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Environmental Science and Pollution... Jul 2023The process of phosphine production by phosphate-reducing bacteria Pseudescherichia sp. SFM4 has been well studied. Phosphine originates from the biochemical stage of...
The process of phosphine production by phosphate-reducing bacteria Pseudescherichia sp. SFM4 has been well studied. Phosphine originates from the biochemical stage of functional bacteria that synthesize pyruvate. Stirring the aggregated bacterial mass and supplying pure hydrogen could lead to an increase of 40 and 44% phosphine production, respectively. Phosphine was produced when bacterial cells agglomerated in the reactor. Extracellular polymeric substances secreted on microbial aggregates promoted the formation of phosphine due to the presence of groups containing phosphorus element. Phosphorus metabolism gene and phosphorus source analysis implied that functional bacteria used anabolic organic phosphorus, especially containing carbon-phosphorus bonds, as a source with [H] as electron donor to produce phosphine.
Topics: Phosphorus; Bacteria; Phosphines; Enterobacteriaceae
PubMed: 37243771
DOI: 10.1007/s11356-023-27293-7 -
Angewandte Chemie (International Ed. in... Oct 2022Herein, cobaloxime is used for the first time as a catalyst for the synthesis of phosphorylated heteroaromatics, which is an intriguing and versatile functional motif....
Herein, cobaloxime is used for the first time as a catalyst for the synthesis of phosphorylated heteroaromatics, which is an intriguing and versatile functional motif. With visible-light irradiation, cobaloxime not only oxidizes phosphine oxides to form phosphorus radicals (P-radicals) for a subsequent reaction with radical acceptor isocyanides or heteroaromatics, but also combines the radical intermediate with β-H elimination, thereby producing phosphorylated heteroaromatics with only H or CH as byproduct. Phosphine oxides with dialkyl, alkylaryl, and diaryl substituents could be directly transformed into phosphorylated phenanthridines, benzothiazoles, isoquinolines, and common heteroaromatics. This catalytic system features extremely mild conditions, broad substrate scope and good to excellent yields. Scale-up reaction and sunlight reaction show the great application potential in the green synthesis of important organophosphorus chemicals.
Topics: Benzothiazoles; Cyanides; Isoquinolines; Organometallic Compounds; Oxides; Phenanthridines; Phosphines; Phosphorus
PubMed: 35912895
DOI: 10.1002/anie.202209293 -
Journal of Inorganic Biochemistry Mar 2023A systematic study of the effect of phosphine and bis-phosphine ligands in the interaction of Ni, Pd, and Pt complexes with two classes of zinc fingers was performed....
A systematic study of the effect of phosphine and bis-phosphine ligands in the interaction of Ni, Pd, and Pt complexes with two classes of zinc fingers was performed. The CysHis, finger 3 of specific protein-1, and the CysHisCys C-terminal zinc finger of nucleocapsid protein 7 of the HIV-1 were used as models of the respective class. In general, phosphine ligands favor the metal binding to the peptide, although the bis-phosphine ligands produce more specific binding than the monodentate. In the case of nickel complexes, the interaction of Ni ions with the sequence SKH, present in CysHis, results in hydrolysis, contrasting to the preferred zinc ejection produced by the Ni complexes with chelating phosphines, producing Ni(bis-phosphine) fingers. In the absence of the SKH sequence, zinc ejection is observed with the formation of nickel fingers, with reactivity dependent on the phosphine. On the other hand, Pd(phosphines) produces Pd fingers in the case of triphenylphosphine with the phosphine coordinated as intermediate species. The bis-phosphine ligands produce very clean spectra and a stable signal Pd(bis-phosphine)finger. Interestingly, phosphines produce very reactive platinum complexes, which eject zinc and promote peptide hydrolysis. The results reported here are relevant to the understanding of the mechanism of these interactions and how to modulate metallocompounds for zinc finger interference.
Topics: Phosphines; Nickel; Ligands; Hydrolysis; Zinc Fingers; Zinc
PubMed: 36635196
DOI: 10.1016/j.jinorgbio.2022.112117 -
Molecules (Basel, Switzerland) Sep 2022This study investigates the mechanism of metal-free pyridine phosphination with P(OEt), PPh, and PArCF using density functional theory calculations. The results show...
This study investigates the mechanism of metal-free pyridine phosphination with P(OEt), PPh, and PArCF using density functional theory calculations. The results show that the reaction mechanism and rate-determining step vary depending on the phosphine and additive used. For example, phosphination of pyridine with P(OEt) occurs in five stages, and ethyl abstraction is the rate-determining step. Meanwhile, 2-Ph-pyridine phosphination with PPh is a four-step reaction with proton abstraction as the rate-limiting step. Energy decomposition analysis of the transition states reveals that steric hindrance in the phosphine molecule plays a key role in the site-selective formation of the phosphonium salt. The mechanism of 2-Ph-pyridine phosphination with PArCF is similar to that with PPh, and analyses of the effects of substituents show that electron-withdrawing groups decreased the nucleophilicity of the phosphine, whereas aryl electron-donating groups increased it. Finally, TfO plays an important role in the C-H fluoroalkylation of pyridine, as it brings weak interactions.
