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Nitroimidazoles

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https://www.readbyqxmd.com/read/27888032/allergy-to-benznidazole-cross-reactivity-with-other-nitroimidazoles
#1
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
#2
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
#3
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
#4
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
#5
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
https://www.readbyqxmd.com/read/27824170/high-performance-carbon-molecular-sieving-membranes-derived-from-pyrolysis-of-metal-organic-framework-zif-108-doped-polyimide-matrices
#6
Wenmei Jiao, Yujie Ban, Zixing Shi, Xuesong Jiang, Yanshuo Li, Weishen Yang
Carbon molecular sieve membranes (CMSMs) were fabricated by pyrolysis of MOF-doped polyimide mixed matrix membranes. ZIF-108 (Zn(2-nitroimidazolate)2) was used as a dopant to tailor the micropores of the as-prepared CMSMs into narrow ultramicropores, providing a remarkable combination of permeability and selectivity of membranes in CO2/CH4, O2/N2 and N2/CH4 separation.
November 8, 2016: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/27818219/removal-of-oxidatively-generated-dna-damage-by-overlapping-repair-pathways
#7
REVIEW
Vladimir Shafirovich, Nicholas E Geacintov
It is generally believed that the mammalian nucleotide excision repair pathway removes DNA helix-distorting bulky DNA lesions, while small non-bulky lesions are repaired by base excision repair (BER). However, recent work demonstrates that the oxidativly generated guanine oxidation products, spiroimininodihydantoin (Sp), 5-guanidinohydantoin (Gh), and certain intrastrand cross-linked lesions, are good substrates of NER and BER pathways that compete with one another in human cell extracts. The oxidation of guanine by peroxynitrite is known to generate 5-guanidino-4-nitroimidazole (NIm) which is structurally similar to Gh, except that the 4-nitro group in NIm is replaced by a keto group in Gh...
November 4, 2016: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/27798206/screening-of-anti-mycobacterial-compounds-in-a-naturally-infected-zebrafish-larvae-model
#8
J P Dalton, B Uy, K S Okuda, C J Hall, W A Denny, P S Crosier, S Swift, S Wiles
OBJECTIVES: Mycobacterium tuberculosis is a deadly human pathogen that causes the lung disease TB. M. tuberculosis latently infects a third of the world's population, resulting in ∼1.5 million deaths per year. Due to the difficulties and expense of carrying out animal drug trials using M. tuberculosis and rodents, infections of the zebrafish Danio rerio with Mycobacterium marinum have become a useful surrogate. However, the infection methods described to date require specialized equipment and a high level of operator expertise...
October 24, 2016: Journal of Antimicrobial Chemotherapy
https://www.readbyqxmd.com/read/27784254/challenges-and-persistent-questions-in-treatment-of-trichomoniasis
#9
Patrícia de Brum Vieira, Tiana Tasca, W Evan Secor
Trichomoniasis is a sexually transmitted disease (STD) caused by infection with the protozoan parasite Trichomonas vaginalis. It is considered the most prevalent non-viral sexually transmitted disease worldwide. Recently, the infection has been associated with adverse outcomes of pregnancy and increased risks of HIV acquisition and transmission, besides the association with cervical and prostate cancers. The consequences of trichomoniasis are likely much greater than previously recognized, both at the individual and the community level...
October 25, 2016: Current Topics in Medicinal Chemistry
https://www.readbyqxmd.com/read/27752036/synthesis-and-biological-evaluation-of-a-new-nitroimidazole-99mtc-complex-for-imaging-of-hypoxia-in-mice-model
#10
Qing Zhang, Qing Zhang, Yanxing Guan, Shaozheng Liu, Qingjie Chen, Xiangmin Li
BACKGROUND This study was specifically designed to develop a new 99mTc compound with 3-amino-4-[2-(2-methyl-5-nitro-1H-imidazol)-ethylamino]-4-oxo-butyrate (5-ntm-asp) and to verify whether this compound is feasible to be a radiopharmaceutical for hypoxic tumors. MATERIAL AND METHODS Metronidazole derivative 5-ntm-asp was synthesized and then radio-labeled by Na [99mTcO4], forming 99mTc-5-ntm-asp. Another two complexes of 99mTc-2- and 99mTc-5-nitroimidazole-iminodiacetic acid (99mTc-2-ntm-IDA and 99mTc-5-ntm-IDA) were also synthesized based on previous studies...
