Unraveling the aflatoxin-FAPY conundrum: structural basis for differential replicative processing of isomeric forms of the formamidopyrimidine-type DNA adduct of aflatoxin B1. Brown KL, Deng JZ, Iyer RS, Iyer LG, Voehler MW, Stone MP, Harris CM, Harris TM (2006) J Am Chem Soc 128: 15188-99 Structural perturbations induced by the alpha-anomer of the aflatoxin B(1) formamidopyrimidine adduct in duplex and single-strand DNA. Brown KL, Voehler MW, Magee SM, Harris CM, Harris TM, Stone MP (2009) J Am Chem Soc 131: 16096-107 Bypass of aflatoxin B1 adducts by the Sulfolobus solfataricus DNA polymerase IV. Banerjee S, Brown KL, Egli M, Stone MP (2011) J Am Chem Soc 133: 12556-68 Reaction of aflatoxin B1 exo-8,9-epoxide with DNA: kinetic analysis of covalent binding and DNA-induced hydrolysis. Johnson WW, Guengerich FP (1997) Proc Natl Acad Sci U S A 94: 6121-5 Evidence for cytochrome P-450NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver. Shimada T, Guengerich FP (1989) Proc Natl Acad Sci U S A 86: 462-5 Activation of amino-alpha-carboline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and a copper phthalocyanine cellulose extract of cigarette smoke condensate by cytochrome P-450 enzymes in rat and human liver microsomes. Shimada T, Guengerich FP (1991) Cancer Res 51: 5284-91 Involvement of cytochrome P450, glutathione S-transferase, and epoxide hydrolase in the metabolism of aflatoxin B1 and relevance to risk of human liver cancer. Guengerich FP, Johnson WW, Ueng YF, Yamazaki H, Shimada T (1996) Environ Health Perspect 104 Suppl 3: 557-62 Elucidation of catalytic specificities of human cytochrome P450 and glutathione S-transferase enzymes and relevance to molecular epidemiology. Guengerich FP, Shimada T, Raney KD, Yun CH, Meyer DJ, Ketterer B, Harris TM, Groopman JD, Kadlubar FF (1992) Environ Health Perspect 98: 75-80 Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes. Guengerich FP, Shimada T, Yun CH, Yamazaki H, Raney KD, Thier R, Coles B, Harris TM (1994) Environ Health Perspect 102 Suppl 9: 49-53 Molecular basis of aflatoxin-induced mutagenesis-role of the aflatoxin B1-formamidopyrimidine adduct. Lin YC, Li L, Makarova AV, Burgers PM, Stone MP, Lloyd RS (2014) Carcinogenesis 35: 1461-8 Kinetics of hydrolysis and reaction of aflatoxin B1 exo-8,9-epoxide and relevance to toxicity and detoxication. Guengerich FP, Johnson WW (1999) Drug Metab Rev 31: 141-58 Error-prone replication bypass of the primary aflatoxin B1 DNA adduct, AFB1-N7-Gua. Lin YC, Li L, Makarova AV, Burgers PM, Stone MP, Lloyd RS (2014) J Biol Chem 289: 18497-506 Purification and characterization of human liver microsomal cytochrome P-450 2A6. Yun CH, Shimada T, Guengerich FP (1991) Mol Pharmacol 40: 679-85 Aflatoxin B1 activation in human lung. Kelly JD, Eaton DL, Guengerich FP, Coulombe RA (1997) Toxicol Appl Pharmacol 144: 88-95 Hepatocellular carcinoma in GNMT-/- mice. Wagner C, Luka Z, Mato JM (2009) Toxicol Appl Pharmacol 237: 246; author reply 247 Activation and detoxication of aflatoxin B1. Guengerich FP, Johnson WW, Shimada T, Ueng YF, Yamazaki H, Langouët S (1998) Mutat Res 402: 121-8 Forging the links between metabolism and carcinogenesis. Guengerich FP (2001) Mutat Res 488: 195-209 Aflatoxin B1 8,9-epoxide hydrolysis in the presence of rat and human epoxide hydrolase. Johnson WW, Yamazaki H, Shimada T, Ueng YF, Guengerich FP (1997) Chem Res Toxicol 10: 672-6 Inherent stereospecificity in the reaction of aflatoxin B(1) 8,9-epoxide with deoxyguanosine and efficiency of DNA catalysis. Brown KL, Bren U, Stone MP, Guengerich FP (2009) Chem Res Toxicol 22: 913-7 Protection against aflatoxin B1-induced cytotoxicity by expression of the cloned aflatoxin B1-aldehyde reductases rat AKR7A1 and human AKR7A3. Bodreddigari S, Jones LK, Egner PA, Groopman