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1.
Molecules ; 27(13)2022 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-35807560

RESUMO

The use of alkynyl gold(I) complexes covers different research fields, such as bioinorganic chemistry, catalysis, and material science, considering the luminescent properties of the complexes. Regarding this last application, we report here the synthesis of three novel dinuclear gold(I) complexes of the general formula [(diNHC)(Au-C≡CPh)2]: two Au-C≡CPh units are connected by a bridging di(N-heterocyclic carbene) ligand, which should favor the establishment of semi-supported aurophilic interactions. The complexes can be easily synthesized through mechanochemistry upon reacting the pristine dibromido complexes [(diNHC)(AuBr)2] with phenylacetylene and KOH. Interestingly, we were also able to isolate the monosubstituted complex [(diNHC)(Au-C≡CPh)(AuBr)]. The gold(I) species were fully characterized by multinuclear NMR spectroscopy and mass spectrometry. The emission properties were also evaluated, and the salient data are comparable to those of analogous compounds reported in the literature.


Assuntos
Complexos de Coordenação/química , Ouro/química , Luminescência , Acetileno/análogos & derivados , Acetileno/química , Dibrometo de Etileno/química , Hidróxidos/química , Ligantes , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Compostos de Potássio/química
2.
Angew Chem Int Ed Engl ; 61(33): e202207623, 2022 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-35731840

RESUMO

Helical polymers such as poly(phenylacetylene)s (PPAs) are interesting materials due to the possibility of tuning their helical scaffold (sense and elongation) once they have been prepared and by the presence of external stimuli. The main limitation in the application of PPAs is their poor photostability. These polymers degrade under visible light exposure through a photochemical electrocyclization process. In this work, it was demonstrated, through a selected example, how the photochemical degradation in PPAs is directly related to their dynamic helical behavior. Thus, while PPAs with dynamic helical structures show poor photostability under UV/Vis light exposure, poly-(R)-1, bearing an enantiopure sulfoxide group as pendant group and designed to have a quasi-static helical behavior, shows a large photostability due to the restricted conformational composition at the polyene backbone, needed to orient the conjugated double bonds prior to the photochemical electrocyclization process and the subsequent degradation of the material.


Assuntos
Parafusos Ósseos , Polímeros , Acetileno/análogos & derivados , Polímeros/química , Estereoisomerismo
3.
Inorg Chem ; 61(24): 9242-9250, 2022 Jun 20.
Artigo em Inglês | MEDLINE | ID: mdl-35684999

RESUMO

One of the major issues regarding long-term human space exploration is the need for a breathable atmosphere. A major component toward achieving this goal is both the removal of exhaled carbon dioxide (CO2) and the generation or recovery of oxygen (O2). NASA's current technology only operates at about 50% efficiency due to the need to vent the methane that is produced during the CO2 reduction process. One method of improving the efficiency of this process is through plasma pyrolysis, wherein the methane is pyrolyzed to produce hydrogen and various dehydrogenated carbon byproducts. In this process, acetylene is one of the main components of this byproduct stream. Unfortunately, while the concentration of this effluent is generally high in hydrogen (>90% typically), the presence of the acetylene waste product can act as a poison for the ruthenium-alumina catalyst used in the CO2-reducing Sabatier process, requiring a removal step. Metal-organic frameworks (MOFs) represent a valuable method for removing these unsaturated hydrocarbons due to their high tunability, particularly through the incorporation of open metal sites. In this study, two common iron-based MOFs, MIL-100 and PCN-250, were studied for their ability to adsorb acetylene. A combination of gas adsorption analysis and density functional theory calculation results shows the ability of these materials to undergo a thermal-induced reduction event, which results in an improvement in gas adsorption performance. This improvement in gas performance appears to be at least partially due to the increased presence of π-backbonding toward the acetylene molecules.


