Disease relevance of Curithane

• Acute myocardiopathy following tripathway exposure to methylenedianiline [1].
• The mutagenic activity of several aromatic amines and aromatic nitro compounds related to 4,4'-methylenedianiline towards Salmonella typhymurium tester strains TA100 and TA98 was evaluated [2].
• Methylenedianiline (DAPM) initially injures epithelial cells of major bile ducts, which is followed by cholestasis, cholangitis, and hepatocellular damage [3].
• Glutathione depletion exacerbates methylenedianiline toxicity to biliary epithelial cells and hepatocytes in rats [3].
• The within- and between-assay coefficients of variation were 4 and 6%, respectively, for samples containing 40 nmol/l. The method was applied for the monitoring of excreted 4,4'-methylenedianiline in urine, during epicutaneous skin hypersensitivity testing (patch testing) [4].

High impact information on Curithane

• 4,4'- Methylenedianiline (CAS: 101-77-9) in the drinking water increased neoplasms of the thyroid gland and liver in F344 rats and B6C3F1 mice [5].
• Oval cells and duct-like structures produced in the livers of rats fed N-2-fluorenylacetamide in a choline-devoid diet differ from bile ducts produced after feeding 4,4'-diaminodiphenylmethane [6].
• The duct-like structures associated with oval cells frequently contain AFP and albumin and are faintly delineated by laminin, whereas normal bile ducts and ducts induced by 4,4'-diaminodiphenylmethane do not contain AFP or albumin and are delineated by an intensely staining layer of laminin [6].
• Products included N,N-dimethyl-4,4'-methylenedianiline, N,N'-dimethyl-4,4'-methylenedianiline, N-methyl-4,4'-methylenedianiline, and 4,4'-methylenedianiline, representing 44.7, 5.3, 11.8, and 6.9%, respectively, of the total radioactivity recovered from the reaction mixture [7].
• A 32P-postlabeling method was used to detect (i), adducts formed by the reaction of the isocyanate group(s) of MDI with DNA; and a 32P-postlabeling method was adapted to detect (ii), a DNA adduct formed by 4,4'- methylenedianiline (MDA), a hydrolysis/decarboxylation product of MDIV [8].

Chemical compound and disease context of Curithane

• Methylene dianiline (4,4'-diaminodiphenylmethane, DAPM) rapidly causes cholestasis and injury to biliary epithelial cells (BEC) in the liver and common bile duct of rats [9].
• We report a patient who developed allergic contact dermatitis to a transitory chemical breakdown product of the isocyanate 4,4'-diphenylmethane diisocyanate (MDI), diaminodiphenylmethane (DDM), although he was not sensitized to the suspected parent compound MDI [10].

Biological context of Curithane

• Gas chromatography-negative-ion chemical ionization mass spectrometry of hydrolysed human urine and blood plasma for the biomonitoring of occupational exposure to 4,4'-methylenebisaniline [11].
• A gas chromatographic-mass spectrometric (GC-MS) method for the biological monitoring of 4,4'-methylenebisaniline (MDA), is presented [11].
• DNA damage induced by 4,4'-methylenedianiline in primary cultures of hepatocytes and thyreocytes from rats and humans [12].
• MDI, like the amine analogue 4,4'-methylenedianiline, is mutagenic in TA 100 after metabolic activation by rat liver enzymes (S-9 mix) [13].
• Decontamination procedures after in vitro topical exposure of human and rat skin to 4,4'-methylenebis[2-chloroaniline] and 4,4'-methylenedianiline [14].

Anatomical context of Curithane

• Modification by antioxidants and p,p'-diaminodiphenylmethane of 7,12-dimethylbenz[a]anthracene-induced carcinogenesis of the mammary gland and ear duct in CD rats [15].
• Methylenedianiline (DAPM) rapidly injures biliary epithelial cells (BEC) in vivo [16].
• Identification of metabolites of 4,4'-methylenedianiline in vascular smooth muscle cells by liquid chromatography-electrospray tandem mass spectrometry [17].
• Intrahepatic bile duct proliferation induced by 4,4'-diaminodiphenylmethane in rats [18].
• Mitochondrial dysfunction occurs before transport or tight junction deficits in biliary epithelial cells exposed to bile from methylenedianiline-treated rats [16].

Associations of Curithane with other chemical compounds

• Rapid elevations of serum alpha-fetoprotein (AFP) occur after feeding N-2-fluorenylacetamide in a choline-devoid diet; no elevations of AFP are seen during 4,4'-diaminodiphenylmethane feeding [6].
• While an MDI-based polymer was shown to be the most hydrolytically stable material, it was the only PCNU that produced its diamine analog, in this case 4,4'-methylene dianiline (MDA), as a degradation product [19].
• Formation of 4,4'-methylenedianiline in polyurethane potting materials by either gamma-ray or autoclave sterilization [20].
• Urinary 4,4'-methylenedianiline (MDA) metabolite was determined after acid hydrolysis as heptafluorobutyric anhydride derivatives by gas chromatography-mass spectrometry using chemical ionisation and monitoring negative ions [21].
• Detectable levels of 2,4-diaminotoluene, 2,6-diaminotoluene and 4,4'-methylenedianiline were found in water food simulant from some of the investigated food packaging materials [22].

Gene context of Curithane

• 4,4'-methylenedianiline-induced hepatotoxicity is modified by N-acetyltransferase 2 (NAT2) acetylator polymorphism in the rat [23].
• Hydrolysis of MDI can yield 4,4'-methylenedianiline (MDA), which is a suspected human carcinogen [24].
• 4,4'-Methylene-dianiline (MDA) and 4,4'-methylene-bis-2-chloroaniline (MOCA) are polycyclic aromatic amines that are currently used in industry [25].
• BACKGROUND: MDA is the abbreviation for methylene dianiline (p,p' diaminodiphenylmethane; 4,4'-methylenedianiline; CAS 101-77-9); and for methylendioxyamphetamine (MDMA, N, alpha-dimethyl-1,3-benzodioxole-5-ethanamine; CAS 42542-10-9) [26].
• D-galactosamine (300 mg/kg b.w., i.p., once a week), a hepatotoxin, significantly inhibited the induction of GST-P positive foci, while 4,4'-diaminodiphenylmethane (DDPM, 0.1% in diet), a bile duct proliferator which is itself a hepatocarcinogen, possessed enhancing activity [27].

Analytical, diagnostic and therapeutic context of Curithane

• Determination of 4,4'-methylenedianiline in hydrolysed human urine using liquid chromatography with UV detection and peak identification by absorbance ratio [28].
• Determination of 4,4'-diaminodiphenylmethane in blood by gas-liquid chromatography with electron-capture detection [29].
• A method is described for the determination of urinary 4,4'-methylenedianiline (MDA) by high-performance liquid chromatography (HPLC) [30].
• Impairment of precursors of oval cells in the liver by administration of 4,4'-diaminodiphenylmethane 24 h before transplantation of hepatocytes did not prevent the appearance of CK-19-positive biliary cells in the spleen [31].
• Diaminodiphenylmethane in standard patch tests [32].

References