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1.
Bioorg Med Chem ; 56: 116627, 2022 02 15.
Article in English | MEDLINE | ID: mdl-35063896

ABSTRACT

As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated that compound 23d exhibited excellently inhibitory activity on LPS-induced NO production in RAW264.7 cells (IC50 = 0.38 ± 0.18 µM). The preliminary structure-activity relationships (SARs) suggested that phenylsulfonyl substituted furoxan moiety had the strongest ability to improve anti-inflammatory activity of lathyrane diterpenoids. Furthermore, compound 23d significantly reduced the level of ROS. Its molecular mechanism was related to inhibiting the transcriptional activation of Nrf2/HO-1 pathway. Based on these considerations, 23d might be a promising anti-inflammatory agent, which is noteworthy for further exploration.


Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Diterpenes/pharmacology , Heterocyclic Compounds/pharmacology , Nitrogen Compounds/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Diterpenes/chemical synthesis , Diterpenes/chemistry , Dose-Response Relationship, Drug , Heme Oxygenase-1/antagonists & inhibitors , Heme Oxygenase-1/metabolism , Heterocyclic Compounds/chemistry , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Membrane Proteins/antagonists & inhibitors , Membrane Proteins/metabolism , Mice , Molecular Structure , NF-E2-Related Factor 2/antagonists & inhibitors , NF-E2-Related Factor 2/metabolism , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Nitrogen Compounds/chemistry , RAW 264.7 Cells , Structure-Activity Relationship
2.
Mol Divers ; 26(2): 1077-1100, 2022 Apr.
Article in English | MEDLINE | ID: mdl-33988806

ABSTRACT

Mono-/dispirocyclotriphosphazenes with pendant arm(s) are robust, but they are less investigated inorganic ring systems. In this study, a series of mono (3 and 4)- and dispirocyclotriphosphazenes with 4-chloro-benzyl pendant arm(s) (13-16) was obtained from the Cl exchange reactions of hexachlorocyclotriphosphazene with sodium (N-benzyl)aminopropanoxides (1 and 2). When compound (3) reacted with excess pyrrolidine, morpholine, tetra-1,4-dioxa-8-azaspiro[4,5]decane (DASD) and piperidine, the fully substituted monospirocyclotriphosphazenes (7, 9, 10 and 12) occurred. But, the reactions of 4 with excess piperidine and morpholine produced the gem-piperidino (5)- and morpholino (6)-substituted monospirocyclotriphosphazenes, whereas the reactions of 4 with excess pyrrolidine and DASD gave the fully substituted monospirocyclotriphosphazenes (8) and (11). However, it should be indicated that these derivatives were obtained to be used for the investigation of their spectral, stereogenic and biological properties. The structures of 5, 7 and 14 were determined crystallographically. X-ray data of 5 and 14 displayed that both of compounds were chiral in solid state, and their absolute configurations were assigned as R and RR. Additionally, the antimicrobial activities of phosphazenes were investigated. Minimum inhibitory concentrations, minimal bacterial concentrations and minimum fungicidal concentrations of phosphazenes were determined. The interactions of phosphazenes with plasmid DNA were evaluated by agarose gel electrophoresis. The cytotoxic activities of compounds were studied against L929 fibroblast and DLD-1 colon cancer cells. In addition, density functional theory calculations of 5, 7 and 14 were reported, and their molecular docking studies with DNA, E. coli DNA gyrase and topoisomerase IV were presented.


Subject(s)
Anti-Infective Agents , Antineoplastic Agents , Anti-Bacterial Agents/chemistry , Anti-Infective Agents/chemistry , Antineoplastic Agents/chemistry , Crystallography, X-Ray , DNA/chemistry , Escherichia coli , Microbial Sensitivity Tests , Molecular Docking Simulation , Morpholines , Nitrogen/chemistry , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Phosphorus/chemistry , Piperidines , Pyrrolidines/pharmacology
3.
Chemistry ; 27(9): 3085-3090, 2021 Feb 10.
Article in English | MEDLINE | ID: mdl-33263935

ABSTRACT

Universal access to clean water has been a global ambition over the years. Photocatalytic water disinfection through advanced oxidation processes has been regarded as one of the promising methods for breaking down microbials. The forefront of this research focuses on the application of metal-free photocatalysts for disinfection to prevent secondary pollution. Graphitic carbon nitride (g-C3 N4 ) has achieved instant attention as a metal-free and visible-light-responsive photocatalyst for various energy and environmental applications. However, the photocatalytic efficiency of g-C3 N4 is still affected by its rapid charge recombination and sluggish electron-transfer kinetics. In this contribution, two-dimensionally protonated g-C3 N4 was employed as metal-free photocatalyst for water treatment and demonstrated 100 % of Escherichia coli within 4 h under irradiation with a 23 W light bulb. The introduction of protonation can modulate the surface charge of g-C3 N4 ; this enhances its conductivity and provides a "highway" for the delocalization of electrons. This work highlights the potential of conjugated polymers in antibacterial application.