Assuntos
Estruturas Metalorgânicas , Acetileno , Adsorção , Dióxido de Carbono , Humanos , Hidrogênio , Ferro , Metano , Temperatura
4.
J Chromatogr A ; 1675: 463164, 2022 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-35660321

RESUMO

An optically-active poly(diphenylacetylene) (PDPA) bearing carboxy pendant groups with left-handed helicity memory (M-h-poly-1), synthesized using the noncovalent helicity-induction-and-memory strategy, was converted into a PDPA bearing optically-active pendant groups through an amide bonding (M-hKT-poly-2S), while maintaining the left-handed helicity memory, by reaction with (S)-1-phenylethylamine ((S)-2) using a condensing reagent at room temperature. Its chiral recognition ability was investigated as a chiral stationary phase (CSP) for high-performance liquid chromatography (HPLC). M-hKT-poly-2S exhibited significantly different chiral recognition ability towards racemates compared to the previously reported corresponding helical PDPA bearing the same optically-active pendant groups (M-hTS-poly-2S) (prepared by the reaction of an optically-inactive PDPA bearing carboxy pendants with (S)-2, followed by thermal annealing, to induce a left-handed helical structure in the polymer main chain). Although the main chains of both M-hKT-poly-2S and M-hTS-poly-2S formed almost completely left-handed helical structures, their higher-order structures varied slightly, as confirmed by various spectroscopic methods (UV-Vis, circular dichroism (CD), IR, and vibrational CD). M-hKT-TS-poly-2S, the PDPA formed on the thermal annealing of M-hKT-poly-2S, exhibited the same higher-order structure and chiral discrimination ability as M-hTS-poly-2S. Therefore, slight differences in the higher-order structures of the kinetically-trapped metastable state (M-hKT-poly-2S) and the thermodynamically-stable state (M-hTS-poly-2S), due to differences in synthetic procedures, significantly impact their chiral recognition abilities as CSPs, even with identical primary structures and helix-sense of the polymer main chain.


Assuntos
Acetileno , Polímeros , Acetileno/análogos & derivados , Acetileno/química , Dicroísmo Circular , Polímeros/química , Estereoisomerismo
5.
Chem Commun (Camb) ; 58(47): 6737-6740, 2022 Jun 09.
Artigo em Inglês | MEDLINE | ID: mdl-35607950

RESUMO

Peptide macrocycles (PMCs) are increasingly popular for the development of inhibitors of protein-protein interactions (PPIs). Large libraries of PMCs are accessible using display technologies like mRNA display and phage display. These technologies require macrocyclization chemistries to be compatible with biological milieu, severely limiting the types of technologies available for cyclization. Here, we introduce the novel non-canonical amino acid (ncAA) p-cyanoacetylene-L-Phe (pCAF), which facilitates spontaneous, co-translational cyclization through Michael addition with cysteine under physiological conditions. This new, robust chemistry creates stable macrocycles of a wide variety of ring sizes including bicyclic structures.


Assuntos
Peptídeos Cíclicos , Fenilalanina , Acetileno/análogos & derivados , Ciclização , Nitrilas , Biblioteca de Peptídeos , Peptídeos/metabolismo , Peptídeos Cíclicos/química , Fenilalanina/metabolismo
6.
Chem Commun (Camb) ; 58(43): 6348-6351, 2022 May 26.
Artigo em Inglês | MEDLINE | ID: mdl-35536025

RESUMO

A visible-light-induced photocatalytic strategy for the synthesis of flavonoids has been developed through the deoxygenative/cyclization reaction of salicylic acid derivatives with aryl acetylene using diphenyl sulfide as an O-transfer reagent. Based on the controlled experiments, the mechanism of visible-light-induced free radical coupling cyclization was proposed. The protocol obtained 51 flavonoids in good yields and has been successfully applied to the synthesis of some natural flavones.


Assuntos
Acetileno , Flavonoides , Ciclização , Luz , Ácido Salicílico
7.
J Org Chem ; 87(9): 5916-5924, 2022 05 06.
Artigo em Inglês | MEDLINE | ID: mdl-35394780

