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Reactivity, SCE induction and mutagenicity of benzyl chloride derivatives
Author(s) -
Hemminki K.,
Falck K.,
Linnainmaa K.
Publication year - 1983
Publication title -
journal of applied toxicology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.784
H-Index - 87
eISSN - 1099-1263
pISSN - 0260-437X
DOI - 10.1002/jat.2550030408
Subject(s) - chemistry , bromide , benzyl chloride , chloride , medicinal chemistry , benzyl bromide , reactivity (psychology) , mutagen , organic chemistry , catalysis , carcinogen , medicine , alternative medicine , pathology
Benzyl chloride, benzyl bromide, p ‐methylbenzyl chloride, and p ‐nitrobenzyl chloride were used to study chemical reactivity with 4‐( p ‐nitrobenzyl)‐pyridine (NBP), and with guanosine in vitro , in relation to mutagenic potency in S. typhimurium and sister chromatid exchange (SCE) induction in CHO cells. Benzyl bromide was found to be the most reactive compound, followed by p ‐methylbenzyl chloride, benzyl chloride and p ‐nitrobenzyl chloride. The order of mutagenicity was p ‐nitrobenzyl chloride ≫ benzyl bromide > benzyl chloride ∽ p ‐methylbenzyl chloride. The compounds tested caused base‐pair mutations only. The order of SCE‐inducing ability decreased as follows: benzyl bromide > benzyl chloride ∽ p ‐nitrobenzyl chloride ∽ p ‐methylbenzyl chloride. The particularly high mutagenicity of p ‐nitrobenzyl chloride in bacteria may be due to reactions other than direct aralkylation, or it may react particularly actively with DNA. Among the other compounds, benzyl bromide was the most active aralkylating compound, mutagen and SCE inducer. The results suggested that reaction of N 2 of guanine, as compared with N‐7 of guanine, failed to show any remarkable mutagenicity or SCE induction, since p ‐methylbenzyl chloride, reacting preferentially at N 2 of guanosine, failed to show unexceptional potency.