Subject(s)
Disinfection/methods , Escherichia coli/chemistry , Escherichia coli/radiation effects , Graphite/chemistry , Graphite/radiation effects , Light , Microbial Viability/radiation effects , Nitrogen Compounds/chemistry , Nitrogen Compounds/radiation effects , Protons , Catalysis/radiation effects , Electrons , Graphite/pharmacology , Microbial Viability/drug effects , Nitrogen Compounds/pharmacology , Photochemistry
4.
Ecotoxicol Environ Saf ; 208: 111712, 2021 Jan 15.
Article in English | MEDLINE | ID: mdl-33396043

ABSTRACT

The photocatalytic process is an environmentally-friendly procedure that has been well known in the destruction of organic pollutants in water. The multiple semiconductor heterojunctions are broadly applied to enhance the photocatalytic performances in comparison to the single semiconductor. Polymeric semiconductors have received much attention as inspiring candidates owing to their adjustable optical absorption features and simply adaptable electronic structure. The shortcomings of the current photocatalytic system, which restricts their technical applications incorporate fast charge recombination, low-utilization of visible radiation, and low immigration capability of the photo-induced electron-hole. This paper indicates the novel fabrication of new CuI/g-C3N4 nanocomposite by hydrothermal and ultrasound-assisted co-precipitation methods. The structure, shape, and purity of the products were affected by different weight percentages and fabrication processes. Electron microscope unveils that CuI nanoparticles are distributed on g-C3N4. The bandgap of pure carbon nitride is estimated at 2.70 eV, and the bandgap of the nanocomposite has increased to 2.8 eV via expanding the amount of CuI. The CuI/C3N4 nanocomposite has a great potential to degrade cationic and anionic dyes in high value because of its appropriate bandgap. It can be a great catalyst for water purification. The photocatalytic efficiency is affected by multiple factors such as types of dyes, fabrication methods, the light sources, mass ratios, and scavengers. The fabricated CuI/C3N4 nanocomposite exposes higher photocatalytic performance than the pure C3N4 and CuI. The photocatalytic efficiency of nanocomposite is enhanced by enhancing the amount of CuI. Besides, the fabricated CuI/C3N4 revealed remarkable reusability without the obvious loss of photocatalytic activity. The antibacterial activity of the specimens reveals that the highest antimicrobial activities are revealed against P. aeruginosa and E. coli. These results prove that the nanocomposite possesses high potential for killing bacteria, and it can be nominated as a suitable agent against bacteria.


Subject(s)
Anti-Bacterial Agents/pharmacology , Copper/chemistry , Graphite/chemistry , Iodides/chemistry , Nitrogen Compounds/chemistry , Water Pollutants, Chemical/isolation & purification , Anti-Bacterial Agents/chemistry , Catalysis , Coloring Agents/chemistry , Coloring Agents/isolation & purification , Coloring Agents/metabolism , Copper/pharmacology , Graphite/pharmacology , Iodides/pharmacology , Light , Nanocomposites/chemistry , Nitrogen Compounds/pharmacology , Water Pollutants, Chemical/chemistry , Water Purification/methods
5.
Small ; 16(10): e1904619, 2020 03.
Article in English | MEDLINE | ID: mdl-31971659

ABSTRACT

Thanks to its photocatalytic property, graphitic carbon nitride (g-C3 N4 ) is a promising candidate in various applications including nanomedicine. However, studies focusing on the suitability of g-C3 N4 for cancer therapy are very limited and possible underlying molecular mechanisms are unknown. Here, it is demonstrated that photoexcitation of g-C3 N4 can be used effectively in photodynamic therapy, without using any other carrier or additional photosensitizer. Upon light exposure, g-C3 N4 treatment kills cancer cells, without the need of any other nanosystem or chemotherapeutic drug. The material is efficiently taken up by tumor cells in vitro. The transcriptome and proteome of g-C3 N4 and light treated cells show activation in pathways related to both oxidative stress, cell death, and apoptosis which strongly suggests that only when combined with light exposure, g-C3 N4 is able to kill cancer cells. Systemic administration of the mesoporous form results in elimination from urinary bladder without any systemic toxicity. Administration of the material significantly decreases tumor volume when combined with local light treatment. This study paves the way for the future use of not only g-C3 N4 but also other 2D nanomaterials in cancer therapy.


