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Explanation of the mechanism of carcinogenesis and syntheses of anticancer agents with high selectivity

Science china {1. 2006年第1期49卷 44-62页

作者： dai qianhuan1,{1., beijing polytechnic university (Now known as beijing Univer-sity of Technology), beijing 100022, china 2. center of Environmental Sciences, Peking university, beijing 1.0871. china 1. center of {1. and bioengineering of cancer research Beijing Polytechnic University Beijing 100022 China 2. center of Environmental Sciences Peking University Beijing 100871 China

In 1.79, the mechanism of chemical carcinogenesis, a challenging anddifficult scientific problem pending for a number of years, was explained by dai {1.. Themechanism named di-region theory predicted that a carcinogen always metabolizes to form a specialbi-functional alky-lating agent. This agent induces cross-linkages between the complementary basepairs in DMA and switches on initial mutageneses in genomes including point and frameshiftmutations. This, in turn, induces further deep mutageneses including the production of variouschimeric chromosomes, deletions and other aberrations found in genomes. In the end this initiatescarcinogenesis of the whole cell through the reverse transcription mechanism after a lengthyincubation period. Recently, this laboratory has verified that physical carcinogenesis, includingthe oncogenesis induced by radiation and asbestos as well as the carcinogenesis induced byendogenous factors such as estrogen or diethyl-stilbestrol switch on carcinogenesis by inducing theformation of cross-linkages between the complementary base pairs in DNA. Di-region theory has nowbeen supported by many experimental observations such as mutational spectra of various *** potential for carcinogenesis, teratogenesis, sterility and mutagenesis lumped together asgenetic toxicity appears to originate almost uniformly from the cross-linking between complementarybases, i.e. malignant cross-linking, which is in accordance with di-region theory. Other forms ofcross-linking between non-complementary bases, benign cross-linkings, show bi-functional alkylationanticancer activity but lack genetic toxicity. The predictable design and synthesis of a highselectivity anticancer agent with high efficacy and low genetic toxicity, a goal long pursued incancer chemotherapy, have been realized for the first time in this laboratory by inhibitingmalignant and heightening benign cross-linking using the principles of di-region theory. A series ofpatented new anticanc

关键词： mechanism of carcinogenesis, di-region theory, minoplatin, selectivity of anticancer agent, cross-linking between DNA bases, anticancer platinum complexes, predictive design of anticancer agent, second generation anticancer agent.

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Experimental verifications on chemical carcinogenesis, a bifunctional alkvlation between DNA interstrands

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Chinese Science Bulletin 2000年第12期45卷 1075-1079页

作者： dai qianhuan, ZHANG Qingrong, WANG Lihui, PEI Shu, WANG Qing &QUBocenter for chemistry and bioengineering of cancer, beijing polytechnic university, beijing 100022, china center for {1. and bioengineering of cancer Beijing Polytechnic University Beijing China

It is evidenced by the filter elution method that two carcinogenic aromatic hydrocarbons, benzo[a]pyrene and dibenzo[a,h]anthracene, two carcinogenic metal salts, beryllium chloride and cadmium chloride, four carcinogenic aromatic amines, 2-aminofluorene, p-naphthylamine, 4-aminobiphenyl and benzidine, can all induce DNA interstrand and DNA-protein cross-link in L1.io culture. However, under the same condition, the corresponding non-carcinogenic compounds, including benzo[k]fluorancene, anthracene, magnesium chloride, zinc chloride, a-naphthylamine, 2-aminobiphenyl and m-toluidine, cannot produce any cross-link adducts. All these results are consistent with the di-region theory that carcinogens are bio-bifunctional alkylation agents. This method can also be used to discriminate carcinogens and non-carcinogens.

关键词： mechanism of chemical carcinogenesis di-region theory DNA interstrand cross-link aromatic amines poiycyclic aromatic hydrocarbons beryllium salt cadmium salt.

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Carcinogenesis switched on by DNA cross-link between complementary bases aroused by aflatoxin and N-nitroso compounds

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Progress in Natural Science:Materials International 2003年第8期 3-9页

作者： dai qianhuan , LU Ping, PENG Shaohua and ZHANG Qingrong (1. center of Environmental Science, Peking university, beijing 100871, china 2. center for chemistry and bioengineering of cancer, beijing polytechnic university, beijing 100022, china)

The di-region theory put forward by dai {1., a molecular mechanism of chemical carcinogenesis, concluded thatthe carcinogenesis induced by most of the environmental carcinogens is switched on by the cross-linking between DNA complementarybases aroused by the bifunctional alkylation of their metabolic intermediates. It was evidenced in this paper with DNA filter elution methodthat one carcinogenic mycotoxin, aflatoxin G1. four carcinogenic N-nitroso compounds, N-nitrosodiethyl-amine, N-nitrosodibutyl-amine,N-nitrosomorpholine and N-nitrosopyrrolidine, one carcinogenic diazo color, 4-dimethylaminodiazobenzene and one carcinogenic nitrogen-containing heterocyclic compound, quinoline, all induced DNA interstrands cross-linking with dosage correlation after metabolic ***, the non-carcinogens in corresponding series for control, aflatoxin B2, N-nitroso-diphenylamine, 4'-bromo-4-dimethylamino-diazobenzene and isoquinoline, cannot induce DNA interstrands cross-linking at all in the same co

关键词： cross-linking between DNA complementary bases di-region theory mycotoxin N-nitroso compounds mechanism of carcinogenesis mutational spectrum.

