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Butallyl-onal 1,4-dioxane hemisolvate.

ABSTRACT: THE ASYMMETRIC UNIT OF THE TITLE COMPOUND [SYSTEMATIC NAME: 5-(1-bromo-prop-2-en-1-yl)-5-sec-butyl-pyrimidine-2,4,6-trione 1,4-dioxane hemisolvate], C(11)H(15)BrN(2)O(3)·0.5C(4)H(8)O(2), contains one half-mol-ecule of 1,4-dioxane and one mol-ecule of butallyl-onal, with an almost planar barbiturate ring [largest deviation from the mean plane = 0.049 (5) Å]. The centrosymmetric dioxane mol-ecule adopts a nearly ideal chair conformation. The barbiturate mol-ecules are linked together by an N-H⋯O hydrogen bond, giving a single-stranded chain. Additionally, each dioxane mol-ecule acts as a bridge between two anti-parallel strands of hydrogen-bonded barbiturate mol-ecules via two hydrogen bonds, N-H⋯O(dioxane)O⋯H-N. Thus, a ladder structure is obtained, with the connected barbiturate mol-ecules forming the 'stiles' and the bridging dioxane mol-ecules the 'rungs'.

SUBMITTER: Gelbrich T

PROVIDER: S-EPMC2983364 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Butallyl-onal 1,4-dioxane hemisolvate.

Gelbrich Thomas T Rossi Denise D Griesser Ulrich J UJ

Acta crystallographica. Section E, Structure reports online 20100930 Pt 10

THE ASYMMETRIC UNIT OF THE TITLE COMPOUND [SYSTEMATIC NAME: 5-(1-bromo-prop-2-en-1-yl)-5-sec-butyl-pyrimidine-2,4,6-trione 1,4-dioxane hemisolvate], C(11)H(15)BrN(2)O(3)·0.5C(4)H(8)O(2), contains one half-mol-ecule of 1,4-dioxane and one mol-ecule of butallyl-onal, with an almost planar barbiturate ring [largest deviation from the mean plane = 0.049 (5) Å]. The centrosymmetric dioxane mol-ecule adopts a nearly ideal chair conformation. The barbiturate mol-ecules are linked together by an N-H⋯O h ...[more]

PMID: 21587656

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Project description:1,4-Dioxane (1,4-DX) is an environmental contaminant found in drinking water throughout the United States (US). While it is a suspected liver carcinogen, there is no federal or state maximum contaminant level for 1,4-DX in drinking water. Very little is known about the mechanisms by which this chemical elicits liver carcinogenicity. In the present study, we performed chronic and short-term dosing studies in female BDF-1 mice to explore the toxic effects of 1,4-DX. Histopathology studies and a multi-omics approach (transcriptomics and metabolomics) were performed to investigate potential mechanisms of toxicity. Mice were exposed to various concentrations of 1,4-DX (0, 50, 500 and 5,000 mg/L) in their drinking water for one or four weeks. Immunohistochemical analysis of the liver revealed an increase in the number of H2AXγ-positive hepatocytes (a marker of DNA double strand breaks) in mice exposed to 5,000 mg/L 1,4-DX for one and four weeks. In addition, an expansion of precholangiocytes was observed after four weeks of 5,000 mg/L 1,4-DX exposure, as reflected by CK-7 immunostaining. An increase in these markers reflect both DNA damage and repair mechanisms. Liver transcriptomics profiling showed that exposure to 5,000 mg/L 1,4-DX for four weeks resulted in the differential expression of 65 genes compared to controls. Pathway analysis of the transcriptomic data revealed 1,4-DX-induced perturbations in multiple signaling pathways in the liver, including those involved in xenobiotic metabolism, nicotine degradation and glutathione-mediated detoxification. Changes to these pathways as a result of 1,4-DX exposure reflect would be predicted to impact the oxidative stress response, detoxification, and DNA damage. Liver, kidney, stool and urine metabolomics profiling revealed no effect of 5,000 mg/L 1,4-DX exposure for one or four weeks on metabolites. We speculate that this may be reflective of DNA damage being counterbalanced by the repair response, with the net result being a null overall effect on the systemic biochemistry of the exposed mice. Our results show a novel approach for the investigation of environmental chemicals that do not elicit cell death, but have activated the repair systems in response to 1,4-DX exposure

Dataset Information

Butallyl-onal 1,4-dioxane hemisolvate.

Publications

Butallyl-onal 1,4-dioxane hemisolvate.

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