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Arsanilic acid

Graham Smith, Urs D Wermuth
Structures having the unusual protonated 4-arsonoanilinium species, namely in the hydrochloride salt, C6H9AsNO3(+)·Cl(-), (I), and the complex salts formed from the reaction of (4-aminophenyl)arsonic acid (p-arsanilic acid) with copper(II) sulfate, i.e. hexaaquacopper(II) bis(4-arsonoanilinium) disulfate dihydrate, (C6H9AsNO3)2[Cu(H2O)6](SO4)2·2H2O, (II), with copper(II) chloride, i.e. poly[bis(4-arsonoanilinium) [tetra-μ-chlorido-cuprate(II)]], {(C6H9AsNO3)2[CuCl4]}n, (III), and with cadmium chloride, i...
April 1, 2017: Acta Crystallographica. Section C, Structural Chemistry
Tista Prasai Joshi, Gong Zhang, Hanyang Cheng, Ruiping Liu, Huijuan Liu, Jiuhui Qu
Aromatic organoarsenic compounds tend to transform into more mobile toxic inorganic arsenic via several processes, and can inadvertently spread toxic inorganic arsenic through the environment to water sources. To gain insight into the transformation mechanisms, we herein investigated how the process of para arsanilic acid (p-ASA) transformation works in detail on the surface of adsorbents by comparing it with phenylarsonic acid (PA) and aniline, which have similar chemical structures. In contrast to the values of 0...
June 1, 2017: Water Research
Wei Sun, Xun Qian, Jie Gu, Xiao-Juan Wang, Li Zhang, Ai-Yun Guo
High concentrations of residual arsanilic acid occur in pig manure due to its use in feed to promote growth and control diseases. This study compared the effects of arsanilic acid at three concentrations (0, 325, and 650mg/kg dry pig manure) on the abundance of antibiotic resistance genes (ARGs) and the microbial community during anaerobic digestion. Addition of 650mg/kg arsanilic acid enhanced the absolute abundances of tetC, sul2, ermB, and gyrA more than twofold in the digestion product. Redundancy analysis indicated that the change in the microbial community structure was the main driver of variation in the ARGs profile...
March 8, 2017: Bioresource Technology
Graham Smith, Urs D Wermuth
The structures of the alkali metal (K, Rb and Cs) complex salts with 4-amino-phenyl-arsonic acid (p-arsanilic acid) manifest an isotypic series with the general formula [M2(C6H7AsNO3)2(H2O)3], with M = K {poly[di-μ3-4-amino-phenyl-arsonato-tri-μ2-aqua-dipotassium], [K2(C6H7AsNO3)2(H2O)3], (I)}, Rb {poly[di-μ3-4-amino-phenyl-arsonato-tri-μ2-aqua-dirubidium], [Rb2(C6H7AsNO3)2(H2O)3], (II)}, and Cs {poly[di-μ3-4-amino-phenyl-arsonato-tri-μ2-aqua-dirubidium], [Cs2(C6H7AsNO3)2(H2O)3], (III)}, in which the repeating structural units lie across crystallographic mirror planes containing two independent and different metal cations and a bridging water mol-ecule, with the two hydrogen p-arsanilate ligands and the second water mol-ecule lying outside the mirror plane...
