Mutagenic and carcinogenic structural alerts and their mechanisms of action

Abstract Knowing the mutagenic and carcinogenic properties of chemicals is very important for their hazard (and risk) assessment. One of the crucial events that trigger genotoxic and sometimes carcinogenic effects is the forming of adducts between chemical compounds and nucleic acids and histones. This review takes a look at the mechanisms related to specific functional groups (structural alerts or toxicophores) that may trigger genotoxic or epigenetic effects in the cells. We present up-to-date information about defined structural alerts with their mechanisms and the software based on this knowledge (QSAR models and classification schemes).

[1]  D. Snodin Genotoxic Impurities: From Structural Alerts to Qualification , 2010 .

[2]  P. Farmer DNA and protein adducts as markers of genotoxicity. , 2003, Toxicology letters.

[3]  Takuji Tanaka,et al.  Chemical-induced Carcinogenesis , 2013 .

[4]  Zhengyin Yan,et al.  Use of a trapping agent for simultaneous capturing and high-throughput screening of both "soft" and "hard" reactive metabolites. , 2007, Analytical chemistry.

[5]  Neal F. Cariello,et al.  Comparison of the computer programs DEREK and TOPKAT to predict bacterial mutagenicity. Deductive Estimate of Risk from Existing Knowledge. Toxicity Prediction by Komputer Assisted Technology. , 2002, Mutagenesis.

[6]  A. Luch,et al.  Reactive species: a cell damaging rout assisting to chemical carcinogens. , 2008, Cancer letters.

[7]  B. Butterworth,et al.  A classification framework and practical guidance for establishing a mode of action for chemical carcinogens. , 2006, Regulatory toxicology and pharmacology : RTP.

[8]  Paolo Vineis,et al.  Bulky DNA adducts and risk of cancer: a meta-analysis. , 2003, Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.

[9]  M. Esteller,et al.  DNA methylation and cancer. , 2010, Advances in genetics.

[10]  L. Möller,et al.  Oxidative DNA Base Modifications and Polycyclic Aromatic Hydrocarbon DNA Adducts in Squamous Cell Carcinoma of Larynx , 2003, Free radical research.

[11]  Linda S Birnbaum,et al.  Cancer and developmental exposure to endocrine disruptors. , 2002, Environmental health perspectives.

[12]  Arnab Mukherjee,et al.  On the molecular mechanism of drug intercalation into DNA: a simulation study of the intercalation pathway, free energy, and DNA structural changes. , 2008, Journal of the American Chemical Society.

[13]  J. Miller,et al.  Covalent intercalative binding to DNA in relation to the mutagenicity of hydrocarbon epoxides and N-acetoxy-2-acetylaminofluorene. , 1978, Cancer research.

[14]  William Arbuthnot Sir Lane,et al.  The critical active-site amine of the human 8-oxoguanine DNA glycosylase, hOgg1: direct identification, ablation and chemical reconstitution. , 1997, Chemistry & biology.

[15]  R. Fuchs,et al.  The processing of a Benzo(a)pyrene adduct into a frameshift or a base substitution mutation requires a different set of genes in Escherichia coli , 2000, Molecular microbiology.

[16]  S. Amin,et al.  Identification and quantification of DNA adducts in the oral tissues of mice treated with the environmental carcinogen dibenzo[a,l]pyrene by HPLC-MS/MS. , 2011, Chemical research in toxicology.

[17]  B. Ketterer,et al.  The role of glutathione in detoxication , 1983, Environmental health perspectives.

[18]  M. Pérez-Prior,et al.  Connecting the chemical and biological reactivity of epoxides. , 2012, Chemical research in toxicology.

[19]  Gilles Klopman,et al.  The MultiCASE Program II. Baseline Activity Identification Algorithm (BAIA) , 1998, J. Chem. Inf. Comput. Sci..

[20]  Christoph Helma,et al.  Lazy structure-activity relationships (lazar) for the prediction of rodent carcinogenicity and Salmonella mutagenicity , 2006, Molecular Diversity.

[21]  A. Luch,et al.  Exposure to polycyclic aromatic hydrocarbons: bulky DNA adducts and cellular responses. , 2012, Experientia supplementum.

[22]  C. Tohyama,et al.  Apoptosis in rat renal proximal tubular cells induced by cadmium. , 1998, Journal of toxicology and environmental health. Part A.

[23]  A. Izzotti,et al.  Environmental carcinogens and mutational pathways in atherosclerosis. , 2015, International journal of hygiene and environmental health.

[24]  Maykel Pérez González,et al.  QSAR modeling of the rodent carcinogenicity of nitrocompounds. , 2008, Bioorganic & medicinal chemistry.

[25]  M T D Cronin,et al.  A review of the electrophilic reaction chemistry involved in covalent DNA binding , 2010, Critical reviews in toxicology.

[26]  G. Almouzni,et al.  Histone metabolic pathways and chromatin assembly factors as proliferation markers. , 2005, Cancer letters.

[27]  Fuart Gatnik Mojca,et al.  Review of QSAR Models and Software Tools for Predicting of Genotoxicity and Carcinogenicity , 2010 .

[28]  J. Schwöbel,et al.  Measurement and estimation of electrophilic reactivity for predictive toxicology. , 2011, Chemical reviews.

[29]  J. Kazius,et al.  Derivation and validation of toxicophores for mutagenicity prediction. , 2005, Journal of medicinal chemistry.

[30]  K. Kolaja,et al.  The role of oxidative stress in chemical carcinogenesis. , 1998, Environmental health perspectives.