RESUMO

An interaction of 1,5-diaryl-3-X-pent-4-yn-1-ones (where X stands for piperidin-1-yl, morpholin-4-yl, 4-methylpiperazin-1-yl) with arylhydrazines proceeds at room temperature and results in 3-aryl-5-arylethynyl-1-phenyl-4,5-dihydro-1H-pyrazoles with up to 57-73% yields. Under similar conditions, the cyclocondensation of conjugated 2,4,1-enynones with arylhydrazine proceeds only in the presence of cyclic amines. 1,5-Diaryl-3-X-pent-4-yn-1-ones are reported as synthetic equivalents of conjugated 2,4,1-enynones in reactions with arylhydrazines. On the basis of obtained data, there are highly efficient methods developed for the synthesis of 5-arylethynyl-substituted 4,5-dihydro-1H-pyrazoles, as well as for similarly structured 1H-pyrazoles prepared by oxidation in AcOH. Presented products possess quite marked fluorescent abilities. Emission maximum wavelengths are located at 453-465 and 363-400 nm, respectively; certain compounds show extremely large Stokes shifts that may reach 91,000 cm-1.


Assuntos
Acetileno , Alcinos , Cetonas , Pargilina/análogos & derivados , Propilaminas , Pirazóis
8.
J Org Chem ; 87(9): 5568-5576, 2022 05 06.
Artigo em Inglês | MEDLINE | ID: mdl-35405075

RESUMO

An efficient synthesis of a variety of 1,2-disubstituted indoles from 2-ethynylanilines was developed. Using 2-ethynylanilines and benzaldehydes as starting materials, the target products (1,2-disubstituted indoles) were obtained smoothly through condensation, reduction, and subsequent cyclization. Various functional groups attached to the aryl ring of 1,2-disubstituted indoles were well tolerated. The protocol features easy performance, easily available starting materials, good yield, and a broad substrate scope, showing potential synthetic value for the preparation of a variety of biologically or pharmaceutically active compounds.


Assuntos
Benzaldeídos , Indóis , Acetileno/análogos & derivados , Compostos de Anilina , Ciclização , Indóis/química , Estrutura Molecular
9.
Angew Chem Int Ed Engl ; 61(26): e202202676, 2022 06 27.
Artigo em Inglês | MEDLINE | ID: mdl-35411566

RESUMO

Well-controlled living polymerization of water-soluble phenylacetylene derivatives in water was achieved for the first time using a multicomponent catalytic system consisting of [Rh(nbd)Cl]2 , an aryl boronic acid, diphenylacetylene having carboxy groups, a tetraalkylammonium hydroxide, and a water-soluble triphenylphosphine. This catalytic system enables a direct synthesis of various water-soluble cis-stereoregular poly(phenylacetylene)s having a narrow molecular weight distribution, the molecular weight of which can be controlled by the initial feed ratio of the monomer to the catalyst. Moreover, the syntheses of water-soluble telechelic poly(phenylacetylene)s having various functional groups at both chain ends as well as a water-soluble block copolymer were achieved.


Assuntos
Polímeros , Água , Acetileno/análogos & derivados , Polimerização
10.
Water Sci Technol ; 85(8): 2389-2397, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35486462

RESUMO

In this study, a mixed precursor system of fly ash (50 wt%) and calcium carbide slag (50 wt%) was used to prepare a geopolymer, and the hydration and hardening mechanism of the whole system and the microscopic characterization of the calcium carbide-fly ash based polymer were investigated after the addition of calcium carbide slag. Ca(OH)2 in calcium carbide slag can effectively excite the volcanic ash activity of fly ash, which leads to a more adequate geopolymerization reaction and produces more hydrated calcium silicate (C-S-H) gels. These gels have very high specific surface area and surface adsorption energy. The results showed that the specific surface area of geopolymer was as high as 79.76 m2/g, and through the study of its adsorption capacity of Cu(II) in aqueous solution, the results showed that its removal efficiency of Cu(II) was 97.63% and its adsorption capacity was 58.58 mg/g. By using fly ash and calcium carbide slag as the auxiliary raw materials for the preparation of geopolymer, it not only can promote the reaction of proceeding, but can also act as an excellent adsorption material, and also as an effective way to utilize industrial waste resources.


