Bright, "Clickable" Porphyrins for the Visualization of Oxygenation under Ambient Light.

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.

• Authors: Emmanuel Roussakis, Zongxi Li, Nicholas H Nowell, Alexander J Nichols, Conor L Evans
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 54 Issue 49 Pg. 14728-31 (Dec 01 2015) ISSN: 1521-3773 [Electronic] Germany
• PMID: 26510549 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
• Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Porphyrins
• Oxygen

Topics

• Click Chemistry
• Light
• Oxygen (chemistry)
• Porphyrins (chemistry)