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Mohamed A Motaleb, Adli A Selim
The selective properties of dioxime compounds were discovered and outlined in the beginning of 20th century by Tschugaeff [L.Z. Tschugaeff, Z. Anorg. Allgem. Chem. 46 (1905) 144]. Dioximes have special properties as analytical reagents for transition metals. Dioximes complexation properties with metals were carried out by many investigations and these complexations showed a wide range of applications such as antimicrobial and theranostic agents. This review will provide general synthetic methods of oximes especially dioximes and brief overview on the applications of dioximes (applications of their metal complexes)...
October 6, 2018: Bioorganic Chemistry
Ligia R Gomes, Marcus V N de Souza, Cristiane F Da Costa, James L Wardell, John Nicolson Low
The crystal structures of three salicyaldoxime compounds, namely 2-hy-droxy-4-methyl-benzaldehyde oxime, C8 H9 NO2 , 1 , 2,4-di-hydroxy-benzaldehyde oxime, C7 H7 NO3 , 2 , and 2-hy-droxy-4-meth-oxy-benzaldehyde oxime, C8 H9 NO3 , 3 , are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The inter-planar angles between the C=N-O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1 , 2 and 3 , respectively...
October 1, 2018: Acta Crystallographica. Section E, Crystallographic Communications
Bin-Qing He, Xiao-Ye Yu, Peng-Zi Wang, Jia-Rong Chen, Wen-Jing Xiao
A photoredox-catalyzed iminyl radical-triggered C-C bond cleavage/addition/Kornblum oxidation cascade of cycloketone oxime esters and styrenes in DMSO is described. This three-component, one-pot procedure features mild conditions, a broad substrate scope, and high functional group tolerance, providing an efficient approach to access diversely functionalized ketonitriles.
October 15, 2018: Chemical Communications: Chem Comm
Hiromi Miyagawa, Takeshi Bamba
The gas chromatography/mass spectrometry (GC/MS)-based metabolomics requires a two-step derivatization procedure consisting of oximation and silylation. However, due to the incomplete derivatization and degeneration of the metabolites, good repeatability is difficult to obtain during the batch derivatization, as the time between completing the derivatization process and GC analysis differs from sample to sample. In this research, we successfully obtained good repeatability for the peak areas of 52 selected metabolites by sequential derivatization and interval injection, in which the oximation and silylation times were maintained at constant values...
October 10, 2018: Journal of Bioscience and Bioengineering
Yu Hirano, Naoshi Kojima, Yasuo Komatsu
Interstrand cross-linking of DNA or RNA inhibits the double strands from dissociating into single strands. This article contains detailed procedures for the synthesis of a novel interstrand cross-linker that comprises a bis-aminooxy naphthalene derivative and a description of its use in the preparation of sequence-specific interstrand cross-linked oligonucleotide duplexes. The interstrand cross-linker covalently connects a pair of apurinic/apyrimidinic sites in DNA/RNA duplexes with bis(aminooxy) groups. The resulting oxime linkages are stable under physiological conditions and greatly improve the thermal stability of the duplex...
October 13, 2018: Current Protocols in Nucleic Acid Chemistry
Gabriele Horn, Martijn Constantijn de Koning, Marco van Grol, Horst Thiermann, Franz Worek
Poisoning by organophosphorus compounds (OP) is characterized by inhibition of the key enzyme acetylcholinesterase (AChE) and potentially fatal outcomes in humans. Insufficient efficacy of the standard therapy with atropine and AChE reactivators (oximes) against certain OP initiated synthesis of novel non-oxime reactivators basing on the common structure 4-amino-2-((diethylamino)methyl)phenol (ADOC). Recently, we reported of a pyrrolidine-bearing ADOC analogue (3 l) with a remarkable ability to reactivate OP-inhibited AChE...
October 9, 2018: Toxicology Letters
Tatiana N Pashirova, Anissa Braïki, Irina V Zueva, Konstantin A Petrov, Vasily M Babaev, Evgenia A Burilova, Darya A Samarkina, Ildar Kh Rizvanov, Eliana B Souto, Ludovic Jean, Pierre-Yves Renard, Patrick Masson, Lucia Ya Zakharova, Oleg G Sinyashin
A novel approach for brain protection against poisoning by organophosphorus agents is developed based on the combination treatment of dual delivery of two oximes. Pralidoxime chloride (2-PAM) and a novel reactivator, 6-(5-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)pentyl)-3-hydroxy picolinaldehyde oxime (3-HPA), have been loaded in solid-lipid nanoparticles (SLNs) to offer distinct release profile and systemic half-life for both oximes. To increase the therapeutic time window of both oximes, SLNs with two different compartments were designed to load each respective drug...
