Molecular modeling of the major benzo[a]pyrene N2-dG adduct in cases where mutagenesis results are known in double stranded DNA.

[1]  Yanbin Zhang,et al.  Effects of base sequence context on translesion synthesis past a bulky (+)-trans-anti-B[a]P-N2-dG lesion catalyzed by the Y-family polymerase pol kappa. , 2003, Biochemistry.

[2]  Wei Yang.  Damage repair DNA polymerases Y. , 2003, Current opinion in structural biology.

[3]  Yanbin Zhang,et al.  Two-step error-prone bypass of the (+)- and (−)-trans-anti-BPDE-N2-dG adducts by human DNA polymerases η and κ , 2002 .

[4]  E. G. Frank,et al.  Translesion replication of benzo[a]pyrene and benzo[c]phenanthrene diol epoxide adducts of deoxyadenosine and deoxyguanosine by human DNA polymerase iota. , 2002, Nucleic acids research.

[5]  Yanbin Zhang,et al.  Lesion Bypass Activities of Human DNA Polymerase μ* , 2002, The Journal of Biological Chemistry.

[6]  E. Loechler,et al.  Molecular modeling of four stereoisomers of the major B[a]PDE adduct (at N(2)-dG) in five cases where the structure is known from NMR studies: molecular modeling is consistent with NMR results. , 2002, Chemical research in toxicology.

[7]  D. Jerina,et al.  Benzo[a]pyrene diol epoxide-deoxyguanosine adducts are accurately bypassed by yeast DNA polymerase zeta in vitro. , 2002, Mutation research.

[8]  Yanbin Zhang,et al.  trans-Lesion Synthesis Past Bulky Benzo[a]pyrene Diol Epoxide N 2-dG and N 6-dA Lesions Catalyzed by DNA Bypass Polymerases* , 2002, The Journal of Biological Chemistry.

[9]  Samuel H. Wilson,et al.  Local deformations revealed by dynamics simulations of DNA polymerase Beta with DNA mismatches at the primer terminus. , 2002, Journal of molecular biology.

[10]  A. R. Srinivasan,et al.  Accurate representation of B-DNA double helical structure with implicit solvent and counterions. , 2002, Biophysical journal.

[11]  M. Radman,et al.  Specialized DNA Polymerases, Cellular Survival, and the Genesis of Mutations , 2002, Science.

[12]  R. Woodgate,et al.  Structure-based interpretation of missense mutations in Y-family DNA polymerases and their implications for polymerase function and lesion bypass. , 2002, DNA repair.

[13]  A. Grollman,et al.  Translesion synthesis by human DNA polymerase kappa on a DNA template containing a single stereoisomer of dG-(+)- or dG-(-)-anti-N(2)-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene). , 2002, Biochemistry.

[14]  J. Essigmann,et al.  The aflatoxin B1 formamidopyrimidine adduct plays a major role in causing the types of mutations observed in human hepatocellular carcinoma , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[15]  Samuel H. Wilson,et al.  Polymerase beta simulations suggest that Arg258 rotation is a slow step rather than large subdomain motions per se. , 2002, Journal of molecular biology.

[16]  D. Jerina,et al.  Preferential Misincorporation of Purine Nucleotides by Human DNA Polymerase η Opposite Benzo[a]pyrene 7,8-Diol 9,10-Epoxide Deoxyguanosine Adducts* , 2002, The Journal of Biological Chemistry.

[17]  Yanbin Zhang,et al.  Response of human REV1 to different DNA damage: preferential dCMP insertion opposite the lesion. , 2002, Nucleic acids research.

[18]  D. Jerina,et al.  Efficiency and Accuracy of SOS-induced DNA Polymerases Replicating Benzo[a]pyrene-7,8-diol 9,10-Epoxide A and G Adducts* , 2002, The Journal of Biological Chemistry.

[19]  T. Kunkel,et al.  The Y-family of DNA polymerases. , 2001, Molecular cell.

[20]  S. Broyde,et al.  Stereochemical, structural, and thermodynamic origins of stability differences between stereoisomeric benzo[a]pyrene diol epoxide deoxyadenosine adducts in a DNA mutational hot spot sequence. , 2001, Journal of the American Chemical Society.