Assuntos
Acetileno , Cinza de Carvão , Acetileno/análogos & derivados , Adsorção , Resíduos Industriais
11.
Mar Drugs ; 20(4)2022 Apr 13.
Artigo em Inglês | MEDLINE | ID: mdl-35447938

RESUMO

A series of twenty-three linear and branched chain mono acetylene lipids were isolated from the Caribbean Sea sponge Cribrochalina vasculum. Seventeen of the compounds, 1-17, are new, while six, 18-23, were previously characterized from the same sponge. Some of the new acetylene-3-hydroxy alkanes 1, 6, 7, 8, 10 were tested for selective cytotoxicity in non-small cell lung carcinoma (NSCLC) cells over WI-38 normal diploid lung fibroblasts. Compound 7, presented clear tumor selective activity while, 1 and 8, showed selectivity at lower doses and 6 and 10, were not active towards NSCLC cells at all. The earlier reported selective cytotoxicity of some acetylene-3-hydroxy alkanes (scal-18 and 23), in NSCLC cells and/or other tumor cell types were also confirmed for 19, 20 and 22. To further study the structure activity relationships (SAR) of this group of compounds, we synthesized several derivatives of acetylene-3-hydroxy alkanes, rac-18, scal-S-18, R-18, rac-27, rac-32, R-32, S-32, rac-33, rac-41, rac-42, rac-43, rac-45, rac-48 and rac-49, along with other 3-substituted derivatives, rac-35, rac-36, rac-37, rac-38, rac-39 and rac-40, and assessed their cytotoxic activity against NSCLC cells and diploid fibroblasts. SAR studies revealed that the alcohol moiety at position 3 and its absolute R configuration both were essential for the tumor cell line selective activity while for its cytotoxic magnitude the alkyl chain length and branching were of less significance.


Assuntos
Antineoplásicos , Carcinoma Pulmonar de Células não Pequenas , Neoplasias Pulmonares , Acetileno/uso terapêutico , Alcanos , Antineoplásicos/química , Carcinoma Pulmonar de Células não Pequenas/tratamento farmacológico , Carcinoma Pulmonar de Células não Pequenas/metabolismo , Humanos , Neoplasias Pulmonares/tratamento farmacológico , Neoplasias Pulmonares/metabolismo , Relação Estrutura-Atividade
12.
Spectrochim Acta A Mol Biomol Spectrosc ; 275: 121179, 2022 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-35344857

RESUMO

Photoinduced charge transfer (CT) mechanisms of two Donor-π-Donor-π-Acceptor conjugates composed of ferrocene (Fc), zinc-porphyrin (ZnP), and fullerene (C60) linked by phenylene-acetylene/acetylene during the one- (OPA) and the two-photon absorption (TPA) processes are analyzed theoretically based on the density functional theory calculations and visualization methods to study the effects of linkage between the two donors on the excitation characteristics. The change of bridge affects the efficiency of superexchange CT from Fc to ZnP in the OPA process. The one-photon excitations are dominated by local transitions of ZnP and Fc, and there is almost no efficient CT from the donors to the acceptor for both the two researched structures. In contrast, the advantage of superexchange CT from ZnP to C60 becomes much larger than the other transition forms during the TPA process when the linkage between ZnP and Fc is changed from acetylene to phenylene-acetylene. This linkage effect in TPA would have great significance in designing novel optoelectronic devices.


Assuntos
Acetileno , Fulerenos , Fulerenos/química
13.
Int J Mol Sci ; 23(5)2022 Mar 02.
Artigo em Inglês | MEDLINE | ID: mdl-35269903

RESUMO

The syntheses of various chemical compounds require heating. The intrinsic release of heat in exothermic processes is a valuable heat source that is not effectively used in many reactions. In this work, we assessed the released heat during the hydrolysis of an energy-rich compound, calcium carbide, and explored the possibility of its usage. Temperature profiles of carbide hydrolysis were recorded, and it was found that the heat release depended on the cosolvent and water/solvent ratio. Thus, the release of heat can be controlled and adjusted. To monitor the released heat, a special tube-in-tube reactor was assembled using joining part 3D-printed with nylon. The thermal effect of the reaction was estimated using a thermoimaging IR monitor. It was found that the kinetics of heat release are different when using mixtures of water with different solvents, and the maximum achievable temperature depends on the type of solvent and the amount of water and carbide. The possibility of using the heat released during carbide hydrolysis to initiate a chemical reaction was tested using a hydrothiolation reaction-the nucleophilic addition of thiols to acetylene. In a model experiment, the yield of the desired product with the use of heat from carbide hydrolysis was 89%, compared to 30% in this intrinsic heating, which was neglected.


