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Journal of Agricultural and Food... Jun 2024In recent decades, the unique structural attributes and purported insecticidal properties of oximes have garnered increasing attention. A variety of insecticides,... (Review)
Review
In recent decades, the unique structural attributes and purported insecticidal properties of oximes have garnered increasing attention. A variety of insecticides, encompassing fluxametamide, fluhexafon, and lepimectin, have been synthesized, all of which incorporate oximes. This review endeavors to encapsulate the insecticidal efficacy, structure-activity correlations, and operative mechanisms of oxime-containing compounds. Furthermore, it delves into the conceptual frameworks underpinning the design of innovative oxime-based insecticides, thereby shedding light on prospective advancements in this field.
PubMed: 38920088
DOI: 10.1021/acs.jafc.4c02096 -
Chemical Communications (Cambridge,... Jun 2024The oxime functional group is pivotal in chemistry, finding extensive applications in medical science, catalysis, organic functional group transformations, and the... (Review)
Review
The oxime functional group is pivotal in chemistry, finding extensive applications in medical science, catalysis, organic functional group transformations, and the recognition of essential and toxic analytes. While the coordination chemistry of oxime derivatives has been thoroughly explored and several reviews have been published on this topic in reputable journals, a comprehensive review encompassing various aspects such as crystal engineering, cation and anion recognition, as well as coordination chemistry activities, is still in demand. This feature article highlights the diverse applications of oxime derivatives across multiple domains of chemistry, including medicine, agriculture, crystal engineering, coordination chemistry, and molecular recognition studies. Each of the oxime derivatives in this feature article are meticulously described in terms of their medicinal applications, crop protection, crystal engineering attributes, analyte recognition capabilities, and coordination chemistry aspects. By providing a comprehensive overview of their versatile applications, this article aims to inspire researchers to explore and develop novel oxime-based derivatives for future applications.
PubMed: 38916274
DOI: 10.1039/d4cc01397b -
Materials Horizons Jun 2024It is challenging for ionic liquid gels to achieve the combination of rapid self-healing with high toughness. Here, ionic liquid gels (DI-PR) were prepared from readily...
It is challenging for ionic liquid gels to achieve the combination of rapid self-healing with high toughness. Here, ionic liquid gels (DI-PR) were prepared from readily available materials. A dynamic covalently bonded oxime-carbamate was prepared from polycaprolactone diol, isophorone diisocyanate and dimethylethyleneglyoxime, followed by addition of the "rigid-flexible" cross-linking agent rutin to chemically cross-link the polymer chains and afford the ionic liquid gels, DI-PR. The tensile strength, elongation at break and toughness of the DI-PR gels were as high as 16.5 MPa, 1132.6%, and 52.6 MJ m, respectively. The toughness is similar to that of natural silkworm silk (70 MJ m) and wool (60 MJ m). After stretching, the DI-PR can rebound within 1 s, their room temperature self-healing rate is as high as 92%, they remain functional over the temperature range -50 °C to 140 °C and the interface with a steel plate has an adhesion toughness of >2000 J m. These properties mean that the DI-PR gels are particularly suitable for use as anticorrosion coatings for submarine and underground gas and oil pipelines. The use of rutin, which combines rigid quercetin-based structural units with flexible glycoside-based structural units, as a cross-linking agent, provides a new method for improving the toughness of soft materials through its synergistic interaction with hard and soft chain fragments of polyurethanes.
PubMed: 38910542
DOI: 10.1039/d4mh00497c -
ACS Medicinal Chemistry Letters Jun 2024In this study, a focused library of oxime ester derivatives of 2,4-dichloro-5-sulfamoylbenzoic acid (lasamide) containing Schiff bases was synthesized and tested for...
In this study, a focused library of oxime ester derivatives of 2,4-dichloro-5-sulfamoylbenzoic acid (lasamide) containing Schiff bases was synthesized and tested for their ability to inhibit the cytosolic human carbonic anhydrases (hCAs) I and II, as well as the transmembrane and tumor-associated IX and XII isoforms. As a result, we obtained a first line of knowledge on lasamide derivatives potentially useful for development as CA inhibitors (CAIs). In particular, we focused our attention on the derivative , which was selective toward hCAs IX and XII over the cytosolic isoenzymes. An study was conducted to assess the binding mode of within hCAs IX and XII. Also, antiproliferative assays highlighted promising derivatives. The data obtained in this study are currently in use for the development of better-performing compounds on the tumor-associated isoforms.
PubMed: 38894925
DOI: 10.1021/acsmedchemlett.4c00206 -
Photochemical & Photobiological... Jun 2024Photoisomerization is a key photochemical reaction in microbial and animal rhodopsins. It is well established that such photoisomerization is highly selective; all-trans...
