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Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors. / Ponomarev, Konstantin Yu; Suslov, Evgeniy V.; Zakharenko, Alexandra L. et al.

In: Bioorganic Chemistry, Vol. 76, 01.02.2018, p. 392-399.

Research output: Contribution to journal › Article › peer-review

Harvard

Ponomarev, KY, Suslov, EV, Zakharenko, AL, Zakharova, OD, Rogachev, AD, Korchagina, DV, Zafar, A, Reynisson, J, Nefedov, AA, Volcho, KP, Salakhutdinov, NF & Lavrik, OI 2018, 'Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors', Bioorganic Chemistry, vol. 76, pp. 392-399. https://doi.org/10.1016/j.bioorg.2017.12.005

APA

Ponomarev, K. Y., Suslov, E. V., Zakharenko, A. L., Zakharova, O. D., Rogachev, A. D., Korchagina, D. V., Zafar, A., Reynisson, J., Nefedov, A. A., Volcho, K. P., Salakhutdinov, N. F., & Lavrik, O. I. (2018). Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors. Bioorganic Chemistry, 76, 392-399. https://doi.org/10.1016/j.bioorg.2017.12.005

Vancouver

Ponomarev KY, Suslov EV, Zakharenko AL, Zakharova OD, Rogachev AD, Korchagina DV et al. Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors. Bioorganic Chemistry. 2018 Feb 1;76:392-399. doi: 10.1016/j.bioorg.2017.12.005

Author

Ponomarev, Konstantin Yu ; Suslov, Evgeniy V. ; Zakharenko, Alexandra L. et al. / Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors. In: Bioorganic Chemistry. 2018 ; Vol. 76. pp. 392-399.

BibTeX

@article{dde78229ab264add89fa457925b91a4f,
title = "Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors",
abstract = "The ability of a number of nitrogen-containing compounds that simultaneously carry the adamantane and monoterpene moieties to inhibit Tdp1, an important enzyme of the DNA repair system, is studied. Inhibition of this enzyme has the potential to overcome chemotherapeutic resistance of some tumor types. Compound (+)-3c synthesized from 1-aminoadamantane and (+)-myrtenal, and compound 4a produced from 2-aminoadamantane and citronellal were found to be most potent as they inhibited Tdp1 with IC50 values of 6 and 3.5 µM, respectively. These compounds proved to have low cytotoxicity in colon HCT-116 and lung A-549 human tumor cell lines (CC50 > 50 µM). It was demonstrated that compound 4a at 10 µM enhanced cytotoxicity of topotecan, a topoisomerase 1 poison in clinical use, against HCT-116 more than fivefold and to a lesser extent of 1.5 increase in potency for A-549.",
keywords = "Adamantanes, Amine, Chemical space, Cytotoxicity, Fluorescent assay, Natural products, Tdp1, molecular modelling, 2-AMINOADAMANTANE DERIVATIVES, EMPIRICAL SCORING FUNCTIONS, CAMPTOTHECINS, TOPOISOMERASE-I, CANCER, PROTEIN-LIGAND DOCKING, DATA-BANK, BIOLOGICAL EVALUATION, ADAMANTANE DERIVATIVES, TDP1 INHIBITORS, Stereoisomerism, Humans, Monoterpenes/chemical synthesis, Adamantane/analogs & derivatives, Binding Sites, HCT116 Cells, Phosphodiesterase Inhibitors/chemical synthesis, Antineoplastic Agents/chemical synthesis, Amines/chemical synthesis, Drug Synergism, Phosphoric Diester Hydrolases/chemistry, Topotecan/pharmacology, Molecular Docking Simulation, Drug Screening Assays, Antitumor",
author = "Ponomarev, {Konstantin Yu} and Suslov, {Evgeniy V.} and Zakharenko, {Alexandra L.} and Zakharova, {Olga D.} and Rogachev, {Artem D.} and Korchagina, {Dina V.} and Ayesha Zafar and J{\'o}hannes Reynisson and Nefedov, {Andrey A.} and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.} and Lavrik, {Olga I.}",
note = "Publisher Copyright: {\textcopyright} 2017",
year = "2018",
month = feb,
day = "1",
doi = "10.1016/j.bioorg.2017.12.005",
language = "English",
volume = "76",
pages = "392--399",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Academic Press Inc.",

}

RIS

TY - JOUR

T1 - Aminoadamantanes containing monoterpene-derived fragments as potent tyrosyl-DNA phosphodiesterase 1 inhibitors

AU - Ponomarev, Konstantin Yu

AU - Suslov, Evgeniy V.