Subject(s)
Graphite , Neoplasms , Nitrogen Compounds , Photochemotherapy , A549 Cells , Animals , Cell Line, Tumor , Cell Survival/drug effects , Cell Survival/radiation effects , Graphite/chemistry , Graphite/pharmacology , Humans , Light , Male , Mice , Mice, Inbred BALB C , Neoplasms/therapy , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Photochemotherapy/methods
6.
Bioorg Chem ; 102: 104086, 2020 09.
Article in English | MEDLINE | ID: mdl-32688114

ABSTRACT

Pipajiains H-J (1-3), three new phenolic derivatives with an unusual sulfone group, pipajiamides A-C (4-6), three new amide derivatives, pipajiaine A (7), one new imidazole analogue, and pipajiaine B (8), a pair of new pyrrolidine derivatives, along with three known compounds were isolated from the insect Blaps japanensis. Their structures were identified by spectroscopic and computational methods. Chiral HPLC was used to separate the (-)- and (+)-antipodes of 4 and 8. Biological activities of all the new compounds against extracellular matrix in rat renal proximal tubular cells, human cancer cells (A549, Huh-7, and K562), COX-2, ROCK1, and JAK3 were evaluated. The results show that compounds 2, (+)-4, and (-)-4 are active against kidney fibrosis, whereas, compound 9 is active toward human cancer cells, inflammation, and JAK3 kinase.


Subject(s)
Coleoptera/chemistry , Nitrogen Compounds/pharmacology , Protein Kinase Inhibitors/pharmacology , Sulfur/pharmacology , Animals , Cells, Cultured , Density Functional Theory , Dose-Response Relationship, Drug , Fibrosis/drug therapy , Humans , Janus Kinase 3/antagonists & inhibitors , Janus Kinase 3/metabolism , Molecular Structure , Nitrogen Compounds/chemistry , Nitrogen Compounds/isolation & purification , Protein Kinase Inhibitors/chemistry , Protein Kinase Inhibitors/isolation & purification , Rats , Structure-Activity Relationship , Sulfur/chemistry , Sulfur/isolation & purification , rho-Associated Kinases/antagonists & inhibitors , rho-Associated Kinases/metabolism
7.
Molecules ; 25(9)2020 Apr 26.
Article in English | MEDLINE | ID: mdl-32357416

ABSTRACT

Water resources contamination has a worldwide impact and is a cause of global concern. The need for provision of clean water is becoming more and more demanding. Nanotechnology may support effective strategies for the treatment, use and reuse of water and the development of next-generation water supply systems. The excellent properties and effectiveness of nanomaterials make them particularly suitable for water/wastewater treatment. This review provides a comprehensive overview of the main categories of nanomaterials used in catalytic processes (carbon nanotubes/graphitic carbon nitride (CNT/g-C3N4) composites/graphene-based composites, metal oxides and composites, metal-organic framework and commercially available nanomaterials). These materials have found application in the removal of different categories of pollutants, including pharmaceutically active compounds, personal care products, organic micropollutants, as well as for the disinfection of bacterial, viral and protozoa microbial targets, in water and wastewater matrices. Apart from reviewing the characteristics and efficacy of the aforementioned nanoengineered materials for the removal of different pollutants, we have also recorded performance limitations issues (e.g., toxicity, operating conditions and reuse) for their practical application in water and wastewater treatment on large scale. Research efforts and continuous production are expected to support the development of eco-friendly, economic and efficient nanomaterials for real life applications in the near future.


Subject(s)
Graphite/pharmacology , Metal-Organic Frameworks/pharmacology , Nanostructures/chemistry , Nanotubes, Carbon/chemistry , Nitrogen Compounds/pharmacology , Water Purification/methods , Catalysis , Disinfection/methods , Graphite/chemistry , Metal-Organic Frameworks/chemistry , Nitrogen Compounds/chemistry , Oxides/chemistry , Wastewater/microbiology , Wastewater/parasitology , Wastewater/toxicity , Wastewater/virology , Water Pollutants, Chemical
8.
Mar Drugs ; 17(12)2019 Dec 03.
Article in English | MEDLINE | ID: mdl-31816961

ABSTRACT

Marine sponge genus Haliclona, one of the most prolific sources of natural products, contains over 600 species but only a small part of them had been classified and chemically investigated. On the basis of extensive literature search, this review firstly summarizes 112 nitrogenous secondary metabolites from classified and unclassified Haliclona sponges as well as from their symbiotic microorganisms. Most of these substances have only been found in Haliclona sponges, and display diverse bioactive properties with potential applications in new drug discovery.


