Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
Тип публикации: Journal Article
Дата публикации: 2019-02-06
scimago Q1
wos Q1
white level БС1
SJR: 1.035
CiteScore: 7.5
Impact factor: 3.9
ISSN: 10431802, 15204812
PubMed ID:
30726065
Organic Chemistry
Pharmacology
Pharmaceutical Science
Biotechnology
Bioengineering
Biomedical Engineering
Краткое описание
A novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin.
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Krasnovskaya O. O. et al. Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug // Bioconjugate Chemistry. 2019. Vol. 30. No. 3. pp. 741-750.
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Krasnovskaya O. O., Malinnikov V. M., Dashkova N. S., Gerasimov V. M., Grishina I. V., Kireev I., Kireev I. I., Lavrushkina S. V., Panchenko P. V., Panchenko P. A., Zakharko M. A., Ignatov P. A., Федорова О. С., Jonusauskas G., Skvortsov D., Skvortsov D. A., Kovalev S. S., Beloglazkina E. K., Zyk N. V., Majouga A. G. Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug // Bioconjugate Chemistry. 2019. Vol. 30. No. 3. pp. 741-750.
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TY - JOUR
DO - 10.1021/acs.bioconjchem.8b00885
UR - https://pubs.acs.org/doi/10.1021/acs.bioconjchem.8b00885
TI - Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
T2 - Bioconjugate Chemistry
AU - Krasnovskaya, Olga O.
AU - Malinnikov, Vladislav M
AU - Dashkova, Natalia S
AU - Gerasimov, Vasily M
AU - Grishina, Irina V
AU - Kireev, I.
AU - Kireev, Igor I
AU - Lavrushkina, Svetlana V
AU - Panchenko, Pavel V.
AU - Panchenko, Pavel A
AU - Zakharko, Marina A.
AU - Ignatov, Pavel A
AU - Федорова, О. С.
AU - Jonusauskas, G.
AU - Skvortsov, Dmitry
AU - Skvortsov, Dmitry A.
AU - Kovalev, Sergey S
AU - Beloglazkina, Elena K.
AU - Zyk, Nikolay V.
AU - Majouga, Alexander G.
PY - 2019
DA - 2019/02/06
PB - American Chemical Society (ACS)
SP - 741-750
IS - 3
VL - 30
PMID - 30726065
SN - 1043-1802
SN - 1520-4812
ER -
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@article{2019_Krasnovskaya,
author = {Olga O. Krasnovskaya and Vladislav M Malinnikov and Natalia S Dashkova and Vasily M Gerasimov and Irina V Grishina and I. Kireev and Igor I Kireev and Svetlana V Lavrushkina and Pavel V. Panchenko and Pavel A Panchenko and Marina A. Zakharko and Pavel A Ignatov and О. С. Федорова and G. Jonusauskas and Dmitry Skvortsov and Dmitry A. Skvortsov and Sergey S Kovalev and Elena K. Beloglazkina and Nikolay V. Zyk and Alexander G. Majouga},
title = {Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug},
journal = {Bioconjugate Chemistry},
year = {2019},
volume = {30},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.bioconjchem.8b00885},
number = {3},
pages = {741--750},
doi = {10.1021/acs.bioconjchem.8b00885}
}
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MLA
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Krasnovskaya, Olga O., et al. “Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug.” Bioconjugate Chemistry, vol. 30, no. 3, Feb. 2019, pp. 741-750. https://pubs.acs.org/doi/10.1021/acs.bioconjchem.8b00885.
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