Bioconjugate Chemistry, volume 30, issue 3, pages 741-750
Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
Krasnovskaya Olga O.
1, 2
,
Malinnikov Vladislav M
1
,
Dashkova Natalia S
1
,
Gerasimov Vasily M
3
,
Grishina Irina V
1
,
Kireev I.
4, 5, 6
,
Panchenko Pavel V.
3, 7
,
Zakharko Marina A.
7
,
Ignatov Pavel A
3
,
Федорова О. С.
3, 7
,
Jonusauskas G.
8
,
Skvortsov Dmitry
1
,
Kovalev Sergey S
1, 9
,
Zyk Nikolay V.
1
,
Majouga Alexander G.
1, 3, 10
Publication type: Journal Article
Publication date: 2019-02-06
Journal:
Bioconjugate Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.7
ISSN: 10431802, 15204812
Organic Chemistry
Pharmacology
Pharmaceutical Science
Biotechnology
Bioengineering
Biomedical Engineering
Abstract
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.
Citations by journals
|
1
2
3
|
|
|
Molecules
|
Molecules
3 publications, 15%
|
|
Bioconjugate Chemistry
|
Bioconjugate Chemistry
2 publications, 10%
|
|
Mendeleev Communications
|
Mendeleev Communications
1 publication, 5%
|
|
Polymers
|
Polymers
1 publication, 5%
|
|
Biosensors
|
Biosensors
1 publication, 5%
|
|
Nature Chemistry
|
Nature Chemistry
1 publication, 5%
|
|
Russian Chemical Bulletin
|
Russian Chemical Bulletin
1 publication, 5%
|
|
Applied Biochemistry and Biotechnology
|
Applied Biochemistry and Biotechnology
1 publication, 5%
|
|
Bioorganic Chemistry
|
Bioorganic Chemistry
1 publication, 5%
|
|
Computer Methods and Programs in Biomedicine
|
Computer Methods and Programs in Biomedicine
1 publication, 5%
|
|
Journal of Pharmaceutical Sciences
|
Journal of Pharmaceutical Sciences
1 publication, 5%
|
|
Bioelectrochemistry
|
Bioelectrochemistry
1 publication, 5%
|
|
Future Medicinal Chemistry
|
Future Medicinal Chemistry
1 publication, 5%
|
|
Green Chemistry
|
Green Chemistry
1 publication, 5%
|
|
Izvestiya Vysshikh Uchebnykh Zavedenii, Seriya Khimiya i Khimicheskaya Tekhnologiya
|
Izvestiya Vysshikh Uchebnykh Zavedenii, Seriya Khimiya i Khimicheskaya Tekhnologiya
1 publication, 5%
|
|
Biomaterials
|
Biomaterials
1 publication, 5%
|
|
International Journal of Molecular Sciences
|
International Journal of Molecular Sciences
1 publication, 5%
|
|
1
2
3
|
Citations by publishers
|
1
2
3
4
5
6
|
|
|
Elsevier
|
Elsevier
6 publications, 30%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
6 publications, 30%
|
|
Springer Nature
|
Springer Nature
3 publications, 15%
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
2 publications, 10%
|
|
Future Medicine
|
Future Medicine
1 publication, 5%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
1 publication, 5%
|
|
Ivanovo State University of Chemistry and Technology
|
Ivanovo State University of Chemistry and Technology
1 publication, 5%
|
|
1
2
3
4
5
6
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0],"codes":[0,0,0,0,0,0],"imageUrls":["","","","","",""],"datasets":[{"label":"Citations number","data":[1,4,5,7,2,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["5","20","25","35","10","5"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Molecules","Bioconjugate Chemistry","Mendeleev Communications","Polymers","Biosensors","Nature Chemistry","Russian Chemical Bulletin","Applied Biochemistry and Biotechnology","Bioorganic Chemistry","Computer Methods and Programs in Biomedicine","Journal of Pharmaceutical Sciences","Bioelectrochemistry","Future Medicinal Chemistry","Green Chemistry","Izvestiya Vysshikh Uchebnykh Zavedenii, Seriya Khimiya i Khimicheskaya Tekhnologiya","Biomaterials","International Journal of Molecular Sciences"],"ids":[1770,4795,5294,11204,5233,17228,10918,331,4196,12663,7218,17177,22201,1017,21625,13732,14627],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/AN2jnDN59NmKaS4CWLHAGstADL2DbnatQScsFA6C_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/PmVbwfUc2aRdrnSFGtkfcabQRXGkjjb14bQC1gcl_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp"],"datasets":[{"label":"","data":[3,2,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[15,10,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Elsevier","Multidisciplinary Digital Publishing Institute (MDPI)","Springer Nature","American Chemical Society (ACS)","Future Medicine","Royal Society of Chemistry (RSC)","Ivanovo State University of Chemistry and Technology"],"ids":[17,202,8,40,6949,123,675],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/AN2jnDN59NmKaS4CWLHAGstADL2DbnatQScsFA6C_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/PmVbwfUc2aRdrnSFGtkfcabQRXGkjjb14bQC1gcl_medium.webp"],"datasets":[{"label":"","data":[6,6,3,2,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[30,30,15,10,5,5,5],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Krasnovskaya O. O. et al. Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug // Bioconjugate Chemistry. 2019. Vol. 30. No. 3. pp. 741-750.
GOST all authors (up to 50)
Copy
Krasnovskaya O. O., Malinnikov V. M., Dashkova N. S., Gerasimov V. M., Grishina I. V., Kireev I., Lavrushkina S. V., Panchenko P. V., Zakharko M. A., Ignatov P. A., Федорова О. С., Jonusauskas G., Skvortsov D., 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.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.bioconjchem.8b00885
UR - https://doi.org/10.1021%2Facs.bioconjchem.8b00885
TI - Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
T2 - Bioconjugate Chemistry
AU - Malinnikov, Vladislav M
AU - Dashkova, Natalia S
AU - Gerasimov, Vasily M
AU - Grishina, Irina V
AU - Ignatov, Pavel A
AU - Kovalev, Sergey S
AU - Zyk, Nikolay V.
AU - Lavrushkina, Svetlana V
AU - Krasnovskaya, Olga O.
AU - Федорова, О. С.
AU - Jonusauskas, G.
AU - Majouga, Alexander G.
AU - Kireev, I.
AU - Panchenko, Pavel V.
AU - Zakharko, Marina A.
AU - Skvortsov, Dmitry
AU - Beloglazkina, Elena K.
PY - 2019
DA - 2019/02/06 00:00:00
PB - American Chemical Society (ACS)
SP - 741-750
IS - 3
VL - 30
SN - 1043-1802
SN - 1520-4812
ER -
Cite this
BibTex
Copy
@article{2019_Krasnovskaya,
author = {Vladislav M Malinnikov and Natalia S Dashkova and Vasily M Gerasimov and Irina V Grishina and Pavel A Ignatov and Sergey S Kovalev and Nikolay V. Zyk and Svetlana V Lavrushkina and Olga O. Krasnovskaya and О. С. Федорова and G. Jonusauskas and Alexander G. Majouga and I. Kireev and Pavel V. Panchenko and Marina A. Zakharko and Dmitry Skvortsov and Elena K. Beloglazkina},
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://doi.org/10.1021%2Facs.bioconjchem.8b00885},
number = {3},
pages = {741--750},
doi = {10.1021/acs.bioconjchem.8b00885}
}
Cite this
MLA
Copy
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://doi.org/10.1021%2Facs.bioconjchem.8b00885.