Photoisomerization is a key photochemical reaction in microbial and animal rhodopsins. It is well established that such photoisomerization is highly selective; all-trans to 13-cis, and 11-cis to all-trans forms in microbial and animal rhodopsins, respectively. Nevertheless, unusual photoisomerization pathways have been discovered recently in microbial rhodopsins. In an enzymerhodopsin NeoR, the all-trans chromophore is isomerized into the 7-cis form exclusively, which is stable at room temperature. Although, the 7-cis form is produced by illumination of retinal, formation of the 7-cis form was never reported for a protonated Schiff base of all-trans retinal in solution. Present HPLC analysis of retinal oximes prepared by hydroxylamine reaction revealed that all-trans and 7-cis forms cannot be separated from the syn peaks under the standard HPLC conditions, while it is possible by the analysis of the anti-peaks. Consequently, we found formation of the 7-cis form by the photoreaction of all-trans chromophore in solution, regardless of the protonation state of the Schiff base. Upon light absorption of all-trans protonated retinal Schiff base in solution, excited-state relaxation accompanies double-bond isomerization, producing 7-cis, 9-cis, 11-cis, or 13-cis form. In contrast, specific chromophore-protein interaction enforces selective isomerization into the 13-cis form in many microbial rhodopsins, but into 7-cis in NeoR.
PubMed: 38886314
DOI: 10.1007/s43630-024-00602-w -
Bioorganic Chemistry Jun 2024In this review, the current progress in the research and development of butyrylcholinesterase (BChE) reactivators is summarised and the advantages or disadvantages of... (Review)
Review
In this review, the current progress in the research and development of butyrylcholinesterase (BChE) reactivators is summarised and the advantages or disadvantages of these reactivators are critically discussed. Organophosphorus compounds such as nerve agents (sarin, tabun, VX) or pesticides (chlorpyrifos, diazinon) cause irreversible inhibition of acetylcholinesterase (AChE) and BChE in the human body. While AChE inhibition can be life threatening due to cholinergic overstimulation and crisis, selective BChE inhibition has presumably no adverse effects. Because BChE is mostly found in plasma, its activity is important for the scavenging of organophosphates before they can reach AChE in the central nervous system. Therefore, this enzyme in combination with its reactivator can be used as a pseudo-catalytic scavenger of organophosphates. Three structural types of BChE reactivators were found, i.e. bisquaternary salts, monoquaternary salts and uncharged compounds. Although the reviewed reactivators have certain limitations, the promising candidates for BChE reactivation were found in each structural group.
PubMed: 38878749
DOI: 10.1016/j.bioorg.2024.107526 -
Angewandte Chemie (International Ed. in... Jun 2024In this work, six benzothioxanthene-based oxime esters were employed as photoinitiators for photopolymerization with visible light (LED) and sunlight. Their abilities to...
High Photoinitiating Efficiency of Benzothioxanthene-based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight.
In this work, six benzothioxanthene-based oxime esters were employed as photoinitiators for photopolymerization with visible light (LED) and sunlight. Their abilities to behave as Type I photoinitiators by mean of a photocleavage mechanism of oxime esters but also in multicomponent photoinitiating system with an iodonium salt (through an electron transfer mechanism) were both explored with the different structures. Due to their broad absorption spectra tailing up 600 nm, photoinitiating properties of the benzothioxanthene-based oxime esters were systematically tested under excitation with low-intensity LED light at wavelengths of 405 nm and 450 nm. Additionally, to the polymerization tests done under artificial light, different benzothioxanthene-based oxime esters were also investigated as solar photoinitiators and displayed a high reactivity in France (Western Europe) even in winter conditions. For the best candidates i.e. the most reactive structures, direct laser write experiments were carried out, evidencing the interest of these structures.
PubMed: 38877857
DOI: 10.1002/anie.202405337 -
BioFactors (Oxford, England) Jun 2024Neuropathy occurs due to damage to the peripheral/central nervous system either due to injury, disease, or drug usage. Increased endoplasmic reticulum (ER) stress is...
