p dimethylaminoazobenzene

Summary

Summary: A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound "may reasonably be anticipated to be a carcinogen." (Merck, 11th ed)

Top Publications

  1. Ohnishi S, Murata M, Degawa M, Kawanishi S. Oxidative DNA damage induced by an N-hydroxy metabolite of carcinogenic 4-dimethylaminoazobenzene. Jpn J Cancer Res. 2001;92:23-9 pubmed
    ..The main reactive species are probably DNA-copper-hydroperoxo complexes. We conclude that oxidative DNA damage may play an important role in the carcinogenic processes of DAB, in addition to DNA adduct formation...
  2. Tyagi S, Kramer F. Molecular beacons: probes that fluoresce upon hybridization. Nat Biotechnol. 1996;14:303-8 pubmed
    ..When introduced into living cells, these probes should enable the origin, movement, and fate of specific mRNAs to be traced...
  3. Caballero F, Gerez E, Oliveri L, Falcoff N, Batlle A, Vazquez E. On the promoting action of tamoxifen in a model of hepatocarcinogenesis induced by p-dimethylaminoazobenzene in CF1 mice. Int J Biochem Cell Biol. 2001;33:681-90 pubmed
    ..To document the long-term effect of TMX in mice treated with p-dimethylaminoazobenzene (DAB), we have investigated the time response action of these drugs on different biochemical parameters...
  4. Gerez E, Vazquez E, Caballero F, Polo C, Batlle A. Altered heme pathway regulation and drug metabolizing enzyme system in a mouse model of hepatocarcinogenesis: effect of veronal. Gen Pharmacol. 1997;29:569-73 pubmed
    ..3. The alterations found here would give rise to a pattern distinctive to that usually observed in the so-called resistant hepatocyte...
  5. Sacca P, Caballero F, Batlle A, Vazquez E. Cell cycle arrest and modulation of HO-1 expression induced by acetyl salicylic acid in hepatocarcinogenesis. Int J Biochem Cell Biol. 2004;36:1945-53 pubmed
    ..We studied the interplay between cell cycle and heme oxygenase-1 (HO-1) and the effect of the acetylsalicylic acid (ASA) in hepatic carcinogenesis...
  6. Martinez Senac M, Webb M. Mechanism of translocation and kinetics of DNA unwinding by the helicase RecG. Biochemistry. 2005;44:16967-76 pubmed
    ..The data support the idea that interactions of the duplex template arm with the protein are the major sites of binding and production of translocation...
  7. Punnonen E, Fages C, Wartiovaara J, Rauvala H. Ultrastructural localization of beta-actin and amphoterin mRNA in cultured cells: application of tyramide signal amplification and comparison of detection methods. J Histochem Cytochem. 1999;47:99-112 pubmed
    ..Especially in the cortical cytoplasm, beta-actin mRNA was associated with actin filaments. Direct localization to microtubules was only rarely seen. (J Histochem Cytochem 47:99-112, 1999)..
  8. Sakagami H, Hosaka M, Arakawa H, Maeda M, Satoh K, Ida Y, et al. Role of hydrogen peroxide in antitumor activity induction by sodium 5,6-benzylidene-L-ascorbate. Anticancer Res. 1998;18:2519-24 pubmed
    ..Addition of ascorbic acid, a degradation product of SBA, showed similar but slightly weaker stimulation effects. These data suggest that antitumor activity of SBA in vivo might, at least in part, be due to H2O2 production...
  9. Spano M, Frei H, Wurgler F, Graf U. Recombinagenic activity of four compounds in the standard and high bioactivation crosses of Drosophila melanogaster in the wing spot test. Mutagenesis. 2001;16:385-94 pubmed
    ..These results demonstrate that the wing spot test in Drosophila is most suited to the detection of recombinagenic activity of genotoxic chemicals...