Topics: Catalysis; Electrons; Metals; Models, Theoretical; Pyridines
PubMed: 36080460
DOI: 10.3390/molecules27175694 -
Drug Research Feb 2022Aluminum phosphide (AlP) toxicity is associated with a high risk of death due to heart, liver, and kidney failure as the target organs. Phosphine gas released due to the...
BACKGROUND
Aluminum phosphide (AlP) toxicity is associated with a high risk of death due to heart, liver, and kidney failure as the target organs. Phosphine gas released due to the ingestion is the main factor involved in the multi-organ failure with various mechanisms. Levosimendan (LEV) is a calcium sensitizer with a pleiotropic effect on multiple organs. This study aimed to investigate whether LEV can alleviate AlP-induced nephrotoxicity in the rat model.
METHOD
Six groups included control group (almond oil only), sole LEV group (48 µg/kg), AlP group (LD50=10 µg/kg), and the poisoned groups treated with LEV at doses of 12, 24, and 48 µg/kg 30 min after AlP gavage. After 24 hours of treatment, serum and kidney samples were taken for biochemical and histopathological analyses.
RESULT
Biochemical analysis of the AlP group showed that the activity of complexes I, II, and IV was significantly reduced, while the levels of lipid peroxidation (LPO) and reactive oxygen species (ROS), lactate, and myeloperoxidase (MPO) activity significantly increased. Also, AlP reduced live renal cells and elevated necrosis. However, the levels of serum creatinine and blood urea nitrogen were not affected by the poisoning. LEV co-treatment could increase mitochondrial complex activity and reduce MPO activity, LPO, ROS, and lactate levels. Additionally, the histopathological analysis showed the detrimental effects of AlP on kidney tissue, which was mitigated by LEV administration.
CONCLUSION
Our findings showed that LEV can potentially improve oxidative stress, imbalance in the redox status, necrosis, and pathological injuries in kidney tissue following AlP-poisoning.
Topics: Animals; Heart; Kidney; Oxidative Stress; Phosphines; Rats; Reactive Oxygen Species; Simendan
PubMed: 34788887
DOI: 10.1055/a-1661-5439 -
International Journal of Environmental... Mar 2023Aluminum phosphide is a highly effective insecticide for fumigation in granaries and is often used in rural grain storage. However, people's awareness of its toxicity is...
Aluminum phosphide is a highly effective insecticide for fumigation in granaries and is often used in rural grain storage. However, people's awareness of its toxicity is not strong. A case of acute inhalation toxicity of phosphine caused by the use of aluminum phosphide to fumigate a granary is reported here. The case presented with aspiration pneumonia and acute left heart failure. The patient was cured using comprehensive life support treatment, including respiratory support, antiarrhythmic treatment, and blood pressure maintenance with vasoactive drugs. There is no specific antidote for phosphine poisoning at present, and the comprehensive application of restricted fluid resuscitation, high-dose glucocorticoid shock, vasoactive drugs and bedside hemofiltration is significant in improving the prognosis of patients. It is also important to remind people to pay attention to their own protection in the process of using aluminum phosphide.
Topics: Humans; Phosphines; Aluminum Compounds; Insecticides
PubMed: 36981930
DOI: 10.3390/ijerph20065021 -
Pest Management Science Feb 2024Stored product protection from insect pests relies heavily on the use of phosphine. The most serious drawback of phosphine is the development of resistance in major...
Development, application and evaluation of three novel TaqMan qPCR assays for phosphine resistance monitoring in major stored product pests Tribolium castaneum and Rhyzopertha dominica.
BACKROUND
Stored product protection from insect pests relies heavily on the use of phosphine. The most serious drawback of phosphine is the development of resistance in major stored product insects worldwide, including the red flour beetle, Tribolium castaneum (Herbst) and the lesser grain borer, Rhyzopertha dominica (F.). Two genetic loci are responsible for phosphine resistance: the rph1 (S349G mutation in the cyt-b5-r homolog) in T. castaneum and the rph2 (P45/49S mutation in the dihydrolipoamide dehydrogenase (dld) gene) in T. castaneum and R. dominica.
RESULTS
In this study, we have developed and applied high-throughput, practical and specific molecular diagnostics (TaqMan qPCR) for monitoring mutations S349G, P45S and P49S. In our pilot monitoring application, we have included phosphine-resistant and susceptible populations from different parts of the world (USA, Australia, Brazil) and European strains from Greece and Serbia. Our results for the resistant T. castaneum showed a P45S mutant allele frequency (MAF) of 100% and 75.0% in the populations from Serbia and Brazil, respectively. Regarding the susceptible T. castaneum, P45S was detected in Greece (MAF = 62.5%) and was absent in Australia (MAF = 0.0%). Additionally, the S349G mutation was found to be fixed in all resistant populations, while it was also detected in susceptible ones (frequencies: 65.0% and 100.0%). The only case where both mutations were fixed (100%) was a resistant population from Serbia. In R. dominica, the P49S mutation was found only in the two resistant R. dominica populations from Serbia and Greece (50.0% and 100%) and was absent from the susceptible one from Greece; thus, P49S seems to be a satisfactory indicator for monitoring phosphine resistance.