Assuntos
Acetileno , Água , Acetileno/análogos & derivados , Acetileno/química , Hidrólise , Solventes
14.
Environ Pollut ; 303: 119076, 2022 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-35240268

RESUMO

Denitrification, as both origins and sinks of N2O, occurs extensively, and is of critical importance for regulating N2O emissions in acidified soils. However, whether soil acidification stimulates N2O emissions, and if so for what reason contributes to stimulate the emissions is uncertain and how the N2O fractions from fungal (ffD) and bacterial (fbD) denitrification change with soil pH is unclear. Thus, a pH gradient (6.2, 7.1, 8.7) was set via manipulating cropland soils (initial pH 8.7) in North China to illustrate the effect of soil acidification on fungal and bacterial denitrification after the addition of KNO3 and glucose. For source partitioning, we used and compared SP/δ18O mapping approach (SP/δ18O MAP) and acetylene inhibition technique combined isotope two endmember mixing model (AIT-IEM). The results showed significantly higher N2O emissions in the acidified soils (pH 6.2 and pH 7.1) compared with the initial soil (pH 8.7). The cumulative N2O emissions during the whole incubation period (15 days) ranged from 7.1 mg N kg-1 for pH 8.7-18.9 mg N kg-1 for pH 6.2. With the addition of glucose, relative to treatments without glucose, this emission also increased with the decrement of pH values, and were significantly stimulated. Similarly, the highest N2O emissions and N2O/(N2O + N2) ratios (rN2O) were observed in the pH 6.2 treatment. But the difference was the highest cumulative N2O + N2 emissions, which were recorded in the pH 7.1 treatment based on SP/δ18O MAP. Based on both approaches, ffD values slightly increased with the acidification of soil, and bacterial denitrification was the dominant pathway in all treatments. The SP/δ18O MAP data indicated that both the rN2O and ffD were lower compared to AIT-IEM. It has been known for long that low pH may lead to high rN2O of denitrification and ffD, but our documentation of a pervasive pH-control of rN2O and ffD by utilizing combined SP/δ18O MAP and AIT-IEM is new. The results of the evaluated N2O emissions by acidified soils are finely explained by high rN2O and enhanced ffD. We argue that soil pH management should be high on the agenda for mitigating N2O emissions in the future, particularly for regions where long-term excessive nitrogen fertilizer is likely to acidify the soils.


Assuntos
Desnitrificação , Solo , Acetileno , Glucose , Concentração de Íons de Hidrogênio , Isótopos , Nitrogênio/análise , Óxido Nitroso/análise
15.
Sci Total Environ ; 824: 153825, 2022 Jun 10.
Artigo em Inglês | MEDLINE | ID: mdl-35157856

RESUMO

Carbonous materials were found to catalyze the dechlorination of trichloroethylene (TCE) by green rust (GR), but the catalytic mechanism was not fully understood. We have developed a facile ball milling method to synthesize N-doped graphene (NG) with various N species, catalyzing fast dechlorination of TCE to acetylene by GR with the highest acetylene production rate of ~0.1 d-1. The adsorption of TCE onto NG is mainly derived from the graphene region of NG, and high pyridinic N is essential for the enhanced TCE reduction by GR. Oxygen species did not enhance the TCE reduction in GR/NG system. High dechlorination rates are correlated to a high amount of defect in NG and a high electron conductivity of NG. Pyridinic N has the highest adsorption energy for TCE among all the N species, which leads to the highest catalytic performance. High electrochemically active surface area resulted from the high content of pyridinic N facilitate the NG-catalyzed dechlorination. The acetylene production rate in real groundwater is still around one-third of that in ultrapure water. This work not only reveals the catalytic mechanism of NG-catalyzed dechlorination by GR, but also provide a feasible approach for practical remediations of TCE-contaminated groundwater using GR-NG mixture.