October 8, 2018: Journal of Controlled Release: Official Journal of the Controlled Release Society
Bharath A Chhabria, Ashish Bhalla, Nusrat Shafiq, Susheel Kumar, Deba Prasad Dhibar, Navneet Sharma
INTRODUCTION: Organophosphate (OP) poisoning is an important public health concern in South-Asia especially in the farming population. Treatment of OP poisoning has remained unchanged since decades and case fatality is 10-40% despite best supportive care, anticholinergic agents and oximes. A new antidote is the need of the hour. Lipid emulsion being inexpensive, easily available and effective in management of other lipid soluble toxins may be a novel option. However, safety has not been established and efficacy is limited to animal studies and case reports in humans with OP poisoning...
October 11, 2018: Clinical Toxicology
Jinwoo Kim, Yashwardhan R Malpani, Jooyun Lee, Jin Soo Shin, Soo Bong Han, Young-Sik Jung
First-line medical treatment against nerve agents consists of co-administration of anticholinergic agents and oxime reactivators, which reactivate inhibited AChE. Pralidoxime, a commonly used oxime reactivator, is effective against some nerve agents but not against others; thus, new oxime reactivators are needed. Novel tacrine-pyridinium hybrid reactivators in which 4-pyridinealdoxime derivatives are connected to tacrine moieties by linear carbon chains of different lengths (C2-C7) were prepared (Scheme 1, 5a-f)...
October 4, 2018: Bioorganic & Medicinal Chemistry Letters
Chuanle Zhu, Fulin Chen, Chi Liu, Hao Zeng, Zhiyi Yang, Wanqing Wu, Huanfeng Jiang
A copper-catalyzed aerobic oxidative C-C single bond cleavage of acyclic unstrained oxime acetates is reported, providing various aryl nitriles and ketones in good yields. Mechanistic studies indicate a radical procedure is involved in this transformation, and the oxygen atom in the ketone products is originated from O2 in the air. Oxime acetates as an internal oxidant have been proved to be an initiator, which may promote the discovery of novel protocol for C-C bond cleavage and dioxygen activation.
October 10, 2018: Journal of Organic Chemistry
Wen-Jing Xiao, Xiao-Ye Yu, Quan-Qing Zhao, Jun Chen, Jia-Rong Chen
A visible light-driven, copper-catalyzed three-component radical cross-coupling of oxime esters, styrenes, and boronic acids have been developed. Key steps of this protocol involve catalytic generation of iminyl radical from redox-active oxime ester and subsequent C-C bond cleavage to cyanoalkyl radical. Upon its addition to styrene, the newly formed benzylic radical undergoes coupling with boronic acid-derived ArCu(II) complex to achieve 1,1-diarylmethane-containing alkylnitriles.
October 8, 2018: Angewandte Chemie
Christopher Bérubé, Alexandre Borgia, Normand Voyer
Two anabaenopeptins, Schizopeptin 791 and anabaenopeptin NZ825, have similar structural features and have been synthesized via a novel acid-catalyzed head-to-side-chain concomitant cyclization/cleavage reaction on oxime resin. The methodology gave rapid access to the anabaenopeptin scaffold by taking advantage of a combined solid-phase/solution-phase synthetic strategy. Also, as side-products of the synthesis, large C2-symmetric 38-member cyclic peptides ring bearing two endocyclic lysine side-chains were isolated, constituting a novel cyclic peptide scaffold...
October 1, 2018: Organic & Biomolecular Chemistry
J Moya Sánchez, M Royo-Villanova Reparaz, A Andreu Ruiz, T Ros Argente Del Castillo, S Sánchez Cámara, J H de Gea García, E Andreu Soler, D Pérez Martínez, M P Olmo Sánchez, C Llamas Lázaro, R H Reyes Marlés, R Jara Rubio
OBJECTIVE: To evaluate the feasibility of using the Sentinella® portable gamma-camera for the diagnosis of brain death (BD). DESIGN: A prospective, observational feasibility study was carried out. SETTING: Intensive Care Unit of a third level hospital. PATIENTS: Consecutive recording was made of the adults diagnosed with brain death based on clinical criteria following admission to the Intensive Care Unit in the period from January to December 2017...
September 27, 2018: Medicina Intensiva
Akihiko Hiyama, Kosuke Morita, Daisuke Sakai, Masahiko Watanabe
BACKGROUND: The aims of this study were to investigate the gene expression of CCN family members in rat intervertebral disc (IVD) cells and to examine whether Wnt-β-catenin signaling regulates the expression of CCN family 2 (CCN2)/connective tissue growth factor (CTGF) in rat nucleus pulposus (NP) cells. METHODS: The gene expression of CCN family members were assessed in rat IVD cells using real-time reverse transcription polymerase chain reaction (RT-PCR). The expression pattern of CCN2 was also assessed in rat IVD cells using western blot and immunohistochemical analyses...
