Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues

Li, Qingyong; Jian, Chen; Luo, Shuyue; Xu, Jialin; Huang, Qiaoxian; Li, Tianyu

doi:10.1016/j.ejmech.2015.02.005

Cited by 63 publications

(37 citation statements)

References 35 publications

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“…The synthesized compounds (2a-d) were evaluated for antioxidant activity using the 2,2-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging method, according to a procedure reported previously, with slight modifications [8,14]. Quercetin and curcumin were used as the standards.…”

Section: Antioxidant Activitymentioning

confidence: 99%

“…Several series of symmetrical monocarbonyl analogs of curcumin (MACs), containing a cyclohexanone or cyclopentanone linker between the two phenyl rings, reportedly have superior anti-inflammatory and antioxidant activity, higher chemical stability, and improved pharmacokinetic profiles compared to curcumin [3,4]. On the other hand, several asymmetrical MAC (AMACs) reportedly exhibit potent anti-inflammatory, antioxidant, and antitumor activities [5][6][7][8]. Finally, our group reported that, while AMACs containing a morpholine Mannich base exhibit low antioxidant activity, two compounds exhibit potent anti-inflammatory activity [9].…”

Section: Introductionmentioning

confidence: 99%

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Anti-Inflammatory and Antioxidant Activity of Synthesized Mannich Base Derivatives of (2e,6e)-2-[(4-Hydroxy-3-Methoxyphenyl)methylidene]-6-(Phenyl Methylidene)cyclohexan-1-One

et al. 2019

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Objective: To further understand this compound, we synthesized and evaluated the antioxidant and anti-inflammatory activity of a series of itsMannich base derivatives.Methods: We synthesized the compounds via the previously reported Mannich reaction method. Their structures were elucidated by Fouriertransforminfrared,1H-NMR,13C-NMR, and high-resolution mass spectra. The derivatives’ anti-inflammatory and antioxidant activities were testedusing the inhibition of protein denaturation method and the 2,2-diphenyl-2-picrylhydrazyl free radical scavenging assay.Results: The IC50 values for the anti-inflammatory activity of the 2,6-dimethylmorpholine, pyrrolidine, 1-methylpiperazine, and dimethylamineMannich base derivatives 2a–d were 10.67, 10.72, 37.75, and 1.93 μM, respectively; for (2E,6E)-2-({4-hydroxy-3-methoxyphenyl}methylidene)-6-(phenylmethylidene)cyclohexan-1-one (1), diclofenac sodium, and curcumin, the IC50 values were 56.29, 1.52, and 8.43 μM, respectively. The IC50values for the antioxidant activity of compounds 2a–2d were 229.62, 57.29, 280.43, and 219.22 μM, respectively; for compound 1, quercetin, andcurcumin, the IC50 values were 144.22, 27.28, and 26.45 μM, respectively.Conclusion: Substituting Mannich bases into (2E,6E)-2-[(4-hydroxy-3-methoxyphenyl) methylidene]-6-(phenylmethylidene)cyclohexan-1-oneenhanced its anti-inflammatory activity, but lowered its antioxidant activity. Compound 2d, (2E,6E)-2-({3-[(dimethylamino)methyl]-4-hydroxy-5-methoxyphenyl}methylidene)-6-(phenyl methylidene)cyclohexan-1-one, exhibited potent anti-inflammatory activity comparable to diclofenacsodium and four times higher than curcumin. However, further investigation of this compound’s mechanism of action and toxicity is warranted.

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Section: Antioxidant Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Antioxidant Activity of Synthesized Mannich Base Derivatives of (2e,6e)-2-[(4-Hydroxy-3-Methoxyphenyl)methylidene]-6-(Phenyl Methylidene)cyclohexan-1-One

et al. 2019

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“…Our previous findings have revealed that terminal basic nitrogen-containing heteroaromatic rings are obviously beneficial to the enhanced cytotoxic and anti-proliferative potency and that the 1,5-diheteroarylpenta-1,4-dien-3-one is the most promising class of curcumin-based anti-prostate cancer agents, with the most potent compounds being over 100 folds more potent than curcumin against prostate cancer cell lines [6,7]. Most monoketone curcumin mimics are symmetric with two identical terminal aromatic rings, but a few of recent reports suggest that asymmetric monoketone curcumin mimics might exhibit more desirable biological profile as compared to the corresponding symmetric counterparts [10,11]. All 1,5-diheteroarylpenta-1,4-dien-3-ones previously reported by us are symmetric with two identical terminal nitrogen-containing heteroaromatic rings [7], but we have noticed from our previous data that different terminal heteroaromatic rings can bring in varied benefits to the scaffold of 1,5-diheteroarylpenta-1,4-dien-3-one.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies

Zhang

Guo

Chen

et al. 2017

European Journal of Medicinal Chemistry

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To further engineer dienones with optimal combinations of potency and bioavailability, thirty-four asymmetric 1,5-diarylpenta-1,4-dien-3-ones (25–58) have been designed and synthesized for the evaluation of their in vitro anti-proliferative activity in three human prostate cancer cell lines and one non-neoplastic prostate epithelial cell line. All these asymmetric dienones are sufficiently more potent than curcumin and their corresponding symmetric counterparts. The optimal dienone 58, with IC50 values in the range of 0.03–0.12 μM, is 636-, 219-, and 454-fold more potent than curcumin in three prostate cancer cell models. Dienones 28 and 49 emerged as the most promising asymmetric dienones that warrant further preclinical studies. The two lead compounds demonstrated substantially improved potency in cell models and superior bioavailability in rats, while exhibiting no acute toxicity in the animals at the dose of 10 mg/kg. Dienones 28 and 46 can induce PC-3 cell cycle regulation at the G0/G1 phase. However, dienone 28 induces PC-3 cell death in a different way from 46 even though they share the same scaffold, indicating that terminal heteroaromatic rings are critical to the action of mechanism for each specific dienone.

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“…Nowadays, some of the asymmetrical MACs (AMACs) with different constituents on the two phenyl rings have been developed and reported to show antioxidant, anti-inflammatory, antimicrobial [11][12][13][14][15] and antitumor properties [16]. However, the study of the Mannich bases of AMACs as an anti-cancer agent has never been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Activity of Diethylamine Mannich Base of Asymmetrical Mono-Carbonyl Curcumin Analogs against HeLa Cell Lines

Prasetyaningrum¹,

Bahtiar²,

Hayun³

2017

Preprint

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Synthesis and assessment of the antioxidant and antitumor properties of asymmetric curcumin analogues

Cited by 63 publications

References 35 publications

Anti-Inflammatory and Antioxidant Activity of Synthesized Mannich Base Derivatives of (2e,6e)-2-[(4-Hydroxy-3-Methoxyphenyl)methylidene]-6-(Phenyl Methylidene)cyclohexan-1-One

Anti-Inflammatory and Antioxidant Activity of Synthesized Mannich Base Derivatives of (2e,6e)-2-[(4-Hydroxy-3-Methoxyphenyl)methylidene]-6-(Phenyl Methylidene)cyclohexan-1-One

Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies

Synthesis and Antiproliferative Activity of Diethylamine Mannich Base of Asymmetrical Mono-Carbonyl Curcumin Analogs against HeLa Cell Lines

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