Ionization potentials and metabolic activations of carbazole and acridine derivatives.
Ionization potentials and metabolic activations of carbazole and acridine derivatives.
复制标题
咔唑和吖啶衍生物的电离势和代谢活化。
DOI：
10.1021/tx9802623
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发表时间：
1999
影响因子：
4.1
通讯作者：
Warshawsky,D
中科院分区：
文献类型：
--
作者：
Xue,W;Zapien,D;Warshawsky,D
7h -二苯并[c，g]咔唑（DBC）和二苯并[a，j]吖啶（DBA）代表环境氮杂环芳香族（NHA）的基因毒物具有不同的代谢、不同的DNA结合模式和不同的致癌活性。测定了18个咔唑和吖啶衍生物的阳极峰电位（Epa）和最大吸收能（ECT）两个化学氧化相关参数。在文献中已有的咔唑和吖啶的epaandect值和电离电位数据的基础上，通过线性回归分析，首次报道了18个咔唑和吖啶的电离电位值。从epaorect2中确定的两组IP值对大多数化合物是一致的。咔唑类化合物的IP值（范围为7.2 ~ 7.6 eV）低于吖啶类化合物（即7.8 ~ 8.1 eV）。这些数据与咔唑和/或吖啶衍生物的潜在活化一致。对于具有~ 7.3 eV的IP的DBC，单电子氧化和单氧合途径都参与代谢激活。相比之下，高IP （~ 8.0 eV）的DBA仅通过单氧途径被激活。因此，正如已知的致癌多环芳烃一样，IP似乎是预测环境中遗传毒性NHA代谢激活的重要参数。
7H-Dibenzo[c,g]carbazole (DBC) and dibenz[a,j]acridine (DBA) representing environmental nitrogen-heterocyclic aromatic (NHA) genotoxicants undergo differing metabolism and exhibit differing DNA binding patterns and carcinogenic activities. Two chemical oxidation-related parameters, anodic peak potentials (Epa) and maximum absorption energies (ECT) of the charge-transfer complexes, were measured for a series of 18 derivatives of carbazole and acridine. On the basis of theEpaandECTvalues and the ionization potential (IP) data of the parent carbazole and acridine that are available in the literature, with linear regression analyses, IP values of the 18 carbazoles and acridines were reported for the first time. The two sets of IP values determined from eitherEpaorECTagreed with one another for most of the compounds. Carbazoles possessed IP values (ranging from 7.2 to 7.6 eV) that are lower than those of acridines (i.e., 7.8−8.1 eV). These data are consistent with the potential activation of carbazole and/or acridine derivatives. For DBC having an IP of ∼7.3 eV, both one-electron oxidation and monooxygenation pathways are involved in the metabolic activation. In contrast, DBA with a high IP of ∼8.0 eV is activated through the monooxygenation pathway only. Therefore, just as it is known for carcinogenic PAHs, IP appears to be an important parameter in predicting the metabolic activation for genotoxic NHA in the environment.