FarFaR - Pharmacy Repository
University of Belgrade, Faculty of Pharmacy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   FarFaR
  • Pharmacy
  • Radovi istraživača / Researchers’ publications
  • View Item
  •   FarFaR
  • Pharmacy
  • Radovi istraživača / Researchers’ publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids

Thumbnail
2011
1481.pdf (531.3Kb)
Authors
Savić, Jelena
Dilber, Sanda
Marković, Bojan
Milenković, Marina
Vladimirov, Sote
Juranić, Ivan O.
Article (Published version)
Metadata
Show full item record
Abstract
Six beta-hydroxy-beta-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the beta-hydroxy-beta-aryl propanoic acids, and to elucidate the effect a-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED(50) values is between 127 mu mol/kg and 15 mu mol/kg, while the result for ibuprofen is 51.7 mu mol/kg. Only slight hyperaemia or few petechiae were spotted on rat's stomach. T...he results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenylpropanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions.

Keywords:
beta-hydroxy-beta-arylpropanoic acids / Reformatsky reaction / anti-inflammatory activity / molecular docking simulations / COX-2 selective inhibitor
Source:
Molecules, 2011, 16, 8, 6645-6655
Publisher:
  • MDPI, Basel
Projects:
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.3390/molecules16086645

ISSN: 1420-3049

PubMed: 25134768

WoS: 000294249100036

Scopus: 2-s2.0-80052214202
[ Google Scholar ]
7
5
URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1483
Collections
  • Radovi istraživača / Researchers’ publications
Institution
Pharmacy
TY  - JOUR
AU  - Savić, Jelena
AU  - Dilber, Sanda
AU  - Marković, Bojan
AU  - Milenković, Marina
AU  - Vladimirov, Sote
AU  - Juranić, Ivan O.
PY  - 2011
UR  - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1483
AB  - Six beta-hydroxy-beta-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the beta-hydroxy-beta-aryl propanoic acids, and to elucidate the effect a-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED(50) values is between 127 mu mol/kg and 15 mu mol/kg, while the result for ibuprofen is 51.7 mu mol/kg. Only slight hyperaemia or few petechiae were spotted on rat's stomach. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenylpropanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions.
PB  - MDPI, Basel
T2  - Molecules
T1  - Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids
VL  - 16
IS  - 8
SP  - 6645
EP  - 6655
DO  - 10.3390/molecules16086645
ER  - 
@article{
author = "Savić, Jelena and Dilber, Sanda and Marković, Bojan and Milenković, Marina and Vladimirov, Sote and Juranić, Ivan O.",
year = "2011",
url = "http://farfar.pharmacy.bg.ac.rs/handle/123456789/1483",
abstract = "Six beta-hydroxy-beta-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the beta-hydroxy-beta-aryl propanoic acids, and to elucidate the effect a-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED(50) values is between 127 mu mol/kg and 15 mu mol/kg, while the result for ibuprofen is 51.7 mu mol/kg. Only slight hyperaemia or few petechiae were spotted on rat's stomach. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenylpropanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions.",
publisher = "MDPI, Basel",
journal = "Molecules",
title = "Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids",
volume = "16",
number = "8",
pages = "6645-6655",
doi = "10.3390/molecules16086645"
}
Savić J, Dilber S, Marković B, Milenković M, Vladimirov S, Juranić IO. Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids. Molecules. 2011;16(8):6645-6655
Savić, J., Dilber, S., Marković, B., Milenković, M., Vladimirov, S.,& Juranić, I. O. (2011). Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids.
MoleculesMDPI, Basel., 16(8), 6645-6655.
https://doi.org/10.3390/molecules16086645
Savić Jelena, Dilber Sanda, Marković Bojan, Milenković Marina, Vladimirov Sote, Juranić Ivan O., "Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids" 16, no. 8 (2011):6645-6655,
https://doi.org/10.3390/molecules16086645 .

DSpace software copyright © 2002-2015  DuraSpace
About FarFaR - Pharmacy Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About FarFaR - Pharmacy Repository | Send Feedback

OpenAIRERCUB