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Nitroimidazoles

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https://www.readbyqxmd.com/read/28223799/hypoxia-responsive-ionizable-liposome-delivery-sirna-for-glioma-therapy
#1
Hong-Mei Liu, Ya-Fei Zhang, Yan-Dong Xie, Yi-Fan Cai, Bai-Yang Li, Wen Li, Ling-Yu Zeng, Yu-Ling Li, Ru-Tong Yu
Here, we report the hypoxia-responsive ionizable liposomes to deliver small interference RNA (siRNA) anticancer drugs, which can selectively enhance cellular uptake of the siRNA under hypoxic and low-pH conditions to cure glioma. For this purpose, malate dehydrogenase lipid molecules were synthesized, which contain nitroimidazole groups that impart hypoxia sensitivity and specificity as hydrophobic tails, and tertiary amines as hydrophilic head groups. These malate dehydrogenase molecules, together with DSPE-PEG2000 and cholesterol, were self-assembled into O'(1),O(1)-(3-(dimethylamino)propane-1,2-diyl) 16-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl) di(hexadecanedioate) liposomes (MLP) to encapsulate siRNA through electrostatic interaction...
2017: International Journal of Nanomedicine
https://www.readbyqxmd.com/read/28213209/molecularly-imprinted-solid-phase-extraction-method-for-simultaneous-determination-of-seven-nitroimidazoles-from-honey-by-hplc-ms-ms
#2
Xiu-Chun Guo, Zhao-Yang Xia, Hai-Hui Wang, Wen-Yi Kang, Li-Ming Lin, Wen-Qing Cao, Hong-Wei Zhang, Wen-Hui Zhou
In this work, a selective sample cleanup procedure that combined molecular imprinting technique with solid phase extraction was developed for the simultaneous extraction of the seven nitroimidazoles (NMZs) from honey samples. The molecular imprinting polymers for NMZs were prepared through bulk polymerization method using 2-methyl-5-nitroimidazole as template molecule, methacrylic acid as the functional monomer and ethylene glycol dimethacrylate as the cross linking agent. The obtained molecular imprinting polymers showed high affinity to template molecule and was used as selective sorbent for simultaneously selective extraction of the seven NMZs from honey matrix...
May 1, 2017: Talanta
https://www.readbyqxmd.com/read/28180110/assessing-tumor-oxygenation-for-predicting-outcome-in-radiation-oncology-a-review-of-studies-correlating-tumor-hypoxic-status-and-outcome-in-the-preclinical-and-clinical-settings
#3
REVIEW
Florence Colliez, Bernard Gallez, Bénédicte F Jordan
Tumor hypoxia is recognized as a limiting factor for the efficacy of radiotherapy, because it enhances tumor radioresistance. It is strongly suggested that assessing tumor oxygenation could help to predict the outcome of cancer patients undergoing radiation therapy. Strategies have also been developed to alleviate tumor hypoxia in order to radiosensitize tumors. In addition, oxygen mapping is critically needed for intensity modulated radiation therapy (IMRT), in which the most hypoxic regions require higher radiation doses and the most oxygenated regions require lower radiation doses...
2017: Frontiers in Oncology
https://www.readbyqxmd.com/read/28178618/medicinal-plants-and-their-isolated-compounds-showing-anti-trichomonas-vaginalis-activity
#4
REVIEW
Mozhgan Mehriardestani, Atousa Aliahmadi, Tayebeh Toliat, Roja Rahimi
Trichomonas vaginalis is a major of non-viral sexually-transmitted infection and an important cause of serious obstetrical and gynecological complications. Treatment options for trichomoniasis are limited to nitroimidazole compounds. The increasing resistance and allergic reactions to nitroimidazole and recurrent trichomoniasis make it essential to identify and develop new drugs against trichomoniasis. Medicinal plants are an important source for discovery of new medications. This review discusses the anti-trichomonas effects of medicinal plants and their chemical constituents to find better options against this pathogenic protozoon...
February 5, 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/28164233/the-use-of-quinacrine-in-nitroimidazole-resistant-giardia-duodenalis-an-old-drug-for-an-emerging-problem
#5
Ana Requena-Méndez, Pilar Goñi, Encarnación Rubio, Diana Pou, Victoria Fumadó, Silvia Lóbez, Edelweiss Aldasoro, Juan Cabezos, Maria Eugenia Valls, Begoña Treviño, Antonio Federico Martínez Montseny, Antonio Clavel, Joaquim Gascon, José Muñoz
No abstract text is available yet for this article.
