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Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.

Yokoyama T, Kosaka Y, Mizuguchi M
J Med Chem 57 8928-35 (2014)
Related entries: 4pwe, 4pwf, 4pwg, 4pwh, 4pwi, 4pwj, 4qrf

Cited: 19 times
EuropePMC logo PMID: 25314129

Abstract

Transthyretin (TTR) is a homotetrameric serum protein associated with amyloidoses such as familial amyloid polyneuropathy and senile systemic amyloidosis. The amyloid fibril formation of TTR can be inhibited through stabilization of the TTR tetramer by the binding of small molecules. In this study, we examined the inhibitory potency of caffeic acid phenethyl ester (CAPE) and its derivatives. Thioflavin T assay showed that CAPE suppressed the amyloid fibril formation of TTR. Comparative analysis of the inhibitory potencies revealed that phenethyl ferulate was the most potent among the CAPE derivatives. The binding of phenethyl ferulate and the selected compounds to TTR were confirmed by the 8-anilino-1-naphthalenesulfonic acid displacement and X-ray crystallography. It was also demonstrated that Bio 30, which is a CAPE-rich commercially available New Zealand propolis, inhibited TTR amyloidogenesis and stabilized the TTR tetramer. These results suggested that a propolis may be efficient for preventing TTR amyloidosis.

Reviews - 4pwk mentioned but not cited (1)

  1. Natural compounds as inhibitors of transthyretin amyloidosis and neuroprotective agents: analysis of structural data for future drug design. Ciccone L, Tonali N, Nencetti S, Orlandini E. J Enzyme Inhib Med Chem 35 1145-1162 (2020)


Reviews citing this publication (6)

  1. The A-Z of Zika drug discovery. Mottin M, Borba JVVB, Braga RC, Torres PHM, Martini MC, Proenca-Modena JL, Judice CC, Costa FTM, Ekins S, Perryman AL, Horta Andrade C. Drug Discov Today 23 1833-1847 (2018)
  2. Therapeutic Implications of Caffeic Acid in Cancer and Neurological Diseases. Alam M, Ahmed S, Elasbali AM, Adnan M, Alam S, Hassan MI, Pasupuleti VR. Front Oncol 12 860508 (2022)
  3. Uncovering the Neuroprotective Mechanisms of Curcumin on Transthyretin Amyloidosis. Ferreira N, Saraiva MJ, Almeida MR. Int J Mol Sci 20 E1287 (2019)
  4. Recent progresses in the pharmacological activities of caffeic acid phenethyl ester. Lv L, Cui H, Ma Z, Liu X, Yang L. Naunyn Schmiedebergs Arch Pharmacol 394 1327-1339 (2021)
  5. Kazakh Ziziphora Species as Sources of Bioactive Substances. Šmejkal K, Malaník M, Zhaparkulova K, Sakipova Z, Ibragimova L, Ibadullaeva G, Žemlička M. Molecules 21 E826 (2016)
  6. Molecular insight into the therapeutic potential of phytoconstituents targeting protein conformation and their expression. Tiwari V. Phytomedicine 52 225-237 (2019)

Articles citing this publication (12)

  1. Targeting Different Transthyretin Binding Sites with Unusual Natural Compounds. Ortore G, Orlandini E, Braca A, Ciccone L, Rossello A, Martinelli A, Nencetti S. ChemMedChem 11 1865-1874 (2016)
  2. Tetrabromobisphenol A Is an Efficient Stabilizer of the Transthyretin Tetramer. Iakovleva I, Begum A, Brännström K, Wijsekera A, Nilsson L, Zhang J, Andersson PL, Sauer-Eriksson AE, Olofsson A. PLoS One 11 e0153529 (2016)
  3. Structural Stabilization of Human Transthyretin by Centella asiatica (L.) Urban Extract: Implications for TTR Amyloidosis. Eze FN, Leelawatwattana L, Prapunpoj P. Biomolecules 9 E128 (2019)
  4. Discovery of γ-Mangostin as an Amyloidogenesis Inhibitor. Yokoyama T, Ueda M, Ando Y, Mizuguchi M. Sci Rep 5 13570 (2015)
  5. New Hydroxycinnamic Acid Esters as Novel 5-Lipoxygenase Inhibitors That Affect Leukotriene Biosynthesis. Boudreau LH, Boudreau LH, Lassalle-Claux G, Cormier M, Blanchard S, Doucet MS, Surette ME, Touaibia M. Mediators Inflamm 2017 6904634 (2017)
  6. Rational Design, Synthesis, Characterization and Evaluation of Iodinated 4,4'-Bipyridines as New Transthyretin Fibrillogenesis Inhibitors. Dessì A, Peluso P, Dallocchio R, Weiss R, Andreotti G, Allocca M, Aubert E, Pale P, Mamane V, Cossu S. Molecules 25 E2213 (2020)
  7. Letter Stability and crystal structures of His88 mutant human transthyretins. Yokoyama T, Hanawa Y, Obita T, Mizuguchi M. FEBS Lett 591 1862-1871 (2017)
  8. Modulating inhibitors of transthyretin fibrillogenesis via sulfation: polychlorinated biphenyl sulfates as models. Grimm FA, Grimm FA, Lehmler HJ, He X, Robertson LW, Duffel MW. Chem Biol Interact 228 1-8 (2015)
  9. Transthyretin Anti-Amyloidogenic and Fibril Disrupting Activities of Bacopa monnieri (L.) Wettst (Brahmi) Extract. Eze FN, Ingkaninan K, Prapunpoj P. Biomolecules 9 E845 (2019)
  10. Insight on the microscopic binding mechanism of bisphenol compounds (BPs) with transthyretin (TTR) based on multi-spectroscopic methods and computational simulations. Huang M, Huang X, Yong L, Jia D, Miao W, Liu H, Yi Z. Anal Bioanal Chem 414 3765-3780 (2022)
  11. Omega-3 PUFAs as a Dietary Supplement in Senile Systemic Amyloidosis. Ciccone L, Nencetti S, Rossello A, Barlettani L, Tonali N, Nieri P, Orlandini E. Nutrients 15 749 (2023)
  12. Peppermint extract inhibits protein aggregation. Kasi PB, Molnár K, László L, Kotormán M. Biol Futur 72 367-372 (2021)


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