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AFB 1 -dGuo Adduct Opposite dCyd. O. O. P. O. O. O. H. O. H. O. Reactions of AFB 1 -dGuo adduct. O. O. O. O. C. H. 3. H. O. hydrolysis. H. H. O. H. O. O. O. O. depurination. O. O. C. H. 3. formamidopyrimidine (Fapy). H. O. H. H. O. O. O. N. H. N. N.
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O O P O O O H O H O Reactions of AFB1-dGuo adduct O O O O C H 3 H O hydrolysis H H O H O O O O depurination O O C H 3 formamidopyrimidine (Fapy) H O H H O O O N H N N H N N 2 apurinic site
Ring-opened formamido pyrimidine (FAPy) of AFB1 adduct at dGuo N7
ADDUCT OF 2-CHLOROOXIRANE WITH dGuo AND OTHER dNUCLEOSIDES = “etheno”
REACTIVE ALDEHYDES FROM LIPID PEROXIDATION AND TRICYCLIC ADDUCTS
Quinone redox cycling is a source of reactive oxygen species (ROS)
GENERATION OF HYDROXYL RADICAL (HO•) BY SUPEROXIDE DISMUTASE (eq. 1) and the FENTON REACTION (eq. 2) SOD 2O2-/ + 2H+ H2O2 + O2 H2O2 + Mn+ HO + HO- + M(n+1)+ (1) (2)
O O O , H O O O N N H N H O N - H O 2 2 N 2 2 H N 2 N H N H N H O 2 2 2 N H H N N H N H N N 2 H N N C H H N N N 3 2 2 O H O H N N O H H N O H d I z d Z O H O O H O N O N H O O N H H H O N d R d R H N d R O N O H N N H O H N N dThyd glycol 5-hydroxy dCyd 5,6-dihydroxy-5,6-dihydro 2 O N 2 O H N 8 - o x o - d G u o H N H N N dCyd 2 O d G u o H H N H N N N 2 H N C H O r e d u c t i o n N H H N N 2 F a p y G PRODUCTS OF ATTACK OF HYDROXYL RADICAL ON NUCLEOBASES
Formation of base propenal Reaction of base propenal with dAdo to form M1G
Review of PAH adduct structures by NMR spectrometry: Nicholas E. Geacintov, et al., Chem. Res. Toxicol., 1997, 10, 112. UNC has a license for all ACS journals, and anyone with an ONYEN can access this paper from UNC on the ACS web site or through the UNC Libraries web site.