[21]  S. Broyde,et al.  Evading the proofreading machinery of a replicative DNA polymerase: induction of a mutation by an environmental carcinogen. , 2001, Journal of molecular biology.

[22]  Yanbin Zhang,et al.  Error-prone lesion bypass by human DNA polymerase eta. , 2000, Nucleic acids research.

[23]  E. Cavalieri,et al.  Evidence that error-prone DNA repair converts dibenzo[a,l]pyrene-induced depurinating lesions into mutations: formation, clonal proliferation and regression of initiated cells carrying H-ras oncogene mutations in early preneoplasia. , 2000, Mutation research.

[24]  J. Wagner,et al.  All three SOS‐inducible DNA polymerases (Pol II, Pol IV and Pol V) are involved in induced mutagenesis , 2000, The EMBO journal.

[25]  P. Kollman,et al.  Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models. , 2000, Accounts of chemical research.

[26]  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.

[27]  E. Loechler,et al.  Factors that influence the mutagenic patterns of DNA adducts from chemical carcinogens. , 2000, Mutation research.

[28]  R. Kozack,et al.  Toward an understanding of the role of DNA adduct conformation in defining mutagenic mechanism based on studies of the major adduct (formed at N(2)-dG) of the potent environmental carcinogen, benzo[a]pyrene. , 2000, Mutation research.

[29]  D. Jerina,et al.  Characterization of the mutational profile of (+)-7R,8S-dihydroxy-9S, 10R-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene at the hypoxanthine (guanine) phosphoribosyltransferase gene in repair-deficient Chinese hamster V-H1 cells. , 1999, Carcinogenesis.

[30]  S. Broyde,et al.  Origins of conformational differences between cis and trans DNA adducts derived from enantiomeric anti-benzo[a]pyrene diol epoxides. , 1999, Chemical research in toxicology.

[31]  S. Broyde,et al.  Stereochemical origin of opposite orientations in DNA adducts derived from enantiomeric anti-benzo[a]pyrene diol epoxides with different tumorigenic potentials. , 1999, Biochemistry.

[32]  D. Jerina,et al.  The ratio of deoxyadenosine to deoxyguanosine adducts formed by (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene in purified calf thymus DNA and DNA in V-79 cells is independent of dose. , 1999, International journal of oncology.

[33]  N. Geacintov,et al.  The major, N2-dG adduct of (+)-anti-B[a]PDE induces G-->A mutations in a 5'-AGA-3' sequence context. , 1999, Carcinogenesis.

[34]  S. Amin,et al.  Mutagenic potential of stereoisomeric bay region (+)- and (-)-cis-anti-benzo[a]pyrene diol epoxide-N2-2'-deoxyguanosine adducts in Escherichia coli and simian kidney cells. , 1998, Biochemistry.

[35]  D. Jerina,et al.  Sequence context profoundly influences the mutagenic potency of trans-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-purine nucleoside adducts in site-specific mutation studies. , 1998, Biochemistry.

[36]  M. Tang,et al.  Slow repair of bulky DNA adducts along the nontranscribed strand of the human p53 gene may explain the strand bias of transversion mutations in cancers , 1998, Oncogene.

[37]  N. Geacintov,et al.  How stereochemistry affects mutagenesis by N2-deoxyguanosine adducts of 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene: configuration of the adduct bond is more important than those of the hydroxyl groups. , 1997, Biochemistry.

[38]  N. Geacintov,et al.  The major, N2-dG adduct of (+)-anti-B[a]PDE shows a dramatically different mutagenic specificity (predominantly, G --> A) in a 5'-CGT-3' sequence context. , 1997, Biochemistry.

[39]  R. Kozack,et al.  Molecular modeling of the conformational complexity of (+)-anti-B[a]PDE-adducted DNA using simulated annealing. , 1997, Carcinogenesis.

[40]  D. Patel,et al.  NMR solution structures of stereoisometric covalent polycyclic aromatic carcinogen-DNA adduct: principles, patterns, and diversity. , 1997, Chemical research in toxicology.