February 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
Graham Smith, Urs D Wermuth
(4-Aminophenyl)arsonic acid (p-arsanilic acid) is used as an antihelminth in veterinary applications and was earlier used in the monosodium salt dihydrate form as the antisyphilitic drug atoxyl. Examples of complexes with this acid are rare. The structures of the alkaline earth metal (Mg, Ca, Sr and Ba) complexes with (4-aminophenyl)arsonic acid (p-arsanilic acid) have been determined, viz. hexaaquamagnesium bis[hydrogen (4-aminophenyl)arsonate] tetrahydrate, [Mg(H2O)6](C6H7AsNO3)·4H2O, (I), catena-poly[[[diaquacalcium]-bis[μ2-hydrogen (4-aminophenyl)arsonato-κ(2)O:O']-[diaquacalcium]-bis[μ2-hydrogen (4-aminophenyl)arsonato-κ(2)O:O]] dihydrate], {[Ca(C6H7AsNO3)2(H2O)2]·2H2O}n, (II), catena-poly[[triaquastrontium]-bis[μ2-hydrogen (4-aminophenyl)arsonato-κ(2)O:O']], [Sr(C6H7AsNO3)2(H2O)3]n, (III), and catena-poly[[triaquabarium]-bis[μ2-hydrogen (4-aminophenyl)arsonato-κ(2)O:O']], [Ba(C6H7AsNO3)2(H2O)3]n, (IV)...
January 1, 2017: Acta Crystallographica. Section C, Structural Chemistry
Birget Moe, Hanyong Peng, Xiufen Lu, Baowei Chen, Lydia W L Chen, Stephan Gabos, Xing-Fang Li, X Chris Le
The occurrence of a large number of diverse arsenic species in the environment and in biological systems makes it important to compare their relative toxicity. The toxicity of arsenic species has been examined in various cell lines using different assays, making comparison difficult. We report real-time cell sensing of two human cell lines to examine the cytotoxicity of fourteen arsenic species: arsenite (As(III)), monomethylarsonous acid (MMA(III)) originating from the oxide and iodide forms, dimethylarsinous acid (DMA(III)), dimethylarsinic glutathione (DMAG(III)), phenylarsine oxide (PAO(III)), arsenate (As(V)), monomethylarsonic acid (MMA(V)), dimethylarsinic acid (DMA(V)), monomethyltrithioarsonate (MMTTA(V)), dimethylmonothioarsinate (DMMTA(V)), dimethyldithioarsinate (DMDTA(V)), 3-nitro-4-hydroxyphenylarsonic acid (Roxarsone, Rox), and 4-aminobenzenearsenic acid (p-arsanilic acid, p-ASA)...
November 2016: Journal of Environmental Sciences (China)
Anjing Geng, Xu Wang, Lishu Wu, Fuhua Wang, Yan Chen, Hui Yang, Zhan Zhang, Xiaoli Zhao
P-arsanilic acid (AsA) is a emerging but less concerned contaminant used in animal feeding operations, for it can be degraded to more toxic metabolites after being excreted by animals. Rice is the staple food in many parts of the world, and also more efficient in accumulating arsenic (As) compared to other cereals. However, the uptake and transformation of AsA by rice is unclear. This study aimed to evaluate the potential risk of using AsA as a feed additive and using the AsA contaminated animal manure as a fertilizer...
March 2017: Ecotoxicology and Environmental Safety
Suqi Li, Jing Xu, Wei Chen, Yingtan Yu, Zizheng Liu, Jinjun Li, Feng Wu
p-Arsanilic acid (p-ASA) is widely used in China as livestock and poultry feed additive for promoting animal growth. The use of organoarsenics poses a potential threat to the environment because it is mostly excreted by animals in its original form and can be transformed by UV-Vis light excitation. This work examined the initial rate and efficiency of p-ASA phototransformation under UV-C disinfection lamp. Several factors influencing p-ASA phototransformation, namely, pH, initial concentration, temperature, as well as the presence of NaCl, NH4(+), and humic acid, were investigated...
September 2016: Journal of Environmental Sciences (China)
Jian Chen, Barry P Rosen
Microbes play a critical role in the global arsenic biogeocycle. Most studies have focused on redox cycling of inorganic arsenic in bacteria and archaea. The parallel cycles of organoarsenical biotransformations are less well characterized. Here we describe organoarsenical biotransformations in the environmental microbe Shewanella putrefaciens. Under aerobic growth conditions, S. putrefaciens reduced the herbicide MSMA (methylarsenate or MAs(V)) to methylarsenite (MAs(III)). Even though it does not contain an arsI gene, which encodes the ArsI C-As lyase, S...
