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首页> 外文期刊>Chemical research in toxicology >Identification of adducts formed in reactions of 2-deoxyadenosine and calf thymus DNA with the bacterial mutagen 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone.
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Identification of adducts formed in reactions of 2-deoxyadenosine and calf thymus DNA with the bacterial mutagen 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone.

机译：鉴定2-脱氧腺苷和小牛胸腺DNA与细菌诱变剂3-氯-4-（氯甲基）-5-羟基-2（5H）-呋喃酮形成的加合物。

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摘要

3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF) is a strong direct acting bacterial mutagen found in chlorine-disinfected drinking water. We studied the reaction of CMCF with 2-deoxyadenosine in buffered aqueous solutions and found that three main adducts were formed. The adducts were isolated and purified by C18 column chromatography and HPLC, and characterized on the basis of their UV absorbance, fluorescence emission, (1)H and (13)C NMR spectroscopic, and mass spectrometric features. The adducts were identified as 3-(2-deoxy-beta-D-ribofuranosyl)-7H-8-formyl[2, 1-i]pyrimidopurine (pfA-dR), 3-(2-deoxy-beta-D-ribofuranosyl)-7H-8-carboxy[2,1-i]pyrimidopurine++ + (pcA-dR), and 4-(N(6)-2-deoxyadenosinyl)-3-formyl-2-hydroxy-3-butenoic acid (OH-fbaA-dR). In the reactions performed at pH 7.4 and 37 degrees C, the yields of pfA-dR, pcA-dR, and OH-fbaA-dR were 1.1, 6.7, and 5.5 mol %, respectively. The adduct pfA-dR was detected also in calf thymus DNA reacted with CMCF. The yield was about six adducts per 10(5) bases. To elucidate the mechanisms of formation of the adducts, (13)C-3-labeled CMCF was reacted with 2'-deoxyadenosine. The adducts are structurally related to the adducts previously identified in the reactions of structurally analogous chlorohydroxyfuranones with 2-deoxyadenosine.
机译：3-氯-4-（氯甲基）-5-羟基-2（5H）-呋喃酮（CMCF）是一种在氯消毒的饮用水中发现的强直接作用的细菌诱变剂。我们研究了CMCF与2-脱氧腺苷在缓冲水溶液中的反应，发现形成了三个主要的加合物。通过C18柱色谱和HPLC分离和纯化加合物，并根据它们的UV吸光度，荧光发射，（1）H和（13）C NMR光谱以及质谱特征进行表征。加合物被鉴定为3-（2-脱氧-β-D-呋喃呋喃糖基）-7H-8-甲酰基[2，1-i]嘧啶嘌呤（pfA-dR），3-（2-脱氧-β-D-呋喃呋喃糖基） ）-7H-8-羧基[2,1-i]嘧啶嘌呤++ +（pcA-dR）和4-（N（6）-2-脱氧腺苷）-3-甲酰基-2-羟基-3-丁烯酸（OH -fbaA-dR）。在pH 7.4和37℃下进行的反应中，pfA-dR，pcA-dR和OH-fbaA-dR的产率分别为1.1mol％，6.7mol％和5.5mol％。在与CMCF反应的小牛胸腺DNA中也检测到加合物pfA-dR。每10（5）个碱的收率约为6个加合物。为了阐明加合物的形成机理，使（13）C-3标记的CMCF与2'-脱氧腺苷反应。加合物在结构上与先前在结构类似的氯羟基呋喃酮与2-脱氧腺苷的反应中鉴定的加合物相关。

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