More Information

Publications62

  1. Wu Z, Tong W. Sensitive absorbance detection method for capillary electrophoresis based on laser wave-mixing. J Chromatogr A. 1997;773:291-8 pubmed
    ..5.10(-8) M, mass detection limit of 13 amol and an absorbance-unit detection limit of 1.35.10(-5) AU are determined for dabsyl-glycine using this absorbance detection method...
  2. Soares M, Carvalho F, Bastos M. Determination of amphetamine and its metabolite p-hydroxyamphetamine in rat urine by reversed-phase high-performance liquid chromatography after dabsyl derivatization. Biomed Chromatogr. 2001;15:452-6 pubmed
    ..The principal advantages of the present proposed method are the stability of the dabsyl derivatives at room temperature and the detection carried out in the visible region, reducing the interferences detected...
  3. Medvedev Z, Crowne H, Medvedeva M. Age related variations of hepatocarcinogenic effect of azo dye (3'-MDAB) as linked to the level of hepatocyte polyploidization. Mech Ageing Dev. 1988;46:159-74 pubmed
    ..It is suggested that the higher resistance of older mice to the carcinogenic effect could be linked to the higher level of hepatocyte polyploidization and that the increase of LSP 1 and 2 is relevant to the toxic effect of the azo dye...
  4. Srinivasan K, Levine W, Bhargava M. Noncovalent binding of 3'-methyl-N,N-dimethyl-4-aminoazobenzene and its metabolites to liver cytosolic proteins and its role in their nuclear translocation. Drug Metab Dispos. 1987;15:504-10 pubmed
    ..Five per cent of translocated radioactivity was irreversibly bound to DNA, 3% to RNA, 67% to non-histone proteins, and 7.5% to histones; the remaining was not associated with any of these macromolecules...
  5. Sun X, Chang J. Heparin binding domain of human antithrombin III inferred from the sequential reduction of its three disulfide linkages. An efficient method for structural analysis of partially reduced proteins. J Biol Chem. 1989;264:11288-93 pubmed
  6. Shen Y, Mackey G, Rupcich N, Gloster D, Chiuman W, Li Y, et al. Entrapment of fluorescence signaling DNA enzymes in sol-gel-derived materials for metal ion sensing. Anal Chem. 2007;79:3494-503 pubmed
    ..Extension of the solid-phase DNAzyme assay toward a multiplexed assay format for metal detection is demonstrated, and shows that sol-gel technology can provide new opportunities for the development of DNAzyme-based biosensors...
  7. Kitamura Y, Kawase M, Ohmori S. Formate excretion in urine of rats fed dimethylaminoazobenzene-rich diets: the possibility of formate formation from D-lactate. Acta Med Okayama. 2008;62:193-203 pubmed
    ..The degradation of D-lactate, an end product of the methylglyoxal bypass, into acetaldehyde and formate was suggested as a possible way to explain the results...
  8. Ribeiro B, Andrade P, Silva B, Baptista P, Seabra R, Valentão P. Comparative study on free amino acid composition of wild edible mushroom species. J Agric Food Chem. 2008;56:10973-9 pubmed publisher
    ..A combination of different mushroom species in the diet would offer good amounts of amino acids and a great diversity of palatable sensations...
  9. Mack D, Reed V, Smith L. Retinyl acetate inhibition of 3'-methyl-4-dimethyl-aminoazobenzene induced hepatic neoplasia. Int J Biochem. 1990;22:359-65 pubmed
    ..06% 3'-Me-DAB. 5. The effect of retinyl acetate on the lower level of 3'-Me-DAB was to prevent formation of nodules through 71 weeks by which time the unprotected rats fed 0.01% 3'-Me-DAB alone had extensive hepatic nodular development...
  10. Dalmas O, Do Cao M, Lugo M, Sharom F, Di Pietro A, Jault J. Time-resolved fluorescence resonance energy transfer shows that the bacterial multidrug ABC half-transporter BmrA functions as a homodimer. Biochemistry. 2005;44:4312-21 pubmed
  11. Comparelli R, Cozzoli P, Curri M, Agostiano A, Mascolo G, Lovecchio G. Photocatalytic degradation of methyl-red by immobilised nanoparticles of TiO2 and ZnO. Water Sci Technol. 2004;49:183-8 pubmed
    ..Several intermediate by-products were identified by HPLC-MS, showing that two different mechanisms were operative during the photocatalytic oxidation...
