Alkylation of RNA by vinyl chloride metabolites in vitro and in vivo: Formation of 1-N6-etheno-adenosine

Mechanisms of vinyl chloride carcinogenicity/mutagenicity

“…At the same time as the foregoing, Laib & Bolt (1977 provided chromatographic evidence for the presence of the correspondingly modified ribonucleosides in fractions of the enzymic hydrolysate of the liver RNA of rats which had been exposed to a large, single radioactive dose of 14C-vinyl chloride, and they confirmed their results with incubations of rat-liver microsomes, 14C-vinyl chloride and the appropriate polynucleotide, fortified with NADPH. From the time-course experiments, these authors (1978) showed relative persistence of etheno-C compared with etheno-A in rat-liver DNA, suggesting its greater biological significance.…”

Mechanisms of vinyl chloride carcinogenicity/mutagenicity

“…At the same time as the foregoing, Laib & Bolt (1977 provided chromatographic evidence for the presence of the correspondingly modified ribonucleosides in fractions of the enzymic hydrolysate of the liver RNA of rats which had been exposed to a large, single radioactive dose of 14C-vinyl chloride, and they confirmed their results with incubations of rat-liver microsomes, 14C-vinyl chloride and the appropriate polynucleotide, fortified with NADPH. From the time-course experiments, these authors (1978) showed relative persistence of etheno-C compared with etheno-A in rat-liver DNA, suggesting its greater biological significance.…”

Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde

“…structures of isolated adducts are consistent with alkylation by either compound (Green & Hathway, 1975; Watanabe et al, 1976;Jones & Hathway, 1978; Barrio et al, 1972;Laib & Bolt, 1977.…”

Nucleobase adducts bind MR1 and stimulate MR1-restricted T cells

“…These adducts can originate from the reaction of products of oxidative stress and lipid peroxidation with nucleic acids. Etheno-A is formed by the adduction of adenosine with lipid peroxidation products ( 66 ), whereas M 1 Ado is formed by the condensation of adenosine with MDA ( 67 ), another carbonyl generated during lipid peroxidation ( 68 ). Elevated levels of these nucleoside adducts have been detected upon oxidative stress in human and mouse tissues ( 58 – 61 ).…”

Mechanisms of vinyl chloride carcinogenicity/mutagenicity

“…At the same time as the foregoing, Laib & Bolt (1977 provided chromatographic evidence for the presence of the correspondingly modified ribonucleosides in fractions of the enzymic hydrolysate of the liver RNA of rats which had been exposed to a large, single radioactive dose of 14C-vinyl chloride, and they confirmed their results with incubations of rat-liver microsomes, 14C-vinyl chloride and the appropriate polynucleotide, fortified with NADPH. From the time-course experiments, these authors (1978) showed relative persistence of etheno-C compared with etheno-A in rat-liver DNA, suggesting its greater biological significance.…”

Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde

“…structures of isolated adducts are consistent with alkylation by either compound (Green & Hathway, 1975; Watanabe et al, 1976;Jones & Hathway, 1978; Barrio et al, 1972;Laib & Bolt, 1977.…”

Nucleobase adducts bind MR1 and stimulate MR1-restricted T cells

“…These adducts can originate from the reaction of products of oxidative stress and lipid peroxidation with nucleic acids. Etheno-A is formed by the adduction of adenosine with lipid peroxidation products ( 66 ), whereas M 1 Ado is formed by the condensation of adenosine with MDA ( 67 ), another carbonyl generated during lipid peroxidation ( 68 ). Elevated levels of these nucleoside adducts have been detected upon oxidative stress in human and mouse tissues ( 58 – 61 ).…”

Mechanisms of vinyl chloride carcinogenicity/mutagenicity

“…At the same time as the foregoing, Laib & Bolt (1977 provided chromatographic evidence for the presence of the correspondingly modified ribonucleosides in fractions of the enzymic hydrolysate of the liver RNA of rats which had been exposed to a large, single radioactive dose of 14C-vinyl chloride, and they confirmed their results with incubations of rat-liver microsomes, 14C-vinyl chloride and the appropriate polynucleotide, fortified with NADPH. From the time-course experiments, these authors (1978) showed relative persistence of etheno-C compared with etheno-A in rat-liver DNA, suggesting its greater biological significance.…”

Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde

“…structures of isolated adducts are consistent with alkylation by either compound (Green & Hathway, 1975; Watanabe et al, 1976;Jones & Hathway, 1978; Barrio et al, 1972;Laib & Bolt, 1977.…”

Nucleobase adducts bind MR1 and stimulate MR1-restricted T cells

“…These adducts can originate from the reaction of products of oxidative stress and lipid peroxidation with nucleic acids. Etheno-A is formed by the adduction of adenosine with lipid peroxidation products ( 66 ), whereas M 1 Ado is formed by the condensation of adenosine with MDA ( 67 ), another carbonyl generated during lipid peroxidation ( 68 ). Elevated levels of these nucleoside adducts have been detected upon oxidative stress in human and mouse tissues ( 58 – 61 ).…”