A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain

Tanase, Constantin I.; Pintilie, Lucia; Mihai, Elena

Constantin I. Tanase, Lucia Pintilie, Elena Mihai

A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain

Abstract:

Prostaglandins with cytoprotective activity were studied for a long time and a few PGE1 and PGE2 stable analogs were promoted as drugs: arbaprostil, enprostil, misoprostol and rioptostol. Nocloprost, a 9β-chlorine prostaglandin analog, has been also promoted as a cytoprotective drug; the succes with this compound stimulated the reserches, and many 9β- or 11β-substituted prostaglandins were synthesized and studied for their biological activity. In the same dirrection we previously synthesized new 9β-halogenated prostaglandins having also an ester group at the carbon atom 6. These compounds were now used in a molecular docking study to predict their potential cytoprotective (anti-ulcer) activity. The study has been done with CLC Drug Discovery Workbench 2.4. software and an oxidoreductase enzyme receptor, chosen from the Protein Data Bank, ID: 4KEW. Two recognized drugs, omeprazole (co-crystallized with the enzyme) and nocloprost were used as standard in the study. The 9β-halogenated prostaglandin analogs were finally docked. Nocloprost and all 9β-halogenated compounds had docking score greater than that of omeprazole. The majority of the 9β-halogenated analogs have a docking score even greater than that of nocloprost, indicating that these compounds could have potential cytoprotective activity. Correlations between docking score and substituents on the prostaglandin skeleton have been done.

Keywords:
9β-halogenated prostaglandins; molecular docking; nocloprost; omeprazole; oxidoreductase enzyme receptor 4KEW; docking score; cytoprotective (anti-ulcer) activity.

Issue: 2020, Volume 71, Issue 4

Pages: 101-110

Publication date: 2020/5/5

https://doi.org/10.37358/RC.20.4.8048

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
TANASE, C.I., PINTILIE, L., MIHAI, E., A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain, Rev. Chim., 71(4), 2020, 101-110.

Vancouver
Tanase CI, Pintilie L, Mihai E. A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain. Rev. Chim.[internet]. 2020 Apr;71(4):101-110. Available from: https://doi.org/10.37358/RC.20.4.8048

APA 6th edition
Tanase, C.I., Pintilie, L. & Mihai, E. (2020). A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain. Revista de Chimie, 71(4), 101-110. https://doi.org/10.37358/RC.20.4.8048

Harvard
Tanase, C.I., Pintilie, L., Mihai, E. (2020). 'A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain', Revista de Chimie, 71(4), pp. 101-110. https://doi.org/10.37358/RC.20.4.8048

IEEE
C.I. Tanase, L. Pintilie, E. Mihai, "A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain". Revista de Chimie, vol. 71, no. 4, pp. 101-110, 2020. [online]. https://doi.org/10.37358/RC.20.4.8048

Text
Constantin I. Tanase, Lucia Pintilie, Elena Mihai,
A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain,
Revista de Chimie,
Volume 71, Issue 4,
2020,
Pages 101-110,
ISSN 2668-8212,
https://doi.org/10.37358/RC.20.4.8048.
(https://revistadechimie.ro/Articles.asp?ID=8048)
Keywords: 9β-halogenated prostaglandins; molecular docking; nocloprost; omeprazole; oxidoreductase enzyme receptor 4KEW; docking score; cytoprotective (anti-ulcer) activity.

RIS
TY - JOUR
T1 - A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain
A1 - Tanase, Constantin I.
A2 - Pintilie, Lucia
A3 - Mihai, Elena
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2020
VL - 71
IS - 4
SP - 101
EP - 110
UR - https://doi.org/10.37358/RC.20.4.8048
KW - 9β-halogenated prostaglandins; molecular docking; nocloprost; omeprazole; oxidoreductase enzyme receptor 4KEW; docking score; cytoprotective (anti-ulcer) activity.
ER -

BibTex
@article{RevCh2020P101,
author = {Tanase Constantin I. and Pintilie Lucia and Mihai Elena},
title = {A Molecular Docking of New 9β-Halogenated Prostaglandin Analogs with an Ester Group at C-6 Atom of the α-Side Chain},
journal = {Revista de Chimie},
volume = {71},
number = {4},
pages = {101-110},
year = {2020},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.20.4.8048},
url = {https://revistadechimie.ro/Articles.asp?ID=8048}
}

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