August 2, 2016: Environmental Science & Technology
Graham Smith, Urs D Wermuth
In the structure of the brucinium salt of 4-amino-phenyl-arsonic acid (p-arsanilic acid), systematically 2,3-dimeth-oxy-10-oxostrychnidinium 4-amino-phenyl-ar-son-ate tetra-hydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water mol-ecules of solvation are accommodated between the layers and are linked to them through a primary cation N-H⋯O(anion) hydrogen bond, as well as through water O-H⋯O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure...
May 1, 2016: Acta Crystallographica. Section E, Crystallographic Communications
Jin-Biao Lin, Shoujun Yuan, Wei Wang, Zhen-Hu Hu, Han-Qing Yu
Roxarsone (ROX) and arsanilic acid (ASA) have been extensively used as organoarsenic animal feed additives. Organic arsenic compounds and their degradation products, arsenate (As(V)) and arsenite (As(III)), exist in the effluent from anaerobic reactors treating animal manure contaminated by ROX or ASA with ammonium (NH4(+)-N) and phosphate (PO4(3-)-P) together. Therefore, arsenic species in the effluent might be involved in the struvite formation process. In this study, the involvement of organic arsenic compounds and their degradation products As(V) and As(III) in the struvite crystallization was investigated...
November 5, 2016: Journal of Hazardous Materials
Wen-ze Xu, Chun-feng Yang, Jing Li, Jian-fei Li, Hui-fang Liu, Cheng-zhi Hu
The p-arsanilic acid (ASA) is an important organoarsenical compound and its removal is more difficult compared to inorganic arsenic, however, little attention has been paid to the removal of ASA in aqueous environment. The influence of P25 on the adsorption of ASA, effect of P25 dosage, pH and illumination intensity on the photo-catalysis, the production analysis and main mechanism of photo-degradation were investigated in this study. The results showed that in the P25 catalysis process, simulated natural light could degrade ASA into As (V) by oxidation...
January 15, 2016: Huan Jing Ke Xue= Huanjing Kexue
Xiande Xie, Yuanan Hu, Hefa Cheng
Being highly water-soluble, phenylarsonic feed additives discharged in animal wastes can easily accumulate in surface water bodies. The photodegradation mechanism, kinetics, and pathways of p-arsanilic acid (p-ASA), 4-hydrophenylarsonic acid (4-HPAA), and phenylarsonic acid (PAA) in water under simulated and natural sunlight irradiation were investigated. The -AsO(OH)2 group was cleaved from the aromatic ring during photodegradation, and p-benzoquinone and p-hydroquinone were formed as the major organic degradation intermediates...
June 1, 2016: Water Research
Zonglin Yang, Hanyong Peng, Xiufen Lu, Qingqing Liu, Rongfu Huang, Bin Hu, Gary Kachanoski, Martin J Zuidhof, X Chris Le
The poultry industry has used organoarsenicals, such as 3-nitro-4-hydroxyphenylarsonic acid (Roxarsone, ROX), to prevent disease and to promote growth. Although previous studies have analyzed arsenic species in chicken litter after composting or after application to agricultural lands, it is not clear what arsenic species were excreted by chickens before biotransformation of arsenic species during composting. We describe here the identification and quantitation of arsenic species in chicken litter repeatedly collected on days 14, 24, 28, 30, and 35 of a Roxarsone-feeding study involving 1600 chickens of two strains...
July 5, 2016: Environmental Science & Technology
Xiande Xie, Yuanan Hu, Hefa Cheng
Although banned in some developed countries, p-arsanilic acid (p-ASA) is still used widely as a feed additive for swine production in many countries. With little uptake and transformation in animal bodies, nearly all the p-ASA administered to animals is excreted chemically unchanged in animal wastes, which can subsequently release the more toxic inorganic arsenic species upon degradation in the environment. For safe disposal of the animal wastes laden with p-ASA, we proposed a method of leaching the highly water-soluble p-ASA out of the manure first, followed by treatment of the leachate using the Fenton process to achieve fast oxidation of p-ASA and removal of the inorganic arsenic species released (predominantly arsenate) from solution simultaneously...
