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Design, Synthesis and Tumour-Selective Toxicity of Novel 1-[3-{3,5-Bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone Oximes and Related Quaternary Ammonium Salts.

ABSTRACT: A novel series of 1-[3-{3,5-bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes 3a-h and related quaternary ammonium salts 4a-h were prepared as candidate antineoplastic agents. Evaluation against neoplastic Ca9-22, HSC-2 and HSC-4 cells revealed the compounds in series 3 and 4 to be potent cytotoxins with submicromolar CC₅₀ values in virtually all cases. In contrast, the compounds were less cytocidal towards HGF, HPLF and HPC non-malignant cells revealing their tumour-selective toxicity. Quantitative structure-activity relationships revealed that, in general, both cytotoxic potency and selectivity index figures increased as the magnitude of the Hammett sigma values rose. In addition, 3a-h are cytotoxic towards a number of leukemic and colon cancer cells. 4b,c lowered the mitochondrial membrane potential in CEM cells, and 4d induced transient G2/M accumulation in Ca9-22 cells. Five compounds, namely 3c,d and 4c-e, were identified as lead molecules that have drug-like properties.

SUBMITTER: Roayapalley PK

PROVIDER: S-EPMC8659243 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Hydrogenation of Alkynes and Olefins Catalyzed by Quaternary Ammonium Salts.

Project description:Catalytic hydrogenation of unsaturated hydrocarbons to alkenes and alkanes using molecular hydrogen is one of the most fundamental transformations in organic synthesis. While methodologies involving transition metals as catalysts in homogeneous and heterogeneous processes have been well developed, metal-free catalytic hydrogenation offers an ideal approach for future chemistry. Herein, the common and inexpensive quaternary ammonium salts are first introduced as catalysts in the catalytic hydrogenation system for the transformations from alkynes or olefins into the corresponding olefins or alkanes. Interestingly, the hydrogenation process of alkynes can be controlled to selectively produce alkenes or alkanes under different conditions. Moreover, the possible mechanism is discussed in new insights into the catalytic behavior of quaternary ammonium salts.

| S-EPMC10870019 | biostudies-literature

Synthesis, physiochemical property and antimicrobial activity of novel quaternary ammonium salts.

Project description:Twenty-four novel 5-phenyl-1,3,4-oxadiazole-2-thiol (POT) analogues, benzo[d]oxazole-2-thiol, benzo[d]thiazole-2-thiol and 5-methyl-1,3,4-thiadiazole-2-thiol-substituted N,N-bis(2-hydroxyethyl) quaternary ammonium salts (QAS) (5a-d, 6a-d, 7a-d, 10a-d, 13a-d, 16a-d) were prepared and characterised by FTIR, NMR and elemental analysis. Part of target compounds (5d, 6d, 7d, 10d, 13d, 16d) displayed potent antimicrobial effect against ten common pathogens (S. aureus, ?-H-tococcus, ?-H-tococcus, E. coli, P. aeruginosa, Proteus vulgaris, Canidia Albicans, Cytospora mandshurica, Physalospora piricola, Aspergillus niger) and had relatively low cytotoxity against two human cell lines (HaCat and LO2). TEM and SEM images of E. coli and S. aureus morphologies treated with 7d showed that the antibacterial mechanism might be the QAS fixing on cell wall surfaces and puncturing to result in the release of bacterial cytoplasm. This study provides new information of QAS, which could be used to design novel antimicrobial agents applied in clinic or agriculture.

| S-EPMC6010013 | biostudies-literature

Synthesis and Antimicrobial Evaluation of Bis-morpholine Triazine Quaternary Ammonium Salts.

Project description:Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis-morpholino triazine quaternary ammonium salts (bis-mTQAS) is reported, starting from 2,4,6-trichloro-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine and various N-alkylmorpholines. Bis-mTQAS were tested as antimicrobials against Gram-negative and Gram-positive bacterial strains. The best-performing bis-mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 μg/mL, respectively. Distinctively, bis-mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity.

| S-EPMC8596621 | biostudies-literature

Quaternary ammonium salts based on (-)-borneol as effective inhibitors of influenza virus.