Subject(s)
Biological Products/isolation & purification , Haliclona/metabolism , Nitrogen Compounds/isolation & purification , Animals , Biological Products/chemistry , Biological Products/pharmacology , Drug Discovery/methods , Humans , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Secondary Metabolism , Symbiosis
9.
Phytother Res ; 33(10): 2661-2684, 2019 Oct.
Article in English | MEDLINE | ID: mdl-31453659

ABSTRACT

Several reviews have been published on Artemisia's derived natural products, but it is the first attempt to review the chemistry and pharmacology of more than 80 alkaloids and allied nitrogen compounds obtained from various Artemisia species (covering the literature up to June 2018). The pharmacological potential and unique skeleton types of certain Artemisia's alkaloids provoke the importance of analyzing Artemisia species for bioactive alkaloids and allied nitrogen compounds. Among the various types of bioactive Artemisia's alkaloids, the main classes were the derivatives of rupestine (pyridine-sesquiterpene), lycoctonine (diterpene), pyrrolizidine, purines, polyamine, peptides, indole, piperidine, pyrrolidine, alkamides, and flavoalkaloids. The rupestine derivatives are Artemisia's characteristic alkaloids, whereas the rest are common alkaloids found in the family Asteraceae and chemotaxonomically links the genus Artemisia with the tribes Anthemideae. The most important biological activities of Artemisia's alkaloids are including hepatoprotective, local anesthetic, ß-galactosidase, and antiparasitic activities; treatment of angina pectoris, opening blocked arteries, as a sleep-inducing agents and inhibition of HIV viral protease, CYP450, melanin biosynthesis, human carbonic anhydrase, [3H]-AEA metabolism, kinases, and DNA polymerase ß1 . Some of the important nitrogen metabolites of Artemisia include pellitorine, zeatin, tryptophan, rupestine, and aconitine analogs, which need to be optimized and commercialized further.


Subject(s)
Alkaloids/pharmacology , Artemisia/chemistry , Alkaloids/analysis , Humans , Nitrogen Compounds/pharmacology , Plant Extracts/pharmacology
10.
Biol Lett ; 14(7)2018 07.
Article in English | MEDLINE | ID: mdl-29997188

ABSTRACT

Ocean acidification (OA) and nutrient enrichment threaten the persistence of near shore ecosystems, yet little is known about their combined effects on marine organisms. Here, we show that a threefold increase in nitrogen concentrations, simulating enrichment due to coastal eutrophication or consumer excretions, offset the direct negative effects of near-future OA on calcification and photophysiology of the reef-building crustose coralline alga, Porolithon onkodes Projected near-future pCO2 levels (approx. 850 µatm) decreased calcification by 30% relative to ambient conditions. Conversely, nitrogen enrichment (nitrate + nitrite and ammonium) increased calcification by 90-130% in ambient and high pCO2 treatments, respectively. pCO2 and nitrogen enrichment interactively affected instantaneous photophysiology, with highest relative electron transport rates under high pCO2 and high nitrogen. Nitrogen enrichment alone increased concentrations of the photosynthetic pigments chlorophyll a, phycocyanin and phycoerythrin by approximately 80-450%, regardless of pCO2 These results demonstrate that nutrient enrichment can mediate direct organismal responses to OA. In natural systems, however, such direct benefits may be counteracted by simultaneous increases in negative indirect effects, such as heightened competition. Experiments exploring the effects of multiple stressors are increasingly becoming important for improving our ability to understand the ramifications of local and global change stressors in near shore ecosystems.


Subject(s)
Nitrogen Compounds/pharmacology , Rhodophyta/physiology , Seawater/chemistry , Calcification, Physiologic , Carbon Dioxide/adverse effects , Photosynthesis/physiology , Rhodophyta/metabolism , Water Pollutants, Chemical/adverse effects
11.
Nucleic Acids Res ; 44(14): 6935-48, 2016 08 19.
Article in English | MEDLINE | ID: mdl-27166377

