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Descubrimiento de una lactona derivada del epoxiisoprostano, un antiinflamatorio muy potente

Julian Egger¹, Peter Bretscher, Stefan Freigang

¹Laboratory of Organic Chemistry, ETH Zurich , HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland.

Journal of the American Chemical Society

|December 5, 2014

Resumen

Los epoxiisoprostanos EI y EC inhiben eficazmente las citoquinas proinflamatorias. Se identificó un potente derivado de la lactona, probablemente formado por EI y EC, revelando un nuevo mecanismo molecular.

Área de la Ciencia:

La bioquímica es la bioquímica.
Inmunología Inmunología.
Química orgánica es la química orgánica.

Sus antecedentes:

Los epoxiisoprostanos (EI y EC) son inhibidores conocidos de la secreción proinflamatoria de citoquinas.
La interleucina-6 (IL-6) e interleucina-12 (IL-12) son citoquinas clave que están involucradas en las respuestas inflamatorias.

Objetivo del estudio:

Investigar el mecanismo molecular de acción de los epoxiisoprostanos EI y EC.
Identificar nuevos derivados y comprender sus vías de formación.

Principales métodos:

Se realizaron estudios químicos detallados sobre los epoxiisoprostanos EI (1) y EC (2).
El análisis consistió en investigar las reacciones intramoleculares e identificar los compuestos resultantes.

Principales resultados:

Se identificó un derivado de la lactona muy potente (3).
Los isoprostanoides EI (1) y EC (2) se proponen como precursores de la lactona (3).
Lactona (3) se forma a través de una reacción intramolecular entre el epoxido y el ácido carboxílico en EC (2).

Conclusiones:

Los epoxiisoprostanos EI y EC exhiben potentes propiedades antiinflamatorias al inhibir la secreción de IL-6 e IL-12.
Se ha identificado un nuevo derivado de la lactona altamente potente (3), derivado de EI y EC.
La formación de lactona (3) a partir de EI y EC proporciona información sobre las vías moleculares de estos compuestos.

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