European Journal of Medicinal Chemistry, volume 222, pages 113589
Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide - A new caspase-activating proapoptotic agent.
Publication type: Journal Article
Publication date: 2021-10-01
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 6.7
ISSN: 02235234, 17683254
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
Herein we report the synthesis of a set of seventeen 3-sulfonamide substituted coumarin derivatives. Prepared compounds were tested in vitro for inhibition of four physiologically relevant isoforms of the metalloenzyme human carbonic anhydrase ( h CA, EC 4.2.1.1). Several coumarin sulfonamides displayed low nanomolar K I values against therapeutically relevant h CA II, IX, and XII, whereas they did not potently inhibit h CA I. Some of these compounds exerted a concentration-dependent antiproliferative action toward RT4 human bladder cancer and especially A431 human epidermoid carcinoma cell lines. In the meantime, the viability of non-tumorigenic hTERT immortalized human foreskin fibroblast cell line Bj-5ta was not significantly affected by the obtained derivatives. Interestingly, compound 10q (2-oxo-2 H -benzo [ h ]chromene-3-sulfonamide) showed a profound and selective dose-dependent inhibition of A431 cell growth with low nanomolar IC 50 values. We demonstrated that 10q possessed a concentration-dependent apoptosis induction activity associated with caspase 3/7 activation in cancer cells. As carbonic anhydrase isoforms in question were not potently inhibited by this compound, its antiproliferative effects likely involve other mechanisms, such as DNA intercalation. Compound 10q clearly represents a viable lead for further development of new-generation anticancer agents. • Carbonic anhydrase IX and XII isoforms are cancer targets. • Primary sulfonamides and coumarins are known to inhibit these isoforms. • A set of hybrid compounds combining the two motifs was investigated. • The most promising compound was not the strongest CA IX/XII inhibitor. • It activated caspases and induced apoptosis in dose-dependent manner.
Citations by journals
|
1
2
3
4
5
|
|
|
Journal of Enzyme Inhibition and Medicinal Chemistry
|
Journal of Enzyme Inhibition and Medicinal Chemistry
5 publications, 31.25%
|
|
Archiv der Pharmazie
|
Archiv der Pharmazie
4 publications, 25%
|
|
Molecules
|
Molecules
3 publications, 18.75%
|
|
Medicinal Chemistry Research
|
Medicinal Chemistry Research
1 publication, 6.25%
|
|
Journal of the Iranian Chemical Society
|
Journal of the Iranian Chemical Society
1 publication, 6.25%
|
|
ChemMedChem
|
ChemMedChem
1 publication, 6.25%
|
|
Expert Opinion on Investigational Drugs
|
Expert Opinion on Investigational Drugs
1 publication, 6.25%
|
|
1
2
3
4
5
|
Citations by publishers
|
1
2
3
4
5
6
|
|
|
Taylor & Francis
|
Taylor & Francis
6 publications, 37.5%
|
|
Wiley
|
Wiley
5 publications, 31.25%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 18.75%
|
|
Springer Nature
|
Springer Nature
2 publications, 12.5%
|
|
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":[2021,2022,2023],"ids":[0,0,0],"codes":[0,0,0],"imageUrls":["","",""],"datasets":[{"label":"Citations number","data":[4,8,4],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6"],"percentage":["25","50","25"],"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":["Journal of Enzyme Inhibition and Medicinal Chemistry","Archiv der Pharmazie","Molecules","Medicinal Chemistry Research","Journal of the Iranian Chemical Society","ChemMedChem","Expert Opinion on Investigational Drugs"],"ids":[864,15226,1770,6106,15384,1430,1879],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp"],"datasets":[{"label":"","data":[5,4,3,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[31.25,25,18.75,6.25,6.25,6.25,6.25],"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":["Taylor & Francis","Wiley","Multidisciplinary Digital Publishing Institute (MDPI)","Springer Nature"],"ids":[18,11,202,8],"codes":[0,0,0,0],"imageUrls":["\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp"],"datasets":[{"label":"","data":[6,5,3,2],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[37.5,31.25,18.75,12.5],"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
Cite this
GOST
Copy
Darin D. et al. Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide - A new caspase-activating proapoptotic agent. // European Journal of Medicinal Chemistry. 2021. Vol. 222. p. 113589.
GOST all authors (up to 50)
Copy
Darin D., Bunev A. S., Ostapenko G. I., Nocentini A., T Supuran C., Krasavin M., Sharonova T., Sharoyko V., Kantin G., Kalinin S. Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide - A new caspase-activating proapoptotic agent. // European Journal of Medicinal Chemistry. 2021. Vol. 222. p. 113589.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.ejmech.2021.113589
UR - https://doi.org/10.1016%2Fj.ejmech.2021.113589
TI - Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide - A new caspase-activating proapoptotic agent.
T2 - European Journal of Medicinal Chemistry
AU - Darin, Dmitry
AU - Bunev, Alexander S.
AU - Ostapenko, Gennady I.
AU - Nocentini, Alessio
AU - T Supuran, Claudiu
AU - Krasavin, Mikhail
AU - Sharonova, Tatiana
AU - Sharoyko, Vladimir
AU - Kantin, Grigory
AU - Kalinin, Stanislav
PY - 2021
DA - 2021/10/01 00:00:00
PB - Elsevier
SP - 113589
VL - 222
SN - 0223-5234
SN - 1768-3254
ER -
Cite this
BibTex
Copy
@article{2021_Darin,
author = {Dmitry Darin and Alexander S. Bunev and Gennady I. Ostapenko and Alessio Nocentini and Claudiu T Supuran and Mikhail Krasavin and Tatiana Sharonova and Vladimir Sharoyko and Grigory Kantin and Stanislav Kalinin},
title = {Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide - A new caspase-activating proapoptotic agent.},
journal = {European Journal of Medicinal Chemistry},
year = {2021},
volume = {222},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016%2Fj.ejmech.2021.113589},
pages = {113589},
doi = {10.1016/j.ejmech.2021.113589}
}