aminobiphenyl compounds

Summary

Summary: Biphenyl compounds substituted in any position by one or more amino groups. Permitted are any substituents except fused rings.

Top Publications

  1. Shahab U, Moinuddin -, Ahmad S, Dixit K, Abidi S, Alam K, et al. Acquired immunogenicity of human DNA damaged by N-hydroxy-N-acetyl-4-aminobiphenyl. IUBMB Life. 2012;64:340-5 pubmed publisher
    ..Possible role of N-OH-AABP-DNA in the induction of antibodies in cancer patients and the related consequences have been discussed. ..
  2. Lindner D, Smith S, Leroy C, Tricker A. Comparison of exposure to selected cigarette smoke constituents in adult smokers and nonsmokers in a European, multicenter, observational study. Cancer Epidemiol Biomarkers Prev. 2011;20:1524-36 pubmed publisher
    ..This research provides a comprehensive evaluation of smoke constituent exposure of adult cigarette smokers and nonsmokers in three European countries. ..
  3. Beland F, Doerge D, Churchwell M, Poirier M, Schoket B, Marques M. Synthesis, characterization, and quantitation of a 4-aminobiphenyl-DNA adduct standard. Chem Res Toxicol. 1999;12:68-77 pubmed
    ..When the 32P-postlabeling analyses and the DELFIA were conducted using the DNA modified in vitro with dG-C8-4-ABP as a quantitation standard, accurate estimations of the extent of in vivo formation of dG-C8-4-ABP were obtained. ..
  4. Burger M, Torino J, Swaminathan S. DNA damage in human transitional cell carcinoma cells after exposure to the proximate metabolite of the bladder carcinogen 4-aminobiphenyl. Environ Mol Mutagen. 2001;38:1-11 pubmed
  5. Butler M, Guengerich F, Kadlubar F. Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4'-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases. Cancer Res. 1989;49:25-31 pubmed
    ..Therefore, individual profiles of cytochromes P-450, affected by both environmental and genetic factors, may be significant determinants of individual susceptibility to arylamine carcinogenesis...
  6. Al Atrash J, Zhang Y, Lin D, Kadlubar F, Santella R. Quantitative immunohistochemical analysis of 4-aminobiphenyl-DNA in cultured cells and mice: comparison to gas chromatography/mass spectroscopy analysis. Chem Res Toxicol. 1995;8:747-52 pubmed
    ..Immunohistochemistry should be useful for analysis of 4-ABP-DNA adducts in human tissue biopsies as well as exfoliated cells from the oral mucosa and urinary bladder. ..
  7. Snyderwine E, Sinha R, Felton J, Ferguson L. Highlights of the eighth international conference on carcinogenic/mutagenic N-substituted aryl compounds. Mutat Res. 2002;506-507:1-8 pubmed
  8. Cho Y, Takahashi S, Asamoto M, Suzuki S, Inaguma S, Hokaiwado N, et al. Age-dependent histopathological findings in the prostate of probasin/SV40 T antigen transgenic rats: lack of influence of carcinogen or testosterone treatment. Cancer Sci. 2003;94:153-7 pubmed
    ..These results suggest that our TG rats are suitable for clarification of mechanisms in early stages of prostate carcinogenesis, that is, from prostatic intraepithelial neoplasia (PIN) to non-invasive and then invasive lesions. ..
  9. Luo W, Fan W, Xie H, Jing L, Ricicki E, Vouros P, et al. Phenotypic anchoring of global gene expression profiles induced by N-hydroxy-4-acetylaminobiphenyl and benzo[a]pyrene diol epoxide reveals correlations between expression profiles and mechanism of toxicity. Chem Res Toxicol. 2005;18:619-29 pubmed
    ..Differences in the transcriptional response of TK6 cells to N-OH-AABP or BPDE exposure may explain the dramatic differences in the toxicity and mutagenicity of these human carcinogens. ..

