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Molecules 2019, 24(8), 1476;

In Silico Evaluation of Ibuprofen and Two Benzoylpropionic Acid Derivatives with Potential Anti-Inflammatory Activity

Graduate Program of Pharmaceutical Innovation, Federal University of Amapá, Macapá-AP 68902-280, Brazil
Laboratory of Modeling and Computational Chemistry, Department of Biological and Health Sciences, Federal University of Amapá, Macapá-AP 68902-280, Brazil
Laboratory of Molecular Modeling, State University of Feira de Santana, Feira de Santana-BA 44036-900, Brazil
Laboratory of Bioinformatics and Molecular Modeling, School of Pharmacy, Federal University of Bahia, Barão de Jeremoabo Street, Salvador 40170-115, BA, Brazil
Computational Laboratory of Pharmaceutical Chemistry, University of Sao Paulo, Av. Prof. do Café, s/n - Monte Alegre, Ribeirão Preto, São Paulo 14040-903, Brazil
Nucleus of Studies and Selection of Bioactive Molecules, Institute of Health Sciences, Federal University of Pará, Belém-PA 66075-110, Brazil
Laboratory Cellular Immunology Applied to Health, Oswaldo Cruz Foundation, FIOCRUZ Rondônia, Rua da Beira, 7671 BR-364, Porto Velho-RO 78912-000, Brazil
Department of Pharmaceutical and Organic Chemistry, Faculty of Pharmacy, Institute of Biosanitary Research ibs.GRANADA. University of Granada, 18071 Granada, Spain
Author to whom correspondence should be addressed.
Academic Editor: Simone Brogi
Received: 23 March 2019 / Revised: 7 April 2019 / Accepted: 11 April 2019 / Published: 15 April 2019
(This article belongs to the Special Issue Computational Approaches for Drug Discovery)
PDF [1951 KB, uploaded 15 April 2019]


Inflammation is a complex reaction involving cellular and molecular components and an unspecific response to a specific aggression. The use of scientific and technological innovations as a research tool combining multidisciplinary knowledge in informatics, biotechnology, chemistry and biology are essential for optimizing time and reducing costs in the drug design. Thus, the integration of these in silico techniques makes it possible to search for new anti-inflammatory drugs with better pharmacokinetic and toxicological profiles compared to commercially used drugs. This in silico study evaluated the anti-inflammatory potential of two benzoylpropionic acid derivatives (MBPA and DHBPA) using molecular docking and their thermodynamic profiles by molecular dynamics, in addition to predicting oral bioavailability, bioactivity and toxicity. In accordance to our predictions the derivatives proposed here had the potential capacity for COX-2 inhibition in the human and mice enzyme, due to containing similar interactions with the control compound (ibuprofen). Ibuprofen showed toxic predictions of hepatotoxicity (in human, mouse and rat; toxicophoric group 2-arylacetic or 3-arylpropionic acid) and irritation of the gastrointestinal tract (in human, mouse and rat; toxicophoric group alpha-substituted propionic acid or ester) confirming the literature data, as well as the efficiency of the DEREK 10.0.2 program. Moreover, the proposed compounds are predicted to have a good oral bioavailability profile and low toxicity (LD50 < 700 mg/kg) and safety when compared to the commercial compound. Therefore, future studies are necessary to confirm the anti-inflammatory potential of these compounds. View Full-Text
Keywords: inflammation; molecular docking; molecular dynamics; bioavailability; toxicity inflammation; molecular docking; molecular dynamics; bioavailability; toxicity

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Bittencourt, J.A.H.M.; Neto, M.F.A.; Lacerda, P.S.; Bittencourt, R.C.V.S.; Silva, R.C.; Lobato, C.C.; Silva, L.B.; Leite, F.H.A.; Zuliani, J.P.; Rosa, J.M.C.; Borges, R.S.; Santos, C.B.R. In Silico Evaluation of Ibuprofen and Two Benzoylpropionic Acid Derivatives with Potential Anti-Inflammatory Activity. Molecules 2019, 24, 1476.

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