Proteasome inhibition and cytostatic effects on human cancer cells by pyrazolone-enamines: a combined crystallographic, structural and computational study

Yan, Xingchen; Xu, Jiakun; Wu, Xiaojing; Zhang, Zhongyu; Zhang, Xia; Yu, Fan; Bi, Caifeng

doi:10.1039/c4nj01906g

Cited by 11 publications

(7 citation statements)

References 47 publications

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“…For decades, Schiff bases have been considered important ligands due to their coordination chemistry, and they can be easily prepared and linked with a different kind of metal ions 18 . Due to the existence of an amine group, analogous to the natural biological systems, Schiff bases show a crucial role in observing the conversion mechanism and racemization reaction in biological systems 19 – 25 . Schiff bases have been used for various essential biological activities including antitumor, anti HIV, antibacterial, antifertility activities, antimosquito larval, antiinflammatory, and anticancer 26 – 33 .…”

Section: Introductionmentioning

confidence: 99%

In vitro cytotoxicity activity of novel Schiff base ligand–lanthanide complexes

Andiappan

Sanmugam

Easwaramoorthy

et al. 2018

Sci Rep

130

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A Schiff base ligand (SBL), N2, N3-bis (anthracen-9-ylmethylene) pyridine-2, 3-diamine, was synthesized through the condensation of 2,6-diaminopyridine and anthracene-9-carbaldehyde using a 1:2 ratio. 1H NMR spectra confirmed the observation of non-involvement aromatic carboxylic proton in SBL. A novel series of lanthanide (i.e., praseodymium (Pr), erbium (Er), and ytterbium (Yb))-based SBL metal complexes was successfully synthesized, and their functional groups were elaborately demonstrated using UV–visible, Fourier transform infrared (FT-IR), and fluorescence spectroscopy analyses. FT-IR spectral studies revealed that SBL behaved as a bidentate ligand and it was structured with metal ions by the two azomethine nitrogens. The synthesized SBL-based metal complexes were elaborately performed for cytotoxicity activity versus Vero, human breast cancer (MCF7), and cervical (HeLa) anticancer cell lines.

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Section: Introductionmentioning

confidence: 99%

In vitro cytotoxicity activity of novel Schiff base ligand–lanthanide complexes

Andiappan

Sanmugam

Easwaramoorthy

et al. 2018

Sci Rep

130

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“…[150][151][152] They have been extensively used as key intermediates in organic synthesis [153][154][155] and as ligands in coordination chemistry, [156][157][158] and can be synthons in bioactive natural products. [16,[162][163][164][165][166][167][168][169][170][171][172] Ag reat deal of evidence has been collected by using various spectroscopic techniques such and X-ray analyses, showing that b-enaminones are stabilized in the tautomeric form A.T hus, the RAHB can be responsible for the observedu sual equilibrium shift towards the Z-isomer. [16,[162][163][164][165][166][167][168][169][170][171][172] Ag reat deal of evidence has been collected by using various spectroscopic techniques such and X-ray analyses, showing that b-enaminones are stabilized in the tautomeric form A.T hus, the RAHB can be responsible for the observedu sual equilibrium shift towards the Z-isomer.…”

Section: Synthesis Of B-enaminonesmentioning

confidence: 99%

“…[171] X-ray analysis showedt hat all of them adopted the RAHB-supported pyrazolone-enamine tautomeric form in the solid state. [171] X-ray analysis showedt hat all of them adopted the RAHB-supported pyrazolone-enamine tautomeric form in the solid state.…”

Section: Synthesis Of B-enaminonesmentioning

confidence: 99%

“…They have been extensively used as key intermediates in organic synthesis and as ligands in coordination chemistry, and can be synthons in bioactive natural products . β‐Enaminones are related to β‐diketones, containing the RAHB system described in Scheme . A great deal of evidence has been collected by using various spectroscopic techniques such and X‐ray analyses, showing that β‐enaminones are stabilized in the tautomeric form A .…”

Section: Rahb As a Driving Force In Synthesismentioning

confidence: 99%

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Resonance‐Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials

Mahmudov

Pombeiro

2016

Chemistry A European J

140

100

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Resonance-assisted hydrogen bonding (RAHB), a concept introduced by Gilli and co-workers in 1989, concerns a kind of intramolecular H-bonding strengthened by a conjugated π-system, usually in 6-, 8-, or 10-membered rings. This Review highlights the involvement of RAHB as a driving force in the synthesis of organic, coordination, and organometallic compounds, as a handy tool in the activation of covalent bonds, and in starting moieties for synthetic transformations. The unique roles of RAHB in molecular recognition and switches, E/Z isomeric resolution, racemization and epimerization of amino acids and chiral amino alcohols, solvatochromism, liquid-crystalline compounds, and in synthons for crystal engineering and polymer materials are also discussed. The Review can provide practical guidance for synthetic chemists that are interested in exploring and further developing RAHB-assisted synthesis and design of materials.

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“…Creaven et al, 14 reported that the coumarin-derived Schiff bases and their copper (II) complexes, were cytotoxic to the breast cancer-derived MCF-7 mammalian cell line, at concentrations which were comparable to the cytotoxic activity of the commercially used drug, mitoxantrone. Apart from this, there are most of the Schiff base shows a crucial role in observing the conversion mechanism and racemization reaction in biological systems [15][16][17][18][19][20][21] . Many study reports state that there is a wide number of Schiff bases have been used for various essential biological activities, including antitumor, anti-HIV, antibacterial, antifertility activities, antimosquito larval, anti-inflammatory, and anticancer [22][23][24][25][26][27][28][29] .…”

mentioning

confidence: 99%

Untitled

2020

IJPSR

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Coumarin and its analogs have a wide range of attention in the treatment of hormone-dependent breast cancer by blocking the formation of estrogen through the inhibition of estrogen receptor. However, the Schiff bases are an important class of compounds with structural similarities of natural biological substances and also due to their presence of imine (-N=CH-), which have an impact on a biological system. Considering the above all facts, the present research work is aimed to design the series of building blocks of coumarin Schiff base moiety as target candidates for estrogen receptor. The designed molecules ensured their reliability through the in-silico drug designing model and subjected to a preliminary study by screening their violation of Lipinski rule of five, if any, predicted for their ADMET profile study by using online available tools. Later an attempt was made to synthesize the proposed compounds, and structural elucidation was done by IR, NMR, and Mass spectroscopy. Besides to this, an in-vitro cytotoxicity study by using human breast cancer cell lines also carried out to evaluate the anti-tumor potency of the synthesized coumarin conjugates as a promising candidate for treating the breast cancer. The results obtained from these tools show there is no Lipinski rule violation, and no toxicity is predicted for these synthesized compounds. Thus, the designed coumarin Schiff base derivatives might serve as the best leads for treating the breast cancer, which is additionally confirmed by performing their docking study via Accelrys discovery studio for inhibiting the production of estrogen. INTRODUCTION: There is a cancer burden worldwide and have been raised to 18.1 million of new cases, and among them, 9.6 million deaths were recorded in the year of 2018.

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Proteasome inhibition and cytostatic effects on human cancer cells by pyrazolone-enamines: a combined crystallographic, structural and computational study

Abstract: Interactions are possibly through hydrogen bonding of the pyrazolone ring and the hydroxyl, or the intercalation of conjugated plane.

Cited by 11 publications

References 47 publications

In vitro cytotoxicity activity of novel Schiff base ligand–lanthanide complexes

In vitro cytotoxicity activity of novel Schiff base ligand–lanthanide complexes

Resonance‐Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials

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