More Information

Publications62

  1. Loehle J, Cornish V, Wakefield L, Doll M, Neale J, Zang Y, et al. N-acetyltransferase (Nat) 1 and 2 expression in Nat2 knockout mice. J Pharmacol Exp Ther. 2006;319:724-8 pubmed
    ..The Nat2 KO model will be useful in future studies to assess the role of Nat2 in arylamine carcinogenesis. ..
  2. Imaida K, Tamano S, Kato K, Ikeda Y, Asamoto M, Takahashi S, et al. Lack of chemopreventive effects of lycopene and curcumin on experimental rat prostate carcinogenesis. Carcinogenesis. 2001;22:467-72 pubmed
    ..Neither summational nor synergistic chemoprevention was evident. It is concluded from the present data that, overall, neither lycopene nor curcumin can consistently prevent rat prostate carcinogenesis. ..
  3. Hsieh M, Chou C. Mutagenicity and antimutagenic effect of soymilk fermented with lactic acid bacteria and bifidobacteria. Int J Food Microbiol. 2006;111:43-7 pubmed
  4. Bessette E, Goodenough A, Langouet S, Yasa I, Kozekov I, Spivack S, et al. Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer. Anal Chem. 2009;81:809-19 pubmed publisher
  5. Shirai T, Takahashi S, Cui L, Yamada Y, Tada M, Kadlubar F, et al. Use of polyclonal antibodies against carcinogen-DNA adducts in analysis of carcinogenesis. Toxicol Lett. 1998;102-103:441-6 pubmed
    ..Thus, the antibodies can be applied as tools to clarify tissue or cell-specific carcinogenesis, carcinogen-exposure levels and metabolic activation in various species, including man after tissue transplantation. ..
  6. Baghbanzadeh M, Pilger C, Kappe C. Rapid nickel-catalyzed Suzuki-Miyaura cross-couplings of aryl carbamates and sulfamates utilizing microwave heating. J Org Chem. 2011;76:1507-10 pubmed publisher
    ..High-speed and scalable nickel-catalyzed cross-coupling of arylboronic acids with aryl carbamates and sulfamates is achieved by using sealed-vessel microwave processing. ..
  7. Yuen J, Gohel M. The dual roles of Ganoderma antioxidants on urothelial cell DNA under carcinogenic attack. J Ethnopharmacol. 2008;118:324-30 pubmed publisher
    ..Water-soluble and water-insoluble components of Ganoderma lucidum exhibited dual roles in oxidative DNA damage. Oxidative DNA damage may be an underlying mechanism of Lingzhi-induced apoptosis in bladder chemoprevention. ..
  8. Qi S, Wang X, Yang Z, Xu X. Effect of N7-protonated purine nucleosides on formation of C8 adducts in carcinogenic reactions of arylnitrenium ions with purine nucleosides: a quantum chemistry study. J Phys Chem B. 2009;113:5645-52 pubmed publisher
    ..iv) The rate constant of the C8 deprotonation process becomes larger when N7-protonated purine bases are involved in these carcinogenic reactions. ..
  9. Sentchouk V, Grintsevich E. Oxidation of benzidine and its derivatives by thyroid peroxidase. Biochemistry (Mosc). 2004;69:201-7 pubmed
    ..Straight correlation between the carcinogenicity of aminobiphenyls and genotoxicity of their peroxidation products was shown by the electrophoresis detecting the formation of covalent DNA cross-linking. ..
  10. Lewis D, Ioannides C, Parke D. A quantitative structure-activity relationship (QSAR) study of mutagenicity in several series of organic chemicals likely to be activated by cytochrome P450 enzymes. Teratog Carcinog Mutagen. 2003;Suppl 1:187-93 pubmed
  11. Inaguma S, Takahashi S, Imaida K, Suzuki S, Shirai T. p-Nonylphenol pretreatment during the late neonatal period has no effect on 3,2'-dimethyl-4-aminobiphenyl-induced prostate carcinogenesis in male F344 rats. Cancer Lett. 2004;212:159-66 pubmed
    ..These results indicate that late neonatal treatment with NP has no modulating effects on DMAB-induced rat prostatic carcinogenesis. ..
