Design, Synthesis, Computational Investigations, and Antitumor Evaluation of N-Rhodanine Glycosides Derivatives as Potent DNA Intercalation and Topo II Inhibition against Cancer Cells.

Nitrogen and sulfur glycosylation was carried out via the reaction of rhodanine (1) with α-acetobromoglucose 3 under basic conditions. Deacetylation of the protected nitrogen nucleoside 4 was performed with CH3ONa in CH3OH without cleavage of the rhodanine ring to afford the deprotected nitrogen nucleoside 6. Further, deacetylation of the protected sulfur nucleoside 5 was performed with CH3ONa in CH3OH with the cleavage of the rhodanine ring to give the hydrolysis product 7. The protected nitrogen nucleosides 11a-f were produced by condensing the protected nitrogen nucleoside 4 with the aromatic aldehydes 10a-f in C2H5OH while using morpholine as a secondary amine catalyst. Deacetylation of the protected nitrogen nucleosides 11a-f was performed with NaOCH3/CH3OH without cleavage of the rhodanine ring to afford the deprotected nitrogen nucleosides 12a-f. NMR spectroscopy was used to designate the anomers' configurations. To examine the electrical and geometric properties derived from the stable structure of the examined compounds, molecular modeling and DFT calculations using the B3LYP/6-31+G (d,p) level were carried out. The quantum chemical descriptors and experimental findings showed a strong connection. The IC50 values for most compounds were very encouraging when evaluated against MCF-7, HepG2, and A549 cancer cells. Interestingly, IC50 values for 11a, 12b, and 12f were much lower than those for Doxorubicin (7.67, 8.28, 6.62 µM): (3.7, 8.2, 9.8 µM), (3.1, 13.7, 21.8 µM), and (7.17, 2.2, 4.5 µM), respectively. Against Topo II inhibition and DNA intercalation, when compared to Dox (IC50 = 9.65 and 31.27 µM), compound 12f showed IC50 values of 7.3 and 18.2 µM, respectively. In addition, compound 12f induced a 65.6-fold increase in the rate of apoptotic cell death in HepG2 cells, with the cell cycle being arrested in the G2/M phase as a result. Additionally, it upregulated the apoptosis-mediated genes of P53, Bax, and caspase-3,8,9 by 9.53, 8.9, 4.16, 1.13, and 8.4-fold change, while it downregulated the Bcl-2 expression by 0.13-fold. Therefore, glucosylated Rhodanines may be useful as potential therapeutic candidates against cancer because of their topoisomerase II and DNA intercalation activity.

Hydrothermal assisted synthesis of hierarchical SnO2 micro flowers with CdO nanoparticles based membrane for energy storage applications.

Hierarchical nanostructures with appropriate morphology and surface functionalities are highly desired to achieve an optimized electrochemical property for active electrode materials. This work renders the facile hydrothermal synthesis of CdO, SnO2, and CdO-SnO2 nanocomposite, and their capacitive performance was tested. The formation of the pure samples and their composite was committed by low-temperature Raman spectroscopy and x-ray diffraction studies which revealed the tetragonal and cubic structures of CdO and SnO2 powder samples with good crystallinity and purity. The morphological postmortem reveals the formation of nanoparticles morphology of CdO with a highly smooth surface appearance. Besides, the SnO2 illustrates the morphology of the micro flowers composed of ultrathin nanosheets. More specifically, the electrochemical properties indicate the pseudocapacitive charge storage mechanism based on cyclic voltammetry and chronopotentiometry analysis. The CdO-SnO2 composite electrode displayed a higher capacitance due to additional pores/space offered for active sites and continuously allowed electrolyte ions to interact with the inner/outer surface of the electrode. These exciting findings led us to design and fabricate battery hybrid supercapacitors (BHSC) from CdO-SnO2, and activated carbon (AC), referred to as CdO-SnO2//AC BHSC, attains a high power delivery (5717 W/kg), and a maximum energy density of 42 Wh/kg at low discharge rate. Noteworthy, a stable cycling performance was obtained with only 91.3% retention after 8000 cycling at a large discharge current of 10 A/g, denoting the magnificent durability of the active electrode material.

Design, synthesis, molecular modelling and antitumor evaluation of S-glucosylated rhodanines through topo II inhibition and DNA intercalation.

In the present study, 5-arylidene rhodanine derivatives 3a-f, N-glucosylation rhodanine 6, S-glucosylation rhodanine 7, N-glucoside rhodanine 8 and S-glucosylation 5-arylidene rhodanines 13a-c were synthesised and screened for cytotoxicity against a panel of cancer cells with investigating the effective molecular target and mechanistic cell death. The anomers were separated by flash column chromatography and their configurations were assigned by NMR spectroscopy. The stable structures of the compounds under study were modelled on a molecular level, and DFT calculations were carried out at the B3LYP/6-31 + G (d,p) level to examine their electronic and geometric features. A good correlation between the quantum chemical descriptors and experimental observations was found. Interestingly, compound 6 induced potent cytotoxicity against MCF-7, HepG2 and A549 cells, with IC50 values of 11.7, 0.21, and 1.7 µM, compared to Dox 7.67, 8.28, and 6.62 µM, respectively. For the molecular target, compound 6 exhibited topoisomerase II inhibition and DNA intercalation with IC50 values of 6.9 and 19.6 µM, respectively compared to Dox (IC50 = 9.65 and 31.27 µM). Additionally, compound 6 treatmnet significantly activated apoptotic cell death in HepG2 cells by 80.7-fold, it induced total apoptosis by 34.73% (23.07% for early apoptosis, 11.66% for late apoptosis) compared to the untreated control group (0.43%) arresting the cell population at the S-phase by 49.6% compared to control 39.15%. Finally, compound 6 upregulated the apoptosis-related genes, while it inhibted the Bcl-2 expression. Hence, glucosylated rhodanines may serve as a promising drug candidates against cancer with promising topoisomerase II and DNA intercalation.