Supramolecular complexation between cucurbit[7]uril and folate and analytical applications

Folate (FA) plays a key role in the biosynthesis of amino acids, purines, and pyrimidines in the human body, and intracellular folate metabolism has become an attractive target of tumor chemotherapy. In this work, an inclusion interaction was found between FA and cucurbit[7]uril (CB[7]), and the formation of a CB[7]-FA 2:1 supramolecular inclusion complex was confirmed by fluorescence spectra, UV-Vis absorption spectroscopy, 1H NMR, and molecular modeling calculations. In addition, FA is generally determined through the indirect fluorescent method because it shows weak fluorescence in aqueous solution. Therefore, a simple, direct fluorescence probe method for rapidly measuring FA was investigated, and the linear equation of FA was ΔF = 14.691C + 37.366 within the concentration ranges of 0.82 ~ 18.31 µg mL–1. The proposed direct fluorescence method was applied to the determination of spiked plasma. We demonstrated that this method could provide an experimental basis for the targeted administration of the CB[7]-FA complex, and it could be extended as a promising fluorescence detection method for drugs in vivo.

The solubilities of benzoic acid and its nitro-derivatives, 3-nitro and 3,5-dinitrobenzoic acids

The solubilities of benzoic acid and its nitrated derivatives (3-nitrobenzoic acid and 3,5-dinitrobenzoic acid) in seven pure solvents—water, methanol, ethanol, acetonitrile, dichloromethane, toluene, and ethyl acetate—were determined experimentally over a temperature range from 273.15 K to 323.15 K under 101.3 kPa. The solubility of the above substances in these solvents increased with temperature. The solubility values of benzoic acid in these seven solvents follow the following order: ethanol > ethanol > acetonitrile > ethyl acetate > dichloromethane > toluene > water, while the solubility values of its nitrification derivatives in these seven solvents follow the following order: methanol > ethanol > ethyl acetate > acetonitrile > dichloromethane > toluene > water. The solubility of benzoic acid, 3-nitrobenzoic acid, and 3,5-dinitrobenzoic acid were significantly different in the same solvent. The solubilities obtained are very helpful in improving the recrystallization and yields of 3-nitrobenzoic acid and 3,5-dinitrobenzoic acid.

A palladium-catalyzed cascade approach for the synthesis of 3,3a,4,6,7,8,9,9a-octahydro-1H-benzo[f]isoindole-1,5(2H)-diones

A synthetic method for the preparation of 3,3a,4,6,7,8,9,9a-octahydro-1 H-benzo[ f]isoindole-1,5(2 H)-diones from 1,6-dienes and vinyl iodides is developed using PdCl2(PPh3)2 as the catalyst. The presented approach exhibits a good functional group tolerance and affords moderate yields of the products. A mechanism is also proposed.

Facile synthesis and biological evaluation of chrysin derivatives

In this paper, novel synthetic methods, including microwave O-alkylation, were used to produce several chrysin derivatives. These compounds were purified, characterised and tested on different cell lines and bacterial strains. From this family, 7-(2,4-dinitrophenoxy)-5-hydroxy-3-phenyl-4H-chromen-4-one (C3) was shown to be extremely active on bacterial strains methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae as well as having anticancer activity on a range of cancer cell lines with IC50 values less than 30 µM. Chrysin has been known for their anticancer and antimicrobial properties, and this study not only corroborates this but also shows that it is possible to synthesise new improved derivatives with therapeutic possibilities.

Enhanced photoelectrochemical performance of NiO-doped TiO2 nanotubes prepared by an impregnation–calcination method

To improve the photocatalytic activity of TiO2, a series of NiO–TiO2 nanotubes (NTbs) is prepared by impregnating TiO2 nanotubes in a solution of NiCl2·6H2O at different concentrations. Self-organized TiO2 nanotubes are prepared by a two-step anodization process. Scanning electron microscopy images show that large particle agglomerates are formed for higher precursor concentrations, and X-ray energy-dispersive spectroscopy results indicate that the atomic percentages of Ni in the NiO–TiO2 NTbs prepared with precursor concentrations of 100 and 300 mM are 1.95% and 4.23%, respectively. Electronic lifetime measurements show that the recombination rate of photogenerated electron–hole pairs is lower for NiO–TiO2 NTbs compared to that of TiO2. Specifically, the recombination rate of the sample prepared at 50 mM is the lowest, which is associated with the longest electron lifetime. Compared to unmodified TiO2 nanotubes, NiO–TiO2 NTbs exhibit improved results for the photocatalytic degradation of rhodamine B.

