Warshawsky D, Kerns E, Bissell M J, Calvin M
Biochem J. 1977 Jun 15;164(3):481-6. doi: 10.1042/bj1640481.
A common impurity of 7,12-dimethylbenz[alpha]anthracene was more effective than 7,12-dimethylbenz[alpha]anthracene in inducing morphological alterations, and in causing an increase in glucose uptake, DNA synthesis and cell number in chick-embryo fibroblasts. Gradual morphological transformation follows the increase in DNA synthesis after 2 days when either primary or secondary cultures are treated with 3 microgram of the compound/ml. The compound, isolated from 7,12-dimethylbenz[alpha]anthracene by alumina column chromatography, was characterized by t.l.c., mass spectroscopy, carbon-hydrogen analysis, u.v. and nuclear-magnetic-resonance spectroscopy and thermal decomposition. It was the photo-oxidation product of 7,12-dimethylbenz[alpha]anthracene, 7,12-epidioxy-7,12-dimethylbenz[alpha]anthracene. It is suggested that some of the biological effects observed after treatment of cultures with 7,12-dimethylbenz[alpha]anthracene may be due in part to the presence of the photo-oxidation product.
7,12-二甲基苯并[a]蒽的一种常见杂质在诱导形态学改变以及使鸡胚成纤维细胞的葡萄糖摄取、DNA合成和细胞数量增加方面比7,12-二甲基苯并[a]蒽更有效。当原代或传代培养物用3微克该化合物/毫升处理时,2天后DNA合成增加,随后逐渐发生形态学转变。通过氧化铝柱色谱从7,12-二甲基苯并[a]蒽中分离出的该化合物,通过薄层层析、质谱分析、碳氢分析、紫外光谱和核磁共振光谱以及热分解进行了表征。它是7,12-二甲基苯并[a]蒽的光氧化产物,7,12-环氧-7,12-二甲基苯并[a]蒽。有人提出,用7,12-二甲基苯并[a]蒽处理培养物后观察到的一些生物学效应可能部分归因于光氧化产物的存在。