[41]  S. Spiegel,et al.  Fidelity of translesional synthesis past benzo[a]pyrene diol epoxide-2'-deoxyguanosine DNA adducts: marked effects of host cell, sequence context, and chirality. , 1996, Biochemistry.

[42]  M. Tang,et al.  Preferential Formation of Benzo[a]pyrene Adducts at Lung Cancer Mutational Hotspots in P53 , 1996, Science.

[43]  D. Patel,et al.  Solution conformation of the (-)-cis-anti-benzo[a]pyrenyl-dG adduct opposite dC in a DNA duplex: intercalation of the covalently attached BP ring into the helix with base displacement of the modified deoxyguanosine into the major groove. , 1996, Biochemistry.

[44]  E. Cavalieri,et al.  Expanded analysis of benzo[a]pyrene-DNA adducts formed in vitro and in mouse skin: their significance in tumor initiation. , 1996, Chemical research in toxicology.

[45]  D. Patel,et al.  Structural alignments of (+)- and (-)-trans-anti-benzo[a]pyrene-dG adducts positioned at a DNA template-primer junction. , 1995, Biochemistry.

[46]  J. Pelling,et al.  Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras mutations in mouse skin papillomas: the role of apurinic sites. , 1995, Proceedings of the National Academy of Sciences of the United States of America.

[47]  N. Geacintov,et al.  The major, N2-Gua adduct of the (+)-anti-benzo[a]pyrene diol epoxide is capable of inducing G-->A and G-->C, in addition to G-->T, mutations. , 1995, Biochemistry.

[48]  E. Loechler.  How are potent bulky carcinogens able to induce such a diverse array of mutations? , 1995, Molecular carcinogenesis.

[49]  D. Jerina,et al.  Multiple fluorescence lifetimes for oligonucleotides containing single, site-specific modifications at guanine and adenine corresponding to trans addition of exocyclic amino groups to (+)-(7R,8S,9S,10R)- and (+)-(7S,8R,9R,10S) -7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. , 1995, Chemical Research in Toxicology.

[50]  T. Krugh,et al.  Structural characterization of a (+)-trans-anti-benzo[a]pyrene-DNA adduct using NMR, restrained energy minimization, and molecular dynamics. , 1995, Biochemistry.

[51]  R. Lloyd,et al.  In vivo and in Vitro Replication Consequences of Stereoisomeric Benzo[a]pyrene-7,8-dihydrodiol 9,10-Epoxide Adducts on Adenine N6 at the Second Position of N-ras Codon 61 (*) , 1995, The Journal of Biological Chemistry.

[52]  N. Geacintov,et al.  Flanking base effects on the structural conformation of the (+)-trans-anti-benzo[a]pyrene diolepoxide adduct to N2-dG in sequence-defined oligonucleotides. , 1994, Carcinogenesis.

[53]  D. Patel,et al.  Solution conformation of the (-)-trans-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: intercalation of the covalently attached benzo[a]pyrene into the helix with base displacement of the modified deoxyguanosine into the minor groove. , 1994, Biochemistry.

[54]  S. Y. Zhang,et al.  Murine squamous cell carcinoma cell lines produced by a complete carcinogenesis protocol with benzo[a]pyrene exhibit characteristic p53 mutations and the absence of H-ras and cyl 1/cyclin D1 abnormalities. , 1994, Carcinogenesis.

[55]  D. Jerina,et al.  Mutagenic selectivity at the HPRT locus in V-79 cells: comparison of mutations caused by bay-region benzo[a]pyrene 7,8-diol-9,-10-epoxide enantiomers with high and low carcinogenic activity. , 1994, Carcinogenesis.

[56]  B. Hingerty,et al.  Molecular Dynamics Simulation of a Tumorigenic Benzo[a]pyrene Metabolite Bound to DNA at a Single Strand‐Double Strand Junction a , 1994, Annals of the New York Academy of Sciences.

[57]  R. Lloyd,et al.  The replication fate of R- and S-styrene oxide adducts on adenine N6 is dependent on both the chirality of the lesion and the local sequence context. , 1993, The Journal of biological chemistry.

