KEGG   PATHWAY: map05204
Entry
map05204                    Pathway                                
Name
Chemical carcinogenesis - DNA adducts
Description
It has been estimated that exposure to environmental chemical carcinogens may contribute significantly to the causation of a sizable fraction, perhaps a majority, of human cancers. Human carcinogens act through a variety of genotoxic and non-genotoxic mechanisms. Genotoxic carcinogens can attack biological macromolecules such as DNA and RNA either directly or indirectly through metabolism, resulting in the formation of adducts with these macromolecules. If DNA adducts escape cellular repair mechanisms and persist, they may lead to miscoding, resulting in permanent mutations. Mutations cause an undefined number of cell changes, translated into aberrant protein expression and in changes in cell cycle control.
Class
Human Diseases; Cancer: overview
Pathway map
map05204  Chemical carcinogenesis - DNA adducts
map05204

Reference
  Authors
Luch A.
  Title
Nature and nurture - lessons from chemical carcinogenesis.
  Journal
Nat Rev Cancer 5:113-25 (2005)
DOI:10.1038/nrc1546
Reference
  Authors
Hecht SS
  Title
Tobacco carcinogens, their biomarkers and tobacco-induced cancer.
  Journal
Nat Rev Cancer 3:733-44 (2003)
DOI:10.1038/nrc1190
Reference
  Authors
Oliveira PA, Colaco A, Chaves R, Guedes-Pinto H, De-La-Cruz P LF, Lopes C
  Title
Chemical carcinogenesis.
  Journal
An Acad Bras Cienc 79:593-616 (2007)
DOI:10.1590/S0001-37652007000400004
Reference
  Authors
Wogan GN, Hecht SS, Felton JS, Conney AH, Loeb LA.
  Title
Environmental and chemical carcinogenesis.
  Journal
Semin Cancer Biol 14:473-86 (2004)
DOI:10.1016/j.semcancer.2004.06.010
Reference
  Authors
Hang B
  Title
Formation and repair of tobacco carcinogen-derived bulky DNA adducts.
  Journal
J Nucleic Acids 2010:709521 (2010)
DOI:10.4061/2010/709521
Reference
  Authors
Tsuneoka Y, Dalton TP, Miller ML, Clay CD, Shertzer HG, Talaska G, Medvedovic M, Nebert DW
  Title
4-aminobiphenyl-induced liver and urinary bladder DNA adduct formation in Cyp1a2(-/-) and Cyp1a2(+/+) mice.
  Journal
J Natl Cancer Inst 95:1227-37 (2003)
DOI:10.1093/jnci/djg025
Reference
  Authors
Kawanishi S, Hiraku Y, Murata M, Oikawa S
  Title
The role of metals in site-specific DNA damage with reference to carcinogenesis.
  Journal
Free Radic Biol Med 32:822-32 (2002)
DOI:10.1016/S0891-5849(02)00779-7
Reference
  Authors
Patterson AD, Gonzalez FJ, Idle JR
  Title
Xenobiotic metabolism: a view through the metabolometer.
  Journal
Chem Res Toxicol 23:851-60 (2010)
DOI:10.1021/tx100020p
Reference
PMID:9202760
  Authors
Turesky RJ, Box RM, Markovic J, Gremaud E, Snyderwine EG
  Title
Formation and persistence of DNA adducts of 2-amino-3-methylimidazo[4,5-f]quinoline in the rat and nonhuman primates.
  Journal
Mutat Res 376:235-41 (1997)
DOI:10.1016/S0027-5107(97)00048-1
Reference
  Authors
Immonen E, Kummu M, Petsalo A, Pihlaja T, Mathiesen L, Nielsen JK, Knudsen LE, Vahakangas K, Myllynen P
  Title
Toxicokinetics of the food-toxin IQ in human placental perfusion is not affected by ABCG2 or xenobiotic metabolism.
  Journal
Placenta 31:641-8 (2010)
DOI:10.1016/j.placenta.2010.05.002
Reference
PMID:8702479
  Authors
Solomon MS, Morgenthaler PM, Turesky RJ, Essigmann JM
  Title
Mutational and DNA binding specificity of the carcinogen 2-amino-3, 8-dimethylimidazo[4,5-f]quinoxaline.
