Synthesis and Biological Evaluation of Curcumin-Nitroxide-Based Molecular Hybrids as Antioxidant and Anti-Proliferative Agents

Bognár, Balázs; Kuppusamy, M. Lakshmi; Madan, Esha; Kálai, Tamás; Balog, Mária; Jekő, József; Kuppusamy, Periannan; Hideg, Kálmán

doi:10.2174/1871520617666170522124712

Cited by 4 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

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

Zsidó

Balog

Erős

et al. 2020

IJMS

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

Zsidó

Balog

Erős

et al. 2020

IJMS

View full text Add to dashboard Cite

show abstract

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

et al. 2019

View full text Add to dashboard Cite

The structure-activity relationships of newly prepared caffeates, containing nitroxide moieties as potential antioxidants have been investigated and compared to those of known natural (caffeic acid phenethyl ester, CAPE) and unnatural (N-acetylcysteine, paramagnetic alcohols) antioxidants. The in vitro antioxidant activity was tested by 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging, while assays of cell protection against reactive oxygen species were carried out in the presence of 2′,7′-dichlorofluorescein diacetate and H 2 O 2 . Paramagnetic esters without phenol motifs exhibited the lowest antioxidant activity, followed by paramagnetic alcohols with moderate activity. Among the compounds investigated, paramagnetic phenolic compounds were the best antioxidants. As the new paramagnetic CAPE analogs were less cytotoxic than CAPE at 10 µM in NIH3T3 fibroblast cells but had similar antioxidant activity, they can be considered promising antioxidants. Graphic abstract

show abstract

Selective Induction of Cellular Toxicity and Anti-tumor Efficacy by N-Methylpiperazinyl Diarylidenylpiperidone and its Pro-nitroxide Conjugate through ROS-mediated Mitochondrial Dysfunction and G2/M Cell-cycle Arrest in Human Pancreatic Cancer

Mast

Hinds

Tse

et al. 2020

Cell Biochem Biophys

View full text Add to dashboard Cite

Synthesis and Biological Evaluation of Curcumin-Nitroxide-Based Molecular Hybrids as Antioxidant and Anti-Proliferative Agents

Abstract: Among the compounds synthesized and investigated the spin-labeled curcumin and 3,5-bis(4-hydroxy-3-methoxybenzylidene)piperidin-4-one derivatives were the most effective antiproliferative and antioxidant derivatives.

Cited by 4 publications

References 0 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

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

Selective Induction of Cellular Toxicity and Anti-tumor Efficacy by N-Methylpiperazinyl Diarylidenylpiperidone and its Pro-nitroxide Conjugate through ROS-mediated Mitochondrial Dysfunction and G2/M Cell-cycle Arrest in Human Pancreatic Cancer

Contact Info

Product

Resources

About