Sawicki JT, Moschel RC, & Dipple A (1983) Involvement of both syn and antidihydrodiol-epoxides in the binding of 7,12-dimethylbenz [a]anthracene to DNA in mouse embryo cell cultures.
Rojas M, Alexandrov K, Auburtin G, Wastiaux-Denamur A, Mayer L, Mahieu B, Sebastien P, & Bartsch H (1995) Anti-benzo(a)pyrene diolepoxide-DNA adduct levels in pheripheral mononuclear cells from coke oven workers and the enhancing effect of smoking.
Amin S, Desai D, & Hecht SS (1993) Tumor-initiating activity on mouse skin of bay region diol-epoxides of 5,6-dimethylchrysene and benzo(c)phenanthrene.
93-147) (in German) Backer JM & Weinstein IB (1980) Mitochondrial DNA is a major cellular target for a dihydrodiol-epoxide derivative of benzo [a]pyrene.
Agarwal SK, Sayer JM, Yeh HJC, Pannell LK, Hilton BD, Pigott MA, Dipple A, Yagi H, & Jerina DM (1987) Chemical characterization of DNA adducts derived from the configurationally isomeric benzo [c]phenanthrene-3,4-diol 1,2-epoxides.
Buening MK, Levin W, Karle JM, Yagi H, Jerina DM, & Conney AH (1979) Tumorigenicity of bay-region epoxides and other derivatives of chrysene and phenanthrene in newborn mice.
8.3.5 DNA adducts DNA adducts with reactive metabolites (mainly diol epoxides) of benzo [a]pyrene and other PAH have been identified in numerous studies (see Section 6).
The mechanisms of immunosuppressive action that have been proposed include formation of active metabolites (including diol epoxides), alterations in cytokine levels, disruption of membrane fluidity, interaction with the Ah receptor, and alterations in calcium ion flux.
In a study of the binding of 3H-labelled anti-5- and anti-6-methylchrysene-1,2-diol-3,4-epoxide to DNA in liver and lung of newborn mice after intraperitoneal administration on day 1 of life and sacrifice after 24 h, 1.1 pmol/mg DNA were found with the benzo [a]pyrene analogue, 0.5 pmol/mg DNA with the 5-methyl compound, and < 0.01 pmol/mg DNA with the 6-methyl compound, consistent with their known tumorigenic activities.
Carmichael PL, Platt KL, Ni She M, Lecoq S, Oesch F, Phillips DH, & Grover PL (1993) Evidence for the involvement of a bis-diol-epoxide in the metabolic activation of dibenz [a,h]anthracene to DNA-binding species in mouse skin.
A methyl group in the same bay region as the epoxide ring leads to exceptional activity, and this may occur a consequence of DNA adduct conformation (Amin et al., 1991b).
The tumorigenicity of racemic anti-1,2-diol-3,4-epoxides of chrysene, 5-methyl-, 5-ethyl-, and 5-propylchrysene was determined in newborn mice.
Cavalieri EL, Rogan EG, Ramakrishna NVS, & Devanesan PD (1993) Mechanisms of benzo(a)pyrene and 7,12-dimethylbenz(a)anthracene activation: Qualitative aspects of the stable and depurination DNA adducts obtained from radical cations and diol epoxides.
5-Methylchrysene 1,2-diol and the 1,2-diol-3,4-epoxide are major proximate and ultimate carcinogens; the corresponding 6-methylchrysene-1,2-diol is also a major metabolite but is much less tumorigenic, perhaps because of the different activity of the corresponding 3,4-epoxides.
Chang RL, Levin W, Wood AW, Lehr RE, Kumar S, Yagi H, Jerina DM, & Conney AH (1981) Tumorigenicity of the diastereomeric bay-region benzo(e)pyrene 9,10-diol-11,12-epoxides in newborn mice.