February 1, 2016: Water Research
Dapeng Peng, Liang Feng, Yuanhu Pan, Yulian Wang, Dongmei Chen, Juan Wang, Zonghui Yuan
For the first time in this study, we used molecular modelling to design a suitable hapten (arsanilic acid, ASA) and produced a broad-specificity monoclonal antibody (mAb). This mAb exhibited the IC50 for ASA was 913.7 μg L(-1) and showed the cross-reactivity to ASA (100%), carbarsone (849.2%), and nitarsone (1159.5%), respectively. Based on this mAb, an optimised indirect competitive enzyme linked immunosorbent assay (ic-ELISA) protocol was developed to monitor organoarsenic compounds (OAs) in edible chicken and pork and feed, which the detection limit for OAs in a muscle matrix ranged from 74...
April 15, 2016: Food Chemistry
Han Young Eom, Dong-Hyug Yang, Joon Hyuk Suh, Unyong Kim, Junghyun Kim, Hyun-Deok Cho, Sang Beom Han
A simple and sensitive derivatization method using toluene-3,4-dithiol as a derivatization reagent for the simultaneous analysis of seven arsenic compounds (roxarsone, nitarsone, p-arsanilic acid, o-arsanilic acid, phenylarsonic acid, phenylarsine oxide, and mono-methylarsonic acid) in chicken muscle was developed and validated by ultra-performance liquid chromatography coupled with ultraviolet detection (UPLC-UV). The structure of the derivatized arsenic compounds was confirmed by liquid chromatography-ion trap mass spectrometry or gas chromatography-mass spectrometry...
December 1, 2015: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
Marianna Czaplicka, Katarzyna Jaworek, Marta Bąk
The paper presents the kinetics and proposed pathways photodegradation and photooxidation of p-arsanilic acid, in a neutral environment by ozone and hydrogen peroxide. The results showed that in a neutral environment, photoozonation process was characterized by the highest decomposition rate constant (k) (k = 31.8 × 10(-3) min(-1)). The rate constants decreased in the order UV/O3 > O3 > UV/H2O2 > H2O2 > UV. It was also found that under pH = 7, decomposition of p-arsanilic acid leads mainly to the formation of aniline, which undergoes secondary reactions...
November 2015: Environmental Science and Pollution Research International
Wenfeng Zhang, Yuanan Hu, Hefa Cheng
Response surface methodology was applied to optimize the parameters for microwave-assisted extraction of six major inorganic and organic arsenic species (As(III), As(V), dimethyl arsenic acid, monomethyl arsenic acid, p-arsanilic acid, and roxarsone) from chicken tissues, followed by detection using a high-performance liquid chromatography with inductively coupled mass spectrometry detection method, which allows the simultaneous analysis of both inorganic and organic arsenic species in the extract in a single run...
September 2015: Journal of Separation Science
Mi-Jeong Kwon, Seok-Jin Kang, Young-Il Park, Yool-Hee Yang, Sa-Ik Bang, Yong Ho Park, ByungJae So, Myung-Haing Cho, Hwan-Goo Kang
In the present study, we differentiated hepatocyte-like cells (HLCs) from human adipose tissue-derived mesenchymal stem cells (AT-MSCs). The hepatic differentiation was confirmed by increases in hepatic proteins or genes, the cytochrome P450 (CYP) activities, albumin secretion, and glycogen storage. To determine the developmental toxic effect of arsanilic acid (Ars) and acetaminophen (AAP) on the hepatic development, the differentiating cells were treated with the test chemicals (below IC12.5) from day 4 to day 13...
June 2015: Cell Biology and Toxicology
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