ABSTRACT

Here, we report the characterization of a set of small, regulatory RNAs (sRNAs) expressed from an Escherichia coli locus we have denoted sdsN located adjacent to the LuxR-homolog gene sdiA Two longer sRNAs, SdsN137 and SdsN178 are transcribed from two σ(S)-dependent promoters but share the same terminator. Low temperature, rich nitrogen sources and the Crl and NarP transcription factors differentially affect the levels of the SdsN transcripts. Whole genome expression analysis after pulse overexpression of SdsN137 and assays of lacZ fusions revealed that the SdsN137 directly represses the synthesis of the nitroreductase NfsA, which catalyzes the reduction of the nitrogroup (NO2) in nitroaromatic compounds and the flavohemoglobin HmpA, which has aerobic nitric oxide (NO) dioxygenase activity. Consistent with this regulation, SdsN137 confers resistance to nitrofurans. In addition, SdsN137 negatively regulates synthesis of NarP. Interestingly, SdsN178 is defective at regulating the above targets due to unusual binding to the Hfq protein, but cleavage leads to a shorter form, SdsN124, able to repress nfsA and hmpA.


Subject(s)
Cytoprotection/drug effects , Escherichia coli Proteins/metabolism , Nitrogen Compounds/pharmacology , RNA, Bacterial/metabolism , Sigma Factor/metabolism , Trans-Activators/metabolism , Base Sequence , DNA, Intergenic/genetics , Escherichia coli/drug effects , Escherichia coli/genetics , Escherichia coli/growth & development , Escherichia coli/metabolism , Escherichia coli Proteins/genetics , Gene Expression Regulation, Bacterial/drug effects , Host Factor 1 Protein/metabolism , Nucleic Acid Conformation , RNA, Bacterial/chemistry , RNA, Messenger/genetics , RNA, Messenger/metabolism , Uridine/metabolism
12.
Molecules ; 23(10)2018 Oct 03.
Article in English | MEDLINE | ID: mdl-30282927

ABSTRACT

A selection of 1-amino-2-arylidenamine-1,2-(dicyano)ethenes 3 was synthesized and cyclized to 2-aryl-4,5-dicyano-1H-imidazoles 4 upon reflux in ethyl acetate/acetonitrile, in the presence of manganese dioxide. These compounds were tested for their antioxidant capacity by cyclic voltammetry, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and deoxyribose degradation assays. The minimum inhibitory concentration of all compounds was evaluated against two yeast species, Saccharomyces cerevisiae and Candida albicans. Their toxicity was tested in mammal fibroblasts. Among the synthesised compounds, two presented dual antioxidant/antifungal activity without toxic effects in fibroblasts. The new compounds synthesized in this work are potential biochemical tools and/or therapeutic drugs.


Subject(s)
Antifungal Agents/chemistry , Antioxidants/chemistry , Nitrogen Compounds/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Antioxidants/chemical synthesis , Antioxidants/pharmacology , Biphenyl Compounds/chemistry , Candida albicans/drug effects , Candida albicans/pathogenicity , Imidazoles/chemistry , Microbial Sensitivity Tests , Nitrogen Compounds/chemical synthesis , Nitrogen Compounds/pharmacology , Phenols/chemical synthesis , Phenols/chemistry , Picrates/chemistry , Plant Extracts/chemistry , Saccharomyces cerevisiae/drug effects , Structure-Activity Relationship
13.
Chem Pharm Bull (Tokyo) ; 65(2): 178-185, 2017.
Article in English | MEDLINE | ID: mdl-28154310

ABSTRACT

Fatty acid synthesis (FAS) is an essential metabolism during the whole growth and development process of the bacterial. Several key enzymes which involved in this biosynthetic pathway have been considered as useful targets for the development of new antibacterial agents. Among them, ß-ketoacyl-acyl carrier protein synthase III (FabH) is the most magnetic target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved of both Gram-positive and Gram-negative bacteria. Following the previous researches, Schiff-based derivatives with dioxygenated rings and N-heterocycle were synthesized in succession, and their biological activities as potential FabH inhibitors were evaluated in this paper. Among these 15 compounds, compound 2E exhibited the best antibacterial activities with minimum inhibitory concentration (MIC) values 1.56-3.13 mg/mL against the tested bacterial strains and showed the most powerful Escherichia coli (E. coli) FabH inhibitory activities with IC50 of 2.1 µM. Also the conceivable binding conformation of placing compound 2E into the E. coli FabH active site was affirmed docking simulation.


