Bioorganic and Medicinal Chemistry Letters, volume 29, issue 16, pages 2229-2235
Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates
Machulkin Alexey E.
1, 2
,
Beloglazkina Elena K
,
Nimenko Ekaterina A.
3
,
Uspenskaya Anastasia A
,
Ber Anton P
3
,
Shafikov Radik R
,
Skvortsov Dmitry A.
,
Zyk Nikolay V.
3
,
Zyk Nikolay U
3
,
Plotnikova Ekaterina A.
4
,
Yakubovskaya Raisa I.
4
,
Koteliansky Victor E.
3
,
Kavalchuk Mikhail V
3
,
Skvortsov Dmitry
3
,
Aladinskaya Anastasia V.
5
,
Shafikov Radik R
3
,
Publication type: Journal Article
Publication date: 2019-08-01
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.7
ISSN: 0960894X, 14643405
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
Prostate cancer (PC) is the second most commonly occurring cancer in men. Conventional chemotherapy has wide variety of disadvantages such as high systemic toxicity and low selectivity. Targeted drug delivery is a promising approach to decrease side effects of therapy. Prostate specific membrane antigen (PSMA) is overexpressed in prostate cancer cells while low level of expression is observed in normal cells. In this study we describe the development of Glu-urea-Lys based PSMA-targeting conjugates with paclitaxel. A series of new PSMA targeting conjugates with paclitaxel was designed and synthesized. The cytotoxicity of conjugates was evaluated against prostate (LNCaP, 22Rv1 and PC-3) and non-prostate (Hek293T, VA13, A549 and MCF-7) cell lines. The most promising conjugate 21 was examined in vivo using 22Rv1 xenograft mice model. It demonstrated good efficiency comparable with paclitaxel, while reduced toxicity. 3D molecular docking study was also performed to understand underlying mechanism of binding and further optimization of the linker substructure and conjugates structure for improving the target affinity. These conjugates may be useful for further design of novel PSMA targeting delivery systems for PC.
Citations by journals
|
1
2
|
|
|
European Journal of Medicinal Chemistry
|
European Journal of Medicinal Chemistry
2 publications, 9.09%
|
|
International Journal of Nanomedicine
|
International Journal of Nanomedicine
2 publications, 9.09%
|
|
Molecules
|
Molecules
1 publication, 4.55%
|
|
Mendeleev Communications
|
Mendeleev Communications
1 publication, 4.55%
|
|
Journal of Molecular Structure
|
Journal of Molecular Structure
1 publication, 4.55%
|
|
Journal of Medicinal Chemistry
|
Journal of Medicinal Chemistry
1 publication, 4.55%
|
|
Bioorganic and Medicinal Chemistry Letters
|
Bioorganic and Medicinal Chemistry Letters
1 publication, 4.55%
|
|
Medicinal Chemistry Research
|
Medicinal Chemistry Research
1 publication, 4.55%
|
|
Current Medicinal Chemistry
|
Current Medicinal Chemistry
1 publication, 4.55%
|
|
Scientific Reports
|
Scientific Reports
1 publication, 4.55%
|
|
Biophysical Reviews
|
Biophysical Reviews
1 publication, 4.55%
|
|
Journal of Drug Delivery Science and Technology
|
Journal of Drug Delivery Science and Technology
1 publication, 4.55%
|
|
Journal of Controlled Release
|
Journal of Controlled Release
1 publication, 4.55%
|
|
Chemistry - A European Journal
|
Chemistry - A European Journal
1 publication, 4.55%
|
|
Biomaterials Science
|
Biomaterials Science
1 publication, 4.55%
|
|
Pharmaceuticals
|
Pharmaceuticals
1 publication, 4.55%
|
|
International Journal of Molecular Sciences
|
International Journal of Molecular Sciences
1 publication, 4.55%
|
|
Frontiers in Chemistry
|
Frontiers in Chemistry
1 publication, 4.55%
|
|
1
2
|
Citations by publishers
|
1
2
3
4
5
6
7
|
|
|
Elsevier
|
Elsevier
7 publications, 31.82%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 13.64%
|
|
Springer Nature
|
Springer Nature
3 publications, 13.64%
|
|
Dove Medical Press
|
Dove Medical Press
2 publications, 9.09%
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
1 publication, 4.55%
|
|
Bentham Science
|
Bentham Science
1 publication, 4.55%
|
|
Wiley
|
Wiley
1 publication, 4.55%
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
1 publication, 4.55%
|
|
Frontiers Media S.A.
|
Frontiers Media S.A.
