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Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins. / Kremis, Stepan A.; Baev, Dmitry S.; Lipeeva, Alla V. et al.

In: Journal of Biochemical and Molecular Toxicology, Vol. 33, No. 11, e22396, 01.11.2019, p. e22396.

Research output: Contribution to journalArticlepeer-review

Harvard

Kremis, SA, Baev, DS, Lipeeva, AV, Shults, EE, Tolstikova, TG, Sinitsyna, OI, Kochetov, AV & Frolova, TS 2019, 'Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins', Journal of Biochemical and Molecular Toxicology, vol. 33, no. 11, e22396, pp. e22396. https://doi.org/10.1002/jbt.22396

APA

Kremis, S. A., Baev, D. S., Lipeeva, A. V., Shults, E. E., Tolstikova, T. G., Sinitsyna, O. I., Kochetov, A. V., & Frolova, T. S. (2019). Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins. Journal of Biochemical and Molecular Toxicology, 33(11), e22396. [e22396]. https://doi.org/10.1002/jbt.22396

Vancouver

Kremis SA, Baev DS, Lipeeva AV, Shults EE, Tolstikova TG, Sinitsyna OI et al. Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins. Journal of Biochemical and Molecular Toxicology. 2019 Nov 1;33(11):e22396. e22396. doi: 10.1002/jbt.22396

Author

Kremis, Stepan A. ; Baev, Dmitry S. ; Lipeeva, Alla V. et al. / Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins. In: Journal of Biochemical and Molecular Toxicology. 2019 ; Vol. 33, No. 11. pp. e22396.

BibTeX

@article{e8cb6c9f3ab14cfcbe4b655139595b64,
title = "Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins",
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.",
keywords = "crosslinking of DNA, furocoumarins, genotoxicity, mutagenicity, peucedanin, ASSAY, DNA-DAMAGE, PSORALEN",
author = "Kremis, {Stepan A.} and Baev, {Dmitry S.} and Lipeeva, {Alla V.} and Shults, {Elvira E.} and Tolstikova, {Tatiana G.} and Sinitsyna, {Olga I.} and Kochetov, {Alexey V.} and Frolova, {Tatiana S.}",
note = "Publisher Copyright: {\textcopyright} 2019 Wiley Periodicals, Inc. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2019",
month = nov,
day = "1",
doi = "10.1002/jbt.22396",
language = "English",
volume = "33",
pages = "e22396",
journal = "Journal of Biochemical and Molecular Toxicology",
issn = "1095-6670",
publisher = "Wiley-Blackwell",
number = "11",

}

RIS

TY - JOUR

T1 - Genotoxic activity of 1,2,3-triazolyl modified furocoumarins and 2,3-dihydrofurocoumarins

AU - Kremis, Stepan A.

AU - Baev, Dmitry S.

AU - Lipeeva, Alla V.

AU - Shults, Elvira E.

AU - Tolstikova, Tatiana G.

AU - Sinitsyna, Olga I.

AU - Kochetov, Alexey V.

AU - Frolova, Tatiana S.

N1 - Publisher Copyright: © 2019 Wiley Periodicals, Inc. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2019/11/1

Y1 - 2019/11/1

N2 - 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.

AB - 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.

KW - crosslinking of DNA

KW - furocoumarins

KW - genotoxicity

KW - mutagenicity

KW - peucedanin

KW - ASSAY

KW - DNA-DAMAGE

KW - PSORALEN

UR - http://www.scopus.com/inward/record.url?scp=85073989138&partnerID=8YFLogxK

U2 - 10.1002/jbt.22396

DO - 10.1002/jbt.22396

M3 - Article

C2 - 31557364

AN - SCOPUS:85073989138

VL - 33

SP - e22396

JO - Journal of Biochemical and Molecular Toxicology

JF - Journal of Biochemical and Molecular Toxicology

SN - 1095-6670

IS - 11

M1 - e22396

ER -

ID: 21993243