February 6, 2017: Journal of Infectious Diseases
https://www.readbyqxmd.com/read/28151652/kinetic-study-of-hydroxyl-and-sulfate-radical-mediated-oxidation-of-pharmaceuticals-in-wastewater-effluents
#6
Lushi Lian, Bo Yao, Shaodong Hou, Jingyun Fang, Shuwen Yan, Weihua Song
Advanced oxidation processes (AOPs), such as hydroxyl radical (HO(•))- and sulfate radical (SO4(•-))-mediated oxidation, are alternatives for the attenuation of pharmaceuticals and personal care products (PPCPs) in wastewater effluents. However, the kinetics of these reactions needs to be investigated. In this study, kinetic models for 15 PPCPs were built to predict the degradation of PPCPs in both HO(•)- and SO4(•-)-mediated oxidation. In the UV/H2O2 process, a simplified kinetic model involving only steady state concentrations of HO(•) and its biomolecular reaction rate constants is suitable for predicting the removal of PPCPs, indicating the dominant role of HO(•) in the removal of PPCPs...
February 13, 2017: Environmental Science & Technology
https://www.readbyqxmd.com/read/28137470/nitroimidazole-derivatives-of-polypyridyl-ruthenium-complexes-towards-understanding-their-anticancer-activity-and-mode-of-action
#7
Olga Mazuryk, Oksana Krysiak-Foria, Agnieszka Żak, Franck Suzenet, Agata Ptak-Belowska, Tomasz Brzozowski, Grażyna Stochel, Małgorzata Brindell
The mechanism of cell death induced by the ruthenium polypyridyl complexes comprising two 4,7-diphenyl-1,10-phenanthroline ligands as well as one unmodified 2,2'-bipyridyl or modified with 2-nitroimidazole moiety attached by shorter (C3H6) or longer (C6H12) linker was investigated. Cytotoxicity and proliferation assays revealed that the studied Ru polypyridyl complexes are more toxic against human pancreas carcinoma PANC-1 cell line than normal human keratinocytes HaCaT with IC50 of 3-5μM. The Ru complexes despite accumulation in mitochondria do not lead to mitochondrial disfunction, though decreasing of mitochondrial Ca(2+) causes mitochondria membrane hyperpolarization...
January 28, 2017: European Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/28127094/efficient-preparation-of-2-nitroimidazole-nucleosides-as-precursors-for-hypoxia-pet-tracers
#8
Petra Križková, Anna Wieczorek, Friedrich Hammerschmidt
ABSTRACT: 2-Deoxy-D-ribose was converted to α/β-mixtures of methyl 3-O-acetyl- and methyl 3-O-benzoyl-2-deoxy-5-(p-toluenesulfonyl)-D-ribofuranosides. These were reacted with boron trichloride to generate ribofuranosyl chlorides, which afforded precursors for tracers to image tumor hypoxia on substitution with salts of 2-nitroimidazole. The anomeric ratio of the nucleosides was delicately influenced by the reaction conditions. GRAPHICAL ABSTRACT: HASH(0x43adb10) ...
2017: Monatshefte Für Chemie
https://www.readbyqxmd.com/read/28110684/hydrothermal-synthesis-of-polyethylenimine-protected-high-luminescent-pt-nanoclusters-and-their-application-to-the-detection-of-nitroimidazoles
#9
Na Xu, Hong-Wei Li, Yuqing Wu
A novel one-step hydrothermal synthesis of highly fluorescent platinum nanoclusters protected by polyethylenimine (Pt-NCs@PEI) is described. The products are characterized well by UV-vis absorption, fluorescence spectra, X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM) imaging. The Pt-NCs@PEI possess high quantum yield at 28%, which is the relatively high one among the reported Pt-NCs; especially, the synthesis is in one-step and the reaction time is much shorter (<1 h) than the related methods...
March 15, 2017: Analytica Chimica Acta
https://www.readbyqxmd.com/read/28088075/development-of-a-hypoxia-triggered-and-hypoxic-radiosensitized-liposome-as-a-doxorubicin-carrier-to-promote-synergetic-chemo-radio-therapy-for-glioma
#10
Hongmei Liu, Yandong Xie, Yafei Zhang, Yifan Cai, Baiyang Li, Honglin Mao, Yingguo Liu, Jun Lu, Longzhen Zhang, Rutong Yu
The treatment of malignant primary brain tumors is challenging. Concomitant radiochemotherapy has become the standard clinical treatment for malignant glioma, but there are two critical challenges to overcome in order to increase efficacy. First, glioma is known to have increased resistant to radiation due to its intra-tumoral hypoxia. In addition, the blood-brain barrier (BBB) restricts the distribution of the chemotherapeutic agent to the brain. Therefore, we developed a hypoxic radiosensitizer-prodrug liposome (MLP), in order to deliver DOX to the tumor and to overcome the above challenges, achieving a synergistic chemo-/radiotherapy treatment of malignant glioma...
