Bright, "Clickable" Porphyrins for the Visualization of Oxygenation under Ambient Light. (29th October 2015)

• Record Type: Journal Article
• Authors: Roussakis, Emmanuel; Li, Zongxi; Nowell, Nicholas H.; Nichols, Alexander J.; Evans, Conor L.
• Is Part Of: Angewandte Chemie. Volume 127:Number 49(2015)
• Page Start: 14941
• Page End: 14944
• Publication Date: 2015-10-29
• Subjects: Biotechnologie -- Dendrimere -- Lumineszenz -- Porphyrine -- Sensoren; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201506847
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A new group of "clickable" and brightly emissive metalloporphyrins has been developed for the visualization of oxygenation under ambient light with the naked eye. These alkynyl‐terminated compounds permit the rapid and facile synthesis of oxygen‐sensing dendrimers through azide–alkyne click chemistry. With absorption maxima overlapping with the wavelengths of common commercial laser sources, they are readily applicable to biomedical imaging of tissue oxygenation. An efficient synthetic methodology, featuring the stable trimethylacetyl (pivaloyl) protecting group, is described for their preparation. A paint‐on liquid bandage containing a new, click‐synthesized porphyrin dendrimer has been used to map oxygenation across an ex vivo porcine skin burn model. Abstract : Rotes Licht, grünes Licht : Das Leuchten sauerstoffempfindlicher Metalloporphyrine, die Gruppen für die Funktionalisierung durch Klick‐Reaktionen tragen, ist unter O2 ‐Ausschluss mit bloßem Auge zu beobachten. Um den Einsatz als Sensoren zu illustrieren, wurde ein Porphyrin in ein Dendrimer eingebunden und in Verbandformulierung für die transdermale Kartierung des O2 ‐Verbrauchs in einem Verbrennungsmodell eingesetzt.