The metabolism of 4-hydroxy-3-nitrophenylarsonic acid in hens

Moody, J. P.; Williams, R. T.

doi:10.1016/s0015-6264(64)80422-3

Cited by 37 publications

(24 citation statements)

References 4 publications

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“…There are several literature reports of Roxarsone and two metabolic products, the nitro-reduced AHBA arising from microbial sources [13], and the N-acetylated Acetarsone from animal [12] and human sources [23]. These three compounds, Roxarsone, AHBA and Acetarsone (Figure 1), are the focus of data presented here on proliferative effects, flow cytometry analysis, and Transwell studies, employing the Caco-2 cell culture model.…”

Section: Resultsmentioning

confidence: 99%

“…However, aromatic nitro reduction is commonly attributed to liver CYPs, NADPH-quinone oxidoreductase, or intestinal anaerobic microbes [22]. Production of AHBA from Roxarsone by poultry had been reported many years ago, [12]. Evidence for anaerobic microbial conditions that produce AHBA from Roxarsone was provided [14].…”

Section: Discussionmentioning

confidence: 99%

“…The Roxarsone reduction product, AHBA (3-amino-4-hydroxybenzenearsonate), has been identified by poultry excretions [12] and produced by anaerobic bacterial action [13]. The structural formulas for Roxarsone biotransformations to the reduced AHBA and N-acetylated Acetarsone are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Permeation of roxarsone and its metabolites increases caco-2 cell proliferation

Bayse¹,

Hammonds-Odie²,

Jackson³

et al. 2013

ABC

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The benzenearsonate, Roxarsone, has been used since 1944 as an antimicrobial, growth-promoting poultry feed additive. USGS and EPA report that Roxarsone (4-hydroxy-3-nitrobenzenearsonate) and metabolites, including AHBA (3-amino-4-hydroxybenzenearsonate), contaminate waterways at greater than 1100 tons annually. To assess human impact of these organic arsenic water contaminants, it was important to study their potential absorption. The human adenocarcinoma cell line, Caco-2, is a model for intestinal absorption. We found proliferative effects on Caco-2 cells at micromolar levels of these compounds, as monitored by [3H]-thymidine incorporation into DNA. Flow cytometry cell cycle analysis confirmed accumulation in S phase from 21% (control) to 36% (24 hour exposure to 10 μM AHBA). Confluent Caco-2 cells grown on collagen-coated Transwell plates were dosed on the apical side. After exposure, media from apical and basolateral sides were collected separately. Following removal of FBS by 30K centrifugal filtration, the benzenearsonates in the collected media were analyzed by HPLC. Analyses were at wavelengths in the ultraviolet/visible range where the absorbance values were linear with respect to concentration. Concentrations were calculated by comparison with analytically-prepared commercial standards. Results from cells dosed at 10 μM for 24 hours with AHBA, Roxarsone, or Acetarsone indicated 6% - 29% permeation occurring from apical to basolateral side, modeling absorption across intestinal epithelium to the circulatory system. Benzenearsonate feed additives are frequently applied in combination with antibiotics, raising additional health concerns. We conclude that micromolar levels of these benzenearsonates are adequate to stimulate Caco-2 cell proliferation.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Permeation of roxarsone and its metabolites increases caco-2 cell proliferation

Bayse¹,

Hammonds-Odie²,

Jackson³

et al. 2013

ABC

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“…Poultry litter has been reported to contain concentrations of roxarsone ranging from 14 to 54 mg/kg (equivalent to 36 to 93% of the total arsenic) [4, 6, 7]. Fresh poultry litter was also shown to contain 4-hydroxy-3-aminophenylarsonic acid (HAPA), a reduced biotransformation product of roxarsone, accounting for 25% of the species identified [10]. Animal waste is currently not classified as hazardous waste by the U.S. EPA, and land application of manure tainted with organoarsenic compounds is a common practice in crop growing fields near to poultry and swine houses which can contribute to environmental emissions of arsenic.…”

Section: Introductionmentioning

confidence: 99%

“…Arsenate (As V ) is formed from roxarsone during composting of poultry litter [6] and during incubation of contaminated swine waste [15] and soil [16]. In poultry litter, 4-hydroxyphenylarsonic acid, phenylarsonic acid, and methylated arsenic species have been detected in addition to HAPA and inorganic arsenic [5–7, 10, 17]. High concentrations of phenylarsonic acid and other phenyl arsenicals have also been detected in soil and groundwater at several former ammunition depots and warfare agent production sites worldwide [18–20].…”

Section: Introductionmentioning

confidence: 99%

Methanogenic inhibition by roxarsone (4-hydroxy-3-nitrophenylarsonic acid) and related aromatic arsenic compounds

Sierra-Álvarez

Cortinas

Field

2010

Journal of Hazardous Materials

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Roxarsone (4-hydroxy-3-nitro-phenylarsonic acid) and p-arsanilic acid (4-aminophenylarsonic acid) are feed additives widely used in the broiler and swine industry. This study evaluated the inhibitory effect of roxarsone, p-arsanilic, and other phenylarsonic compounds on the activity of acetate-and H 2 -utilizing methanogenic microorganisms. Roxarsone, p-arsanilic, and 4-hydroxy-3-aminophenylarsonic acid (HAPA) inhibited acetoclastic and hydrogenotrophic methanogens when supplemented at concentrations of 1 mM, and their inhibitory effect increased sharply with incubation time. Phenylarsonic acid (1 mM) inhibited acetoclastic but not H 2 -utilizing methanogens. HAPA, a metabolite from the anaerobic biodegradation of roxarsone, was found to be sensitive to autooxidation by oxygen. The compound (2.6 mM) caused low methanogenic inhibition (only 14.2%) in short-term assays of 12 h when autooxidation was prevented by supplementing HAPA solutions with ascorbate. However, ascorbate-free HAPA solutions underwent spontaneous autooxidation in the presence of oxygen, leading to the formation of highly inhibitory compounds. These results confirm the microbial toxicity of organoarsenic compounds, and they indicate that biotic as well as abiotic transformations can potentially impact the fate and microbial toxicity of these contaminants in the environment.

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Arsenic

Rossman

2008

Environmental Toxicants

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The metabolism of 4-hydroxy-3-nitrophenylarsonic acid in hens

Cited by 37 publications

References 4 publications

Permeation of roxarsone and its metabolites increases caco-2 cell proliferation

Permeation of roxarsone and its metabolites increases caco-2 cell proliferation

Methanogenic inhibition by roxarsone (4-hydroxy-3-nitrophenylarsonic acid) and related aromatic arsenic compounds

Arsenic

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