JD, Sutter CH, Roebuck BD, Guengerich FP, Kensler TW, Sutter TR (2008) Chem Res Toxicol 21: 1134-42 Guanine alkylation by the potent carcinogen aflatoxin B1: quantum chemical calculations. Bren U, Guengerich FP, Mavri J (2007) Chem Res Toxicol 20: 1134-40 DNA Sequence Modulates Geometrical Isomerism of the trans-8,9- Dihydro-8-(2,6-diamino-4-oxo-3,4-dihydropyrimid-5-yl-formamido)- 9-hydroxy Aflatoxin B1 Adduct. Li L, Brown KL, Ma R, Stone MP (2015) Chem Res Toxicol 28: 225-37 Structural refinement of the 8,9-dihydro-8-(N7-guanyl)-9-hydroxy-aflatoxin B(1) adduct in a 5'-Cp(AFB)G-3' sequence. Giri I, Jenkins MD, Schnetz-Boutaud NC, Stone MP (2002) Chem Res Toxicol 15: 638-47 Glutathione conjugation of aflatoxin B1 exo- and endo-epoxides by rat and human glutathione S-transferases. Raney KD, Meyer DJ, Ketterer B, Harris TM, Guengerich FP (1992) Chem Res Toxicol 5: 470-8 Comparison of rates of enzymatic oxidation of aflatoxin B1, aflatoxin G1, and sterigmatocystin and activities of the epoxides in forming guanyl-N7 adducts and inducing different genetic responses. Baertschi SW, Raney KD, Shimada T, Harris TM, Guengerich FP (1989) Chem Res Toxicol 2: 114-2 Reduction of aflatoxin B1 dialdehyde by rat and human aldo-keto reductases. Guengerich FP, Cai H, McMahon M, Hayes JD, Sutter TR, Groopman JD, Deng Z, Harris TM (2001) Chem Res Toxicol 14: 727-37 Structure of the aflatoxin B(1) dialdehyde adduct formed from reaction with methylamine. Guengerich FP, Voehler M, Williams KM, Deng Z, Harris TM (2002) Chem Res Toxicol 15: 793-8 Reaction of aflatoxin B(1) oxidation products with lysine. Guengerich FP, Arneson KO, Williams KM, Deng Z, Harris TM (2002) Chem Res Toxicol 15: 780-92 The endo-8,9-epoxide of aflatoxin B1: a new metabolite. Raney KD, Coles B, Guengerich FP, Harris TM (1992) Chem Res Toxicol 5: 333-5 Oxidation of aflatoxins and sterigmatocystin by human liver microsomes: significance of aflatoxin Q1 as a detoxication product of aflatoxin B1. Raney KD, Shimada T, Kim DH, Groopman JD, Harris TM, Guengerich FP (1992) Chem Res Toxicol 5: 202-10 Oxidation of aflatoxin B1 by bacterial recombinant human cytochrome P450 enzymes. Ueng YF, Shimada T, Yamazaki H, Guengerich FP (1995) Chem Res Toxicol 8: 218-25 Conjugation of highly reactive aflatoxin B1 exo-8,9-epoxide catalyzed by rat and human glutathione transferases: estimation of kinetic parameters. Johnson WW, Ueng YF, Widersten M, Mannervik B, Hayes JD, Sherratt PJ, Ketterer B, Guengerich FP (1997) Biochemistry 36: 3056-60 Mispairing of the 8,9-dihydro-8-(N7-guanyl)-9-hydroxy-aflatoxin B1 adduct with deoxyadenosine results in extrusion of the mismatched dA toward the major groove. Giri I, Johnston DS, Stone MP (2002) Biochemistry 41: 5462-72 Wobble dC.dA pairing 5' to the cationic guanine N7 8,9-dihydro-8-(N7-guanyl)-9-hydroxyaflatoxin B1 adduct: implications for nontargeted AFB1 mutagenesis. Giri I, Stone MP (2003) Biochemistry 42: 7023-34 Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Ueng YF, Kuwabara T, Chun YJ, Guengerich FP (1997) Biochemistry 36: 370-81 Cytochrome P450 oxidations in the generation of reactive electrophiles: epoxidation and related reactions. Guengerich FP (2003) Arch Biochem Biophys 409: 59-71 Principles of covalent binding of reactive metabolites and examples of activation of bis-electrophiles by conjugation. Guengerich FP (2005) Arch Biochem Biophys 433: 369-78 Thermal stabilization of the DNA duplex by adducts of aflatoxin B1. Giri I, Stone MP (2002) Biopolymers 65: 190-201 Reactive intermediates in biological systems: what have we learned and where are we going? Guengerich FP, Cai H, Johnson WW, Parikh A (2001) Adv Exp Med Biol 500: 639-50
Hints: (1) double-click or double-tap to navigate to a node. (2) Grab a node and move it to arrange the graph.