March 2017: Biomaterials
https://www.readbyqxmd.com/read/28054455/development-and-validation-of-a-liquid-chromatography-with-tandem-mass-spectrometry-method-for-the-determination-of-nitroimidazole-residues-in-beeswax
#11
Kamila Mitrowska, Maja Antczak
In this study a new method for the determination of 12 nitroimidazoles and their hydroxymetabolites (metronidazole, hydroxymetronidazole, dimetridazole, ronidazole, hydroxydimetridazole, ipronidazole, hydroxyipronidazole, carnidazole, ornidazole, secnidazole, ternidazole, tinidazole) in beeswax has been developed and validated. The optimized sample preparation procedure included melting and dilution of beeswax in a mixture of n-hexane and isopropanol followed by extraction with 2% acetic acid. The extracts were purified on strong cation exchange based solid-phase extraction cartridges and evaporated in a vacuum system with vortex motion...
January 5, 2017: Journal of Separation Science
https://www.readbyqxmd.com/read/28043690/covalent-triazine-framework-1-as-adsorbent-for-inline-solid-phase-extraction-high-performance-liquid-chromatographic-analysis-of-trace-nitroimidazoles-in-porcine-liver-and-environmental-waters
#12
Cheng Zhong, Beibei Chen, Man He, Bin Hu
In this study, covalent triazine framework-1 (CTF-1) was adopted as solid phase extraction (SPE) sorbents, and a method of SPE inline coupled with high performance liquid chromatography-ultraviolet (HPLC-UV) detection was developed for trace analysis of three nitroimidazolaes (including metronidazole, ronidazole and dimetridazole) in porcine liver and environmental water samples. CTF-1 has rich π-electron and N containing triazine, thus can form π-π interaction and intermolecular hydrogen bond with three target polar nitroimidazoles, resulting in high extraction efficiency (87%-98%)...
February 3, 2017: Journal of Chromatography. A
https://www.readbyqxmd.com/read/28007448/bioreductively-activatable-prodrug-conjugates-of-phenstatin-designed-to-target-tumor-hypoxia
#13
Blake A Winn, Zhe Shi, Graham J Carlson, Yifan Wang, Benson L Nguyen, Evan M Kelly, R David Ross, Ernest Hamel, David J Chaplin, Mary L Trawick, Kevin G Pinney
A variety of solid tumor cancers contain significant regions of hypoxia, which provide unique challenges for targeting by potent anticancer agents. Bioreductively activatable prodrug conjugates (BAPCs) represent a promising strategy for therapeutic intervention. BAPCs are designed to be biologically inert until they come into contact with low oxygen tension, at which point reductase enzyme mediated cleavage releases the parent anticancer agent in a tumor-specific manner. Phenstatin is a potent inhibitor of tubulin polymerization, mimicking the chemical structure and biological activity of the natural product combretastatin A-4...
February 1, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27988333/delamanid-is-not-metabolized-by-salmonella-or-human-nitroreductases-a-possible-mechanism-for-the-lack-of-mutagenicity
#14
Erina Hanaki, Mikayo Hayashi, Makoto Matsumoto
Nitro-containing compounds such as nitrofuran and nitroimidazole are drugs used for the treatment of infectious diseases. However, many of these nitro-containing drugs are positive in the bacterial reverse mutation assay (Ames test). The recently approved anti-multidrug-resistant tuberculosis (MDR-TB) drug, delamanid (Deltyba™; OPC-67683), a derivative of 4-nitroimidazole, was negative for mutagenicity in the Ames assay. In Salmonella typhimurium, mutagenicity of nitro compounds has been closely associated with the ability of nitroreductase to metabolize (degradation)these compounds...
December 14, 2016: Regulatory Toxicology and Pharmacology: RTP
https://www.readbyqxmd.com/read/27983649/design-and-synthesis-of-vandetanib-derivatives-containing-nitroimidazole-groups-as-tyrosine-kinase-inhibitors-in-normoxia-and-hypoxia
#15
Huiqiang Wei, Deguan Li, Xiangbo Yang, Haihua Shang, Saijun Fan, Yiliang Li, Dan Song
Sixteen novel epidermal growth factor receptor (EGFR)/vascular endothelial growth factor (VEGF)-2 inhibitors (nitroimidazole-substituted 4-anilinoquinazoline derivatives (16a-p)) were designed and prepared via the introduction of a nitroimidazole group in the piperidine side chain and modification on the aniline moiety of vandetanib. Preliminary biological tests showed that comparing with vandetanib, some target compounds exhibited excellent EGFR inhibitory activities and anti-proliferative over A549/H446 cells in hypoxia...