  12. Glende C, Klein M, Schmitt H, Erdinger L, Boche G. Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. Part II: alkylation far away from the amino function. Mutat Res. 2002;515:15-38 pubmed
    ..To predict the correct mutagenicities of such compounds, it is necessary to introduce steric parameters in the respective QSAR equations which will be done in a forthcoming paper. ..
  13. Grimmer G, Dettbarn G, Seidel A, Jacob J. Detection of carcinogenic aromatic amines in the urine of non-smokers. Sci Total Environ. 2000;247:81-90 pubmed
    ..The detected urinary levels of aromatic amines arising from sources other than tobacco smoke or diesel exhaust may play a role in the bladder cancer etiology of non-smokers. ..
  14. Kimura S, Kawabe M, Ward J, Morishima H, Kadlubar F, Hammons G, et al. CYP1A2 is not the primary enzyme responsible for 4-aminobiphenyl-induced hepatocarcinogenesis in mice. Carcinogenesis. 1999;20:1825-30 pubmed
    ..In vitro studies using CYP1A2-null and wild-type mouse liver microsomes revealed that CYP1A2 is not the sole P450 required for 4-ABP N-hydroxylation and that another, yet to be identified, P450 is likely to be involved. ..
  15. Sugamori K, Brenneman D, Wong S, Gaedigk A, Yu V, Abramovici H, et al. Effect of arylamine acetyltransferase Nat3 gene knockout on N-acetylation in the mouse. Drug Metab Dispos. 2007;35:1064-70 pubmed
    ..Thus, Nat3 is unlikely to play a significant role in the N-acetylation of arylamines either in wild-type mice or in mice lacking Nat1 and Nat2 activities. ..
  16. Hein D, Doll M, Nerland D, Fretland A. Tissue distribution of N-acetyltransferase 1 and 2 catalyzing the N-acetylation of 4-aminobiphenyl and O-acetylation of N-hydroxy-4-aminobiphenyl in the congenic rapid and slow acetylator Syrian hamster. Mol Carcinog. 2006;45:230-8 pubmed
    ..These conclusions are important for interpretation of molecular epidemiological investigations into the role of N-acetyltransferase polymorphisms in various diseases including cancer. ..
  17. Saletta F, Matullo G, Manuguerra M, Arena S, Bardelli A, Vineis P. Exposure to the tobacco smoke constituent 4-aminobiphenyl induces chromosomal instability in human cancer cells. Cancer Res. 2007;67:7088-94 pubmed
  18. Seyler T, Reyes L, Bernert J. Analysis of 4-aminobiphenyl hemoglobin adducts in smokers and nonsmokers by pseudo capillary on-column gas chromatography- tandem mass spectrometry. J Anal Toxicol. 2010;34:304-11 pubmed
    ..Our study shows that 4-aminobiphenyl Hb adducts remain the preferred biomarker for identifying people exposed to aromatic amines from tobacco smoke. ..
  19. Bessette E, Spivack S, Goodenough A, Wang T, Pinto S, Kadlubar F, et al. Identification of carcinogen DNA adducts in human saliva by linear quadrupole ion trap/multistage tandem mass spectrometry. Chem Res Toxicol. 2010;23:1234-44 pubmed publisher
    ..These findings demonstrate that PhIP is a significant DNA-damaging agent in humans. Saliva appears to be a promising biological fluid in which to assay DNA adducts of tobacco and dietary carcinogens by selective LIT MS techniques. ..
  20. Parsons B, Beland F, Von Tungeln L, Delongchamp R, Fu P, Heflich R. Levels of 4-aminobiphenyl-induced somatic H-ras mutation in mouse liver DNA correlate with potential for liver tumor development. Mol Carcinog. 2005;42:193-201 pubmed
    ..This study demonstrates that ACB-PCR can directly measure background levels of somatic oncogene mutation and detect a carcinogen-induced increase in such mutation. ..
  21. Lu Q, Jin Y, Pantuck A, Zhang Z, Heber D, Belldegrun A, et al. Green tea extract modulates actin remodeling via Rho activity in an in vitro multistep carcinogenic model. Clin Cancer Res. 2005;11:1675-83 pubmed
    ..This study shows that GTE exerts an effect on cytoskeletal actin remodeling and provides further support for the use of GTE as a chemopreventive agent. ..