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AM1.computational study on metabolites of l ,3-butadiene interstrand cross-linking DNA

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Chinese Science Bulletin 2000年第3期45卷 212-214页

作者： ZHOU Zhigang, dai qianhuan & ZHONG Rugang1. center of Environmental Science, Peking university, beijing 100871, china 2. center cancer chemistry and bioengineering, beijing polytechnic university beijing 100022, china

The alkylating reactions of 1.2-epoxy-3,4-butene (EB) and 1.2,3,4-diepoxybutane (DEB)-the important metabolites of rodent carcinogenic 1.3-butadiene, with adenine and cytosine andinteraction with fragment of DNA on major groove-have been computed. Results show thatthere are little differences in activation energy between EB and DEB, so it is difficult to explain the fact that the mutagenicity of DEB is greater (about 1.0-fold) than that of EB by the ability of alkylation. it is also known that DEB can interstrand cross-link with DNA through two times alkylating reactions, whereas EB cannot. So this may contribute to the significant different genotoxicity of the two agents. Meanwhile, DEB can interstrand cross-link with many sequences of DNA in major groove vs. two in minor groove, which increases opportunity of interstrand cross-link with DNA in major groove. This difference may be the reason of base selection of DEB mutation. The deformation of some cross-linked DNA may also contribute to this

关键词： 1 3-butadiene carcinogenesis mutagenesis cross-linking with DNA AMI.

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基于双区理论的N-亚硝基化合物结构致癌活性关系的模式辨认资料

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环境化学 1987年第6期 1-12页

作者：戴乾圜钟儒刚高心明北京工业大学癌化学与生物工程中心

借模式辨认,建立了N-亚硝基化合物(NNC)的结构致癌活性关系(SCAR)的双区理论模型,1.3个NNC的计算结果与实验事实的一致达97.4％。实验事实的模式辨认处理揭示: NNC致癌作用的关键步骤是DNA互补碱对的横向交联,其中亲电中心之一是熟知的... 详细信息

借模式辨认,建立了N-亚硝基化合物(NNC)的结构致癌活性关系(SCAR)的双区理论模型,1.3个NNC的计算结果与实验事实的一致达97.4％。实验事实的模式辨认处理揭示: NNC致癌作用的关键步骤是DNA互补碱对的横向交联,其中亲电中心之一是熟知的α-位,而另一个中心则应是β-位或恰好相当于(?)-位的Υ-位。NNC的SCAR可根据结构与化学活性的关系,做出合理的阐释。本文报导了此模式辨认处理的数学方法、数值结果和数据集。

关键词：双区理论亚硝基化合物模式辨认致癌作用致癌性 NNC 致癌活性

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Carcinogenesis of asbestos switched on by inducing cross-linkage between DNA complementary pair bases

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Chinese Science Bulletin 2002年第13期47卷 1086-1091页

作者： dai {1. CHEN Sha LI Yingxia center of Environmental Science Peking UniversityBeijing 100871China center for {1. and bioengineering of cancer Beijing Polytechnic UniversityBeijing 100022China

Since the beginning of the 1.80s, dai {1. predicted based upon his di-region theory that the carcino-genesis switched on by the so-called physical carcinogenic factors including radiation, asbestos and foreign matter implantation, is just initiated through the cross-linking between DNA complementary pair bases induced by them. In this note, it was evidenced with the DNA filter elution method that the oxygenase activated by asbestos induces the cross-linking between DNA inter-strands and DNA-protein with dosage correlation, in which over 80% of DNA inter-strand cross-link ratio account for the total cross-link ratio. Obviously, both of the cross-linkages are just induced by hydroxyl free radical, HO·, because the ferrous ion increased the cross-link ratios up to several times through Fenton reaction and vitamin C inhibited the cross-link ratios with factors of 8-9 by destroying the hydroxyl radical. Non-carcinogen but with lower free radical formation energy, pyrene, by culturing with asbestos

关键词： asbestos mechanism of carcinogenesis di-region theory hydroxyl free radical DNA interstrand cross-link Fenton reaction AM1 molecular orbital calculation.

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PM3 computation for the DNA complementary base paircross-linked by the metabolite of Benzo[a] pyrene

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Chinese Science Bulletin 1998年第2期43卷 175-175页

作者： qianhuan {1. Bo Qu Rugang Zhong Dawei Zheng center for {1. and bioengineering of cancer Beijing Polytechnic University Beijing China

Discusses PM3 computation for DNA complementary base pair cross-linked by the metabolite of Benzo[a]pyrene. Experimental procedure; Distance of positions.

关键词： base PM3 computation for the DNA complementary base paircross-linked by the metabolite of Benzo[a pyrene DNA

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香紫苏醇侧链的氧化降解

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有机化学 2003年第1期23卷 95-99页

作者：王文军戴乾圜陈莎中国石化北京化工研究院北京100013 北京工业大学癌化学与工程中心北京100022

研究了高锰酸钾、高硼酸钠、高碘酸钠等对香紫苏醇侧链的氧化降解 ,并通过IR ,NMR ,MS或元素分析等技术对氧化降解产物的结构进行了表征 .

关键词：侧链香紫苏醇氧化降解天然产物药物高锰酸钾高硼酸钠高碘酸钠

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