Cinnamic acid derivatives as the potential modulators of prion aggregation

Tishina, Sofia A.; Stroylov, Viktor S.; Zanyatkin, Ivan; Melnikova, Aleksandra; Muronetz, Vladimir I.; Stroylova, Yulia Yu.

doi:10.1016/j.mencom.2017.09.021

Cited by 7 publications

(5 citation statements)

References 12 publications

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“…Experimental studies confirmed the results of molecular modeling of the interaction of 3,4-DMCA with a prion monomer. Using various approaches, the effects of 3,4-DMCA, ferulic acid, and 7 chemical derivatives bearing different substituents in o -, m -, and p - positions of cinnamic acid were studied for anti-prion activity [ 119 , 144 ]. Among naturally occurring HCAs, the most promising effect was shown for 3,4-DMCA.…”

Section: Hydroxycinnamic Acid Derivatives Modulating the Pathologimentioning

confidence: 99%

“…In particular, it was shown that they suppress the pathological transformation of PrP under the closest to natural conditions—when preformed amyloid fibrils are added to PrP monomers, i.e., during so-called seeding. The studied derivatives were also able to increase the viability of SH-SY5Y neuroblastoma cells after the addition of prion oligomers, which indicates a decrease in prion neurotoxicity under the influence of some HCA derivatives [ 119 , 144 ].…”

Section: Hydroxycinnamic Acid Derivatives Modulating the Pathologimentioning

confidence: 99%

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Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

et al. 2020

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This review presents the main properties of hydroxycinnamic acid (HCA) derivatives and their potential application as agents for the prevention and treatment of neurodegenerative diseases. It is partially focused on the successful use of these compounds as inhibitors of amyloidogenic transformation of proteins. Firstly, the prerequisites for the emergence of interest in HCA derivatives, including natural compounds, are described. A separate section is devoted to synthesis and properties of HCA derivatives. Then, the results of molecular modeling of HCA derivatives with prion protein as well as with α-synuclein fibrils are summarized, followed by detailed analysis of the experiments on the effect of natural and synthetic HCA derivatives, as well as structurally similar phenylacetic and benzoic acid derivatives, on the pathological transformation of prion protein and α-synuclein. The ability of HCA derivatives to prevent amyloid transformation of some amyloidogenic proteins, and their presence not only in food products but also as natural metabolites in human blood and tissues, makes them promising for the prevention and treatment of neurodegenerative diseases of amyloid nature.

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Section: Hydroxycinnamic Acid Derivatives Modulating the Pathologimentioning

confidence: 99%

Section: Hydroxycinnamic Acid Derivatives Modulating the Pathologimentioning

confidence: 99%

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

et al. 2020

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“…For example, 3,4DMCA (3,4-dimethoxycinnamic acid) has higher solubility in water than curcumin. In our studies, it has been shown that some cinnamic acid derivatives prevent the pathological transformation of amyloidogenic proteins (alpha-synuclein and prion protein) [ 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…Interactions and anti-prion activity have been studied for several cinnamic acids, including 3,4DMCA, whose effect has been considerable on the biologically common compounds [ 9 , 10 ]. The ability of hydroxycinnamic acids to partially inhibit the oligomerization and formation of prion amyloid fibrils has been confirmed by various physicochemical methods, such as isothermal titration calorimetry, dynamic light scattering, thioflavin T fluorescence, and circular dichroism spectroscopy [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Hydroxycinnamic Acid Derivatives from Coffee Extracts Prevent Amyloid Transformation of Alpha-Synuclein

et al. 2022

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Earlier we showed that derivatives of hydroxycinnamic acids prevent amyloid transformation of alpha-synuclein and prion protein. The aim of this work was to determine the content of 3-hydroxycinnamic acid derivatives in coffee extracts and to evaluate their activity in relation to alpha-synuclein amyloid aggregation. Hydroxycinnamic acid derivatives were identified in aqueous and ethanol extracts of coffee beans by quantitative mass spectrometric analysis. Only 3,4-dimethoxycinnamic acid (13–53 μg/mL) was detected in significant amounts in the coffee extracts, while ferulic acid was present in trace amounts. In addition, 3-methoxy-4-acetamidoxycinnamic acid (0.4–0.8 μg/mL) was detected in the roasted coffee extracts. The half-maximum inhibitory concentrations of alpha-synuclein fibrillization reaction in the presence of coffee extracts, as well as inhibitory constants, were determined using thioflavin T assay. The inhibitory effect of black and green coffee extracts on alpha-synuclein fibrillization is dose-dependent, and in a pairwise comparison, the constants of half-maximal inhibition of fibrillization for green coffee extracts are comparable to or greater than those for black coffee. Thus, coffee extracts prevent pathological transformation of alpha-synuclein in vitro, probably due to the presence of 3,4-dimethoxycinnamic acid in them. Consequently, coffee drinks and coffee extracts can be used for the prevention of synucleinopathies including Parkinson’s disease.

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“…Cinnamic acid derivatives are widely used as flavors and fragrance 1,2 . During the last years, compounds holding a cinnamoyl scaffold attracted attention because of their biological activities combined with low toxicity [3][4][5][6][7][8] . However, several of these compounds have also shown cytotoxic [9][10][11][12][13][14] as well as antimicrobial [15][16][17][18][19][20] and anti-oxidant properties [21][22][23][24][25][26] .…”

Section: Introductionmentioning

confidence: 99%

Unexpected cytotoxicity of a triisopropylsilylated syringaldehyde derived cinnamic acid amide

et al. 2019

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A small series of substituted cinnamic acid amides was prepared and screened for their cytotoxic activity. As a rather astonishing and unprecedented result, compound 5 holding a triisopropylsilyl (TIPS) protecting group at position 4 of the aromatic ring was highly cytotoxic (EC50 = 3.2 mM for HT29 human colon adenocarcinoma cells) while analogs with a methoxy or hydroxyl group at this position were of low cytotoxicity or not cytotoxic at all.

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Cinnamic acid derivatives as the potential modulators of prion aggregation

Cited by 7 publications

References 12 publications

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

Hydroxycinnamic Acid Derivatives from Coffee Extracts Prevent Amyloid Transformation of Alpha-Synuclein

Unexpected cytotoxicity of a triisopropylsilylated syringaldehyde derived cinnamic acid amide

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