  12. Castronuovo C, Sacca P, Meiss R, Caballero F, Batlle A, Vazquez E. Homeostatic response under carcinogen withdrawal, heme oxygenase 1 expression and cell cycle association. BMC Cancer. 2006;6:286 pubmed
    ..We analyzed HO-1 cellular localization and the expression of HO-1, Bcl-2 and cell cycle related proteins under these conditions comparing them to hepatocellular carcinoma (HC)...
  13. Pathak S, Khuda Bukhsh A. Assessment of hepatocellular damage and hematological alterations in mice chronically fed p-dimethyl aminoazobenzene and phenobarbital. Exp Mol Pathol. 2007;83:104-11 pubmed
    ..All results clearly indicated that the chronic feeding of the carcinogens induced considerable toxicity and palpable hepato-cellular injuries along with some other changes during the carcinogenetic process in liver...
  14. Kelly J, Cuerrier D, Graham L, Campbell R, Davies P. Profiling of calpain activity with a series of FRET-based substrates. Biochim Biophys Acta. 2009;1794:1505-9 pubmed publisher
    ..However, the activity profiles with the FRET substrate series were significantly different for the cathepsins, particularly cathepsin B...
  15. Tyagi S, Bratu D, Kramer F. Multicolor molecular beacons for allele discrimination. Nat Biotechnol. 1998;16:49-53 pubmed
    ..A comparison of "hairpin probes" with corresponding "linear probes" confirms that the presence of the hairpin stem in molecular beacons significantly enhances their specificity...
  16. Baudys M, Meloun B, Pohl J, Kostka V. Identification of the second (buried) cysteine residue and of the C-terminal disulfide bridge of bovine spleen cathepsin B. Biol Chem Hoppe Seyler. 1988;369 Suppl:169-74 pubmed
    ..As the second important result, a disulfide bridge formed by Cys148 and Cys252 in the C-terminal part of the chain was identified...
  17. Scott R, Chakraborty S, Sell S, Hunt J, Dunsford H. Change in the ploidy state of rat liver cells during chemical hepatocarcinogenesis and its relationship to the increased expression of alpha-fetoprotein. Cancer Res. 1989;49:6085-90 pubmed
    ..In addition, in the cases of hepatocellular carcinoma that were found, a population of cells was detected by flow cytometry that contained altered DNA...
  18. Miyamoto K, Sanae F, Kohei K, Nomura M, Koshiura R. Changes in number of alpha-adrenergic receptor subtypes in hepatocytes from rats fed 3'-methyl-4-dimethylaminoazobenzene. Jpn J Cancer Res. 1990;81:557-9 pubmed
    ..alpha 2-Adrenergic receptors, measured in terms of [3H]clonidine binding, transiently increased 3-fold over the control at 2 weeks. These changes in the early period of the 3'-MeDAB diet intake may be related to hepatocarcinogenesis...
  19. Fang C, Zhang G, Zhu X, Gong J. Distribution of oval cells and c-myc mRNA expression in mouse hepatocarcinogenesis. Hepatobiliary Pancreat Dis Int. 2004;3:433-9 pubmed
  20. Gulnik S, Suvorov L, Majer P, Collins J, Kane B, Johnson D, et al. Design of sensitive fluorogenic substrates for human cathepsin D. FEBS Lett. 1997;413:379-84 pubmed
  21. Zaramella A, Conti N, Dal Cin M, Paio A, Seneci P, Gehanne S. Dansyl and dabsyl analytical constructs as tools for the accurate estimation of compounds in solid-phase synthesis. J Comb Chem. 2001;3:410-20 pubmed
    ..Preliminary studies using the dabsyl moiety as an improved chromophore with higher wavelength and extinction coefficient are also reported...