Neuropathy occurs due to damage to the peripheral/central nervous system either due to injury, disease, or drug usage. Increased endoplasmic reticulum (ER) stress is observed in neuropathy. ER stress also leads to a block in autophagy amplifying neuropathic pain. 6-Bromoindirubin-3'-oxime (6-BIO) is an inhibitor of GSK-3β which suppresses mTOR activity thereby increasing autophagy. Tunicamycin (TM)-mediated ER stress and diabetic rat models were used to elucidate the role of ER stress and autophagy in mitigation of neuropathic pain by 6-BIO. Pain was assessed by behavioral studies in ER stressed/diabetic rats having neuropathy. Western blotting, RT-PCR, and fluorescence microscopy were used to assess the level of autophagy and ER stress after TM and 6-BIO treatment in SH-SY5Y neurons. Intraplantar injection of TM in rats led to peripheral neuropathy which was reduced upon 6-BIO injection. 6-BIO also reduced pain in animals exhibiting diabetic peripheral neuropathy. Modulation in the markers of autophagy (p-mTOR, LC-3, and SQSTM1/p62) shows that 6-BIO induces autophagolysosome formation post TM treatment. Concomitantly, 6-BIO reduces ER stress and c-Fos expression-a neuronal activity and pain marker. Alleviation of pain by the inhibition of ER stress and increased formation of autolysosomes by 6-BIO can be harnessed for treating peripheral neuropathy.
PubMed: 38866585
DOI: 10.1002/biof.2088 -
Chemical Communications (Cambridge,... Jun 2024The total synthesis of 1,4a-di--pancratistatin, a novel stereoisomer of the anti-tumor alkaloid pancratistatin, was achieved in 14 steps starting from D-mannitol. The...
The total synthesis of 1,4a-di--pancratistatin, a novel stereoisomer of the anti-tumor alkaloid pancratistatin, was achieved in 14 steps starting from D-mannitol. The construction of the pancratistatin skeleton involved conjugate addition of organocuprate to a nitrosoolefin, which was generated from inosose oxime. This was followed by stereoselective reduction of the oxime to an amine and site-selective formylation. Biological evaluations revealed that the newly synthesized compounds exhibit cytotoxicity toward cancer cells and significant ferroptosis inhibitory activity. These compounds constitute a promising small-molecule library for the development of potent bioactive agents.
PubMed: 38864269
DOI: 10.1039/d4cc02199a -
Scientific Reports Jun 2024There have been 774,075,242 cases of COVID-19 and 7,012,986 deaths worldwide as of January 2024. In the early stages of the pandemic, there was an urgent need to reduce... (Meta-Analysis)
Meta-Analysis
A systematic review and meta-analysis, investigating dose and time of fluvoxamine treatment efficacy for COVID-19 clinical deterioration, death, and Long-COVID complications.
There have been 774,075,242 cases of COVID-19 and 7,012,986 deaths worldwide as of January 2024. In the early stages of the pandemic, there was an urgent need to reduce the severity of the disease and prevent the need for hospitalization to avoid stress on healthcare systems worldwide. The repurposing of drugs to prevent clinical deterioration of COVID-19 patients was trialed in many studies using many different drugs. Fluvoxamine (an SSRI and sigma-1 receptor agonist) was initially identified to potentially provide beneficial effects in COVID-19-infected patients, preventing clinical deterioration and the need for hospitalization. Fourteen clinical studies have been carried out to date, with seven of those being randomized placebo-controlled studies. This systematic review and meta-analysis covers the literature from the outbreak of SARS-CoV-2 in late 2019 until January 2024. Search terms related to fluvoxamine, such as its trade names and chemical names, along with words related to COVID-19, such as SARS-CoV-2 and coronavirus, were used in literature databases including PubMed, Google Scholar, Scopus, and the ClinicalTrials.gov database from NIH, to identify the trials used in the subsequent analysis. Clinical deterioration and death data were extracted from these studies where available and used in the meta-analysis. A total of 7153 patients were studied across 14 studies (both open-label and double-blind placebo-controlled). 681 out of 3553 (19.17%) in the standard care group and 255 out of 3600 (7.08%) in the fluvoxamine-treated group experienced clinical deterioration. The estimated average log odds ratio was 1.087 (95% CI 0.200 to 1.973), which differed significantly from zero (z = 2.402, p = 0.016). The seven placebo-controlled studies resulted in a log odds ratio of 0.359 (95% CI 0.1111 to 0.5294), which differed significantly from zero (z = 3.103, p = 0.002). The results of this study identified fluvoxamine as effective in preventing clinical deterioration, and subgrouping analysis suggests that earlier treatment with a dose of 200 mg or above provides the best outcomes. We hope the outcomes of this study can help design future studies into respiratory viral infections and potentially improve clinical outcomes.
Topics: Fluvoxamine; Humans; COVID-19 Drug Treatment; COVID-19; SARS-CoV-2; Treatment Outcome; Clinical Deterioration; Selective Serotonin Reuptake Inhibitors
PubMed: 38862591
DOI: 10.1038/s41598-024-64260-9