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(1977) 1,2-Diol-3,4-epoxide 5,6-Oxide S.

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.

KW - pyrene diol epoxides deoxyribonucleoside adducts synthesis structure determination

(1982) 1,10b-Diol-2,3-epoxide S.

Further evidence that the epoxide is an intermediate was presented by Hinson et al.

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.

9,10-epoxide intramammary 1 × 12.2 µmol control 3% (1994) Table 94.

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.

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1,2-Diol- (1979); Chang 3,4-epoxide et al.


Hydrolysis of Epoxides Reaction Type : Nucleophilic Substitution

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).

An epoxide is a cyclic ether with a three-atom ring

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.

Synthesis of 6-methylchrysene-1,2-diol-3,4-epoxides …

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.

Synthesis of an aromatic hydrocarbon diol epoxide…

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.

Synthesis of Epoxides • halohydrin formation is both ..

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).

Epoxide Hydrolases and their Application in Organic Synthesis

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.

Reactions: Alcohols, Ethers and Epoxides - Quizlet

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.

Covalent Bonding of Bay-Region Diol Epoxides to Nucleic Acids

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.

for which a bay-region diol epoxide is not ..

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.

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