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Pares bioortogonales triples y mutuamente ortogonales a través del diseño de cicloalquinas que contienen sulfamato

Yun Hu¹, Jessica M Roberts¹, Henry R Kilgore²

¹Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.

Journal of the American Chemical Society

|October 21, 2020

Resumen

Los investigadores desarrollaron nuevas cicloctinas (SNO-OCT) para la química bioortogonal. Estos compuestos permiten reacciones sintonizables, rápidas y ortogonales para el etiquetado biológico avanzado in vitro e in vivo.

Área de la Ciencia:

Química bioortogonal
Síntesis orgánica
Biología química

Sus antecedentes:

Los reactivos de etiquetado bioortogonales son cruciales para el estudio de los sistemas biológicos.
El desarrollo de pares de reactivos mutuamente excluyentes con reacciones rápidas y predecibles es un desafío continuo.

Objetivo del estudio:

Diseñar y sintetizar nuevas cicloctinas que contengan S, N y O (SNO-OCT) con reactividad ajustable.
Para lograr reactividades divergentes para sistemas de ligadura dual y triple mutuamente ortogonales.
Evaluar la utilidad de estos compuestos para el etiquetado de células vivas.

Principales métodos:

Modificación de los andamios SNO-OCT para ajustar las propiedades electrónicas.
Reacciones de cicloadición con varios dipolos (tipo I-III).
Estudios computacionales y experimentales para comprender la cinética de las reacciones.
Experimentos de captación celular y de etiquetado in situ en células de mamíferos.

Principales resultados:

Los SNO-OCT permiten la sintonización electrónica para influir en las tasas de cicloadición.
Un derivado difluorado de SNO-OCT mostró tasas de reacción mejoradas (k > 5,13 M−1s−1).
Sistemas de triple ligadura diseñados e informados con reactividades ortogonales.
Los SNO-OCT polares son internalizados por las células de los mamíferos y funcionan en el citosol.

Conclusiones:

Los SNO-OCT ofrecen una plataforma versátil para el desarrollo de reactivos bioortogonales sintonizables.
Estos compuestos permiten la creación de sistemas de ligadura ortogonales dobles y triples.
Los SNO-OCT son eficaces para el etiquetado de células vivas, lo que demuestra su potencial para aplicaciones in vitro e in vivo.

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