1 publication, 4.55%
|
|
1
2
3
4
5
6
7
|
- 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":[2020,2021,2022,2023,2024],"ids":[0,0,0,0,0],"codes":[0,0,0,0,0],"imageUrls":["","","","",""],"datasets":[{"label":"Citations number","data":[3,5,11,2,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["13.64","22.73","50","9.09","4.55"],"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":["European Journal of Medicinal Chemistry","International Journal of Nanomedicine","Molecules","Mendeleev Communications","Journal of Molecular Structure","Journal of Medicinal Chemistry","Bioorganic and Medicinal Chemistry Letters","Medicinal Chemistry Research","Current Medicinal Chemistry","Scientific Reports","Biophysical Reviews","Journal of Drug Delivery Science and Technology","Journal of Controlled Release","Chemistry - A European Journal","Biomaterials Science","Pharmaceuticals","International Journal of Molecular Sciences","Frontiers in Chemistry"],"ids":[8171,10956,1770,5294,9347,3673,8828,6106,17087,13767,79,17907,14351,24708,12476,1203,14627,6407],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/wVWp6zaxUsMdR03dYMdOZoesUrVGtNMWkHKByIvT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_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\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp"],"datasets":[{"label":"","data":[2,2,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[9.09,9.09,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55,4.55],"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","Dove Medical Press","American Chemical Society (ACS)","Bentham Science","Wiley","Royal Society of Chemistry (RSC)","Frontiers Media S.A."],"ids":[17,202,8,417,40,39,11,123,208],"codes":[0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/wVWp6zaxUsMdR03dYMdOZoesUrVGtNMWkHKByIvT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp"],"datasets":[{"label":"","data":[7,3,3,2,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[31.82,13.64,13.64,9.09,4.55,4.55,4.55,4.55,4.55],"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
Machulkin A. E. et al. Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates // Bioorganic and Medicinal Chemistry Letters. 2019. Vol. 29. No. 16. pp. 2229-2235.
GOST all authors (up to 50)
Copy
Skvortsov D. A., Majouga A. G., Koteliansky V. E., Zyk N. V., Beloglazkina E. K., Zyk N. U., Nimenko E. A., Yakubovskaya R. I., Plotnikova E. A., Shafikov R. R., Uspenskaya A. A., V. Aladinskaya A., Kavalchuk M. V., Ber A. P., Ivanenkov Y., Machulkin A. E., Skvortsov D., Aladinskaya A. V., Uspenskaya A. A., Shafikov R. R., Beloglazkina E. K. Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates // Bioorganic and Medicinal Chemistry Letters. 2019. Vol. 29. No. 16. pp. 2229-2235.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.bmcl.2019.06.035
UR - https://doi.org/10.1016%2Fj.bmcl.2019.06.035
TI - Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Machulkin, Alexey E.
AU - Skvortsov, Dmitry A.
AU - Ivanenkov, Yan
AU - Ber, Anton P
AU - Kavalchuk, Mikhail V
AU - V. Aladinskaya, Anastasia
AU - Uspenskaya, Anastasia A
AU - Shafikov, Radik R
AU - Plotnikova, Ekaterina A.
AU - Yakubovskaya, Raisa I.
AU - Nimenko, Ekaterina A.
AU - Zyk, Nikolay U
AU - Beloglazkina, Elena K
AU - Zyk, Nikolay V.
AU - Koteliansky, Victor E.
AU - Majouga, Alexander G.
AU - Skvortsov, Dmitry
AU - Aladinskaya, Anastasia V.
AU - Uspenskaya, Anastasia A.
AU - Shafikov, Radik R
AU - Beloglazkina, Elena K.
PY - 2019
DA - 2019/08/01 00:00:00
PB - Elsevier
SP - 2229-2235
IS - 16
VL - 29
SN - 0960-894X
SN - 1464-3405
ER -
Cite this
BibTex
Copy
@article{2019_Machulkin,
author = {Alexey E. Machulkin and Dmitry A. Skvortsov and Yan Ivanenkov and Anton P Ber and Mikhail V Kavalchuk and Anastasia V. Aladinskaya and Anastasia A Uspenskaya and Radik R Shafikov and Ekaterina A. Plotnikova and Raisa I. Yakubovskaya and Ekaterina A. Nimenko and Nikolay U Zyk and Elena K Beloglazkina and Nikolay V. Zyk and Victor E. Koteliansky and Alexander G. Majouga and Dmitry Skvortsov and Anastasia V. Aladinskaya and Anastasia A. Uspenskaya and Radik R Shafikov and Elena K. Beloglazkina},
title = {Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2019},
volume = {29},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016%2Fj.bmcl.2019.06.035},
number = {16},
pages = {2229--2235},
doi = {10.1016/j.bmcl.2019.06.035}
}
Cite this
MLA
Copy
Machulkin, Alexey E., et al. āSynthesis and biological evaluation of PSMA-targeting paclitaxel conjugates.ā Bioorganic and Medicinal Chemistry Letters, vol. 29, no. 16, Aug. 2019, pp. 2229-2235. https://doi.org/10.1016%2Fj.bmcl.2019.06.035.