  Journal
J Biol Chem 271:18368-74 (1996)
DOI:10.1074/jbc.271.31.18368
Reference
  Authors
Nauwelaers G, Bessette EE, Gu D, Tang Y, Rageul J, Fessard V, Yuan JM, Yu MC, Langouet S, Turesky RJ
  Title
DNA adduct formation of 4-aminobiphenyl and heterocyclic aromatic amines in human hepatocytes.
  Journal
Chem Res Toxicol 24:913-25 (2011)
DOI:10.1021/tx200091y
Reference
  Authors
  Title
The Health Consequences of Involuntary Exposure to Tobacco Smoke: A Report of the Surgeon General.
  Journal
The Health Consequences of Involuntary Exposure to Tobacco Smoke: A Report of the  (2006)
Reference
  Authors
Singh R, Sram RJ, Binkova B, Kalina I, Popov TA, Georgieva T, Garte S, Taioli E, Farmer PB
  Title
The relationship between biomarkers of oxidative DNA damage, polycyclic aromatic hydrocarbon DNA adducts, antioxidant status and genetic susceptibility following exposure to environmental air pollution in humans.
  Journal
Mutat Res 620:83-92 (2007)
DOI:10.1016/j.mrfmmm.2007.02.025
Reference
  Authors
Lodovici M, Luceri C, Guglielmi F, Bacci C, Akpan V, Fonnesu ML, Boddi V, Dolara P.
  Title
Benzo(a)pyrene diolepoxide (BPDE)-DNA adduct levels in leukocytes of smokers in relation to polymorphism of CYP1A1, GSTM1, GSTP1, GSTT1, and mEH.
  Journal
Cancer Epidemiol Biomarkers Prev 13:1342-8 (2004)
Reference
  Authors
Androutsopoulos VP, Tsatsakis AM, Spandidos DA
  Title
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.
  Journal
BMC Cancer 9:187 (2009)
DOI:10.1186/1471-2407-9-187
Reference
  Authors
Gonzalez FJ, Kimura S
  Title
Understanding the role of xenobiotic-metabolism in chemical carcinogenesis using gene knockout mice.
  Journal
Mutat Res 477:79-87 (2001)
DOI:10.1016/S0027-5107(01)00109-9
Reference
  Authors
Banoglu E
  Title
Current status of the cytosolic sulfotransferases in the metabolic activation of promutagens and procarcinogens.
  Journal
Curr Drug Metab 1:1-30 (2000)
DOI:10.2174/1389200003339234
Reference
  Authors
Lehner AF, Horn J, Flesher JW
  Title
Mass spectrometric analysis of 7-sulfoxymethyl-12-methylbenz[a]anthracene and related electrophilic polycyclic aromatic hydrocarbon metabolites.
  Journal
J Mass Spectrom 39:1366-78 (2004)
DOI:10.1002/jms.730
Reference
  Authors
Stiborova M, Martinek V, Semanska M, Hodek P, Dracinsky M, Cvacka J, Schmeiser HH, Frei E
  Title
Oxidation of the carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxy-naphthalene (Sudan I) by cytochromes P450 and peroxidases: a comparative study.
  Journal
Interdiscip Toxicol 2:195-200 (2009)
DOI:10.2478/v10102-009-0017-z
Reference
  Authors
Maanen MJ, Smeets CJ, Beijnen JH
  Title
Chemistry, pharmacology and pharmacokinetics of N,N',N" -triethylenethiophosphoramide (ThioTEPA).
  Journal
Cancer Treat Rev 26:257-68 (2000)
DOI:10.1053/ctrv.2000.0170
Reference
  Authors
Hoes I, Van Dongen W, Lemiere F, Esmans EL, Van Bockstaele D, Berneman ZN
  Title
Comparison between capillary and nano liquid chromatography-electrospray mass spectrometry for the analysis of minor DNA-melphalan adducts.
  Journal
J Chromatogr B Biomed Sci Appl 748:197-212 (2000)
DOI:10.1016/S0378-4347(00)00400-X
Reference
  Authors
Lee JC, Son YO, Pratheeshkumar P, Shi X
  Title
Oxidative stress and metal carcinogenesis.
  Journal
Free Radic Biol Med 53:742-57 (2012)
DOI:10.1016/j.freeradbiomed.2012.06.002
Reference
  Authors
Wild CP, Turner PC
  Title
The toxicology of aflatoxins as a basis for public health decisions.