  22. Kato K, Takahashi S, Cui L, Toda T, Suzuki S, Futakuchi M, et al. Suppressive effects of dietary genistin and daidzin on rat prostate carcinogenesis. Jpn J Cancer Res. 2000;91:786-91 pubmed
    ..Thus, the present data suggest that genistin and daidzin possess anti-cancer effects at relatively early stages of prostate cancer development, providing experimental support for epidemiological findings. ..
  23. Yamauchi A, Kawai K, Tsukamoto S, Ideyama Y, Shirai T, Akaza H. Persistence of prostatic intraepithelial neoplasia after effective chemoprevention of microscopic prostate cancer with antiandrogen in a rat model. J Urol. 2006;175:348-52 pubmed
    ..Despite this suppressive effect on microscopic cancer bicalutamide permits the persistence of PIN. The latter finding suggests that the sensitivity of PIN to antiandrogen might be more complicated than previously recognized. ..
  24. Ketelslegers H, Godschalk R, Eskens B, Dallinga J, Gottschalk R, Van Schooten F, et al. Potential role of cytochrome P450-1B1 in the metabolic activation of 4-aminobiphenyl in humans. Mol Carcinog. 2009;48:685-91 pubmed publisher
  25. Chen J, Yu H, Liu Y, Jiang W, Jiang J, Zhang J, et al. Ecotoxicological evaluation of 4-aminobiphenyl using a test battery. Ecotoxicol Environ Saf. 2004;58:104-9 pubmed
  26. Skipper P, Tannenbaum S, Ross R, Yu M. Nonsmoking-related arylamine exposure and bladder cancer risk. Cancer Epidemiol Biomarkers Prev. 2003;12:503-7 pubmed
  27. Gu D, Turesky R, Tao Y, Langouët S, Nauwelaërs G, Yuan J, et al. DNA adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 4-aminobiphenyl are infrequently detected in human mammary tissue by liquid chromatography/tandem mass spectrometry. Carcinogenesis. 2012;33:124-30 pubmed publisher
    ..Our findings, derived from a specific mass spectrometry method, signify that PhIP and 4-ABP are not major DNA-damaging agents in mammary tissue of USA women and raise questions about the roles of these chemicals in breast cancer. ..
  28. Ohnishi S, Murata M, Kawanishi S. Oxidative DNA damage induced by a metabolite of 2-naphthylamine, a smoking-related bladder carcinogen. Jpn J Cancer Res. 2002;93:736-43 pubmed
    ..The oxidative DNA damage by these amino-aromatic compounds may participate in smoking-related bladder cancer, in addition to DNA adduct formation. ..
  29. Schorp M, Leyden D. Biomonitoring of smoke constituents: exposure to 4-aminobiphenyl and 4-aminobiphenyl hemoglobin adduct levels in nonsmokers and smokers. Inhal Toxicol. 2010;22:725-37 pubmed publisher
  30. Beland F, Melchior W, Mourato L, Santos M, Marques M. Arylamine-DNA adduct conformation in relation to mutagenesis. Mutat Res. 1997;376:13-9 pubmed
    ..This increase in biological activity may be due in part to the greater propensity of ortho alkylated adducts to adopt a syn conformation. ..
  31. Gaber K, Harréus U, Matthias C, Kleinsasser N, Richter E. Hemoglobin adducts of the human bladder carcinogen o-toluidine after treatment with the local anesthetic prilocaine. Toxicology. 2007;229:157-64 pubmed
    ..01). In conclusion, prilocaine anesthesia leads to a massive increase of hemoglobin adducts of the carcinogenic arylamine o-toluidine. This implies a carcinogenic risk which should be taken into account in preventive hazard minimization. ..
  32. Murata M, Tamura A, Tada M, Kawanishi S. Mechanism of oxidative DNA damage induced by carcinogenic 4-aminobiphenyl. Free Radic Biol Med. 2001;30:765-73 pubmed
    ..We conclude that, in addition to DNA adduct formation, oxidative DNA damage may play an important role in the carcinogenic process of 4-ABP. ..
