INTERACTIONS OF VINYL-CHLORIDE WITH RAT-LIVER DNA INVIVO
INTERACTIONS OF VINYL-CHLORIDE WITH RAT-LIVER DNA INVIVO
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DOI：
10.1016/0009-2797(78)90126-6
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发表时间：
1978-01-01
影响因子：
5.1
通讯作者：
HATHWAY, DE
中科院分区：
文献类型：
--
作者：
GREEN, T;HATHWAY, DE
9. β- D-2“-脱氧呋喃核糖基-咪唑并-[2，1-i]嘌呤（“乙烯基-脱氧腺苷”）和1 β-在从小牛胸腺DNA获得的酶水解产物中鉴定出D-2“-脱氧呋喃核糖基-1，2-二氢-2-氧代-咪唑并-[1，2-c]-嘧啶（“乙烯基-脱氧胞苷”），小牛胸腺DNA通过与氯乙醛的化学反应进行修饰，大鼠经口暴露于饮用水中的氯乙烯（250 ppm）约2年后，从大鼠制备的肝脏DNA中鉴定出D-2“-脱氧呋喃核糖基-1，2-二氢-2-氧代-咪唑并-[1，2-c]-嘧啶（“乙烯基-脱氧胞苷”）。氯乙烯衍生的环氧氯乙烷和/或氯乙醛作为双功能烷化剂对脱氧腺苷和脱氧胞苷残基的DNA。本文报道了脱氧核糖核苷和2种乙烯脱氧核糖核苷的液相色谱分离，以及乙烯脱氧腺苷和乙烯脱氧胞苷及其O-双（三甲基硅基）衍生物的质谱。在动物实验中，与乙烯脱氧胞苷相比，乙烯脱氧腺苷的比例较小。咪唑并[2，1-i]嘌呤（乙烯基腺嘌呤）在模型实验中修饰的DNA沉降后的上清液中以及氯乙醛和脱氧腺苷之间反应产生的产物中被鉴定。脱氧腺苷和脱氧胞苷残基的咪唑环化和乙烯基脱氧腺苷残基的脱嘌呤对DNA结构的影响进行了讨论，与氯乙烯致癌性。
9.beta.-D-2''-Deoxyribofuranosyl-imidazo-[2,1-i]purine ("etheno-deoxyadenosine") and 1.beta.-D-2''-deoxyribofuranosyl-1,2-dihydro-2-oxo-imidazo-[1,2-c]-pyrimidine ("etheno-deoxycytidine") are identified in the enzyme hydrolysates obtained from calf-thymus DNA which had been modified by chemical reaction with chloroacetaldehyde and from liver DNA prepared from rats which had been exposed orally to vinyl chloride in their drinking water (250 ppm) for approximately 2 yr. Vinyl chloride-derived chloroethylene oxide and/or chloroacetaldehyde behaves as a bifunction alkylating agent towards deoxyadenosine and deoxycytidine residues of DNA. The separation of deoxyribonucleosides and the 2 etheno-deoxyribosyl-nucleosides by liquid chromatography, and the mass spectra of etheno-deoxyadenosine and etheno-deoxycytidine and of their O-bis-(trimethylsilyl) derivatives are described. In the animal experiment, the resulting proportion of etheno-deoxyadenosine is small compared with that of etheno-deoxycytidine. Imidazo[2,1-i]purine (etheno-denine) is identified in the supernatant after sedimentation of the modified DNA in the model experiment, and in the product resulting from the reaction between chloroacetaldehyde and deoxyadenosine. The effect on the structure of DNA of the imidazo-cyclization of deoxyadenosine and deoxycytidine residues and of the depurination of etheno-deoxyadenosine residues is discussed in relation to vinyl chloride oncogenicity.