September 29, 2018: Arthritis Research & Therapy
Khursheed Ali, Bilal Ahmed, Mohammad Saghir Khan, Javed Musarrat
Biogenic hematite (α-Fe2 O3 ) nanoparticles (NPs) of average size <10 nm were synthesized using green approach with Aloe vera extract (ALE). The aim of the study was to assess the protective effect of extracellular polymeric substances (EPS) against antibacterial and antibiofilm activities of ALE-α-Fe2 O3 NPs in normal EPS producers (pristine) and experimentally modified (low-EPS) Pseudomonas aeruginosa (P. aeruginosa) cells and the mechanism of cell killing. Formation of ALE-α-Fe2 O3 NPs has been validated by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM) and Fourier-transformed infrared spectroscopy (FTIR) analysis...
November 2018: Journal of Photochemistry and Photobiology. B, Biology
Ming-Yang Lee, Yi-Zhen Li, Kao-Jean Huang, Hui-Chi Huang, Ching-Yen Lin, Ying-Ray Lee
Cholangiocarcinoma (CCA) is one of the most serious of all cancers and a major public health problem. CCA is an extremely invasive cancer, and the survival rate for CCA patients is only 24 months after diagnosis. Although surgery and chemotherapy can extend the survival rate to 5 years, < 20-40% of CCA patients will survive this long; therefore, it is crucial to discover an effective chemotherapeutic agent for CCA. Indirubin-3'-oxime (I3O), a derivative of indirubin, has been shown to suppress cell proliferation and induce cell-cycle arrest and cell apoptosis in various human cancers...
September 27, 2018: European Journal of Pharmacology
Zhao Wei, Huanglei Bi, Yan-Qin Liu, Hui-Fang Nie, Lin Yao, Sheng-Zheng Wang, Jun Yang, Yong-An Wang, Xueying Liu, Zhi-Bing Zheng
A new series of nonquaternary conjugates for reactivation of both nerve agents and pesticides inhibited hAChE were described in this paper. It was found that substituted salicylaldehydes conjugated to aminobenzamide through piperidine would produce efficient reactivators for sarin, VX and tabun inhibited hAChE, such as L6M1R3, L6M1R5 to L6M1R7, L4M1R3 and L4M1R5 to L4M1R7. The in vitro reactivation experiment for pesticides inhibited hAChE of these new synthesized oximes were conducted for the first time. Despite they were less efficient than obidoxime, some of them were highlighted as equal or more efficient reactivators in comparison to 2-PAM...
September 18, 2018: Bioorganic Chemistry
Stephanie Chapman, Alexander O'Malley, Stewart Parker, Robert Raja
As a key step in nylon-6 synthesis, the Beckmann rearrangement is an ongoing target of catalytic studies that seek to improve the sustainability of polymer manufacture. Whilst solid-acid catalysts (predominantly zeotypes) have proven effective for this transformation, the development of more active and selective systems demands an understanding of fundamental catalytic mechanisms. In this undertaking, in situ and operando characterization techniques can be informative, provided rigorous spectroscopic groundwork is in place...
September 25, 2018: Chemphyschem: a European Journal of Chemical Physics and Physical Chemistry
Tanvir Rizvi, Prem Batchala, Sugoto Mukherjee
Brain death (BD) is an irreversible cessation of functions of the entire brain, including the brainstem. The diagnosis of BD is made on clinical grounds and neurologic examination. In the United States, clinical criteria set by the American Academy of Neurology (AAN) emphasize 3 specific clinical findings to confirm BD, which include coma, absence of brainstem reflexes and apnea. Ancillary tests are needed when neurologic examination or apnea test cannot be performed. AAN recommended ancillary tests include electroencephalogram, which confirms electrical activity loss; catheter cerebral angiogram, which confirms loss of cerebral blood flow; as well as transcranial Doppler and nuclear scintigraphy...
October 2018: Seminars in Ultrasound, CT, and MR
Yang Xu, Yu Wang, Peiyuan Liu, Guo-Chao Chu, Huajian Xu, Yi-Ming Li, Jun Wang, Jing Shi
Bioorthogonal reactions have emerged as valuable tools for site-specific protein labeling and modification in vitro and in vivo. Hydrazone and oxime ligation has recently attracted considerable attention for wide applications in the conjugation of biomolecules. However, this kind of reaction has suffered from slow kinetics under physiological conditions and toxicity or complications of the reaction system due to catalysts. In this work we have developed an electron-deficient benzaldehyde reagent, which can be easily equipped with various types of bio-functional molecules for catalyst-free hydrazone ligation...
October 3, 2018: Organic & Biomolecular Chemistry
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