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Deamination via diazotization reaction

Deamination via diazotization reaction. Deamination by bisulfite reaction. Direct acting mutagens. P450 catalytic cycle. “compound I”. “compound 0”. -. •. Hydroxyl radical from action of superoxide dismutase followed by Fenton chemistry. SOD.

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Deamination via diazotization reaction

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  1. Deamination via diazotization reaction

  2. Deamination by bisulfite reaction

  3. Direct acting mutagens

  4. P450 catalytic cycle “compound I” “compound 0”

  5. - • Hydroxyl radical from action of superoxide dismutase followed by Fenton chemistry SOD 2O2 + 2H+ H2O2 + 02 H202 + Mn+ M(n+1)+ + HO- + HO• Fenton reaction

  6. Quinone redox cycling is a source of reactive oxygen species (ROS) N A D H N A D N A D H N A D . O O H O O H O O semiquinone quinone catechol O O 2 2 - - O O H H O O , , 2 2 2 2 2 2 . . H H O O

  7. N H N H 2 2 H O H N N O H O H O N O N H d R d R 5-hydroxy dCyd O C H 3 H N O H O H O N H d R Products of Hydroxyl Radical Oxidation of Bases 5,6-dihydroxy-5,6-dihydro dCyd dThyd glycol

  8. LIPID PEROXIDATION RADICAL CHAIN

  9. β-CLEAVAGE TO UNSATURATED ALDEHYDES α β

  10. Formation of Malondialdehyde

  11. O O O O H C H acrolein 3 malondialdehyde crotonaldehyde (enol form) O H O O N O H O N N N N N N N N N N N d R N H C N N d R 3 d R + 2 1,N -propeno dG O (M1G) N N N H O N N d R 2 1,N -propano dG, two isomers O O O O H 4-hydroxy-2,3-epoxynonanal O H 4-hydroxy-2-nonenal OH O H O O O N N N N N N H O O + N N N N N N N N N d R d R d R 1,N2-etheno dG 4 isomers 4 isomers

  12. dGuo from initial 2,3-epoxy-4-hydroxynonanal adducts

  13. Formation of base propenal Reaction of base propenal with dGuo to form M1G

  14. M1G FROM BASE PROPENAL

  15. Cation radicals from 1-electron oxidation of BP and 6-MePB benzo[a]pyrene cation radical 6-methylbenzo[a]pyrene cation radical

  16. Adducts of the cation radicals of BP and 7,12-DMBA with dAdo and dGuo

  17. Pathway for formation of adducts of dGuo from the cation radical of DMBA

  18. Pathway to adducts of dAdo from 1-electron oxidation of dibenzo[a,l]pyrene

  19. H1´ abstraction from deoxyribose “ene-diyne” class of antineoplastic drugs From: Chem. Rev.1998, 98, 1089-1107

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