The development of three ruthenium-based antimicrobial metallodrugs: Design, synthesis, and activity evaluation against Staphylococcus aureus

The development of new classes of antimicrobial is urgently needed due to the widespread occurrence of multi-resistant pathogens. In this study, three novel ruthenium complexes: [Ru(dmob)2(BTPIP)](PF6)2 (Ru(II)-1), [Ru(dbp)2(BTPIP)](PF6)2 (Ru(II)-2), and [Ru(dpa)2(BTPIP)](PF6)2 (Ru(II)-3) (dpa = 2,2’-dipyridylamine, dmob = 4,4’-dimethoxy-2,2’-bipyridyl, dbp = 4,4’-di- tert-butyl-2,2’-dipyridyl, BTPIP = 4-(benzo[ b]thiophen-2-yl)phenyl-1 H-imidazo[4,5- f][1,10]phenanthroline) are synthesized and investigated as antimicrobial metallodrugs. We demonstrate that all three complexes have significant antimicrobial activity against Staphylococcus aureus by testing their minimal inhibitory concentrations = 0.0015–0.0125 mg/mL. The antibacterial activity of the best active complex Ru(II)-3 is 13 times that of ofloxacin (minimal inhibitory concentration = 19.5 μg/mL). Importantly, Ru(II)-3 not only increases the susceptibility of Staphylococcus aureus to existing common antibiotics but also shows noticeably delayed and decreased resistance in Staphylococcus aureus since the minimal inhibitory concentration values of Ru(II)-3 only increased eightfold times after 20 passages. Furthermore, the biofilms formation and rabbit erythrocyte hemolysis assays verified that Ru(II)-3 also efficiently inhibit the biofilm formation and toxin secretion of Staphylococcus aureus.

Syntheses, crystal structures, and fluorescent properties of three coordination polymers with 5-sulfoisophthalic acid anion and 4-phenylpyridine

Three coordination polymers—{[Ag2(SIP)(4-pp)]·[Ag(4-pp)2]·H2O}n, [Pb4(SIP)2( μ3-OH)2(H2O)2]n, and {[Zn2(SIP)2(4-pp)4][Zn(4-pp)2(H2O)4]·4H2O}n (SIP = 5-sulfoisophthalic acid anion, 4-pp = 4-phenylpyridine)—are constructed under hydrothermal or solvothermal conditions using sodium m-phthalate 5-sulfonate (NaH2SIP) and 4-phenylpyridine as ligands. The structures of the three complexes are determined by single-crystal X-ray diffraction, powder X-ray diffraction, thermogravimetric analyses, Fourier-transform infrared analysis, and photoluminescence. The fluorescent properties of the complexes in the solid state are investigated at room temperature, and the results indicate that they all show photoluminescent properties.

A cucurbit[7]uril-based supramolecular fluorescent probe for the detection of metronidazole with high sensitivity and strong anti-interference capacity

We propose a new method for the selective detection of the antibiotic metronidazole (MNZ) using CB[7]-JAT (cucurbit[7]uril = CB[7] and JAT = jatrorrhizine) as a fluorescent probe, which is based on the competitive reaction between MNZ and JAT for the occupancy of the CB[7] cavity. The proposed method gives a good calibration curve in the concentration range of 0.38–60 μM, and the limit of detection for MNZ is 65 ng mL−1 with those obtained by the standard curve method. Moreover, the proposed method was successfully applied for the determination of MNZ in liquid milk. Most importantly, due to the high binding affinity between CB[7] and MNZ, the proposed method shows great anti-interference capacity to accurately detect MNZ in the presence of other antibiotics.

Synthesis and antimicrobial activity of aryldiazenyl/arylhydrazono pyrazoles

We report the design, synthesis, and in vitro antimicrobial evaluation of functionalized pyrazoles containing a hydrazono/diazenyl moiety. Among these newly synthesized derivatives, 4-[2-(4-chlorophenyl)hydrazono]-5-methyl-2-[2-(naphthalen-2-yloxy)acetyl]-2,4-dihydro-3 H-pyrazol-3-one is a promising antimicrobial agent against Staphylococcus aureus (minimum inhibitory concentration 0.19 μg mL−1). Structure–activity relationship studies reveal that the electronic environment on the distal phenyl ring has a considerable effect on the antimicrobial potential of the hybrid analogues. Molecular docking studies into the active site of S. aureus dihydrofolate reductase also prove the usefulness of hybridizing a pyrazole moiety with azo and hydrazo groups in the design of new antimicrobial agents.

One-pot synthesis and biological evaluation of (2E,4E)-4-arylidene-2-styryl-5-oxopyrrolidine derivatives

Many marine alkaloids possess interesting structures and antitumor activities. Thus, we have synthesized (2 E,4 E)-4-arylidene-2-styryl-5-oxopyrrolidine derivatives of the marine alkaloids, rhopaladins A–D. The cytotoxicities of these derivatives against C-33A, CaSki, SiHa, HeLa, HepG2, and LO2 cells are evaluated by MTT assays. The results show that (2 E,4 E)-2-(4-chlorostyryl)-4-benzylidene- N-cyclohexyl-1-(4-fluorophenyl)-5-oxopyrrolidine-2-carboxamide significantly inhibits cancer cell proliferation, with IC50 values against C-33A, CaSki, SiHa, HeLa, and HepG2 cells of 5.56, 9.15, 12.5, 21.4, and 14.5 μM, respectively, and an IC50 value of 86.77 μM against the normal LO2 cell line.