CHLOROACETALDEHYDE-TREATED RIBOPOLYNUCLEOTIDE AND DEOXYRIBOPOLYNUCLEOTIDE .1. REACTION-PRODUCTS
CHLOROACETALDEHYDE-TREATED RIBOPOLYNUCLEOTIDE AND DEOXYRIBOPOLYNUCLEOTIDE .1. REACTION-PRODUCTS
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DOI：
10.1021/bi00265a050
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发表时间：
1982-01-01
期刊：
影响因子：
2.9
通讯作者：
SINGER, B
中科院分区：
文献类型：
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作者：
KUSMIEREK, JT;SINGER, B
氯乙烯代谢物氯乙醛（CAA）与核糖和脱氧核糖多核苷酸中的胞嘧啶和腺嘌呤残基的体外反应导致形成相对稳定的水合乙烯基衍生物3，N4-（N4-α-羟基乙烯）胞嘧啶（ε C·H2O）和1，N6-（N6-α-羟基乙烯）腺嘌呤（ε A··H2O）。在生理条件下，水合物缓慢转化为3，N4-乙烯胞嘧啶（ε C）和1，N6-乙烯腺嘌呤（ε A）。pH7.25时ε C·H2O在聚（rC）中的半衰期为4.9小时，50 ℃。在37 ℃下，在聚（rA）中ε A·H2O的溶解度为1.4小时。C.聚合物中的这些脱水速率类似于单体中水合物的脱水速率。在双链聚合物中，A和C残基的反应性被大大抑制。腺嘌呤残基在聚（rA）·聚（rU）中的反应性比单链聚合物中的A低约10倍。在类似的反应条件下，没有检测到poly（rC）·poly（rG）中C残基的反应。在暴露于氯乙烯的细胞中，形成CAA，A和C的环状乙烯基衍生物可能优先出现在核酸的单链区域，水合物形成修饰的主要部分。
The in vitro reaction of the vinyl chloride metabolite chloroacetaldehyde (CAA) with cytosine and adenine residues in ribo- and deoxyribopolynucleotides leads to the formation of the relatively stable hydrated etheno derivatives 3,N4-(N4-.alpha.-hydroxyethene)cytosine (.epsilon.C.cntdot.H2O) and 1,N6-(N6-.alpha.-hydroxyethene)adenine (.epsilon.A.cntdot.H2O). Under physiological conditions the hydrates are slowly converted to 3,N4-ethenocytosine (.epsilon.C) and 1,N6-ethenoadenine (.epsilon.A). The half-life at pH 7.25 of .epsilon.C.cntdot.H2O in poly(rC) is 4.9 h at 50.degree. C and of .epsilon.A.cntdot.H2O in poly(rA) is 1.4 h at 37.degree. C. These dehydration rates in polymers are similar to those for hydrates in monomers. The reactivity of A and C residues is greatly suppressed in double-stranded polymers. Adenine residues are about 10 times less reactive in poly(rA).cntdot.poly(rU) than A in single-stranded polymers. Under similar reaction conditions no reaction of C residues in poly(rC).cntdot.poly(rG) was detected. In vinyl chloride exposed cells, where CAA is formed, the cyclic etheno derivatives of A and C are likely to occur preferentially in single-stranded regions of nucleic acids, with the hydrate forming a major proportion of the modification.