Assuntos
Grafite , Água Subterrânea , Tricloroetileno , Acetileno , Água Subterrânea/química , Ferro/química , Nitrogênio , Tricloroetileno/química
16.
Chemistry ; 28(18): e202104329, 2022 Mar 28.
Artigo em Inglês | MEDLINE | ID: mdl-35133690

RESUMO

The first intermolecular visible light [3+2] cycloaddition reaction performed on a meta photocycloadduct employing acetylenic sulfones is described. The developed methodology exploits the advantages of combining UV and visible-light in a two-step sequence that provides a photogenerated cyclopropane which, through a strain-release process, generates a new cyclopentane ring while significantly increasing the molecular complexity. Mechanistic studies and DFT calculations indicate an energy transfer pathway for the visible light-driven reaction step. This strategy could be extended to simpler vinylcyclopropanes.


Assuntos
Acetileno , Alcinos , Reação de Cicloadição , Luz , Sulfonas
17.
Toxicology ; 468: 153112, 2022 02 28.
Artigo em Inglês | MEDLINE | ID: mdl-35101591

RESUMO

The global increase in the demand for ripe fruits has induced unhealthy use of toxic chemicals in fruit ripening. One of such chemicals in common use is calcium carbide (CaC2). Due to its nature, commercial CaC2 is consistently found to contain impurities such as Arsenic and other toxic and carcinogenic chemicals. Few studies have only reported acute associative effects of CaC2, whereas there is only sparse evidence of its chronic and long-term impact. This article reviewed all the information on the nature of commercial CaC2 used for food processing. Meanwhile, all reports on the acute effects of CaC2, such as skin burns, skin irritations and inflammation, were summarized. Despite reported acute cases, an increase in commercial CaC2 for fruit ripening has been reported in recent times, especially in developing countries, as many vendors may consider the toxic effects/risks as negligible. Therefore, this study highlighted the paucity in research studies on the chronic impact of commercial CaC2 while proposing possible mechanisms for CaC2 induction of cancer, cardiovascular dysfunction, diabetic mellitus and others. Furthermore, suggestions on further studies to unravel the chronic impacts of CaC2 on health and recommendations for viable alternatives of fruit ripening with minimal or zero toxicity were proffered. Finally, other suggestions such as improving CaC2 detection technologies and innovative grassroots educational programs will strengthen national and international agencies to enforce restrictions on the illicit use of the toxicant for fruit ripening.


Assuntos
Acetileno/análogos & derivados , Aditivos Alimentares/toxicidade , Frutas/efeitos dos fármacos , Acetileno/química , Acetileno/toxicidade , Aerossóis , Animais , Arsênio/análise , Arsênio/toxicidade , Contaminação de Medicamentos , Aditivos Alimentares/química , Contaminação de Alimentos/prevenção & controle , Inocuidade dos Alimentos , Doenças Transmitidas por Alimentos/prevenção & controle , Frutas/crescimento & desenvolvimento , Humanos , Pós
18.
Molecules ; 27(3)2022 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-35164242

RESUMO

All-trans-retinoic acid (ATRA), the active metabolite of vitamin A, plays a pivotal role in cell differentiation, proliferation and embryonic development. It is an effective therapy for dermatological disorders and malignancies. ATRA is prone to isomerization and oxidation, which can affect its activity and selectivity. Novel diphenylacetylene-based ATRA analogues with increased stability can help to overcome these problems and may offer significant potential as therapeutics for a variety of cancers and neurodegenerative diseases, including amyotrophic lateral sclerosis. Here, we investigated the effects of these retinoids on cell viability and genotoxicity in the widely used model system of the rapidly proliferating Chinese hamster ovary cell line. DC360 is a fluorescent ATRA analogue and DC324 is a non-active derivative of DC360. EC23, DC525, DC540, DC645, and DC712 are promising analogues with increased bioactivity. The cytotoxic activity of the compounds was evaluated by ATP assay and DNA damage was tested by comet assay. No cytotoxicity was observed in the 10-6-10-5 M concentration range. All compounds induced DNA migration similar to ATRA, but DC324, DC360 and EC23 did so to a greater extent, particularly at higher concentrations. We believe that retinoid receptor-independent genotoxicity is a general characteristic of these compounds; however, further studies are needed to identify the molecular mechanisms and understand their complex biological functions.


