Bright, "Clickable" Porphyrins for the Visualization of Oxygenation under Ambient Light.
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.
Wellman Center for Photomedicine, Massachusetts General Hospital, CNY 149-3210, 13thStreet, Charlestown, MA 02129 (USA).
Emmanuel
E
Roussakis
Wellman Center for Photomedicine, Massachusetts General Hospital, CNY 149-3210, 13thStreet, Charlestown, MA 02129 (USA).
Zongxi
Z
Li
Wellman Center for Photomedicine, Massachusetts General Hospital, CNY 149-3210, 13thStreet, Charlestown, MA 02129 (USA).
Nicholas H
NH
Nowell
Wellman Center for Photomedicine, Massachusetts General Hospital, CNY 149-3210, 13thStreet, Charlestown, MA 02129 (USA).|Harvard University Program in Biophysics, Building C2, Room 112, 240 Longwood Avenue, Boston, MA 02115 (USA).|Harvard-MIT Division of Health Sciences and Technology, 77 Massachusetts Avenue E25-519, Cambridge, MA 02139 (USA).
Alexander J
AJ
Nichols
Wellman Center for Photomedicine, Massachusetts General Hospital, CNY 149-3210, 13thStreet, Charlestown, MA 02129 (USA). evans.conor@mgh.harvard.edu.|Harvard University Program in Biophysics, Building C2, Room 112, 240 Longwood Avenue, Boston, MA 02115 (USA). evans.conor@mgh.harvard.edu.
Conor L
CL
Evans
D057930:Click Chemistry; D008027:Light; D010100:Oxygen / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*
D011166:Porphyrins; D010100:Oxygen
biotechnology; dendrimers; luminescence; porphyrins; sensors