2006, 128, 6784.
         | A highly selective and sensitive inorganic/organic hybrid polymer fluorescence ‘turn-on’ chemosensory system for iron cations.Crossref | GoogleScholarGoogle Scholar |

[25]  CWT Leung, Y Hong, S Chen, E Zhao, JWY Lam, BZ Tang, A photostable AIE luminogen for specific mitochondrial imaging and tracking. J Am Chem Soc 2013, 135, 62.
         | A photostable AIE luminogen for specific mitochondrial imaging and tracking.Crossref | GoogleScholarGoogle Scholar |

[26]  L Mao, Y Liu, S Yang, Y Li, X Zhang, Y Wei, Recent advances and progress of fluorescent bio-/chemosensors based on aggregation-induced emission molecules. Dyes Pigm 2019, 162, 611.
         | Recent advances and progress of fluorescent bio-/chemosensors based on aggregation-induced emission molecules.Crossref | GoogleScholarGoogle Scholar |

[27]  G-F Zha, S-M Wang, KP Rakesh, SNA Bukhari, HM Manukumar, HK Vivek, N Mallesha, H-L Qin, Discovery of novel arylethenesulfonyl fluorides as potential candidates against methicillin-resistant of Staphylococcus aureus (MRSA) for overcoming multidrug resistance of bacterial infections. Eur J Med Chem 2019, 162, 364.
         | Discovery of novel arylethenesulfonyl fluorides as potential candidates against methicillin-resistant of Staphylococcus aureus (MRSA) for overcoming multidrug resistance of bacterial infections.Crossref | GoogleScholarGoogle Scholar |

[28]  AJ Brouwer, N Herrero Álvarez, A Ciaffoni, H van de Langemheen, RMJ Liskamp, Proteasome inhibition by new dual warhead containing peptido vinyl sulfonyl fluorides. Bioorg Med Chem 2016, 24, 3429.
         | Proteasome inhibition by new dual warhead containing peptido vinyl sulfonyl fluorides.Crossref | GoogleScholarGoogle Scholar |

[29]  M-C Giel, S Zhang, Q Hu, D Ding, Y Tang, Y Hong, Synthesis of a β-arylethenesulfonyl fluoride-functionalized AIEgen for activity-based urinary trypsin detection. ACS Appl Bio Mater 2022, 5, 4321.
         | Synthesis of a β-arylethenesulfonyl fluoride-functionalized AIEgen for activity-based urinary trypsin detection.Crossref | GoogleScholarGoogle Scholar |

[30]  Giel M-C, Hong Y. The application of click chemistry in the design of aggregation-induced emission luminogens for activity-based sensing. In: Gu X, Tang BZ, editors Aggregation-Induced Emission: Applications in Biosensing, Bioimaging and Biomedicine. Vol. 1. Berlin, Germany: De Gruyter; 2022. pp. 53–82.
| Crossref |

[31]  TC OwYong, S Ding, N Wu, T Fellowes, S Chen, JM White, WWH Wong, Y Hong, Optimising molecular rotors to AIE fluorophores for mitochondria uptake and retention. Chem Commun 2020, 56, 14853.
         | Optimising molecular rotors to AIE fluorophores for mitochondria uptake and retention.Crossref | GoogleScholarGoogle Scholar |

[32]  S Sasaki, GPC Drummen, G Konishi, Recent advances in twisted intramolecular charge transfer (TICT) fluorescence and related phenomena in materials chemistry. J Mater Chem C 2016, 4, 2731.
         | Recent advances in twisted intramolecular charge transfer (TICT) fluorescence and related phenomena in materials chemistry.Crossref | GoogleScholarGoogle Scholar |