Assuntos
Acetileno/análogos & derivados , Dano ao DNA , Retinoides/farmacologia , Acetileno/química , Trifosfato de Adenosina/metabolismo , Animais , Células CHO , Sobrevivência Celular/efeitos dos fármacos , Ensaio Cometa , Cricetulus , Retinoides/química
19.
Molecules ; 27(3)2022 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-35164158

RESUMO

As part of our continuous studies involving the prospection of natural products from Brazilian flora aiming at the discovery of prototypes for the development of new antiparasitic drugs, the present study describes the isolation of two natural acetylene acetogenins, (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11'-yn-19'-enyl)butanolide (1) and (2S,3R,4R)-3-hydroxy-4-methyl-2-(n-eicos-11'-ynyl)butanolide (2), from the seeds of Porcelia macrocarpa (Warm.) R.E. Fries (Annonaceae). Using an ex-vivo assay, compound 1 showed an IC50 value of 29.9 µM against the intracellular amastigote forms of Leishmania (L.) infantum, whereas compound 2 was inactive. These results suggested that the terminal double bond plays an important role in the activity. This effect was also observed for the semisynthetic acetylated (1a and 2a) and eliminated (1b and 2b) derivatives, since only compounds containing a double bond at C-19 displayed activity, resulting in IC50 values of 43.3 µM (1a) and 23.1 µM (1b). In order to evaluate the effect of the triple bond in the antileishmanial potential, the mixture of compounds 1 + 2 was subjected to catalytic hydrogenation to afford a compound 3 containing a saturated side chain. The antiparasitic assays performed with compound 3, acetylated (3a), and eliminated (3b) derivatives confirmed the lack of activity. Furthermore, an in-silico study using the SwissADME online platform was performed to bioactive compounds 1, 1a, and 1b in order to investigate their physicochemical parameters, pharmacokinetics, and drug-likeness. Despite the reduced effect against amastigote forms of the parasite to the purified compounds, different mixtures of compounds 1 + 2, 1a + 2a, and 1b + 2b were prepared and exhibited IC50 values ranging from 7.9 to 38.4 µM, with no toxicity for NCTC mammalian cells (CC50 > 200 µM). Selectivity indexes to these mixtures ranged from >5.2 to >25.3. The obtained results indicate that seeds of Porcelia macrocarpa are a promising source of interesting prototypes for further modifications aiming at the discovery of new antileishmanial drugs.


Assuntos
Acetogeninas/farmacologia , Acetileno/farmacologia , Annonaceae/química , Antiprotozoários/farmacologia , Leishmania/efeitos dos fármacos , Acetogeninas/química , Acetileno/análogos & derivados , Antiprotozoários/química , Humanos , Leishmaniose/tratamento farmacológico , Sementes/química
20.
Int J Mol Sci ; 23(1)2022 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-35008988

RESUMO

Hospital-acquired infections are responsible for a significant part of morbidity and mortality. Among the possible modes of transmission, this study focuses on environmental surfaces by developing innovative antibacterial coatings that can be applied on interior fittings in hospitals. This work aims to optimize a coating made of an amorphous carbon matrix doped with silver (a-C:H:Ag) produced by a hybrid PVD/PECVD process and to evaluate its antibacterial activity. We present a coating characterization (chemical composition and morphology) as well as its stability in an ageing process and after multiple exposures to bacteria. The antibacterial activity of the coatings is demonstrated against Escherichia coli (Gram-negative) and Staphylococcus aureus (Gram-positive) bacteria through several bioassays. Moreover, the data suggest a crucial role of silver diffusion towards the surface and nanoparticle formation to explain the very promising anti-bacterial activities reported in this work.


Assuntos
Acetileno , Antibacterianos/química , Antibacterianos/farmacologia , Carbono , Materiais Revestidos Biocompatíveis , Prata , Acetileno/química , Carbono/química , Fenômenos Químicos , Testes de Sensibilidade Microbiana/métodos , Nanoestruturas/química , Tamanho da Partícula , Prata/química , Análise Espectral , Propriedades de Superfície
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