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苯并[e]芘和(±)-反式二苯并[a,l]芘二环氧物-DNA加合物的固体基质荧光猝灭

Solid-matrix fluorescence quenching of benzo[e]pyrene and (+/-)-anti-dibenzo[a, l]pyrene diolepoxide-DNA adducts.

作者信息

Thompson Allison L, Hurtubise Robert J

机构信息

Department of Chemistry, University of Wyoming, Laramie, WY 82971, USA.

出版信息

Appl Spectrosc. 2005 Jan;59(1):126-33. doi: 10.1366/0003702052940602.

DOI:10.1366/0003702052940602
PMID:15720748
Abstract

The solid-matrix fluorescence (SMF) quenching of benzo[e]pyrene and (+/-)-anti-dibenzo[a, l]pyrene-11,12-diol-13,14-epoxide ((+/-)-antiDB[a, l]PDE)-DNA adducts with thallium nitrate (TlNO(3)) and sodium iodide (NaI) was examined and several SMF quenching models were developed. The SMF quenching data for B[e]P with either TlNO(3) or NaI fit a two-independent-binding-site model. However, the SMF quenching of (+/-)-anti-DB[a, l]PDE-DNA adducts with TlNO(3) fits a sphere of action model, but quenching with NaI was modeled with the two-independent-binding-site model. The data were compared with earlier SMF quenching data for 7,8,9,10-tetrahydroxytetrahydro-benzo[a]pyrene (tetrol I-1) and (+/-)-anti-benzo[a]pyrene-trans-7,8-dihydrodiol-9,10-epoxide ((+/-)-anti-BPDE)DNA adducts. The interpretation of the SMF quenching data for the (+/-)-anti-DB[a, l]PDE-DNA adducts was distinctively different than the interpretation of the SMF quenching data for the (+/-)-antiBPDE-DNA adducts. This initial study shows that SMF quenching has the potential to characterize polycyclic aromatic hydrocarbonDNA adducts with different numbers of aromatic rings. In addition, the data indicated that external and intercalated DNA adducts interacted with heavy-atom salts in dissimilar fashions. The new SMF methodology developed is useful for the characterization of both polycyclic aromatic hydrocarbon-DNA adducts and metabolites from polycyclic aromatic hydrocarbons.

摘要

研究了硝酸铊(TlNO₃)和碘化钠(NaI)对苯并[e]芘以及(±)-反式二苯并[a,l]芘-11,12-二醇-13,14-环氧化物((±)-反式DB[a,l]PDE)-DNA加合物的固体基质荧光(SMF)猝灭作用,并建立了几种SMF猝灭模型。苯并[e]芘与TlNO₃或NaI的SMF猝灭数据符合双独立结合位点模型。然而,(±)-反式-DB[a,l]PDE-DNA加合物与TlNO₃的SMF猝灭符合作用球模型,但与NaI的猝灭则用双独立结合位点模型进行模拟。将这些数据与早期关于7,8,9,10-四羟基四氢苯并[a]芘(四醇I-1)和(±)-反式苯并[a]芘-反式-7,8-二氢二醇-9,10-环氧化物((±)-反式BPDE)-DNA加合物的SMF猝灭数据进行了比较。(±)-反式-DB[a,l]PDE-DNA加合物的SMF猝灭数据的解释与(±)-反式BPDE-DNA加合物的SMF猝灭数据的解释明显不同。这项初步研究表明,SMF猝灭有潜力表征具有不同芳环数的多环芳烃-DNA加合物。此外,数据表明外部和插入的DNA加合物与重原子盐以不同方式相互作用。所开发的新SMF方法对于多环芳烃-DNA加合物以及多环芳烃代谢物的表征都很有用。

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