Subject(s)
3-Oxoacyl-(Acyl-Carrier-Protein) Synthase/antagonists & inhibitors , Anti-Bacterial Agents/chemistry , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Heterocyclic Compounds/chemistry , Nitrogen Compounds/chemistry , Schiff Bases/chemistry , Anti-Bacterial Agents/pharmacology , Heterocyclic Compounds/pharmacology , Microbial Sensitivity Tests , Nitrogen Compounds/pharmacology , Schiff Bases/pharmacology , Structure-Activity Relationship
14.
Molecules ; 22(12)2017 Dec 09.
Article in English | MEDLINE | ID: mdl-29232847

ABSTRACT

It has been proven that specific isoforms of human carbonic anhydrase (hCA) are able to fine-tune physiological pathways connected to signal processing, and that decreased CAs expression negatively influences cognition, leading to mental retardation, Alzheimer's disease, and aging-related cognitive dysfunctions. For this reason, a small library of natural and synthetic nitrogen containing cyclic derivatives was assayed as activators of four human isoforms of carbonic anhydrase (hCA I, II, IV and VII). Most of the compounds activated hCA I, IV and VII in the micromolar range, with KAs ranging between 3.46 and 80.5 µM, whereas they were not active towards hCA II (KAs > 100 µM). Two natural compounds, namely l-(+)-ergothioneine (1) and melatonin (2), displayed KAs towards hCA VII in the nanomolar range after evaluation by a CO2 hydration method in vitro, showing a rather efficient and selective activation profile with respect to histamine, used as a reference compound. Corroborated with the above in vitro findings, a molecular modelling in silico approach has been performed to correlate these biological data, and to elucidate the binding interaction of these activators within the enzyme active site.


Subject(s)
Carbonic Anhydrases/metabolism , Enzyme Activation , Nitrogen Compounds/chemical synthesis , Small Molecule Libraries/chemical synthesis , Carbonic Anhydrases/chemistry , Catalytic Domain/drug effects , Computer Simulation , Ergothioneine/chemistry , Ergothioneine/pharmacology , Humans , Melatonin/chemistry , Melatonin/pharmacology , Models, Molecular , Molecular Docking Simulation , Molecular Structure , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Small Molecule Libraries/chemistry , Small Molecule Libraries/pharmacology , Structure-Activity Relationship
15.
Z Naturforsch C J Biosci ; 70(3-4): 75-8, 2015.
Article in English | MEDLINE | ID: mdl-26052135

ABSTRACT

Chemical investigation of an unknown marine sponge, which was collected in the Gulf of Aqaba (Jordan), afforded a new brominated alkaloid 3-amino-1-(2-amino-4-bromophenyl)propan-1-one (1), as well as 7-bromoquinolin-4(1H)-one (2) which had previously only been reported as a synthetic compound. In addition, caulerpin (6), previously only known to be produced by algae, was likewise isolated. Furthermore, three known alkaloids including (Z)-5-(4-hydroxybenzylidene)-hydantoin, (Z)-6-bromo-3'-deimino-2',4'-bis(demethyl)-3'-oxoaplysinopsin, and 6-bromoindole-3-carbaldehyde (3-5), were also obtained. All compounds were unambiguously elucidated based on extensive 1D and 2D NMR spectroscopy, LCMS, as well as by comparison with the literature and tested for their cytotoxic activity toward the mouse lymphoma cell line L5178Y.


Subject(s)
Alkaloids/chemistry , Nitrogen Compounds/chemistry , Porifera/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Animals , Cell Line, Tumor , Mice , Nitrogen Compounds/isolation & purification , Nitrogen Compounds/pharmacology
16.
Appl Environ Microbiol ; 80(19): 6046-53, 2014 Oct.
Article in English | MEDLINE | ID: mdl-25063657

ABSTRACT

Conidial germination is fundamentally important to the growth and dissemination of most fungi. It has been previously shown (K. Hayer, M. Stratford, and D. B. Archer, Appl. Environ. Microbiol. 79:6924-6931, 2013, http://dx.doi.org/10.1128/AEM.02061-13), using sugar analogs, that germination is a 2-stage process involving triggering of germination and then nutrient uptake for hyphal outgrowth. In the present study, we tested this 2-stage germination process using a series of nitrogen-containing compounds for the ability to trigger the breaking of dormancy of Aspergillus niger conidia and then to support the formation of hyphae by acting as nitrogen sources. Triggering and germination were also compared between A. niger and Aspergillus nidulans using 2-deoxy-D-glucose (trigger), D-galactose (nontrigger in A. niger but trigger in A. nidulans), and an N source (required in A. niger but not in A. nidulans). Although most of the nitrogen compounds studied served as nitrogen sources for growth, only some nitrogen compounds could trigger germination of A. niger conidia, and all were related to L-amino acids. Using L-amino acid analogs without either the amine or the carboxylic acid group revealed that both the amine and carboxylic acid groups were essential for an L-amino acid to serve as a trigger molecule. Generally, conidia were able to sense and recognize nitrogen compounds that fitted into a specific size range. There was no evidence of uptake of either triggering or nontriggering compounds over the first 90 min of A. niger conidial germination, suggesting that the germination trigger sensors are not located within the spore.