December 14, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/27888032/allergy-to-benznidazole-cross-reactivity-with-other-nitroimidazoles
#16
Blanca Noguerado-Mellado, Patricia Rojas-Pérez-Ezquerra, María Calderón-Moreno, Cristina Morales-Cabeza, Pilar Tornero-Molina
No abstract text is available yet for this article.
November 22, 2016: Journal of Allergy and Clinical Immunology in Practice
https://www.readbyqxmd.com/read/27886776/synthesis-and-performance-of-chiral-ferrocene-modified-silica-gel-for-mixed-mode-chromatography
#17
Lijun Qiao, Xiaohua Zhou, Xue Li, Wenrui Du, Ajuan Yu, Shusheng Zhang, Yangjie Wu
A brush-type chiral stationary phase, N-ferrocenyl benzoyl-(1S, 2R)-1, 2-diphenyl ethanol-bonded on the silica gel (NFcBEs) for high performance liquid chromatography (HPLC), was prepared using γ-glycidoxypropyltrimethoxysilane as coupling reagent. The structure of this novel material was characterized by infrared spectroscopy, elemental analysis and thermogravimetric analysis. Mechanism involved in the chromatographic separation is the multi-interaction including hydrophobic, π-π, hydrogen-bonding, π-charge transfer, dipole-dipole and acid-base equilibrium interactions...
January 15, 2017: Talanta
https://www.readbyqxmd.com/read/27886759/capillary-electrophoresis-tandem-mass-spectrometry-combined-with-molecularly-imprinted-solid-phase-extraction-as-useful-tool-for-the-monitoring-of-5-nitroimidazoles-and-their-metabolites-in-urine-samples
#18
Maykel Hernández-Mesa, Carmen Cruces-Blanco, Ana M García-Campaña
A novel capillary electrophoresis-tandem mass spectrometry approach is proposed for the determination of eleven 5-nitroimidazoles in urine samples for therapeutical drug monitoring purposes. A comparison between two separation modes, namely micellar electrokinetic chromatography and capillary zone electrophoresis was carried out, obtaining higher selectivity when 1M formic acid (pH 1.8) was selected as background electrolyte. 5-Nitroimidazoles were hydrodynamically injected in water for 40s at 50mbar and their separation was performed at 28kV and 25°C...
January 15, 2017: Talanta
https://www.readbyqxmd.com/read/27875881/communication-position-does-matter-the-photofragmentation-of-the-nitroimidazole-isomers
#19
P Bolognesi, A R Casavola, A Cartoni, R Richter, P Markus, S Borocci, J Chiarinelli, S Tošić, H Sa'adeh, M Masič, B P Marinković, K C Prince, L Avaldi
A combined experimental and theoretical approach has been used to disentangle the fundamental mechanisms of the fragmentation of the three isomers of nitroimidazole induced by vacuum ultra-violet (VUV) radiation, namely, 4-, 5-, and 2-nitroimidazole. The results of mass spectrometry as well as photoelectron-photoion coincidence spectroscopy display striking differences in the radiation-induced decomposition of the different nitroimidazole radical cations. Based on density functional theory (DFT) calculations, a model is proposed which fully explains such differences, and reveals the subtle fragmentation mechanisms leading to the release of neutral species like NO, CO, and HCN...
November 21, 2016: Journal of Chemical Physics
https://www.readbyqxmd.com/read/27827934/practical-and-metal-free-synthesis-of-novel-enantiopure-amides-containing-the-potentially-bioactive-5-nitroimidazole-moiety
#20
Cédric Spitz, Fanny Mathias, Alain Gamal Giuglio-Tonolo, Thierry Terme, Patrice Vanelle
We report here a practical and metal-free synthesis of novel enantiopure amides containing the drug-like 5-nitroimidazole scaffold. The first step was a metal-free diastereoselective addition of 4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole to enantiomerically pure N-tert-butanesulfinimine. Then, the N-tert-butanesulfinyl-protected amine was easily deprotected under acidic conditions. Finally, the primary amine was coupled with different acid chlorides or acids to give the corresponding amides...
November 4, 2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
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