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Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation

The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to...

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Main Authors: Kamal, Rullah, Mohd Aluwi, Mohd Fadhlizil Fasihi, M. Yamin, Bohari, Abdul Bahari, Mohd Nazri, Sze Wei, Leong, Ahmad, Syahida, Abas, Faridah, Ismail, Nor Hadiani, Jantan, Ibrahim, Lam, Kok Wai
Format: Article
Language:English
Published: Elsevier 2014
Subjects:
QD Chemistry
RS403 Materia Medica-Pharmaceutical Chemistry
Online Access:http://irep.iium.edu.my/72070/1/Paper%20BMCL%20%28full%29.pdf
http://irep.iium.edu.my/72070/
https://www.sciencedirect.com/science/article/pii/S0960894X14006891
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spelling my.iium.irep.720702023-09-13T02:08:31Z http://irep.iium.edu.my/72070/ Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation Kamal, Rullah Mohd Aluwi, Mohd Fadhlizil Fasihi M. Yamin, Bohari Abdul Bahari, Mohd Nazri Sze Wei, Leong Ahmad, Syahida Abas, Faridah Ismail, Nor Hadiani Jantan, Ibrahim Lam, Kok Wai QD Chemistry RS403 Materia Medica-Pharmaceutical Chemistry The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 lM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites. Elsevier 2014-08-15 Article PeerReviewed application/pdf en http://irep.iium.edu.my/72070/1/Paper%20BMCL%20%28full%29.pdf Kamal, Rullah and Mohd Aluwi, Mohd Fadhlizil Fasihi and M. Yamin, Bohari and Abdul Bahari, Mohd Nazri and Sze Wei, Leong and Ahmad, Syahida and Abas, Faridah and Ismail, Nor Hadiani and Jantan, Ibrahim and Lam, Kok Wai (2014) Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation. Bioorganic & Medicinal Chemistry Letters, 24 (16). pp. 3826-3834. ISSN 0960-894X https://www.sciencedirect.com/science/article/pii/S0960894X14006891 10.1016/j.bmcl.2014.06.061
institution Universiti Islam Antarabangsa Malaysia
building IIUM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider International Islamic University Malaysia
content_source IIUM Repository (IREP)
url_provider http://irep.iium.edu.my/
language English
topic QD Chemistry
RS403 Materia Medica-Pharmaceutical Chemistry
spellingShingle QD Chemistry
RS403 Materia Medica-Pharmaceutical Chemistry
Kamal, Rullah
Mohd Aluwi, Mohd Fadhlizil Fasihi
M. Yamin, Bohari
Abdul Bahari, Mohd Nazri
Sze Wei, Leong
Ahmad, Syahida
Abas, Faridah
Ismail, Nor Hadiani
Jantan, Ibrahim
Lam, Kok Wai
Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
description The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 lM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.
format Article
author Kamal, Rullah
Mohd Aluwi, Mohd Fadhlizil Fasihi
M. Yamin, Bohari
Abdul Bahari, Mohd Nazri
Sze Wei, Leong
Ahmad, Syahida
Abas, Faridah
Ismail, Nor Hadiani
Jantan, Ibrahim
Lam, Kok Wai
author_facet Kamal, Rullah
Mohd Aluwi, Mohd Fadhlizil Fasihi
M. Yamin, Bohari
Abdul Bahari, Mohd Nazri
Sze Wei, Leong
Ahmad, Syahida
Abas, Faridah
Ismail, Nor Hadiani
Jantan, Ibrahim
Lam, Kok Wai
author_sort Kamal, Rullah
title Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
title_short Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
title_full Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
title_fullStr Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
title_full_unstemmed Inhibition of prostaglandin E-2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
title_sort inhibition of prostaglandin e-2 production by synthetic minor prenylated chalcones and flavonoids: synthesis, biological activity, crystal structure, and in silico evaluation
publisher Elsevier
publishDate 2014
url http://irep.iium.edu.my/72070/1/Paper%20BMCL%20%28full%29.pdf
http://irep.iium.edu.my/72070/
https://www.sciencedirect.com/science/article/pii/S0960894X14006891
_version_ 1778160466277695488
score 13.211869

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