Evaluation and Theoretical Study on the Anti-inflammatory Mechanism
                    of 1-Nitro-2-phenylethane

Joyce K. L. Vale; Anderson B. Lima; Bruno G. Pinheiro; Alessandra S. Cardoso; Joyce K. R. Silva; José G. S. Maia; Gloria E. P. de Sousa; Albérico B. F. da Silva; Pergentino J. C. Sousa; Rosivaldo S. Borges

doi:10.1055/s-0032-1328402

Planta Medica, Table of Contents

Planta Med 2013; 79(8): 628-633
DOI: 10.1055/s-0032-1328402

Biological and Pharmacological Activity

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Evaluation and Theoretical Study on the Anti-inflammatory Mechanism of 1-Nitro-2-phenylethane

Joyce K. L. Vale

¹Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil

,

Anderson B. Lima

¹Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil

,

Bruno G. Pinheiro

¹Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil

,

Alessandra S. Cardoso

²Faculdade de Farmácia, Universidade Federal do Pará, Belém, PA, Brasil

,

Joyce K. R. Silva

³Faculdade de Engenharia Química, Universidade Federal do Pará, Belém, PA, Brasil

,

José G. S. Maia

³Faculdade de Engenharia Química, Universidade Federal do Pará, Belém, PA, Brasil

,

Gloria E. P. de Sousa

⁴Faculdade de Ciências Farmacêutica de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brasil

,

Albérico B. F. da Silva

⁵Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brasil

,

Pergentino J. C. Sousa

¹Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil

,

Rosivaldo S. Borges

¹Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Belém, PA, Brasil

⁵Instituto de Química de São Carlos, Universidade de São Paulo, São Carlos, SP, Brasil

› Author Affiliations

Abstract

In this study, 1-nitro-2-phenylethane was evaluated with respect to its effects in edema models of acute inflammation induced with carrageenan, dextran, and croton oil. 1-Nitro-2-phenylethane produced inhibition of rat paw edema induced by carrageenan and dextran at the doses of 25 and 50 mg/kg. The same doses caused an inhibition of croton oil-induced ear edema in mice. Our results suggest that 1-nitro-2-phenylethane has anti-inflammatory activity, probably of peripheral origin, acting in the synthesis and/or release of inflammatory mediators. A conformational study of 1-nitro-2-phenylethane was carried out using density functional theory calculations, showing three different groups of conformers corresponding to energy minimum geometries. The stereoelectronic repulsions are responsible for conformational preferences and the one most stable conformer. The prostaglandin endoperoxide synthase mechanism is related more to electrophilic than nucleophilic properties.

Key words

anti-inflammatory - Lauraceae - Aniba canelilla - DFT - 1-nitro-2-phenylethane - SAR

Full Text

References

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