October 18, 2016: Medical Science Monitor: International Medical Journal of Experimental and Clinical Research
https://www.readbyqxmd.com/read/27722939/experimental-and-molecular-docking-investigation-on-metal-organic-framework-mil-101-cr-as-a-sorbent-for-vortex-assisted-dispersive-micro-solid-phase-extraction-of-trace-5-nitroimidazole-residues-in-environmental-water-samples-prior-to-uplc-ms-ms-analysis
#11
Nan Lu, Ting Wang, Pan Zhao, Lianjun Zhang, Xiaowen Lun, Xueli Zhang, Xiaohong Hou
In the presented work, metal-organic framework (MOF) material MIL-101(Cr) (MIL, Matérial Institute Lavoisier) was used as a sorbent for vortex assisted dispersive micro-solid-phase extraction (VA-D-μ-SPE) of trace amount of metronidazole (MNZ), ronidazole (RNZ), secnidazole (SNZ), dimetridazole (DMZ), tinidazole (TNZ), and ornidazole (ONZ) in different environmental water samples. Ultra-high-performance liquid chromatography coupled with tandem mass spectrometry (UPLC-MS/MS) was used to quantify the target analytes...
November 2016: Analytical and Bioanalytical Chemistry
https://www.readbyqxmd.com/read/27709564/the-potential-of-lactobacillus-casei-and-entercoccus-faecium-combination-as-a-preventive-probiotic-against-entamoeba
#12
Nitya Sarjapuram, Niharika Mekala, Meetali Singh, Utpal Tatu
Travellers' diarrhoea caused by enteric protozoa like Entamoeba histolytica is among the most common protozoan diseases in developing countries. In developing countries, amoebiasis is the second most prevalent protozoan disease. This protozoan parasite is often known to coexist as a part of the normal gut microbiota. It is estimated that around 50-60 % of population in developing countries might be harbouring Entamoeba in an asymptomatic manner. Due to physiological perturbation or upon immuno-compromise, it can become virulent and then cause diarrhoea, bloody stools and may invade other organs if left untreated...
October 5, 2016: Probiotics and Antimicrobial Proteins
https://www.readbyqxmd.com/read/27706901/targeting-a-targeted-drug-an-approach-toward-hypoxia-activatable-tyrosine-kinase-inhibitor-prodrugs
#13
Claudia Karnthaler-Benbakka, Diana Groza, Bettina Koblmüller, Alessio Terenzi, Katharina Holste, Melanie Haider, Dina Baier, Walter Berger, Petra Heffeter, Christian R Kowol, Bernhard K Keppler
Tyrosine kinase inhibitors (TKIs), which have revolutionized cancer therapy over the past 15 years, are limited in their clinical application due to serious side effects. Therefore, we converted two approved TKIs (sunitinib and erlotinib) into 2-nitroimidazole-based hypoxia-activatable prodrugs. Kinetics studies showed very different stabilities over 24 h; however, fast reductive activation via E. coli nitroreductase could be confirmed for both panels. The anticancer activity and signaling inhibition of the compounds against various human cancer cell lines were evaluated in cell culture...
October 5, 2016: ChemMedChem
https://www.readbyqxmd.com/read/27698790/glioblastoma-multiforme-effect-of-hypoxia-and-hypoxia-inducible-factors-on-therapeutic-approaches
#14
Wen-Juan Huang, Wei-Wei Chen, Xia Zhang
Central nervous system-based cancers have a much higher mortality rate with the 2016 estimates at 6.4 for incidence and 4.3 for deaths per 100,000 individuals. Grade IV astrocytomas, known as glioblastomas are highly aggressive and show a high proliferation index, diffused infiltration, angiogenesis, microvascular proliferation and pleomorphic vessels, resistance to apoptosis, and pseudopalisading necrosis. Extensive hypoxic regions in glioblastomas contribute to the highly malignant phenotype of these tumors...
October 2016: Oncology Letters
https://www.readbyqxmd.com/read/27698320/topological-characterization-of-electron-density-electrostatic-potential-and-intermolecular-interactions-of-2-nitroimidazole-an-experimental-and-theoretical-study
#15
Chinnasamy Kalaiarasi, Mysore S Pavan, Poomani Kumaradhas
An experimental charge density distribution of 2-nitroimidazole was determined from high-resolution X-ray diffraction and the Hansen-Coppens multipole model. The 2-nitroimidazole compound was crystallized and a high-angle X-ray diffraction intensity data set has been collected at low temperature (110 K). The structure was solved and further, an aspherical multipole model refinement was performed up to octapole level; the results were used to determine the structure, bond topological and electrostatic properties of the molecule...
October 1, 2016: Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
https://www.readbyqxmd.com/read/27697044/challenges-and-persistent-questions-in-treatment-of-trichomoniasis
#16
Patrícia de Brum Vieira, Tiana Tasca, W Evan Secor
Trichomoniasis is a sexually transmitted disease (STD) caused by infection with the protozoan parasite Trichomonas vaginalis. It is considered the most prevalent non-viral sexually transmitted disease worldwide. Recently, the infection has been associated with adverse outcomes of pregnancy and increased risks of HIV acquisition and transmission, besides the association with cervical and prostate cancers. The consequences of trichomoniasis are likely much greater than previously recognized, both at the individual and the community level...
