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Cicloctinas difluoradas de segunda generación para la química de clic sin cobre

Julian A Codelli¹, Jeremy M Baskin, Nicholas J Agard

¹Departments of Chemistry, University of California, Berkeley, California 94720, USA.

Journal of the American Chemical Society

|August 6, 2008

Resumen

Los nuevos reactivos de cicloctina difluorada (DIFO) permiten una química de clic sin cobre para el etiquetado de biomoléculas. Estos compuestos DIFO mejorados ofrecen una mayor accesibilidad sintética y mantienen tasas de reacción rápidas para aplicaciones in vivo.

Área de la Ciencia:

Biología Química Biología química.
Química orgánica es la química orgánica.
Biotecnología La biotecnología es la biotecnología.

Sus antecedentes:

Las reacciones de cicloadición 1,3-dipolar, particularmente con azidas y alquinas, son cruciales para el etiquetado selectivo del sitio de las biomoléculas.
La química de clics catalizada por el cobre, aunque es efectiva, está limitada en aplicaciones biológicas debido a la toxicidad del metal.
En trabajos anteriores se introdujeron reactivos de cicloctina difluorada (DIFO) para la química de clics sin cobre en sistemas vivos.

Objetivo del estudio:

Desarrollar nuevos y sintéticamente tratables reactivos de cicloctina difluorada (DIFO) para la química de clics sin cobre.
Evaluar la reactividad y la utilidad de estos nuevos análogos DIFO en el etiquetado biológico y la obtención de imágenes.

Principales métodos:

Síntesis de una nueva clase de análogos de cicloctina difluorada (DIFO).
Evaluación de la cinética de reacción de los reactivos DIFO con azidas en una cicloadición [3 + 2] sin cobre.
Aplicación de los reactivos DIFO para la obtención de imágenes de glicanos en células vivas.

Principales resultados:

Se sintetizó una nueva serie de reactivos DIFO con una mejor tratabilidad.
Los nuevos análogos DIFO exhibieron rápidas tasas de cicloadición [3 + 2] comparables a las del compuesto madre.
Se logró una imagen exitosa de los glicanos en células vivas utilizando los reactivos DIFO de segunda generación.

Conclusiones:

Los reactivos DIFO de segunda generación proporcionan una plataforma más accesible para la química de clic sin cobre.
Estos reactivos mantienen una alta reactividad, lo que permite un etiquetado e imágenes bioortogonales eficientes en los sistemas vivos.
La utilidad expandida de estos compuestos DIFO facilitará una adopción más amplia de la química de clic sin cobre por parte de los biólogos.

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