van Houte L P, Retèl J, Westra J G, van Grondelle R
Free University, Department of Biophysics, The Netherlands.
Carcinogenesis. 1990 Apr;11(4):701-4. doi: 10.1093/carcin/11.4.701.
The reactive metabolites of the carcinogenic N-acetyl-2-aminofluorene (AAF) form adducts with the guanine base of DNA. The fluorescence emission characteristics of N-(deoxy-guanosin-8-yl)-N-acetyl-2-aminofluorene (dGuo-C8-AAF), N-(deoxyguanosin-8-yl)-2-aminofluorene (dGuo-C8-AF) and the two N7 = C8 imidazole ring-opened products of dGuo-C8-AF (ro-dGuo-C8-AF I + II) were investigated and related to their conformational properties. The dGuo-C8-AF adduct (phi F congruent to 4-5 X 10(-4) shows a broad and structureless emission band, which is attributed to the formation of an excited-state complex. In contrast, the emission spectra of dGuo-C8-AAF (phi F congruent to 1.10(-4] and both ro-dGuo-C8-AF compounds [phi F(ro-dGuo-C8-AF I) congruent to 4.10(-3); phi F(ro-dGuo-C8-AF II) congruent to 4.10(-4)] are narrow. This indicates that dGuo-C8-AAF and ro-dGuo-C8-AF I + II do not decay into an exciplex as occurs in dGuo-C8-AF. The spectroscopic features are discussed in terms of the differences in the dynamic structure of the various compounds.
致癌物质N-乙酰-2-氨基芴(AAF)的反应性代谢产物与DNA的鸟嘌呤碱基形成加合物。研究了N-(脱氧鸟苷-8-基)-N-乙酰-2-氨基芴(dGuo-C8-AAF)、N-(脱氧鸟苷-8-基)-2-氨基芴(dGuo-C8-AF)以及dGuo-C8-AF的两种N7 = C8咪唑环开环产物(ro-dGuo-C8-AF I + II)的荧光发射特性,并将其与它们的构象性质相关联。dGuo-C8-AF加合物(φF约为4 - 5×10⁻⁴)显示出宽且无结构的发射带,这归因于激发态复合物的形成。相比之下,dGuo-C8-AAF(φF约为1.10⁻⁴)以及两种ro-dGuo-C8-AF化合物[φF(ro-dGuo-C8-AF I)约为4.10⁻³;φF(ro-dGuo-C8-AF II)约为4.10⁻⁴]的发射光谱较窄。这表明dGuo-C8-AAF和ro-dGuo-C8-AF I + II不会像dGuo-C8-AF那样衰变为激基复合物。根据各种化合物动态结构的差异对光谱特征进行了讨论。