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Detection/quantification of amyloid aggregation in solution using the novel fluorescent benzofuranone-derivative compounds as amyloid fluorescent probes: synthesis and in vitro characterization

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Abstract

Neurodegenerative diseases are characterized by the presence of amyloid deposition. Thioflavin T (ThT) has been one of the molecules of choice to attempt the detection of the amyloid deposits, but ThT is unable to cross blood–brain barrier, due to its low lipophilicity. Therefore, there is strong motivation to design and develop new compounds for in vitro fibril detection as well as for in vivo amyloid imaging. Additionally, the importance and critical role of oxidative stress in the onset/progression of some neurodegenerative disorders, and therefore, the efficacy of aurone compounds in inhibiting the resulting toxicity have been frequently reported. In this study, we report the synthesis of some benzofuranone compounds and examine their antioxidant inhibitory property. Furthermore, to establish the potential detection of synthesized compounds to amyloid aggregates, their in vitro binding to some non-disease related amyloidogenic proteins were characterized. Analyses of the in vitro binding studies showed that compounds 3 and 4 bind to the fibril structures successfully while compounds 1, 2 and 5 indicated a low affinity binding to amyloid. Additionally, compounds 3 and 4 exhibited very good antioxidant properties. Furthermore, these compounds have a great potential as fluorescent probes for detecting amyloid aggregation for further investigations.

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Abbreviations

AD:

Alzheimer’s disease

MS:

Mass spectrometry

ROS:

Reactive oxygen species

ThT:

Thioflavin T

TEM:

Transmission electron microscopy

AFM:

Atomic force microscopy

PMSF:

Phenyl methyl sulphonyl fluoride

DMSO:

Dimethyl sulphoxide

TFE:

2,2,2-Trifluoroethanol

TMB:

3,3′,5,5′-Tetramethylbenzidine

TMS:

Tetramethylsilane

SDS-PAGE:

Sodium dodecyl sulfate polyacrylamide gel electrophoresis

β-Lg:

β-Lactoglobulin

BSA:

Bovine serum albumin

DPPH:

2,2-Diphenyl-1-picrylhydrazyl radical

FRAP:

Ferric reducing antioxidant power

PET:

Positron emission tomography

PCs:

Phenolic compounds

BBB:

Blood brain barrier

CR:

Congo red

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Authors and Affiliations

  1. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Sirvan Abbasbeigi, Seyyed Abolghasem Ghadami & Reza Khodarahmi

  2. Department of Biology and Biochemistry, Faculty of Science, Islamic Azad University, Sanandaj, Iran

    Sirvan Abbasbeigi

  3. Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Hadi Adibi

  4. Nano Drug Delivery Research Center, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Sajad Moradi

  5. Department of Stem Cells and Developmental Biology, Cell Science Research Center, Royan Institute for Stem Cell Biology and Technology, ACECR, Tehran, Iran

    Seyyed Abolghasem Ghadami

  6. Department of Pharmacognosy and Biotechnology, Faculty of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah, Iran

    Reza Khodarahmi

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  1. Sirvan Abbasbeigi
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  2. Hadi Adibi
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  3. Sajad Moradi
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Correspondence to Seyyed Abolghasem Ghadami or Reza Khodarahmi.

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Abbasbeigi, S., Adibi, H., Moradi, S. et al. Detection/quantification of amyloid aggregation in solution using the novel fluorescent benzofuranone-derivative compounds as amyloid fluorescent probes: synthesis and in vitro characterization. J IRAN CHEM SOC 16, 1225–1237 (2019). https://doi.org/10.1007/s13738-019-01599-1

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