  Journal
Mutagenesis 17:471-81 (2002)
DOI:10.1093/mutage/17.6.471
Reference
PMID:9275165
  Authors
Kobertz WR, Wang D, Wogan GN, Essigmann JM
  Title
An intercalation inhibitor altering the target selectivity of DNA damaging agents: synthesis of site-specific aflatoxin B1 adducts in a p53 mutational hotspot.
  Journal
Proc Natl Acad Sci U S A 94:9579-84 (1997)
DOI:10.1073/pnas.94.18.9579
Reference
PMID:8759017
  Authors
Bailey EA, Iyer RS, Harris TM, Essigmann JM
  Title
A viral genome containing an unstable aflatoxin B1-N7-guanine DNA adduct situated at a unique site.
  Journal
Nucleic Acids Res 24:2821-8 (1996)
DOI:10.1093/nar/24.14.2821
Reference
  Authors
Chiang HC, Wang CY, Lee HL, Tsou TC
  Title
Metabolic effects of CYP2A6 and CYP2A13 on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced gene mutation--a mammalian cell-based mutagenesis approach.
  Journal
Toxicol Appl Pharmacol 253:145-52 (2011)
DOI:10.1016/j.taap.2011.03.022
Reference
  Authors
Bhat SH, Gelhaus SL, Mesaros C, Vachani A, Blair IA
  Title
A new liquid chromatography/mass spectrometry method for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in urine.
  Journal
Rapid Commun Mass Spectrom 25:115-21 (2011)
DOI:10.1002/rcm.4824
Reference
  Authors
Maertens LA, Upadhyaya P, Hecht SS, Zimmerman CL
  Title
Formation and distribution of NNK metabolites in an isolated perfused rat lung.
  Journal
Drug Metab Dispos 38:752-60 (2010)
DOI:10.1124/dmd.109.031492
Reference
PMID:8951235
  Authors
Lee VM, Keefer LK, Archer MC
  Title
An evaluation of the roles of metabolic denitrosation and alpha-hydroxylation in the hepatotoxicity of N-Nitrosodimethylamine.
  Journal
Chem Res Toxicol 9:1319-24 (1996)
DOI:10.1021/tx960077u
Reference
  Authors
Swenberg JA, Lu K, Moeller BC, Gao L, Upton PB, Nakamura J, Starr TB
  Title
Endogenous versus exogenous DNA adducts: their role in carcinogenesis, epidemiology, and risk assessment.
  Journal
Toxicol Sci 120 Suppl 1:S130-45 (2011)
DOI:10.1093/toxsci/kfq371
Reference
  Authors
Yang Y, Nair J, Barbin A, Bartsch H
  Title
Immunohistochemical detection of 1,N(6)-ethenodeoxyadenosine, a promutagenic DNA adduct, in liver of rats exposed to vinyl chloride or an iron overload.
  Journal
Carcinogenesis 21:777-81 (2000)
DOI:10.1093/carcin/21.4.777
Reference
  Authors
Bartsch H, Nair J
  Title
Oxidative stress and lipid peroxidation-derived DNA-lesions in inflammation driven carcinogenesis.
  Journal
Cancer Detect Prev 28:385-91 (2004)
DOI:10.1016/j.cdp.2004.07.004
Reference
  Authors
Kehe K, Szinicz L
  Title
Medical aspects of sulphur mustard poisoning.
  Journal
Toxicology 214:198-209 (2005)
DOI:10.1016/j.tox.2005.06.014
Reference
  Authors
Matijasevic Z, Volkert MR
  Title
Base excision repair sensitizes cells to sulfur mustard and chloroethyl ethyl sulfide.
  Journal
DNA Repair (Amst) 6:733-41 (2007)
DOI:10.1016/j.dnarep.2006.12.014
Related
pathway
map00980  Metabolism of xenobiotics by cytochrome P450
map05210  Colorectal cancer
map05211  Renal cell carcinoma
map05215  Prostate cancer
map05219  Bladder cancer
map05221  Acute myeloid leukemia
map05222  Small cell lung cancer
map05223  Non-small cell lung cancer
map05224  Breast cancer
map05225  Hepatocellular carcinoma
map05226  Gastric cancer
KO pathway
ko05204   

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