Project description:A series of compounds containing a 1,7,7-trimethylbicyclo[2.2.1]heptane fragment were evaluated for their antiviral activity against influenza A virus strain A/Puerto Rico/8/34 (H1N1) in vitro. The most potent antiviral compound proved to be a quaternary ammonium salt based on (-)-borneol, 10a. In in vitro experiments, compound 10a inhibited influenza A viruses (H1, H1pdm09, and H3 subtypes), with an IC50 value of 2.4-16.8 µM (depending on the virus), and demonstrated low toxicity (CC50 = 1311 µM). Mechanism-of-action studies for compound 10a revealed it to be most effective when added at the early stages of the viral life cycle. In direct haemolysis inhibition tests, compound 10a was shown to decrease the membrane-disrupting activity of influenza A virus strain A/Puerto Rico/8/34. According to molecular modelling results, the lead compound 10a can bind to different sites in the stem region of the viral hemagglutinin.

| S-EPMC8116641 | biostudies-literature

Crystal structures of three new N-halo-methyl-ated quaternary ammonium salts.

Project description:In the crystals of the title N-halo-methyl-ated quaternary ammonium salts, C19H23IN(+)·I(-), (I) [systematic name: N-(4,4-di-phenyl-but-3-en-1-yl)-N-iodo-methyl-N,N-di-methyl-ammonium iodide], C20H25IN(+)·I(-), (II) [systematic name: N-(5,5-di-phenyl-pent-4-en-1-yl)-N-iodo-methyl-N,N-di-methyl-ammonium iodide], and C21H27IN(+)·I(-), (III) [systematic name: N-(6,6-di-phenyl-hex-5-en-1-yl)-N-iodo-methyl-N,N-di-methyl-ammonium iodide], there are short I⋯I(-) inter-actions of 3.564 (4), 3.506 (1) and 3.557 (1) Å for compounds (I), (II) and (III), respectively. Compound (I) crystallizes in the Sohncke group P21 as an 'enanti-opure' compound and is therefore a potential material for NLO properties. In the crystal of compound (I), mol-ecules are linked by C-H⋯I(-) and C-H⋯π inter-actions which, together with the I⋯I(-) inter-actions, lead to the formation of ribbons along [100]. In (II), there are only C-H⋯I(-) inter-actions which, together with the I⋯I(-) inter-actions, lead to the formation of helices along [010]. In (III), apart from the I⋯I(-) inter-actions, there are no significant inter-molecular inter-actions present.

| S-EPMC4647383 | biostudies-literature

Polyamide 6 Nanocomposites with Inorganic Particles Modified with Three Quaternary Ammonium Salts.

Project description:The purpose of this study was to obtain polyamide 6 nanocomposites with national organically modified clay with three quaternary ammonium salts. The obtained results confirm the intercalation of molecules of salt in the clay layers, and a good interaction with the polymer, showing the formation of intercalated and/or partially exfoliated structures. The nanocomposites showed similar thermal stability compared to pure polymer, and the mechanical properties presented interesting and promising results.

| S-EPMC5448849 | biostudies-other

Design, Synthesis, Antibacterial, Antifungal and Anticancer Evaluations of Novel β-Pinene Quaternary Ammonium Salts.

Project description:β-pinene is a monoterpene isolated from turpentine oil and numerous other plants' essential oils, which has a broad spectrum of biological activities. In the current work, six novel β-pinene quaternary ammonium (β-PQA) salts were synthesized and evaluated in vitro for their antifungal, antibacterial and anticancer activities. The in vitro assay results revealed that compounds 4a and 4b presented remarkable antimicrobial activity against the tested fungi and bacteria. In particular, compound 4a showed excellent activities against F. oxysporum f.sp. niveum, P. nicotianae var.nicotianae, R. solani, D. pinea and Fusicoccumaesculi, with EC50 values of 4.50, 10.92, 9.45, 10.82 and 6.34 μg/mL, respectively. Moreover, compound 4a showed the best antibacterial action against E. coli, P. aeruginosa, S. aureus and B. subtilis, with MIC at 2.5, 0.625, 1.25 and 1.25 μg/mL, respectively. The anticancer activity results demonstrated that compounds 4a, 4b, 4c and 4f exhibited remarkable activity against HCT-116 and MCF-7 cell lines, with IC50 values ranged from 1.10 to 25.54 μM. Notably, the compound 4c displayed the strongest cytotoxicity against HCT-116 and MCF-7 cell lines, with the IC50 values of 1.10 and 2.46 μM, respectively. Furthermore, preliminary antimicrobial mechanistic studies revealed that compound 4a might cause mycelium abnormalities of microbial, cell membrane permeability changes and inhibition of the activity of ATP. Altogether, these findings open interesting perspectives to the application of β-PQA salts as a novel leading structure for the development of effective antimicrobial and anticancer agents.