  33. Wang S, Chung J, Chen C, Chen S. 2- and 4-Aminobiphenyls induce oxidative DNA damage in human hepatoma (Hep G2) cells via different mechanisms. Mutat Res. 2006;593:9-21 pubmed
    ..Taken together, our finding indicated the mechanisms of induced oxidative DNA damage in Hep G2 cell by 2-ABP and 4-ABP are different, although both tested compounds are isomers. ..
  34. Dickerson T, Tremblay M, Hoffman T, Ruiz D, Janda K. Catalysis of the photo-Fries reaction: antibody-mediated stabilization of high energy states. J Am Chem Soc. 2003;125:15395-401 pubmed
    ..Furthermore, despite the observed photodecay, turnover of the antibody was present; this represents the first case in which true turnover of a photochemical reaction using a catalytic antibody could be observed. ..
  35. Rami H, Thompson M, Wyman P, Jerman J, Egerton J, Brough S, et al. Discovery of small molecule antagonists of TRPV1. Bioorg Med Chem Lett. 2004;14:3631-4 pubmed
    ..Study of a quaternary salt of 5 supports a mode of action in which compounds from this series cause inhibition via an extracellularly accessible binding site on the TRPV1 receptor. ..
  36. Tripathy N, Wurgler F, Frei H. Genetic toxicity of six carcinogens and six non-carcinogens in the Drosophila wing spot test. Mutat Res. 1990;242:169-80 pubmed
    ..The data for the non-carcinogens demonstrate that non-genotoxic compounds can be identified in the wing spot test with a reasonable experimental effort. ..
  37. Sheikh I, Beg M, Yasir M. Molecular Interactions of Carcinogenic Aromatic Amines, 4-Aminobiphenyl and 4,4'-Diaminobiphenyl, with Lactoperoxidase - Insight to Breast Cancer. Anticancer Res. 2017;37:6245-6249 pubmed
    ..LPO catalyzes their oxidation and converts them into reactive products which bind to DNA and form adducts. These DNA adducts subsequently lead to breast cancer...
  38. Williams G, Iatropoulos M, Jeffrey A, Shirai T. Protective effect of acetaminophen against colon cancer initiation effects of 3,2'-dimethyl-4-aminobiphenyl in rats. Eur J Cancer Prev. 2002;11:39-48 pubmed
    ..APAP reduced this by 94-fold. Thus, APAP produced a marked protective effect in colonic enterocytes against several parameters of neoplastic development by the carcinogen. ..
  39. Roemer E, Schorp M, Piadé J, Seeman J, Leyden D, Haussmann H. Scientific assessment of the use of sugars as cigarette tobacco ingredients: a review of published and other publicly available studies. Crit Rev Toxicol. 2012;42:244-78 pubmed publisher
    ..In conclusion, thorough examination of the data available suggests that the use of sugars as ingredients in cigarette tobacco does not increase the inherent risk and harm of cigarette smoking. ..
  40. Faraglia B, Chen S, Gammon M, Zhang Y, Teitelbaum S, Neugut A, et al. Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: the influence of tobacco smoke. Carcinogenesis. 2003;24:719-25 pubmed
    ..In this study, genetic polymorphisms did not significantly affect the formation of 4-ABP-DNA adducts in breast cancer cases, perhaps due to the small number of samples. ..
  41. Steele D, el Kabbani O, Dunten P, Windsor L, Kammlott R, Crowther R, et al. Expression, characterization and structure determination of an active site mutant (Glu202-Gln) of mini-stromelysin-1. Protein Eng. 2000;13:397-405 pubmed
    ..The inhibitor makes no specific interactions with the active site glutamate and a comparison of the wild-type and mutant structures revealed no major structural changes resulting from the glutamate to glutamine substitution. ..
  42. Bafana A, Chakrabarti T, Devi S. Azoreductase and dye detoxification activities of Bacillus velezensis strain AB. Appl Microbiol Biotechnol. 2008;77:1139-44 pubmed
    ..Thus, the culture seems to be a suitable candidate for further study for both decolourization and detoxification of azo dyes, resulting in their safe disposal. ..
