Synthesis, cytotoxicity and computational study of novel protoberberine derivatives

Simić, Milena; Damjanović, Ana B.; Kalinić, Marko D.; Tasić, Gordana; Erić, Suzana; Antić-Stanković, Jelena; Savić, Vladimir

doi:10.2298/jsc150525090s

Cited by 6 publications

(3 citation statements)

References 66 publications

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“…Starting from isoquinoline, diene 4 was prepared in several high yielding steps as reported previously. 41,42 Scheme 2. Emetine and some related derivatives.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

Simić¹,

Petković²,

Jovanović³

et al. 2017

JSCS

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Pd-catalysed arylation-acetoxylation cascade, a previously reported methodology, was applied in the functionalisation of unsymmetrical dienes. Both explored classes of compounds, isoquinoline and β-carboline-derived dienes, afforded single regioisomers. Although further improvements of the process are necessary, primarily due to lower yields, the described functionalisation of the studied compounds might be useful in the synthesis of emetine and related naturally occurring compounds.

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“…Starting from isoquinoline, diene 4 was prepared in several high yielding steps as reported previously. 41,42 Scheme 2. Emetine and some related derivatives.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

Simić¹,

Petković²,

Jovanović³

et al. 2017

JSCS

Self Cite

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“…Within this procedure, a cubic grid box and grid maps were created in order to represent the active region in which the native molecular structure is embedded. 35 A grid of 40 points in x-, y-and z-direction with grid spacing of 0.375 Å was built centred on a ligand. The maximum number of energy evaluations was 2.500.000.…”

Section: Molecular Dockingmentioning

confidence: 99%

Molecular docking study on biomolecules isolated from endophytic fungi

Ignjatović

Đajić

Krmar

et al. 2021

JSCS

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Recently, growing interest is devoted to investigation of compounds with antimicrobial activity due to rising cases of resistance of microbes to known therapy. Reliable and versatile source of novel drug discovery was recently found among endophytic fungi. Up to now, the research usually enclosed with in vitro evaluation of antimicrobial activity and chemical structure elucidation of biomolecules extracted from fungal material. Therefore, this research was designed as an extension to previous investigations of endophytic fungi growing on conifer needles by means of conducting a molecular docking study. The in silico methods were used with the main goal to make a contribution to the understanding of the mechanisms underlying the interaction of biomolecules isolated from fungus Phomopsis species and eight different types of receptors that belong to usually multidrug resistant bacterial pathogens. The results revealed valuable interactions with receptors 3G7B (Staphylococcus aureus?s gyrase B), 1F0K (1.9 ? structure of Escherichia Coli?s transferase) and 1SHV (Klebsiella pneumoniae?s SHV-1 ? -lactamase) thus pointing out to the receptors which trigger antibiotic response upon activation by the most potent compounds 325-3, 325-5, phomoenamide and phomol. These findings also recommended further discovery of novel potent and broad-spectrum antibiotics based on the structure of selected molecules.

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“…Cancer is a lethal disease typically caused by mutations that result in uncontrolled cell growth that subsequently invades surrounding tissues; such systemic metastasis is now the second leading cause of death worldwide [1,2]. Natural products from many species (including microorganisms, marine organisms, and other plants) have proved valuable resources for securing molecular treatments for cancer [3][4][5][6][7][8][9][10][11][12]. Indeed, many anti-cancer drugs derived from natural products (such as paclitaxel, doxorubicin, and rapamycin) are currently either in clinical use or preclinical evaluation to treat cancer patients [4,5,13].…”

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confidence: 99%

Raphanus sativus Sprout Causes Selective Cytotoxic Effect on p53-Deficient Human Lung Cancer Cells in vitro

Baeka

Rohb

Choi

et al. 2017

Natural Product Communications

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Raphanus sativus L. (Brassicaceae) is widely consumed in many different forms worldwide. Its sprouts, in particular, are commonly consumed as a health food. R. sativus sprout has recently been shown to have anti-tumor activity on human colon cancer cells, suggesting that it may have potential use in cancer prevention and treatment. The extent of this anti-tumor activity and its underlying mechanisms, however, remain to be investigated in other types of cancer cells. In this study, we showed that the MeOH extract from R. sativus sprout exhibits significant but variable cytotoxic effects on human lung adenocarcinoma cells depending on their p53 status. The MeOH extract decreased the viability of p53-deleted human lung cancer cells (H1299 and Calu-6) by inducing apoptosis; this effect, however, did not occur for wild-type p53 cancer cells (A549), for cells expressing a p53 mutant lacking the C terminus (H1264), or for non-tumor fibroblast cells (NIH3T3). Phytochemical analyses of the MeOH extract allowed us to identify and isolate β-sitosterol as a major component of the MeOH extract. Direct treatment with β-sitosterol significantly reduced the viability of Calu-6 cells, suggesting that it may, in part, contribute to R. sativus sprout's anti-tumor activity. This work provides experimental evidence for a novel biological application of R. sativus sprout in treating human lung cancer, and it identifies the main component involved in this effect, further supporting its potential use as a functional food for cancer management.

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Synthesis, cytotoxicity and computational study of novel protoberberine derivatives

Cited by 6 publications

References 66 publications

Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

Molecular docking study on biomolecules isolated from endophytic fungi

Raphanus sativus Sprout Causes Selective Cytotoxic Effect on p53-Deficient Human Lung Cancer Cells in vitro

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