Genotoxic activity of 1,2,3‐triazolyl modified furocoumarins and 2,3‐dihydrofurocoumarins

Kremis Stepan A.; Baev Dmitry S.; Lipeeva Alla V.; Shults Elvira E.; Tolstikova Tatiana G.; Sinitsyna Olga I.; Kochetov Alexey V.; Frolova Tatiana S.

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Genotoxic activity of 1,2,3‐triazolyl modified furocoumarins and 2,3‐dihydrofurocoumarins

机译：1,2,3-三唑基改性呋喃香草和2,3-二氢呋喃脲草林的基因毒性活性

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Abstract The furocoumarin backbone is a promising platform for chemical modifications aimed at creating new pharmaceutical agents. However, the high level of biological activity of furocoumarins is associated with a number of negative effects. For example, some of the naturally occurring ones and their derivatives can show genotoxic and mutagenic properties as a result of their forming crosslinks with DNA molecules. Therefore, a particularly important area for the chemical modification of natural furocoumarins is to reduce the negative aspects of their bioactivity. By studying a group of 21 compounds—1,2,3‐triazolyl modified derivatives of furocoumarin and peucedanin—using the SOS chromotest, the Ames test, and DNA‐comet assays, we revealed modifications that can neutralize the structure's genotoxic properties. Theoretical aspects of the interaction of the compound library were studied using molecular modeling and this identified the leading role of the polyaromatic molecular core that takes part in stacking‐interactions with the pi‐systems of the nitrogenous bases of DNA.

机译：摘要Furocoumarin骨干是一个有希望的化学修改平台，旨在创造新的药剂。然而，Furocoumarins的高水平生物活性与许多负面影响有关。例如，由于它们的形成与DNA分子的交联，一些天然存在的衍生物和它们的衍生物可以显示出遗传毒性和致突变性的特性。因此，对天然呋喃香林氏素的化学改性的特别重要的区域是减少其生物活性的负面方面。通过研究一组21种化合物-1,2,3-三唑基改性呋喃甲蛋白和Peuceanin的衍生物，使用SOS Chromotest，AMES测试和DNA-彗星测定，我们揭示了可以中和结构的遗传毒性的修饰。使用分子建模研究了复合文库的相互作用的理论方面，这鉴定了多芳族分子核的主要作用，其参与与DNA含氮基部的PI-Systems的堆叠相互作用。

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《Journal of biochemical and molecular toxicology》 |2019年第11期|共6页
作者
Kremis Stepan A.; Baev Dmitry S.; Lipeeva Alla V.; Shults Elvira E.; Tolstikova Tatiana G.; Sinitsyna Olga I.; Kochetov Alexey V.; Frolova Tatiana S.;
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作者单位

Federal Research Center of Fundamental and Translational Medicine SB RASNovosibirsk Russia;

Novosibirsk State UniversityNovosibirsk Russia;

Novosibirsk Institute of Organic Chemistry SB RASNovosibirsk Russia;

Novosibirsk State UniversityNovosibirsk Russia;

Novosibirsk State UniversityNovosibirsk Russia;

Novosibirsk State UniversityNovosibirsk Russia;

Novosibirsk State UniversityNovosibirsk Russia;

Federal Research Center of Fundamental and Translational Medicine SB RASNovosibirsk Russia;

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正文语种 eng
中图分类生物化学;
关键词
crosslinking of DNA; furocoumarins; genotoxicity; mutagenicity; peucedanin;

机译：DNA的交联;Furocoumarins;基因毒性;致突变性;Peuceanin;

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专利

1. Genotoxic activity of 1,2,3‐triazolyl modified furocoumarins and 2,3‐dihydrofurocoumarins [J] . Kremis Stepan A., Baev Dmitry S., Lipeeva Alla V., Journal of biochemical and molecular toxicology . 2019,第11期

机译：1,2,3-三唑基改性呋喃香草和2,3-二氢呋喃脲草林的基因毒性活性
2. Antitumor and antiviral activities of 4-substituted 1,2,3-triazolyl-2,3-dibenzyl-L-ascorbic acid derivatives [J] . Macan Andrijana Mescic, Harej Anja, Cazin Ines, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2019,第期

机译：4-取代的1,2,3-三唑基-2,3-二苄基-1-抗坏血酸衍生物的抗肿瘤和抗病毒活性
3. Synthesis and antiplasmodial activity of glyco-conjugate hybrids of phenylhydrazono-indolinones and glycosylated 1,2,3-triazolyl-methyl-indoline-2,3-diones [J] . Ravi Kumar Thakur, Prince Joshi, Pragati Baranwal, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2018,第期

机译：苯肼 - 吲哚酮和糖基化杂交杂交液的合成及抗溶液活性，糖基化1,2,3-三唑基 - 甲基 - 吲哚-2,3-炔酮
4. Synthesis, Crystal Structure, NLO and Hirshfeld Surface Analysis of 1,2,3-triazolyl chalcone Single Crystal [C] . C. Shruthi, V. Ravindrachary, B. Guruswamy, International Conference on Condensed Matter and Applied Physics . 2017

机译：1,2,3-三唑基Chalcone单晶的合成，晶体结构，NLO和HIRSHFELD表面分析
5. Bio-Inspired Modulation of Tris(triazolyl)borate's Electronic Properties Resulting in Enhanced Reactivity of Cu(I/II) and Other Transition Metal Complexes. [D] . Dixon, Natalie Anne. 2014

机译：生物启发性调节三（三唑基）硼酸酯的电子性质，导致Cu（I / II）和其他过渡金属配合物的反应性增强。
6. Design Synthesis and Antibacterial Activity of Coumarin-123-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin [O] . Alla V. Lipeeva, Danila O. Zakharov, Liubov G. Burova, 2019

机译：从天然呋喃香豆素Peucedanin中获得的香豆素-123-三唑杂种的设计合成和抑菌活性
7. Antitumor and antiviral activities of 4-substituted 1,2,3-triazolyl-2,3-dibenzyl-L-ascorbic acid derivatives [O] . Andrijana Meščić Macan, Anja Harej, Ines Cazin, 2019

机译：4-取代的1,2,3-三唑基-2,3-二苄基-1-抗坏血酸衍生物的抗肿瘤和抗病毒活性
8. Reaction of Bis(triethylphosphine)Platinum and Pentakis(t-butyl isocyanide)-Ruthenium with Dicarba-nido-hexaboranes(8): Molecular Structures of (Nido-micron(4,5)-(Trans-(Et3P)2 Pt(H))-micron(5,6)-H-2,3-C2B4H6), (Closo-1,1-(Et3P)2-2,3-Me2-1,2,3-PtC2B4H4), and (RuH(ButNC)5)(+) (Nido-2,3-Me2-2,3-C2B4H5)(-). [R] . Barker, G. K., Green, M., Onak, T. P., 1977

机译：双（三乙基膦）铂和pentakis（叔丁基异氰化物） - 钌与Dicarba-nido-hexaboranes的反应（8）：（Nido-微米（4,5） - （反式 - （Et3p）2 pt（H）的分子结构）） - 微米（5,6）-H-2,3-C2B4H6），（Closo-1,1-（Et3p）2-2,3-me2-1,2,3-ptC2B4H4）和（RuH（但NC）5）（+）（Nido-2,3-me2-2,3-C2B4H5）（ - ）。

Genotoxic activity of 1,2,3‐triazolyl modified furocoumarins and 2,3‐dihydrofurocoumarins

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