Dataset Information

Quinoxaline-3-amino-phenol-water (2/1/2).

ABSTRACT: The asymmetric unit of the title compound, 2C(8)H(6)N(2)·C(6)H(7)NO·2H(2)O, contains two quinoxaline mol-ecules, one mol-ecule of 3-amino-phenol and two water mol-ecules which are hydrogen bonded to form a two-dimensional polymeric structure. Each of the symmetry-independent quinoxaline mol-ecules forms separate stacks of different symmetry. In one set of stacks, the mol-ecules are related by a screw axis and are slightly tilted [dihedral angle = 7.12 (1)°]. In the second set of stacks, adjacent mol-ecules are parallel and related by an inversion center [inter-planar distances = 3.376 (4) and 3.473 (4) Å].

SUBMITTER: Czapik A

PROVIDER: S-EPMC2961097 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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Publications

Quinoxaline-3-amino-phenol-water (2/1/2).

Czapik Agnieszka A Gdaniec Maria M

Acta crystallographica. Section E, Structure reports online 20080423 Pt 5

The asymmetric unit of the title compound, 2C(8)H(6)N(2)·C(6)H(7)NO·2H(2)O, contains two quinoxaline mol-ecules, one mol-ecule of 3-amino-phenol and two water mol-ecules which are hydrogen bonded to form a two-dimensional polymeric structure. Each of the symmetry-independent quinoxaline mol-ecules forms separate stacks of different symmetry. In one set of stacks, the mol-ecules are related by a screw axis and are slightly tilted [dihedral angle = 7.12 (1)°]. In the second set of stacks, adjacent ...[more]

PMID: 21202378

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Project description:2-Amino-1,7-dimethylimidazo[4,5-g]quinoxaline (MeIgQx) is a recently discovered heterocyclic aromatic amine (HAA) that is formed during the cooking of meats. MeIgQx is an isomer of 2-amino-3,8-dimethylmidazo[4,5-f]quinoxaline (MeIQx), a rodent carcinogen and possible human carcinogen that also occurs in cooked meats. MeIgQx is a bacterial mutagen, but knowledge about its metabolism and carcinogenic potential is lacking. Metabolism studies on MeIgQx and MeIQx were conducted with human and mouse liver microsomes, and recombinant human P450s. DNA binding studies were also investigated in mice to ascertain the genotoxic potential of MeIgQx in comparison to MeIQx. Both HAAs underwent comparable rates of N-oxidation to form genotoxic N-hydroxylated metabolites with mouse liver microsomes (0.2-0.3 nmol/min/mg protein). The rate of N-oxidation of MeIQx was 4-fold greater than the rate of N-oxidation of MeIgQx with human liver microsomes (1.7 vs 0.4 nmol/min/mg protein). The rate of N-oxidation, by recombinant human P450 1A2, was comparable for both substrates (6 pmol/min/pmol P450 1A2). MeIgQx also underwent N-oxidation by human P450s 1A1 and 1B1 at appreciable rates, whereas MeIQx was poorly metabolized by these P450s. The potential of MeIgQx and MeIQx to form DNA adducts was assessed in female C57BL/6 mice given [(14)C]-MeIgQx (10 μCi, 9.68 mg/kg body wt) or [(14)C]-MeIQx (10 μCi, 2.13 mg/kg body wt). DNA adduct formation in the liver, pancreas, and colorectum was measured by accelerator mass spectrometry at 4, 24, or 48 h post-treatment. Variable levels of adducts were detected in all organs. The adduct levels were similar for both HAAs, when adjusted for dose, and ranged from 1 to 600 adducts per 10(7) nucleotides per mg/kg dose. Thus, MeIgQx undergoes metabolic activation and binds to DNA at levels that are comparable to MeIQx. Given the high amounts of MeIgQx formed in cooked meats, further investigations are warranted to assess the carcinogenic potential of this HAA.

Dataset Information

Quinoxaline-3-amino-phenol-water (2/1/2).

Publications

Quinoxaline-3-amino-phenol-water (2/1/2).

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