| S-EPMC8539267 | biostudies-literature

The smallest quaternary ammonium salts with ether groups for high-performance electrochemical double layer capacitors.

Project description:Electrochemical double layer capacitors (EDLCs) are energy storage devices that have been used for a wide range of electronic applications. In particular, the electrolyte is one of the important components, directly related to the capacitance and stability. Herein, we first report a series of the smallest quaternary ammonium salts (QASs), with ether groups on tails and tetrafluoroborate (BF4) as an anion, for use in EDLCs. To find the optimal structure, various QASs with different sized head groups and ether-containing tail groups were systematically compared. Comparing two nearly identical structures with and without ether groups, QASs with oxygen atoms showed improved capacitance, proving that ions with oxygen atoms move more easily than their counterparts at lower electric fields. Moreover, the ether containing QASs showed low activation energy values of conductivities, leading to smaller IR drops during the charge and discharge processes, resulting in an overall higher capacitance.

| S-EPMC5604401 | biostudies-literature

Formation and shape-control of hierarchical cobalt nanostructures using quaternary ammonium salts in aqueous media.

Project description:Aggregation and self-assembly are influenced by molecular interactions. With precise control of molecular interactions, in this study, a wide range of nanostructures ranging from zero-dimensional nanospheres to hierarchical nanoplates and spindles have been successfully synthesized at ambient temperature in aqueous solution. The nanostructures reported here are formed by aggregation of spherical seed particles (monomers) in presence of quaternary ammonium salts. Hydroxide ions and a magnetic moment of the monomers are essential to induce shape anisotropy in the nanostructures. The cobalt nanoplates are studied in detail, and a growth mechanism based on collision, aggregation, and crystal consolidation is proposed based on a electron microscopy studies. The growth mechanism is generalized for rods, spindles, and nearly spherical nanostructures, obtained by varying the cation group in the quaternary ammonium hydroxides. Electron diffraction shows different predominant lattice planes on the edge and on the surface of a nanoplate. The study explains, hereto unaddressed, the temporal evolution of complex magnetic nanostructures. These ferromagnetic nanostructures represent an interesting combination of shape anisotropy and magnetic characteristics.

| S-EPMC5331312 | biostudies-literature

Synthesis, Structure, Surface and Antimicrobial Properties of New Oligomeric Quaternary Ammonium Salts with Aromatic Spacers.

Project description:New dimeric, trimeric and tetrameric quaternary ammonium salts were accomplished by reaction of tertiary alkyldimethyl amines with appropriate bromomethylbenzene derivatives. A series of new cationic surfactants contain different alkyl chain lengths (C4-C18), aromatic spacers and different numbers of quaternary nitrogen atoms. The structure of the products was confirmed by spectral analysis (FT-IR, ¹H-NMR, 13C-NMR and 2D-NMR), mass spectroscopy (ESI-MS), elemental analysis, as well as PM5 semiempirical methods. Compound (21) was also analyzed using X-ray crystallography. Critical micelle concentration (CMC) of 1,4-bis-[N-(1-alkyl)-N,N-dimethylammoniummethyl]benzene dibromides (3-9) was determined to characterize the aggregation behavior. The antimicrobial properties of novel QACs (Quaternary Ammonium Salts) were examined to set their minimal inhibitory concentration (MIC) values against fungi Aspergillus niger, Candida albicans, Penicillium chrysogenum and bacteria Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa.

| S-EPMC6150277 | biostudies-literature

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