Fluorescent Isoindole Crosslink (FlICk) Chemistry: A Rapid, User-friendly Stapling Reaction
Mihajlo Todorovic
Chemistry Department, UBC, 2036 Main Mall, Vancouver, B.C., V6T1Z1 Canada
Search for more papers by this authorKaterina D. Schwab
Chemistry Department, UBC, 2036 Main Mall, Vancouver, B.C., V6T1Z1 Canada
Search for more papers by this authorDr. Jutta Zeisler
B.C. Cancer Agency Research Centre, 675 West 10th Avenue, Vancouver, BC, V5Z 1L3 Canada
Search for more papers by this authorDr. Chengcheng Zhang
B.C. Cancer Agency Research Centre, 675 West 10th Avenue, Vancouver, BC, V5Z 1L3 Canada
Search for more papers by this authorProf. Dr. Francois Bénard
B.C. Cancer Agency Research Centre, 675 West 10th Avenue, Vancouver, BC, V5Z 1L3 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. David M. Perrin
Chemistry Department, UBC, 2036 Main Mall, Vancouver, B.C., V6T1Z1 Canada
Search for more papers by this authorMihajlo Todorovic
Chemistry Department, UBC, 2036 Main Mall, Vancouver, B.C., V6T1Z1 Canada
Search for more papers by this authorKaterina D. Schwab
Chemistry Department, UBC, 2036 Main Mall, Vancouver, B.C., V6T1Z1 Canada
Search for more papers by this authorDr. Jutta Zeisler
B.C. Cancer Agency Research Centre, 675 West 10th Avenue, Vancouver, BC, V5Z 1L3 Canada
Search for more papers by this authorDr. Chengcheng Zhang
B.C. Cancer Agency Research Centre, 675 West 10th Avenue, Vancouver, BC, V5Z 1L3 Canada
Search for more papers by this authorProf. Dr. Francois Bénard
B.C. Cancer Agency Research Centre, 675 West 10th Avenue, Vancouver, BC, V5Z 1L3 Canada
Search for more papers by this authorCorresponding Author
Prof. Dr. David M. Perrin
Chemistry Department, UBC, 2036 Main Mall, Vancouver, B.C., V6T1Z1 Canada
Search for more papers by this authorAbstract
The stabilization of peptide secondary structure via stapling is a ubiquitous goal for creating new probes, imaging agents, and drugs. Inspired by indole-derived crosslinks found in natural peptide toxins, we employed ortho-phthalaldehydes to create isoindole staples, thus transforming inactive linear and monocyclic precursors into bioactive monocyclic and bicyclic products. Mild, metal-free conditions give an array of macrocyclic α-melanocyte-stimulating hormone (α-MSH) derivatives, of which several isoindole-stapled α-MSH analogues (Ki≈1 nm) are found to be as potent as α-MSH. Analogously, late-stage intra-annular isoindole stapling furnished a bicyclic peptide mimic of α-amanitin that is cytotoxic to CHO cells (IC50=70 μm). Given its user-friendliness, we have termed this approach FlICk (fluorescent isoindole crosslink) chemistry.
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