  22. Seidenari S, Mantovani L, Manzini B, Pignatti M. Cross-sensitizations between azo dyes and para-amino compound. A study of 236 azo-dye-sensitive subjects. Contact Dermatitis. 1997;36:91-6 pubmed
    ..Cross-sensitizations between azo dyes and para-amino compounds can partially be explained on the basis of structural affinities...
  23. Velanganni A, Dharaneedharan S, Geraldine P, Balasundram C. Dietary supplementation of vitamin A, C and E prevents p-dimethylaminoazobenzene induced hepatic DNA damage in rats. Indian J Biochem Biophys. 2007;44:157-63 pubmed
    ..The results indicate that there is a significant advantage in mixed vitamins therapy at low dose over the treatment with individual vitamins...
  24. Borges C, Watson J. Recognition of cysteine-containing peptides through prompt fragmentation of the 4-dimethylaminophenylazophenyl-4'-maleimide derivative during analysis by MALDI-MS. Protein Sci. 2003;12:1567-72 pubmed
  25. Nakamura H, Ubuka T. Determination of taurine and hypotaurine in animal tissues by reversed-phase high-performance liquid chromatography after derivatization with dabsyl chloride. Adv Exp Med Biol. 2003;526:221-8 pubmed
  26. Boer H, Simolin H, Cottaz S, Söderlund H, Koivula A. Heterologous expression and site-directed mutagenesis studies of two Trichoderma harzianum chitinases, Chit33 and Chit42, in Escherichia coli. Protein Expr Purif. 2007;51:216-26 pubmed
  27. Caballero F, Meiss R, Gimenez A, Batlle A, Vazquez E. Immunohistochemical analysis of heme oxygenase-1 in preneoplastic and neoplastic lesions during chemical hepatocarcinogenesis. Int J Exp Pathol. 2004;85:213-22 pubmed
    ..In our experimental model, down modulation of HO-1 expression correlated with malignancy progression. Thus, our data point to activation of HO-1 as a potential therapeutic tool...
  28. Rasmussen F, Yeung N, Kiefer L, Murphy G, Lopez Otin C, Vitek M, et al. Use of a multiple-enzyme/multiple-reagent assay system to quantify activity levels in samples containing mixtures of matrix metalloproteinases. Biochemistry. 2004;43:2987-95 pubmed
    ..Some of the best substrates tested have specific activities for collagenase 3 that are 37,000-, 17,000-, 90-, and 200-fold selective over stromelysin 1, collagenase 1, and gelatinases A and B, respectively...
  29. Burton B, Economo M, Lee G, White J. Development of theta rhythmicity in entorhinal stellate cells of the juvenile rat. J Neurophysiol. 2008;100:3144-57 pubmed publisher
    ..Our data predict that functions that rely on theta rhythmicity in the hippocampal network are limited until at least P18...
  30. Biswas S, Khuda Bukhsh A. Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice. BMC Complement Altern Med. 2002;2:4 pubmed
  31. Tsuda S, Murakami M, Matsusaka N, Kano K, Taniguchi K, Sasaki Y. DNA damage induced by red food dyes orally administered to pregnant and male mice. Toxicol Sci. 2001;61:92-9 pubmed
    ..N-nitrosodiethylamine at 14 mg/kg did not induce DNA damage in any organs examined. Because the 3 azo additives we examined induced colon DNA damage at a very low dose, more extensive assessment of azo additives is warranted...
  32. Krieglstein K, Henschen A, Weller U, Habermann E. Arrangement of disulfide bridges and positions of sulfhydryl groups in tetanus toxin. Eur J Biochem. 1990;188:39-45 pubmed
    ..During the progress of the investigations about 20% of the amino acid sequence previously predicted from DNA analysis was confirmed by protein-chemical methods...
  33. Rizzo J, Gifford L, Zhang X, Gewirtz A, Lu P. Chimeric RNA-DNA molecular beacon assay for ribonuclease H activity. Mol Cell Probes. 2002;16:277-83 pubmed
    ..This method permits real-time detection of RNase H activity and a convenient approach to RNase H kinetic and mechanistic study...