[31]  T. Schultz,et al.  Verification of the structural alerts for Michael acceptors. , 2007, Chemical research in toxicology.

[32]  Judith C. Madden,et al.  Assessment of Methods To Define the Applicability Domain of Structural Alert Models , 2011, J. Chem. Inf. Model..

[33]  E C Miller,et al.  Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules , 1981, Cancer.

[34]  Shaoyu Zhou,et al.  Oxidative stress and oxidative damage in chemical carcinogenesis. , 2011, Toxicology and applied pharmacology.

[35]  Aixia Yan,et al.  Carcinogenicity prediction of noncongeneric chemicals by a support vector machine. , 2013, Chemical research in toxicology.

[36]  Romualdo Benigni,et al.  Structure alerts for carcinogenicity, and the Salmonella assay system: a novel insight through the chemical relational databases technology. , 2008, Mutation research.

[37]  H. Allgayer,et al.  Modulation of Base Hydroxylation by Bile Acids and Salicylates in a Model of Human Colonic Mucosal DNA (Putative Implications in Colonic Cancer) , 1999, Digestive Diseases and Sciences.

[38]  Lutz Müller,et al.  Photochemical genotoxicity: principles and test methods. Report of a GUM task force. , 2004, Mutation research.

[39]  P. Darbre Environmental oestrogens, cosmetics and breast cancer. , 2006, Best practice & research. Clinical endocrinology & metabolism.

[40]  B. Epe DNA damage spectra induced by photosensitization , 2012, Photochemical & Photobiological Sciences.

[41]  J. McLachlan,et al.  Epigenetics, evolution, endocrine disruption, health, and disease. , 2006, Endocrinology.

[42]  Manel Esteller,et al.  The role of histone deacetylases (HDACs) in human cancer , 2007, Molecular oncology.

[43]  R C Garner,et al.  The role of DNA adducts in chemical carcinogenesis. , 1998, Mutation research.

[44]  B. Lee,et al.  Toxicological Characteristics of Endocrine-Disrupting Chemicals: Developmental Toxicity, Carcinogenicity, and Mutagenicity , 2004, Journal of toxicology and environmental health. Part B, Critical reviews.

[45]  H. Ellinger-Ziegelbauer,et al.  Comparison of the expression profiles induced by genotoxic and nongenotoxic carcinogens in rat liver. , 2005, Mutation research.

[46]  J. Swenberg,et al.  DNA adducts: biological markers of exposure and potential applications to risk assessment. , 1996, Mutation research.

[47]  Romualdo Benigni,et al.  Structural Alerts of Mutagens and Carcinogens , 2006 .

[48]  Mark T D Cronin,et al.  The Use of a Chemistry-based Profiler for Covalent DNA Binding in the Development of Chemical Categories for Read-across for Genotoxicity , 2011, Alternatives to laboratory animals : ATLA.

[49]  M. Ehrlich,et al.  DNA methylation in cancer: too much, but also too little , 2002, Oncogene.

[50]  Kap-Hoon Han,et al.  The nsdD gene encodes a putative GATA‐type transcription factor necessary for sexual development of Aspergillus nidulans , 2001, Molecular microbiology.

[51]  Ian Johnson,et al.  Approaches to the assessment of toxicity data with endpoints related to endocrine disruption , 2002, Journal of applied toxicology : JAT.

[52]  J. Essigmann,et al.  Biological properties of single chemical-DNA adducts: a twenty year perspective. , 2008, Chemical research in toxicology.

[53]  M T D Cronin,et al.  Development of new structural alerts suitable for chemical category formation for assigning covalent and non-covalent mechanisms relevant to DNA binding. , 2012, Mutation research.

[54]  Horst Spielmann,et al.  In Vitro Phototoxicity Testing , 1994 .

[55]  Lapenna Silvia,et al.  A Framework for assessing in silico Toxicity Predictions: Case Studies with selected Pesticides , 2011 .

[56]  Romualdo Benigni,et al.  The Benigni / Bossa rulebase for mutagenicity and carcinogenicity - a module of Toxtree , 2008 .

[57]  K. Gates,et al.  Sequence specificity of DNA alkylation by the antitumor natural product leinamycin. , 2003, Chemical research in toxicology.

[58]  T. Ferrari,et al.  An open source multistep model to predict mutagenicity from statistical analysis and relevant structural alerts , 2010, Chemistry Central journal.

[59]  Yu Shyr,et al.  Cytosolic and nuclear protein targets of thiol-reactive electrophiles. , 2006, Chemical research in toxicology.

[60]  Jure Zupan,et al.  Evaluation of toxic endpoints for a set of cosmetic ingredients with CAESAR models. , 2015, Chemosphere.

[61]  L. Marnett,et al.  Endogenous DNA adducts: potential and paradox. , 1993, Chemical research in toxicology.

[62]  B. Halliwell,et al.  DNA damage and cancer: measurement and mechanism. , 1995, Cancer letters.

[63]  R. Benigni,et al.  Nongenotoxic carcinogenicity of chemicals: mechanisms of action and early recognition through a new set of structural alerts. , 2013, Chemical reviews.

[64]  I. Rusyn,et al.  Expression of base excision DNA repair genes as a biomarker of oxidative DNA damage. , 2005, Cancer letters.

[65]  Micha Rautenberg,et al.  lazar: a modular predictive toxicology framework , 2013, Front. Pharmacol..

[66]  Z. Hall Cancer , 1906, The Hospital.