  43. Kuduk S, Di Marco C, Chang R, Wood M, Schirripa K, Kim J, et al. Development of orally bioavailable and CNS penetrant biphenylaminocyclopropane carboxamide bradykinin B1 receptor antagonists. J Med Chem. 2007;50:272-82 pubmed
    ..One of these novel bradykinin B1 antagonists (13b) also exhibited suitable pharmacokinetic properties and efficient ex vivo receptor occupancy for further development as a novel approach for the treatment of pain and inflammation. ..
  44. Chen H, Qin T, Zhao L, Xu X. Effects of lead on 4-aminobiphenyl pharmacokinetics in liver, kidney, spleen, testes, heart, lung and hemoglobin adduct for rat model. Ecotoxicology. 2002;11:255-64 pubmed
  45. Castelao J, Yuan J, Gago Dominguez M, Skipper P, Tannenbaum S, Chan K, et al. Carotenoids/vitamin C and smoking-related bladder cancer. Int J Cancer. 2004;110:417-23 pubmed
    ..The carotenoid-bladder cancer association was not affected by the GSTM1, GSTT1 and GSTP1 genotypes. ..
  46. McQueen C, Chau B, Erickson R, Tjalkens R, Philbert M. The effects of genetic variation in N-acetyltransferases on 4-aminobiphenyl genotoxicity in mouse liver. Chem Biol Interact. 2003;146:51-60 pubmed
    ..Mouse models with variation in both isoforms are needed to adequately assess the role of variation in NATs in susceptibility to 4ABP genotoxicity. ..
  47. Poirier M, Beland F. Aromatic amine DNA adduct formation in chronically-exposed mice: considerations for human comparison. Mutat Res. 1997;376:177-84 pubmed
  48. Riedel K, Scherer G, Engl J, Hagedorn H, Tricker A. Determination of three carcinogenic aromatic amines in urine of smokers and nonsmokers. J Anal Toxicol. 2006;30:187-95 pubmed
    ..In conclusion, the analytical method is suitable for measuring short-term exposure to arylamines in urine of non-occupationally exposed smokers and nonsmokers...
  49. Swaminathan S, Torino J, Burger M. Human urinary bladder epithelial cells lacking wild-type p53 function are deficient in the repair of 4-aminobiphenyl-DNA adducts in genomic DNA. Mutat Res. 2002;499:103-17 pubmed
    ..This implies that in p53 null cells the unrepaired DNA damage could cause accumulation of mutation, which might contribute to increased genomic instability and neoplastic progression. ..
  50. Kumar V, Majumdar C, Roy P. Effects of endocrine disrupting chemicals from leather industry effluents on male reproductive system. J Steroid Biochem Mol Biol. 2008;111:208-16 pubmed publisher
    ..Our data suggests that the effluents from leather industry have potential EDC demonstrating androgenic activities. ..
  51. Flamini G, Romano G, Curigliano G, Chiominto A, Capelli G, Boninsegna A, et al. 4-Aminobiphenyl-DNA adducts in laryngeal tissue and smoking habits: an immunohistochemical study. Carcinogenesis. 1998;19:353-7 pubmed
    ..5% of the polyps. This work demonstrates that 4-ABP-DNA adducts can be evaluated in laryngeal tissue and are related to smoking exposure. ..
  52. Paonessa J, Ding Y, Randall K, Munday R, Argoti D, Vouros P, et al. Identification of an unintended consequence of Nrf2-directed cytoprotection against a key tobacco carcinogen plus a counteracting chemopreventive intervention. Cancer Res. 2011;71:3904-11 pubmed publisher
    ..Thus, CPDT exemplifies a counteracting solution to the dilemma posed by Nrf2. ..
  53. Bradley C, Van Der Meer R, Roodi N, Yan H, Chandrasekharan M, Sun Z, et al. Carcinogen-induced histone alteration in normal human mammary epithelial cells. Carcinogenesis. 2007;28:2184-92 pubmed