  34. Kato T, Matsuda T, Matsui S, Mizutani T, Saeki K. Activation of the aryl hydrocarbon receptor by methyl yellow and related congeners: structure-activity relationships in halogenated derivatives. Biol Pharm Bull. 2002;25:466-71 pubmed
    ..These results suggest that the amide bond is equivalent to the -N=N- or -CH=CH- double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives...
  35. Kamei T, Akiyama H, Morii H, Tamaoki N, Uyeda T. Visible-light photocontrol of (E)/(Z) isomerization of the 4-(dimethylamino)azobenzene pseudo-nucleotide unit incorporated into an oligonucleotide and DNA hybridization in aqueous media. Nucleosides Nucleotides Nucleic Acids. 2009;28:12-28 pubmed publisher
    ..Significant photoregulation of DNA hybridization by visible light was demonstrated under this condition...
  36. Oosterwijk J, Mesker W, Ouwerkerk Van Velzen M, Knepfle C, Wiesmeijer K, Beverstock G, et al. Fetal cell detection in maternal blood: a study in 236 samples using erythroblast morphology, DAB and HbF staining, and FISH analysis. Cytometry. 1998;32:178-85 pubmed
    ..These data indicate that further refinement of NRBC detection is needed before application of noninvasive prenatal diagnosis using maternal blood is feasible...
  37. Mori H, Tanaka T, Sugie S, Kuniyasu T, Iwata H, Ni I H, et al. Hepatocarcinogenic activities of hydroxymethyl derivatives of 4-(N,N-dimethylamino)azobenzene in ACI/N rats. J Natl Cancer Inst. 1987;79:1159-61 pubmed
    ..These data suggest that 3'-CH2OH-DAB is the most potent hepatocarcinogen in the series of azo dyes. Possible reasons for the potency of the chemical are discussed...
  38. Garcia Heras M, Kromka K, Faber J, Karaszkiewicz P, Villegas M. Evaluation of air acidity through optical sensors. Environ Sci Technol. 2005;39:3743-7 pubmed
    ..05, approximately. The sensors can be a very useful analytical tool to alert against acid rain risks in preventive conservation of historical materials, among other applications...
  39. Yu X, Zhu S, Xu Z, Hu X, Zhu T, Chen J, et al. Roles of EGFR-Stat3 signal pathway in carcinogenesis of experimental hepatoma in rats. J Cancer Res Clin Oncol. 2007;133:145-52 pubmed
    ..TGFalpha-EGFR autocrine ring formation may lead to the activation of Stat3 and in turn, promote proliferation and regulate the transcription of genes regulating cell apoptosis and cell cycle...
  40. Kelly M, Styles J, Pritchard N. Analysis of cytological changes in hepatocytes from rats dosed with 3'-methyl-4-dimethylaminoazobenzene: initial response appears to involve cytokinesis of binucleated cells. Cancer Lett. 1990;53:1-4 pubmed
    ..Shortly afterwards nonpolyploidizing growth commences by proliferation of some 2N cells...
  41. Handley M, Hirth W, Phillips J, Ali S, Khan A, Fadnis L, et al. Development of a sensitive and quantitative analytical method for 1H-4-substituted imidazole histamine H3-receptor antagonists utilizing high-performance liquid chromatography and dabsyl derivatization. J Chromatogr B Biomed Sci Appl. 1998;716:239-49 pubmed
    ..This assay has demonstrated it's suitability for the sensitive quantitation of several structurally diverse 1H-4-substituted imidazole HA H3-receptor antagonists in biological matrices for pharmacokinetic and biodistribution studies...