September 30, 2016: Current Topics in Medicinal Chemistry
https://www.readbyqxmd.com/read/27693670/-18-f-fluoro-azomycin-2%C3%A2-deoxy-%C3%AE-d-ribofuranoside-a-new-imaging-agent-for-tumor-hypoxia-in-comparison-with-18-f-faza
#17
Anna Schweifer, Florian Maier, Walter Ehrlichmann, Denis Lamparter, Manfred Kneilling, Bernd J Pichler, Friedrich Hammerschmidt, Gerald Reischl
INTRODUCTION: Radiolabeled 2-nitroimidazoles (azomycins) are a prominent class of biomarkers for PET imaging of hypoxia. [(18)F]Fluoro-azomycin-α-arabinoside ([(18)F]FAZA) - already in clinical use - may be seen as α-configuration nucleoside, but enters cells only via diffusion and is not transported by cellular nucleoside transporters. To enhance image contrast in comparison to [(18)F]FAZA our objective was to (18)F-radiolabel an azomycin-2´-deoxyriboside with β-configuration ([(18)F]FAZDR, [(18)F]-β-8) to mimic nucleosides more closely and comparatively evaluate it versus [(18)F]FAZA...
December 2016: Nuclear Medicine and Biology
https://www.readbyqxmd.com/read/27692854/n-arylsulfonyl-%C3%AE-amino-carboxamides-are-potent-and-selective-inhibitors-of-the-chemokine-receptor-ccr10-that-show-efficacy-in-the-murine-dnfb-model-of-contact-hypersensitivity
#18
Asitha Abeywardane, Gary Caviness, Younggi Choi, Derek Cogan, Amy Gao, Daniel Goldberg, Alexander Heim-Riether, Debra Jeanfavre, Elliott Klein, Jennifer A Kowalski, Wang Mao, Craig Miller, Neil Moss, Philip Ramsden, Ernest Raymond, Donna Skow, Lana Smith-Keenan, Roger J Snow, Frank Wu, Jiang-Ping Wu, Yang Yu
Compound 1 ((4-amino-3,5-dichlorophenyl)-1-(4-methylpiperidin-1-yl)-4-(2-nitroimidazol-1-yl)-1-oxobutane-2-sulfonamido) was discovered to be a 690nM antagonist of human CCR10 Ca(2+) flux. Optimization delivered (2R)-4-(2-cyanopyrrol-1-yl)-S-(1H-indol-4-yl)-1-(4-methylpiperidin-1-yl)-1-oxobutane-2-sulfonamido (eut-22) that is 300 fold more potent a CCR10 antagonist than 1 and eliminates potential toxicity, mutagenicity, and drug-drug-interaction liabilities often associated with nitroaryls and anilines. eut-22 is highly selective over other GPCR's, including a number of other chemokine receptors...
September 21, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27664624/multi-class-method-for-the-determination-of-nitroimidazoles-nitrofurans-and-chloramphenicol-in-chicken-muscle-and-egg-by-dispersive-solid-phase-extraction-and-ultra-high-performance-liquid-chromatography-tandem-mass-spectrometry
#19
Zhiwen Zhang, Yuping Wu, Xiaowei Li, Yingyu Wang, Hui Li, Qin Fu, Yawen Shan, Tianhe Liu, Xi Xia
This study describes the development of a multiresidue method for the efficient identification and quantification of nitroimidazoles, nitrofurans, and chloramphenicol in chicken and egg. After derivatization of nitrofuran metabolites, dispersive-solid phase extraction was used for the extraction of target analytes. An optimization strategy involved the selection of sorbents and extraction solutions for dispersive-solid phase extraction in order to achieve acceptably high recoveries and reduce co-extractives in the final extracts...
February 15, 2017: Food Chemistry
https://www.readbyqxmd.com/read/27647935/the-drug-ornidazole-inhibits-photosynthesis-in-a-different-mechanism-described-for-protozoa-and-anaerobic-bacteria
#20
Yehouda Marcus, Noam Tal, Mordechai Ronen, Raanan Carmieli, Michael Gurevitz
Ornidazole of the 5-nitroimidazole drug family is used to treat protozoan and anaerobic bacterial infections via a mechanism that involves pre-activation by reduction of the nitro group, and production of toxic derivatives and radicals. Metronidazole, another drug family member, has been suggested to affect photosynthesis by draining electrons from the electron carrier, ferredoxin, thus inhibiting NADP(+) reduction and stimulating radical and peroxide production. Here we show, however, that ornidazole inhibits photosynthesis via a different mechanism...
September 19, 2016: Biochemical Journal
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