Abstract
The covalent binding of 3H-styrene oxide to amino acids, and whole human blood was investigated in vitro. After reaction, serum, and red cells were separated, and proteins were digested into amino acids; styrene oxide derivatives were isolated by HPLC. The order of binding to free amino acids was cysteine ≫ histidine > lysine > serine. In serum proteins and hemoglobin cysteine-derivatives predominated. When styrene oxide was reacted with free cysteine and with proteins two isomers were observed. These were likely to present binding through the α and β carbon of styrene oxide, and their abundance was about 2:1.
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Hemminki K (1983) Reactions of methylnitrosourea, epichlorohydrin, styrene oxide and acetoxyacetylaminofluorene with polyamino acids. Carcinogenesis 4: 1–3
Hemminki K, Hesso A (1984) Reaction products of styrene oxide with guanosine in aqueous media. Carcinogenesis 5: 601–607
Neumann H-G (1984) Analysis of hemoglobin as a dose monitor for alkylating and arylating agents. Arch Toxicol 56: 1–6
Pachecka J, Gariboldi P, Cantoni L, Belvedere G, Mussini E, Salmona M (1979) Isolation and structure determination of enzymatically formed styrene oxide glutathione conjugates. Chem-Biol Interact 27: 313–321
Sugiura K, Goto M (1981) Mutagenicities of styrene derivatives on bacterial test systems: relationship between mutagenic potencies and chemical reactivity. Chem-Biol Interact 35: 71–91
World Health Organisation. IPCS. Environmental Health Criteria 26. Styrene, Geneva, 1983
Yagen B, Hernandez O, Bend JR, Cox RH (1981) Synthesis and relative stereochemistry of the four mercapturic acids derived from styrene oxide and N-acetylcysteine. Chem-Biol Interact 34: 57–67
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© 1986 Springer-Verlag
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Hemminki, K. (1986). Binding of Styrene Oxide to Amino Acids, Human Serum Proteins and Hemoglobin. In: Chambers, C.M., Chambers, P.L., Tuomisto, J. (eds) Toxic Interfaces of Neurones, Smoke and Genes. Archives of Toxicology, vol 9. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-71248-7_46
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DOI: https://doi.org/10.1007/978-3-642-71248-7_46
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-16589-7
Online ISBN: 978-3-642-71248-7
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