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 - •
2O H H2O
H Mn M(n+1)+ + HO- + HO•
Fenton reaction

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

8. Products of Hydroxyl Radical Oxidation of Bases2 O d R
5-hydroxy dCyd N H 2 O d R
5,6-dihydroxy-5,6-dihydro
dCyd H N O d R C 3
dThyd glycol

12. LIPID PEROXIDATION RADICAL CHAIN

13. β-CLEAVAGE TO UNSATURATED ALDEHYDESα

14. Formation of Malondialdehyde

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

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

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

18. M1G FROM BASE PROPENAL

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

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

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

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

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