[58]  E. Loechler,et al.  Evidence from in vitro replication that O6-methylguanine can adopt multiple conformations. , 1993, Proceedings of the National Academy of Sciences of the United States of America.

[59]  D. Patel,et al.  Solution conformation of the (+)-cis-anti-[BP]dG adduct in a DNA duplex: intercalation of the covalently attached benzo[a]pyrenyl ring into the helix and displacement of the modified deoxyguanosine. , 1993, Biochemistry.

[60]  E. Loechler,et al.  Mutational specificity of the (+)-anti-diol epoxide of benzo[a]pyrene in a supF gene of an Escherichia coli plasmid: DNA sequence context influences hotspots, mutagenic specificity and the extent of SOS enhancement of mutagenesis. , 1993, Carcinogenesis.

[61]  E. Loechler,et al.  Mutagenesis by the (+)-anti-diol epoxide of benzo[a]pyrene: what controls mutagenic specificity? , 1993, Biochemistry.

[62]  M. Benasutti,et al.  Mutagenesis by (+)-anti-B[a]P-N2-Gua, the major adduct of activated benzo[a]pyrene, when studied in an Escherichia coli plasmid using site-directed methods. , 1992, Carcinogenesis.

[63]  D. Patel,et al.  Influence of benzo[a]pyrene diol epoxide chirality on solution conformations of DNA covalent adducts: the (-)-trans-anti-[BP]G.C adduct structure and comparison with the (+)-trans-anti-[BP]G.C enantiomer. , 1992, Biochemistry.

[64]  D. Patel,et al.  Solution conformation of the major adduct between the carcinogen (+)-anti-benzo[a]pyrene diol epoxide and DNA. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[65]  N. V. Ramakrishna,et al.  Identification and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes in vitro. , 1992, Chemical research in toxicology.

[66]  D. Jerina,et al.  Dose-dependent differences in the profile of mutations induced by an ultimate carcinogen from benzo[a]pyrene. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[67]  U. Singh,et al.  Structures of the (+)- and (-)-trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyre ne adducts to guanine-N2 in a duplex dodecamer. , 1991, Cancer research.

[68]  E. Loechler.  Molecular modeling studies of O2-alkylthymines and O4-alkylthymines in DNA: structures that may be pertinent to the incorporation of the corresponding dAlkTTP into DNA by DNA polymerases in vitro. , 1990, Mutation research.

[69]  B. Glickman,et al.  Induction of specific frameshift and base substitution events by benzo[a]pyrene diol epoxide in excision-repair-deficient Escherichia coli. , 1990, Carcinogenesis.

[70]  B. Brooks,et al.  Molecular mechanics and antibody binding in the structural analysis of polycyclic aromatic hydrocarbon-diol-epoxide--DNA adducts. , 1990, Carcinogenesis.

[71]  J. Essigmann,et al.  Genetic effects of thymine glycol: site-specific mutagenesis and molecular modeling studies. , 1989, Proceedings of the National Academy of Sciences of the United States of America.

[72]  J. M. Roman,et al.  DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide. , 1989, Chemical research in toxicology.

[73]  E. Loechler.  Adduct‐induced base‐shifts: A mechanism by which the adducts of bulky carcinogens might induce mutations , 1989, Biopolymers.

[74]  S. Mohr,et al.  A-DNA accommodates adducts derived from diol epoxides of polycyclic aromatic hydrocarbons bound in a "side-stacking" mode. , 1987, Journal of biomolecular structure & dynamics.

[75]  L. Marnett,et al.  Peroxyl free radicals: potential mediators of tumor initiation and promotion. , 1987, Carcinogenesis.

[76]  J. Mccormick,et al.  Kinds of mutations formed when a shuttle vector containing adducts of (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene replicates in human cells. , 1987, Proceedings of the National Academy of Sciences of the United States of America.

[77]  K. Zakrzewska,et al.  Sequence selectivity, a test of the nature of the covalent adduct formed between benzo[a]pyrene and DNA. , 1987, Journal of biomolecular structure & dynamics.

[78]  D. Phillips,et al.  Aberrant activation of benzo(a)pyrene in cultured rat mammary cells in vitro and following direct application to rat mammary glands in vivo. , 1985, Cancer research.

