European Journal of Medicinal Chemistry, volume 112, pages 114-129
Discovery of antitumor anthra[2,3-b]furan-3-carboxamides: Optimization of synthesis and evaluation of antitumor properties
Lyubov G Dezhenkova
2
,
Vladimir B. Tsvetkov
3, 4
,
Yuri N. Luzikov
2
,
Yulia L Volodina
5
,
Victor Tatarskiy
5
,
Anastasia Kalinina
5
,
Michael I Treshalin
2
,
Helen M. Treshalina
5
,
Vladimir I Romanenko
5
,
Dmitry Kaluzhny
6
,
Michael Kubbutat
7
,
Dominique Schols
8
,
Yves Pommier
9
,
Maria N Preobrazhenskaya
2
7
ProQinase GmbH, Breisacher Str. 117, 79106 Freiburg, Germany.
|
9
Developmental Therapeutics Branch, National Cancer Institute, NIH, 37 Convent Drive, 37-5068, Bethesda, MD 20892, USA.
|
Publication type: Journal Article
Publication date: 2016-04-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 6.7
ISSN: 02235234, 17683254
PubMed ID:
26890118
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
Anthraquinones and their analogues, in particular heteroarene-fused anthracendiones, are prospective scaffolds for new compounds with improved antitumor characteristics. We herein report the use of a 'scaffold hopping' approach for the replacement of the core structure in the previously discovered hit compound naphtho[2,3-f]indole-5,10-dione 2 with an alternative anthra[2,3-b]furan-5,10-dione scaffold. Among 13 newly synthesized derivatives the majority of 4,11-dihydroxy-2-methyl-5,10-dioxoanthra[2,3-b]furan-3-carboxamides demonstrated a high antiproliferative potency against a panel of wild type and drug resistant tumor cell lines, a property superior over the reference drug doxorubicin or lead naphtho[2,3-f]indole-5,10-dione 2. At low micromolar concentrations the selected derivative of (R)-3-aminopyrrolidine 3c and its stereoisomer (S)-3-aminopyrrolidine 3d caused an apoptotic cell death preceded by an arrest in the G2/M phase. Studies of intracellular targets showed that 3c and 3d formed stable intercalative complexes with the duplex DNA as determined by spectral analysis and molecular docking. Both 3c and 3d attenuated topoisomerase 1 and 2 mediated unwinding of the supercoiled DNA via a mechanism different from conventional DNA-enzyme tertiary complex formation. Furthermore, 3d decreased the activity of selected human protein kinases in vitro, indicating multiple targeting by the new chemotype. Finally, 3d demonstrated an antitumor activity in a model of murine intraperitoneally transplanted P388 leukemia, achieving the increase of animal life span up to 262% at tolerable doses. Altogether, the 'scaffold hopping' demonstrated its productivity for obtaining new perspective antitumor drug candidates.
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Citations by publishers
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1 publication, 2.04%
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Taylor & Francis
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5
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Shchekotikhin A. et al. Discovery of antitumor anthra[2,3-b]furan-3-carboxamides: Optimization of synthesis and evaluation of antitumor properties // European Journal of Medicinal Chemistry. 2016. Vol. 112. pp. 114-129.
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Shchekotikhin A., Dezhenkova L. G., Tsvetkov V. B., Luzikov Y. N., Volodina Y. L., Tatarskiy V., Kalinina A., Treshalin M. I., Treshalina H. M., Romanenko V. I., Kaluzhny D., Kubbutat M., Schols D., Pommier Y., Shtil A. A., Preobrazhenskaya M. N. Discovery of antitumor anthra[2,3-b]furan-3-carboxamides: Optimization of synthesis and evaluation of antitumor properties // European Journal of Medicinal Chemistry. 2016. Vol. 112. pp. 114-129.
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TY - JOUR
DO - 10.1016/j.ejmech.2016.01.050
UR - https://doi.org/10.1016/j.ejmech.2016.01.050
TI - Discovery of antitumor anthra[2,3-b]furan-3-carboxamides: Optimization of synthesis and evaluation of antitumor properties
T2 - European Journal of Medicinal Chemistry
AU - Shchekotikhin, Andrey
AU - Dezhenkova, Lyubov G
AU - Tsvetkov, Vladimir B.
AU - Luzikov, Yuri N.
AU - Volodina, Yulia L
AU - Tatarskiy, Victor
AU - Kalinina, Anastasia
AU - Treshalin, Michael I
AU - Treshalina, Helen M.
AU - Romanenko, Vladimir I
AU - Kaluzhny, Dmitry
AU - Kubbutat, Michael
AU - Schols, Dominique
AU - Pommier, Yves
AU - Shtil, Alexander A.
AU - Preobrazhenskaya, Maria N
PY - 2016
DA - 2016/04/01 00:00:00
PB - Elsevier
SP - 114-129
VL - 112
PMID - 26890118
SN - 0223-5234
SN - 1768-3254
ER -
Cite this
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@article{2016_Shchekotikhin,
author = {Andrey Shchekotikhin and Lyubov G Dezhenkova and Vladimir B. Tsvetkov and Yuri N. Luzikov and Yulia L Volodina and Victor Tatarskiy and Anastasia Kalinina and Michael I Treshalin and Helen M. Treshalina and Vladimir I Romanenko and Dmitry Kaluzhny and Michael Kubbutat and Dominique Schols and Yves Pommier and Alexander A. Shtil and Maria N Preobrazhenskaya},
title = {Discovery of antitumor anthra[2,3-b]furan-3-carboxamides: Optimization of synthesis and evaluation of antitumor properties},
journal = {European Journal of Medicinal Chemistry},
year = {2016},
volume = {112},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/j.ejmech.2016.01.050},
pages = {114--129},
doi = {10.1016/j.ejmech.2016.01.050}
}