Subject(s)
Amino Acids/pharmacology , Aspergillus nidulans/drug effects , Aspergillus niger/drug effects , Nitrogen Compounds/pharmacology , Spores, Fungal/drug effects , Aspergillus nidulans/growth & development , Aspergillus niger/growth & development , Carbon Radioisotopes/analysis , Cysteine/pharmacology , Deoxyglucose/pharmacology , Galactose/pharmacology , Hyphae , Serine/pharmacology , Spores, Fungal/growth & development , Valine/pharmacology
17.
J Prosthet Dent ; 112(5): 1103-10, 2014 Nov.
Article in English | MEDLINE | ID: mdl-24836536

ABSTRACT

STATEMENT OF PROBLEM: Titanium has long been used to produce dental implants. Problems related to its manufacturing, casting, welding, and ceramic application for dental prostheses still limit its use, which highlights the need for technologic improvements. The aim of this in vitro study was to evaluate the biologic performance of titanium dental implants coated with zirconium nitride in a murine preosteoblast cellular model. PURPOSE: The purpose of this study was to evaluate the chemical and morphologic characteristics of titanium implants coated with zirconium nitride by means of physical vapor deposition. MATERIAL AND METHODS: Chemical and morphologic characterizations were performed by scanning electron microscopy and energy dispersive x-ray spectroscopy, and the bioactivity of the implants was evaluated by cell-counting experiments. RESULTS: Scanning electron microscopy and energy dispersive x-ray spectroscopy analysis found that physical vapor deposition was effective in covering titanium surfaces with zirconium nitride. Murine MC-3T3 preosteoblasts were seeded onto titanium-coated and zirconium nitride-coated screws to evaluate their adhesion and proliferation. These experiments found a significantly higher number of cells adhering and spreading onto zirconium nitride-coated surfaces (P<.05) after 24 hours; after 7 days, both titanium and zirconium nitride surfaces were completely covered with MC-3T3 cells. CONCLUSIONS: Analysis of these data indicates that the proposed zirconium nitride coating of titanium implants could make the surface of the titanium more bioactive than uncoated titanium surfaces.


Subject(s)
Coated Materials, Biocompatible/pharmacology , Dental Implants , Dental Materials/chemistry , Nitrogen Compounds/pharmacology , Osteoblasts/drug effects , Titanium/chemistry , Zirconium/pharmacology , 3T3 Cells , Animals , Cell Adhesion/drug effects , Cell Count , Cell Culture Techniques , Cell Proliferation/drug effects , Materials Testing , Mice , Microscopy, Electron, Scanning , Osteoblasts/ultrastructure , Pseudopodia/ultrastructure , Spectrometry, X-Ray Emission , Volatilization
18.
ACS Appl Mater Interfaces ; 16(20): 25727-25739, 2024 May 22.
Article in English | MEDLINE | ID: mdl-38742469

ABSTRACT

The development of engineered nanomaterials has been considered a promising strategy to control oral infections. In this study, silver-embedded carbon nitrides (Ag@g-CN) were synthesized and tested against Candida albicans, investigating their antifungal action and biocompatibility in animal cells. Ag@g-CN was synthesized by a simple one-pot thermal polymerization technique and characterized by various analytical techniques. X-ray diffraction (XRD) analysis revealed slight alterations in the crystal structure of g-CN upon the incorporation of Ag. Fourier transform infrared (FT-IR) spectroscopy confirmed the presence of Ag-N bonds, indicating successful silver incorporation and potential interactions with g-CN's amino groups. UV-vis spectroscopy demonstrated a red shift in the absorption edge of Ag@g-CN compared with g-CN, attributed to the surface plasmon resonance effect of silver nanoparticles. Field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM) confirmed the 2D layered sheet like morphology of both materials. The Ag 3d peaks found in X-ray photoelectron spectroscopy (XPS) confirmed the presence of metallic Ag0 nanoparticles in Ag@g-CN. The Ag@g-CN materials exhibited high antifungal activity against reference and oral clinical strains of C. albicans, with minimal inhibitory concentration (MIC) ranges between 16-256 µg/mL. The mechanism of Ag@g-CN on C. albicans was attributed to the disruption of the membrane integrity and disturbance of the biofilm. In addition, the Ag@g-CN material showed good biocompatibility in the fibroblastic cell line and in Galleria mellonella, with no apparent cytotoxicity observed at a concentration up to 1000 µg/mL. These findings demonstrate the potential of the Ag@g-CN material as an effective and safe antifungal agent for the treatment of oral fungal infections.