[79]  J. Dommen,et al.  A Mechanism for the Stereoselectivity and Binding of Benzo[a]pyrene Diol Epoxides to DNA , 1985 .

[80]  E. R. Taylor,et al.  Interactions of molecules with nucleic acids. X. Covalent intercalative binding of the carcinogenic BPDE I(+) to kinked DNA. , 1983, Journal of biomolecular structure & dynamics.

[81]  D. Grunberger,et al.  Molecular Biology of Mutagens and Carcinogens , 1983, Springer US.

[82]  D. Phillips.  Fifty years of benzo(a)pyrene , 1983, Nature.

[83]  A. Conney,et al.  Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. , 1982, Cancer research.

[84]  J. Miller,et al.  Carcinogenic epoxides of benzo[a]pyrene and cyclopenta[cd]pyrene induce base substitutions via specific transversions. , 1982, Proceedings of the National Academy of Sciences of the United States of America.

[85]  N. Dattagupta,et al.  Carcinogen-induced alteration of DNA structure. , 1981, The Journal of biological chemistry.

[86]  F. Kadlubar.  A transversion mutation hypothesis for chemical carcinogenesis by N2-substitution of guanine in DNA. , 1980, Chemico-biological interactions.

[87]  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.

[88]  F. Beland.  Computer-generated graphic models of the N2-substituted deoxyguanosine adducts of 2-acetylaminofluorene and benzo[a]pyrene and the O6-substituted deoxyguanosine adduct of 1-naphthylamine in the DNA double helix. , 1978, Chemico-biological interactions.

[89]  M. Goodman.  Error-prone repair DNA polymerases in prokaryotes and eukaryotes. , 2002, Annual review of biochemistry.

[90]  E. Friedberg.  Why do cells have multiple error‐prone DNA polymerases? , 2001, Environmental and molecular mutagenesis.

[91]  R. Kozack,et al.  A hypothesis for what conformation of the major adduct of (+)-anti-B[a]PDE (N2-dG) causes G-->T versus G-->A mutations based upon a correlation between mutagenesis and molecular modeling results. , 1999, Carcinogenesis.

[92]  R. Kozack,et al.  Molecular modeling of the major adduct of (+)-anti-B[a]PDE (N2-dG) in the eight conformations and the five DNA sequences most relevant to base substitution mutagenesis. , 1999, Carcinogenesis.

[93]  E. Loechler,et al.  Are base substitution and frameshift mutagenesis pathways interrelated? An analysis based upon studies of the frequencies and specificities of mutations induced by the (+)-anti diol epoxide of benzo[a]pyrene. , 1995, Mutation research.

[94]  R. Jankowiak,et al.  Sequence dependence of benzo[a]pyrene diol epoxide-DNA adduct conformer distribution: a study by laser-induced fluorescence/polyacrylamide gel electrophoresis. , 1994, Chemical Research in Toxicology.

[95]  D. Jerina,et al.  Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10-epoxides: structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety , 1991 .

[96]  E. Loechler.  Molecular modeling in mutagenesis and carcinogenesis. , 1991, Methods in enzymology.

[97]  Jia-Ling Yang,et al.  Kinds and location of mutations induced by (±)-7β,8α- dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in the coding region of the hypoxanthine (guanine) phosphoribosyltransferase gene in diploid human fibroblasts , 1991 .

[98]  A. Carothers,et al.  DNA base changes in benzo[a]pyrene diol epoxide-induced dihydrofolate reductase mutants of Chinese hamster ovary cells. , 1990, Carcinogenesis.

[99]  P. Kollman,et al.  Molecular mechanics simulations on covalent complexes between polycyclic carcinogens and B-DNA. , 1989, Carcinogenesis.

[100]  A. Balmain,et al.  Oncogene activation in chemical carcinogenesis. , 1988, Advances in cancer research.

[101]  S. Islam,et al.  Computer modelling studies of the covalent interactions between DNA and the enantiomers of anti-7,8-diol,9,10-epoxy-benzo[a]pyrene. , 1983, Journal of biomolecular structure & dynamics.

[102]  P. Grasso.  Carcinogens in Food , 1983 .