4,8-DiMeIQx
4,8-DiMeIQx is an orally active mutagen, selective dopaminergic neurotoxicant, and DNA damaging agent. 4,8-DiMeIQx can be isolated from cooked beef, sausage, pork, and chicken. 4,8-DiMeIQx induces reverse mutations in *Salmonella typhimurium* TA98 in the presence or absence of S9 mix, and forms DNA adducts in vivo in rat liver. 4,8-DiMeIQx exhibits selective neurotoxicity toward dopaminergic neurons. 4,8-DiMeIQx shows no activity against non-dopaminergic neurons. 4,8-DiMeIQx can be used in studies related to Parkinson's disease and colorectal cancer.
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- No. CAS: 95896-78-9
- Fòrmula: C12H13N5
- Peso molecular:227.27
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Almacenamiento:
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Descripciòn
In Vitro
4,8-DiMeIQx (1 μg per assay) is mutagenic to Salmonella typhimurium TA98 with S9 mix, inducing 206,000 revertants per μg, and accounts for 9% of the total mutagenicity of bacteriological-grade beef extract[1].
4,8-DiMeIQx (100 nM-5 μM; 24 h) is selectively neurotoxic to dopaminergic neurons in E17 rat primary midbrain cultures, with a threshold dose of 100 nM and significant dopaminergic neuron loss observed across all tested concentrations from 100 nM to 5 μM, while non-dopaminergic neurons remain unaffected[2].
4,8-DiMeIQx (100 nM-5 μM; 24 h) does not elicit significant neurite length changes in either dopaminergic or non-dopaminergic neurons in E17 rat primary midbrain cultures at concentrations from 100 nM to 5 μM after 24 h of incubation[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
4,8-DiMeIQx (0.5 mg per rat; p.o.; single dose) oral administration to male AGUS rats results in predominant urinary excretion of radioactivity within 24 hours, with BNF-induced intestinal enzyme activity increasing fecal excretion; major metabolites include hydroxylated and acetylated forms, with varying mutagenic potency relative to the parent compound[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Wistar (male, 8 weeks old, 250 g)[3]
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Dosage:50 mg/kg
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Administration:p.o.; single dose
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Result:Identified three DNA adducts in liver DNA.
Accounted for ~60% of total measured radioactivity via the major adduct N2-(2'-deoxyguanosin-8-yl)-4,8-DiMeIQx.
Had a relative adduct level of 3.54×10-5 for the major adduct.
Had relative adduct levels of 1.43×10-5 and 1.30×10-5 for the two minor adducts.
Matched the in vivo adduct pattern seen in in vitro modified calf thymus DNA.
Chemical Information
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No. CAS 95896-78-9
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Peso molecular 227.27
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Fòrmula C12H13N5
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SMILES
NC(N1C)=NC2=C1C(C)=CC3=C2N=C(C)C=N3
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureza y Documentación
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Ficha de datos (276 KB)
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SDS (252 KB)
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- Español - ES (252 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Takahashi M, et al. Identification and quantification of 2-amino-3,4,8-trimethylimidazo- [4,5-f]quinoxaline (4,8-DiMeIQx) in beef extract. Carcinogenesis. 1985 Oct;6(10):1537-9. [Content Brief]
[2]. Cruz-Hernandez A, et al. Selective dopaminergic neurotoxicity of three heterocyclic amine subclasses in primary rat midbrain neurons. Neurotoxicology. 2018 Mar;65:68-84. [Content Brief]
[3]. Frandsen H, et al. Formation of DNA adducts by the food mutagen 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (4,8-DiMeIQx) in vitro and in vivo. Identification of a N2-(2'-deoxyguanosin-8-yl)-4,8-DiMeIQx adduct. Carcinogenesis. 1994 Nov;15(11):2553-8. [Content Brief]
[4]. Knize MG, et al. The metabolism of 4,8-DiMeIQx in conventional and germ-free rats. Carcinogenesis. 1989 Aug;10(8):1479-84. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
4,8-DiMeIQx Related Classifications
HY-W356181 Related Classifications
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Keywords
- 4,8-DiMeIQx
- 95896-78-9
- DNA Alkylator/Crosslinker
- DNA/RNA Synthesis
- Bacterial
- Salmonella enterica TA98
- parkinson’s disease
- E17 rat primary midbrain cultures
- colorectal cancer
- non-dopaminergic neurons
- calf thymus DNA
- Salmonella typhimurium TA98
- 2'-deoxyguanosine
- AGUS rats
- dopaminergic neurons
- Inhibitor
- inhibitor
- inhibit