Novel Oxindole–Curcumin Hybrid Compound for Antioxidative Stress and Neuroprotection

Hirata, Yoko; Ito, Yuki; Takashima, Madoka; Yagyu, Kazuya; Oh‐hashi, Kentaro; Suzuki, Hiromi; Ono, Ken; Furuta, Kyoji; Sawada, Makoto

doi:10.1021/acschemneuro.9b00619

Cited by 28 publications

(22 citation statements)

References 37 publications

(62 reference statements)

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“…This yellow pigmented powder is derived from rhizome of turmeric via grinding [22]. It is responsible for the yellow color of turmeric and for a long time, this flavoring substance has been widely applied in different regions of Asia for treatment of various disorders [23][24][25][26]. The chemical formula of curcumin is n,1,7-bis-(3-hydroxy-4-methoxyphenyl)-1,6-heptadiene-3,5-dione.…”

Section: Curcumin: Structure and Pharmacokineticsmentioning

confidence: 99%

Polychemotherapy with Curcumin and Doxorubicin via Biological Nanoplatforms: Enhancing Antitumor Activity

et al. 2020

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Doxorubicin (DOX) is a well-known chemotherapeutic agent extensively applied in the field of cancer therapy. However, similar to other chemotherapeutic agents such as cisplatin, paclitaxel, docetaxel, etoposide and oxaliplatin, cancer cells are able to obtain chemoresistance that limits DOX efficacy. In respect to dose-dependent side effect of DOX, enhancing its dosage is not recommended for effective cancer chemotherapy. Therefore, different strategies have been considered for reversing DOX resistance and diminishing its side effects. Phytochemical are potential candidates in this case due to their great pharmacological activities. Curcumin is a potential antitumor phytochemical isolated from Curcuma longa with capacity of suppressing cancer metastasis and proliferation and affecting molecular pathways. Experiments have demonstrated the potential of curcumin for inhibiting chemoresistance by downregulating oncogene pathways such as MMP-2, TGF-β, EMT, PI3K/Akt, NF-κB and AP-1. Furthermore, coadministration of curcumin and DOX potentiates apoptosis induction in cancer cells. In light of this, nanoplatforms have been employed for codelivery of curcumin and DOX. This results in promoting the bioavailability and internalization of the aforementioned active compounds in cancer cells and, consequently, enhancing their antitumor activity. Noteworthy, curcumin has been applied for reducing adverse effects of DOX on normal cells and tissues via reducing inflammation, oxidative stress and apoptosis. The current review highlights the anticancer mechanism, side effects and codelivery of curcumin and DOX via nanovehicles.

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Section: Curcumin: Structure and Pharmacokineticsmentioning

confidence: 99%

Polychemotherapy with Curcumin and Doxorubicin via Biological Nanoplatforms: Enhancing Antitumor Activity

et al. 2020

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“…Several studies have reported that ROS scavenging and iron chelating chemicals such as α-tocopherol and deferoxamine prevent glutamate-or erastin-induced cell death in HT22 cells [21][22][23]. We examined whether ROS scavenging and iron chelating chemicals mitigated enhanced toxicity of sodium chlorate.…”

Section: Effect Of Ros Scavenging and Iron Chelating Chemicals On Sodmentioning

confidence: 99%

Reduced Sulfation Enhanced Oxytosis and Ferroptosis in Mouse Hippocampal HT22 Cells

et al. 2020

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Sulfation is a common modification of extracellular glycans, tyrosine residues on proteins, and steroid hormones, and is important in a wide variety of signaling pathways. We investigated the role of sulfation on endogenous oxidative stress, such as glutamate-induced oxytosis and erastin-induced ferroptosis, using mouse hippocampal HT22 cells. Sodium chlorate competitively inhibits the formation of 3′-phosphoadenosine 5′-phosphosulfate, the high energy sulfate donor in cellular sulfation reactions. The treatment of HT22 cells with sodium chlorate decreased sulfation of heparan sulfate proteoglycans and chondroitin sulfate proteoglycans. Sodium chlorate and β-d-xyloside, which prevents proteoglycan glycosaminoglycan chain attachment, exacerbated both glutamate- and erastin-induced cell death, suggesting that extracellular matrix influenced oxytosis and ferroptosis. Moreover, sodium chlorate enhanced the generation of reactive oxygen species and influx of extracellular Ca2+ in the process of oxytosis and ferroptosis. Interestingly, sodium chlorate did not affect antioxidant glutathione levels. Western blot analysis revealed that sodium chlorate enhanced erastin-induced c-Jun N-terminal kinase phosphorylation, which is preferentially activated by cell stress-inducing signals. Collectively, our findings indicate that sulfation is an important modification for neuroprotection against oxytosis and ferroptosis in neuronal hippocampal cells.

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“…Compounds with radical scavenger properties of curcumin have shown remarkable activities related to the activation of the antioxidant response element (ARE). This controls the expression of genes, whose protein products have key roles in cellular defense against the toxicity of electrophiles and ROS, providing neuroprotective effects [ 4 ]. In addition, several compounds have shown significant inhibitory activities against α-glucosidase (α-Gls) [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

An In Vitro and In Silico Study of Antioxidant Properties of Curcuminoid N-alkylpyridinium Salts: Initial Assessment of Their Antitumoral Properties

et al. 2022

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In this work, we report the synthesis of curcuminoids with ionic liquid characteristics, obtained by incorporating alkyl-substituted pyridinium moiety rather than one phenyl group through a two-step process. The antioxidant capacity of the obtained compounds was evaluated in vitro by 1,1-diphenyl-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) assays, showing that some derivatives are more potent than curcumin. Pyridine curcuminoids (group 4) and curcuminoid N-alkylpyridinium salts with two methoxyl groups in the phenyl ring (group 7), presented the best antioxidant capacity. The experimental results were rationalized by density functional theory (DFT) calculations of the bond dissociation enthalpy (BDE) for O–H in each compound. The computational calculations allowed for insight into the structural–antioxidant properties relationship in these series of compounds. BDEs, obtained in the gas phase and water, showed a notable impact of water solvation on the stabilization of some radicals. The lower values of BDEs in the water solution correspond to the structurally related compounds curcuminoid-pyridine 4c and curcuminoid pyridinium salt 7a, which is consistent with the experimental results. Additionally, an assessment of cell viability and cell migration assays was performed for human colon cancer (HT29), human breast cancer (MCF7) cells, in addition to NIH3T3 murine fibroblast, as a model of non-cancer cell type. These compounds mainly cause inhibition of the cell migration observed in MCF7 cancer cells without affecting the non-tumoral NIH3T3 cell line: Neither in viability nor in migration.

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Novel Oxindole–Curcumin Hybrid Compound for Antioxidative Stress and Neuroprotection

Cited by 28 publications

References 37 publications

Polychemotherapy with Curcumin and Doxorubicin via Biological Nanoplatforms: Enhancing Antitumor Activity

Polychemotherapy with Curcumin and Doxorubicin via Biological Nanoplatforms: Enhancing Antitumor Activity

Reduced Sulfation Enhanced Oxytosis and Ferroptosis in Mouse Hippocampal HT22 Cells

An In Vitro and In Silico Study of Antioxidant Properties of Curcuminoid N-alkylpyridinium Salts: Initial Assessment of Their Antitumoral Properties

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