  42. Polo C, Vazquez E, Caballero F, Gerez E, Battle A. Heme biosynthesis pathway regulation in a model of hepatocarcinogenesis pre-initiation. Comp Biochem Physiol B. 1992;103:251-6 pubmed
  43. Shen Y, Chiuman W, Brennan J, Li Y. Catalysis and rational engineering of trans-acting pH6DZ1, an RNA-cleaving and fluorescence-signaling deoxyribozyme with a four-way junction structure. Chembiochem. 2006;7:1343-8 pubmed
  44. Molinari A, Tursilli R, Casolari A, Maldotti A, Scalia S. Influence of complexation with cyclodextrins on photo-induced free radical production by the common sunscreen agents octyl-dimethylaminobenzoate and octyl-methoxycinnamate. Pharmazie. 2006;61:41-5 pubmed
    ..Therefore, inclusion of ODAB and OMC into the cyclodextrin cavities minimizes their photosensitising potential...
  45. Kittler J, Meisler N, Thanassi J. Azo dye-induced alterations in vitamin B-6 metabolism and in pyridoxal 5'-phosphate-binding proteins in rat liver. J Nutr. 1986;116:588-98 pubmed
    ..Therefore, with respect to vitamin B-6 metabolism and use, it appears likely that azo dye-induced hepatocarcinogenesis involves proliferation of a stem cell type(s) having the phenotypic characteristics of fetal hepatic tissue...
  46. Surjyo B, Anisur K. Protective action of an anti-oxidant (L-Ascorbic acid) against genotoxicity and cytotoxicity in mice during p-DAB-induced hepatocarcinogenesis. Indian J Cancer. 2004;41:72-80 pubmed
    ..Therefore studies involving vitamin supplementation, particularly with those with anti-oxidant activity, in combating cancer have routinely been carried out in both in vivo and in vitro systems, but relatively much less in mice...
  47. Sasaki Y, Tsuda S, Izumiyama F, Nishidate E. Detection of chemically induced DNA lesions in multiple mouse organs (liver, lung, spleen, kidney, and bone marrow) using the alkaline single cell gel electrophoresis (Comet) assay. Mutat Res. 1997;388:33-44 pubmed
    ..We suggest that it may be possible to use the alkaline SCG assay using a homogenization technique to detect the genotoxicity of chemicals in vivo in their target organs...
  48. Sethuraman R, Lee T, Tachibana S. Simple quantitative HPLC method for measuring physiologic amino acids in cerebrospinal fluid without pretreatment. Clin Chem. 2004;50:665-9 pubmed
  49. Ivanov V, Martinson T, Tiuriaeva I. [Tumor-associated hetero-organic antigens as markers of deranged cell differentiation and malignancy]. Vopr Onkol. 2003;49:467-71 pubmed
    ..Their synthesis, following single exposure, was assayed immunocytofluorimetrically. It is suggested that the antigens be used as markers of cell dysdifferentiation and malignancy and testing substances for carcinogenicity...
  50. Gopi H, Ravindra G, Pal P, Pattanaik P, Balaram H, Balaram P. Proteolytic stability of beta-peptide bonds probed using quenched fluorescent substrates incorporating a hemoglobin cleavage site. FEBS Lett. 2003;535:175-8 pubmed
  51. Li J, Tan W, Wang K, Xiao D, Yang X, He X, et al. Ultrasensitive optical DNA biosensor based on surface immobilization of molecular beacon by a bridge structure. Anal Sci. 2001;17:1149-53 pubmed
    ..It was interesting to note that the described biosensor was reproducible after being regenerated by urea...
  52. Kinoshita E, Saito M. Novel histamine measurement by HPLC analysis used to assay histidine decarboxylase inhibitory activity of shoyuflavones from soy sauce. Biosci Biotechnol Biochem. 1998;62:1488-91 pubmed
    ..They showed intense inhibition of the activities of HDC from both mouse mastocytoma P-815 cells and Clostridium perfringens...
  53. Yano M, Higashi T, Kano S, Tateishi N, Kido Y, Mori T, et al. Decreased activation of carcinogens in the liver of carcinogen-resistant rats. Cancer Res. 1989;49:5352-7 pubmed
    ..These data implicate that the hepatic Ah receptor level may be an important factor in determining carcinogen sensitivity in rats...