AU - Zakharenko, Alexandra L.

AU - Zakharova, Olga D.

AU - Rogachev, Artem D.

AU - Korchagina, Dina V.

AU - Zafar, Ayesha

AU - Reynisson, Jóhannes

AU - Nefedov, Andrey A.

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

AU - Lavrik, Olga I.

N1 - Publisher Copyright: © 2017

PY - 2018/2/1

Y1 - 2018/2/1

N2 - The ability of a number of nitrogen-containing compounds that simultaneously carry the adamantane and monoterpene moieties to inhibit Tdp1, an important enzyme of the DNA repair system, is studied. Inhibition of this enzyme has the potential to overcome chemotherapeutic resistance of some tumor types. Compound (+)-3c synthesized from 1-aminoadamantane and (+)-myrtenal, and compound 4a produced from 2-aminoadamantane and citronellal were found to be most potent as they inhibited Tdp1 with IC50 values of 6 and 3.5 µM, respectively. These compounds proved to have low cytotoxicity in colon HCT-116 and lung A-549 human tumor cell lines (CC50 > 50 µM). It was demonstrated that compound 4a at 10 µM enhanced cytotoxicity of topotecan, a topoisomerase 1 poison in clinical use, against HCT-116 more than fivefold and to a lesser extent of 1.5 increase in potency for A-549.

AB - The ability of a number of nitrogen-containing compounds that simultaneously carry the adamantane and monoterpene moieties to inhibit Tdp1, an important enzyme of the DNA repair system, is studied. Inhibition of this enzyme has the potential to overcome chemotherapeutic resistance of some tumor types. Compound (+)-3c synthesized from 1-aminoadamantane and (+)-myrtenal, and compound 4a produced from 2-aminoadamantane and citronellal were found to be most potent as they inhibited Tdp1 with IC50 values of 6 and 3.5 µM, respectively. These compounds proved to have low cytotoxicity in colon HCT-116 and lung A-549 human tumor cell lines (CC50 > 50 µM). It was demonstrated that compound 4a at 10 µM enhanced cytotoxicity of topotecan, a topoisomerase 1 poison in clinical use, against HCT-116 more than fivefold and to a lesser extent of 1.5 increase in potency for A-549.

KW - Adamantanes

KW - Amine

KW - Chemical space

KW - Cytotoxicity

KW - Fluorescent assay

KW - Natural products

KW - Tdp1, molecular modelling

KW - 2-AMINOADAMANTANE DERIVATIVES

KW - EMPIRICAL SCORING FUNCTIONS

KW - CAMPTOTHECINS

KW - TOPOISOMERASE-I

KW - CANCER

KW - PROTEIN-LIGAND DOCKING

KW - DATA-BANK

KW - BIOLOGICAL EVALUATION

KW - ADAMANTANE DERIVATIVES

KW - TDP1 INHIBITORS

KW - Stereoisomerism

KW - Humans

KW - Monoterpenes/chemical synthesis

KW - Adamantane/analogs & derivatives

KW - Binding Sites

KW - HCT116 Cells

KW - Phosphodiesterase Inhibitors/chemical synthesis

KW - Antineoplastic Agents/chemical synthesis

KW - Amines/chemical synthesis

KW - Drug Synergism

KW - Phosphoric Diester Hydrolases/chemistry

KW - Topotecan/pharmacology

KW - Molecular Docking Simulation

KW - Drug Screening Assays, Antitumor

UR - http://www.scopus.com/inward/record.url?scp=85038011816&partnerID=8YFLogxK

U2 - 10.1016/j.bioorg.2017.12.005

DO - 10.1016/j.bioorg.2017.12.005

M3 - Article

C2 - 29248742

AN - SCOPUS:85038011816

VL - 76

SP - 392

EP - 399

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

ER -

ID: 9265041