Subject(s)
Antifungal Agents , Candida albicans , Metal Nanoparticles , Silver , Candida albicans/drug effects , Silver/chemistry , Silver/pharmacology , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/chemical synthesis , Metal Nanoparticles/chemistry , Metal Nanoparticles/toxicity , Animals , Microbial Sensitivity Tests , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Nitrogen Compounds/toxicity , Mice , Nitriles
19.
Colloids Surf B Biointerfaces ; 240: 113998, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38823340

ABSTRACT

Photoactivated therapy has gradually emerged as a promising and rapid method for combating bacteria, aimed at overcoming the emergence of drug-resistant strains resulting from the inappropriate use of antibiotics and the subsequent health risks. In this work, we report the facile fabrication of Zn3[Fe(CN)6]/g-C3N4 nanocomposites (denoted as ZHF/g-C3N4) through the in-situ loading of zinc hexacyanoferrate nanospheres onto two-dimensional g-C3N4 sheets using a simple metal-organic frameworks construction method. The ZHF/g-C3N4 nanocomposite exhibits enhanced antibacterial activity through the synergistic combination of the excellent photothermal properties of ZHF and the photodynamic capabilities of g-C3N4. Under dual-light irradiation (420 nm + 808 nm NIR), the nanocomposites achieve remarkable bactericidal efficacy, eliminating 99.98% of Escherichia coli and 99.87% of Staphylococcus aureus within 10 minutes. Furthermore, in vivo animal experiments have demonstrated the outstanding capacity of the composite in promoting infected wound healing, achieving a remarkable wound closure rate of 99.22% after a 10-day treatment period. This study emphasizes the potential of the ZHF/g-C3N4 nanocomposite in effective antimicrobial applications, expanding the scope of synergistic photothermal/photodynamic therapy strategies.


Subject(s)
Anti-Bacterial Agents , Escherichia coli , Nanocomposites , Staphylococcus aureus , Wound Healing , Nanocomposites/chemistry , Wound Healing/drug effects , Staphylococcus aureus/drug effects , Escherichia coli/drug effects , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Animals , Photochemotherapy , Microbial Sensitivity Tests , Mice , Sterilization/methods , Ferrocyanides/chemistry , Ferrocyanides/pharmacology , Particle Size , Zinc/chemistry , Zinc/pharmacology , Photothermal Therapy , Surface Properties , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Graphite
20.
ACS Appl Bio Mater ; 7(5): 2911-2923, 2024 05 20.
Article in English | MEDLINE | ID: mdl-38619913

ABSTRACT

Protective masks are critical to impeding microorganism transmission but can propagate infection via pathogen buildup and face touching. To reduce this liability, we integrated electrospun photocatalytic graphitic carbon nitride (g-C3N4) nanoflakes into standard surgical masks to confer a self-sanitization capacity. By optimizing the purine/melamine precursor ratio during synthesis, we reduced the g-C3N4 band gap from 2.92 to 2.05 eV, eliciting a 4× increase in sterilizing hydrogen peroxide production under visible light. This narrower band gap enables robust photocatalytic generation of reactive oxygen species from environmental and breath humidity to swiftly eliminate accumulated microbes. Under ambient sunlight, the g-C3N4 nanocomposite mask layer achieved a 97% reduction in the bacterial viability during typical use. Because the optimized band gap also allows photocatalytic activity under shadowless lamp illumination, the self-cleaning functionality could mitigate infection risk from residual pathogens in routine hospital settings. Both g-C3N4 and polycaprolactone demonstrate favorable biocompatibility and biodegradability, making this approach preferable over current commercially available metal-based options. Given the abundance and low cost of these components, this scalable approach could expand global access to reusable self-sanitizing protective masks, serving as a sustainable public health preparedness measure against future pandemics, especially in resource-limited settings.


Subject(s)
Anti-Bacterial Agents , Graphite , Materials Testing , Nitrogen Compounds , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Graphite/chemistry , Graphite/pharmacology , Nitrogen Compounds/chemistry , Nitrogen Compounds/pharmacology , Purines/chemistry , Purines/pharmacology , Particle Size , Escherichia coli/drug effects , Textiles/microbiology , Masks , Microbial Sensitivity Tests , Biocompatible Materials/chemistry , Biocompatible Materials/pharmacology , Staphylococcus aureus/drug effects , Humans
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