CONCLUSIONS
Our P49S detection assay in R. dominica seems to be a viable option in this direction, yet its utilization needs additional large-scale confirmatory work. The identification of additional resistance markers also should be prioritized. © 2023 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
Topics: Animals; Tribolium; Insecticides; Insecticide Resistance; Coleoptera; Phosphines
PubMed: 37671455
DOI: 10.1002/ps.7755 -
Biochemistry Sep 2020Protein biochemistry protocols typically include disulfide bond reducing agents to guard against unwanted thiol oxidation and protein aggregation. Commonly used...
Protein biochemistry protocols typically include disulfide bond reducing agents to guard against unwanted thiol oxidation and protein aggregation. Commonly used disulfide bond reducing agents include dithiothreitol, β-mercaptoethanol, glutathione, and the tris(alkyl)phosphine compounds tris(2-carboxyethyl)phosphine (TCEP) and tris(3-hydroxypropyl)phosphine (THPP). While studying the catalytic activity of the NAD(P)H-dependent enzyme Δ-pyrroline-5-carboxylate reductase, we unexpectedly observed a rapid non-enzymatic chemical reaction between NAD and the reducing agents TCEP and THPP. The product of the reaction exhibits a maximum ultraviolet absorbance peak at 334 nm and forms with an apparent association rate constant of 231-491 M s. The reaction is reversible, and nuclear magnetic resonance characterization (H, C, and P) of the product revealed a covalent adduct between the phosphorus of the tris(alkyl)phosphine reducing agent and the C4 atom of the nicotinamide ring of NAD. We also report a 1.45 Å resolution crystal structure of short-chain dehydrogenase/reductase with the NADP-TCEP reaction product bound in the cofactor binding site, which shows that the adduct can potentially inhibit enzymes. These findings serve to caution researchers when using TCEP or THPP in experimental protocols with NAD(P). Because NAD(P)-dependent oxidoreductases are widespread in nature, our results may be broadly relevant.
Topics: Bacterial Proteins; Burkholderia; Disulfides; Dithiothreitol; NAD; Oxidation-Reduction; Phosphines; Protein Conformation; Protein Domains; Reducing Agents; Short Chain Dehydrogenase-Reductases
PubMed: 32841567
DOI: 10.1021/acs.biochem.0c00490 -
Bioorganic & Medicinal Chemistry Letters Oct 2020The development of both chemotherapeutic drug resistance as well as adverse side effects suggest that the current chemotherapeutic drugs remain ineffective in treating...
The development of both chemotherapeutic drug resistance as well as adverse side effects suggest that the current chemotherapeutic drugs remain ineffective in treating the various types of cancers. The development of new metallodrugs presenting anti-cancer activity is therefore needed. Ruthenium complexes have gained a great deal of interest due to their promising anti-tumour properties and reduced toxicity in vivo. This study highlighted the effective induction of cell death in a malignant melanoma cell by two novel bis-amino-phosphine ruthenium(II) complexes referred to as GA105 and GA113. The IC concentrations were determined for both the complexes, the ligand and cisplatin, for comparison. Both complexes GA105 and GA113 displayed a high anti-cancer selectivity profile as they exhibited low IC values of 6.72 µM and 8.76 µM respectively, with low toxicity towards a non-malignant human cell line. The IC values obtained for both complexes were lower than that of cisplatin. The new complexes were more effective compared to the free ligand, GA103 (IC = >20 µM). Morphological studies on treated cells induced apoptotic features, which with further studies could indicate an intrinsic cell death pathway. Additionally, flow cytometric analysis revealed that the mode of cell death of complex GA113 was apoptosis. The outcomes herein give further insight into the potential use of selected Ru(II) complexes as alternative chemotherapeutic drugs in the future.
Topics: Antineoplastic Agents; Cell Proliferation; Cell Survival; Coordination Complexes; Diamines; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HEK293 Cells; Humans; Ligands; Molecular Structure; Phosphines; Ruthenium; Structure-Activity Relationship
PubMed: 32791194
DOI: 10.1016/j.bmcl.2020.127492 -
The Journal of Organic Chemistry Jul 2021An interesting remote δ-C 1,6-addition and an isomerization cascade reaction for phosphine-catalyzed activated alkynes have been disclosed. The products featuring a...
An interesting remote δ-C 1,6-addition and an isomerization cascade reaction for phosphine-catalyzed activated alkynes have been disclosed. The products featuring a functional diene and a 1,1-diaryl methyl motif have been obtained in moderate to good yields (30-86%) by applying -quinone methides (QMs) and δ-substituted alkynoate with tributylphosphine (PBu) catalysis, along with high regioselectivity and stereoselectivity (dr > 20:1). The wide scope of compatible substrates (35 examples), such as indolyl, oxindolyl, ester, and cinnamyl, expand the utility of this methodology. A plausible mechanism and some applications of it have also been presented.
Topics: Alkynes; Catalysis; Indolequinones; Phosphines
PubMed: 34164976
DOI: 10.1021/acs.joc.1c00226