Synthesis and evaluation of paramagnetic caffeic acid phenethyl ester (CAPE) analogs

Nagane, Masaki; Yamashita, Tadashi; Vörös, Patrik; Kálai, Tamás; Hideg, Kálmán; Bognár, Balázs

doi:10.1007/s00706-019-02458-8

Cited by 8 publications

(11 citation statements)

References 42 publications

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“…Human cervix carcinoma HeLa cells were maintained in DMEM supplemented with 10% fetal bovine serum at 37 • C and 5% CO 2 . To determine the toxicity of BM and SL-BM, the WST-1 cell viability assay was employed as described previously [26]. The cells (NIH3T3: 2000 per well; HeLa: 5000 per well) were seeded into all the wells of 96-well plates.…”

Section: Cell Viability Assaysmentioning

confidence: 99%

“…We have reported in several studies that the modification of biomolecules (caffeic acid phenethyl ester, resveratrol, and curcumin) with nitroxides for use as "in statu nascendi acting" antioxidants may be beneficial on their activity. For instance, better antioxidant, antiproliferative, anti-inflammatory and cell-protective compounds can be achieved by these modifications [26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Spin-Labelled Bergamottin: A Potent CYP3A4 Inhibitor with Antiproliferative Activity

Zsidó

Balog

Erős

et al. 2020

IJMS

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Bergamottin (BM, 1), a component of grapefruit juice, acts as an inhibitor of some isoforms of the cytochrome P450 (CYP) enzyme, particularly CYP3A4. Herein, a new bergamottin containing a nitroxide moiety (SL-bergamottin, SL-BM, 10) was synthesized; chemically characterized, evaluated as a potential inhibitor of the CYP2C19, CYP3A4, and CYP2C9 enzymes; and compared to BM and known inhibitors such as ketoconazole (KET) (3A4), warfarin (WAR) (2C9), and ticlopidine (TIC) (2C19). The antitumor activity of the new SL-bergamottin was also investigated. Among the compounds studied, BM showed the strongest inhibition of the CYP2C9 and 2C19 enzymes. SL-BM is a more potent inhibitor of CYP3A4 than the parent compound; this finding was also supported by docking studies, suggesting that the binding positions of BM and SL-BM to the active site of CYP3A4 are very similar, but that SL-BM had a better ∆Gbind value than that of BM. The nitroxide moiety markedly increased the antitumor activity of BM toward HeLa cells and marginally increased its toxicity toward a normal cell line. In conclusion, modification of the geranyl sidechain of BM can result in new CYP3A4 enzyme inhibitors with strong antitumor effects.

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Section: Cell Viability Assaysmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Spin-Labelled Bergamottin: A Potent CYP3A4 Inhibitor with Antiproliferative Activity

Zsidó

Balog

Erős

et al. 2020

IJMS

Self Cite

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“…The trolox-equivalent antioxidant capacity (TEAC) of the prepared flavonoid-carotenoid conjugates (16)(17)(18)(19)(20)(21)(22)(23)(24)(25) was investigated towards ABTS •+ radical cation in aqueous ethanolic solution (see the experimental section) [31]. The synthetized compounds showed significantly higher TEAC values than their parent flavonoids ( Figure 3, Table 2); the exceptions were the conjugates of 8′-apo-β- Zeaxanthin conjugated with one daidzein (18) or chrysin (23) was found to be weaker antioxidants than zeaxanthin; however, its bistriazole derivatives (17 and 22) exceeded the parent zeaxanthin.…”

Section: Measurement Of Antioxidant Capacitymentioning

confidence: 99%

“…A literature procedure [31] was applied with modifications. The 2,2 -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS •+ ) was produced in aqueous solution by reacting ABTS •+ in 7 mM and potassium persulfate in 2.45 mM concentrations.…”

Section: Assay For the Antioxidant Activity Of The Carotenoids/teac Amentioning

confidence: 99%

Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

et al. 2020

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Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in new amphipathic structures. 7-Azidohexyl ethers of daidzein and chrysin were prepared in five steps, and their azide-alkyne [4 + 2] cycloaddition with pentynoates of 8′-apo-β-carotenol, zeaxanthin, and capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however, were found to exhibit a synergistic enhancement in antioxidant capacities. ECD (electronic circular dichroism) and UV-vis analysis of zeaxanthin–flavonoid conjugates revealed that they form different optically active J-aggregates in acetone/water and tetrahydrofuran/water mixtures depending on the solvent ratio and type of the applied aprotic polar solvent, while the capsanthin derivatives showed no self-assembly. The zeaxanthin bis-triazole conjugates with daidzein and with chrysin, differing only in the position of a phenolic hydroxyl group, showed significantly different aggregation profile upon the addition of water.

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“…Since most single-target drugs have shown unmet results in alleviating the symptoms of PD, it is necessary to further study drugs from multifactorial pathways underlying neuronal degeneration [7]. Caffeic acid phenethyl ester (CAPE), a natural compound extracted from propolis of honeybee hives, has a variety of biological activities, such as antioxidative, anti-inflammatory, and antiatherosclerotic [8]. Previous studies have shown that CAPE has an excellent multi-target neuroprotective effect, which could significantly improve the behavioral animal models of neurodegenerative diseases through regulating several different levels in the signal pathways [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

A Novel Synthetic Precursor of Styryl Sulfone Neuroprotective Agents Inhibits Neuroinflammatory Responses and Oxidative Stress Damage through the P38 Signaling Pathway in the Cell and Animal Model of Parkinson’s Disease

Guo

Ning

et al. 2021

Molecules

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A novel class of styryl sulfones were designed and synthesized as CAPE derivatives by our work team, which showed a multi-target neuroprotective effect, including antioxidative and anti-neuroinflammatory properties. However, the underlying mechanisms remain unclear. In the present study, the anti-Parkinson’s disease (PD) activity of 10 novel styryl sulfone compounds was screened by the cell viability test and the NO inhibition test in vitro. It was found that 4d exhibited the highest activity against PD among them. In a MPTP-induced mouse model of PD, the biological activity of 4d was validated through suppressing dopamine neurotoxicity, microglial activation, and astrocytes activation. With compound 4d, we conducted the mechanistic studies about anti-inflammatory responses through inhibition of p38 phosphorylation to protect dopaminergic neurons, and antioxidant effects through promoting nuclear factor erythroid 2-related factor 2 (Nrf2). The results revealed that 4d could significantly inhibit 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine/1-methyl-4-phenylpyridinium (MPTP/MPP+)-induced p38 mitogen-activated protein kinase (MAPK) activation in both in vitro and in vivo PD models, thus inhibiting the NF-κB-mediated neuroinflammation-related apoptosis pathway. Simultaneously, it could promote Nrf2 nuclear transfer, and upregulate the expression of antioxidant phase II detoxification enzymes HO-1 and GCLC, and then reduce oxidative damage.

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Synthesis and evaluation of paramagnetic caffeic acid phenethyl ester (CAPE) analogs

Cited by 8 publications

References 42 publications

Synthesis of Spin-Labelled Bergamottin: A Potent CYP3A4 Inhibitor with Antiproliferative Activity

Synthesis of Spin-Labelled Bergamottin: A Potent CYP3A4 Inhibitor with Antiproliferative Activity

Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

A Novel Synthetic Precursor of Styryl Sulfone Neuroprotective Agents Inhibits Neuroinflammatory Responses and Oxidative Stress Damage through the P38 Signaling Pathway in the Cell and Animal Model of Parkinson’s Disease

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