F-18 labeling protocol of peptides based on chemically orthogonal strain-promoted cycloaddition under physiologically friendly reaction conditions.
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| Abstract |
We introduce the high-throughput synthesis of various (18)F-labeled peptide tracers by a straightforward (18)F-labeling protocol based on a chemo-orthogonal strain-promoted alkyne azide cycloaddition (SPAAC) using aza-dibenzocyclootyne-substituted peptides as precursors with (18)F-azide synthon to develop peptide based positron emission tomography (PET) molecular imaging probes. The SPAAC reaction and subsequent chemo-orthogonal purification reaction with azide resin proceeded quickly and selectively under physiologically friendly reaction conditions (i.e., toxic chemical reagents-free, aqueous medium, room temperature, and pH ≈7), and provided four (18)F-labeled tumor targetable bioactive peptides such as cyclic Arg-Gly-Asp (cRGD) peptide, bombesin (BBN), c-Met binding peptide (cMBP), and apoptosis targeting peptide (ApoPep) in high radiochemical yields as direct injectable solutions without any HPLC purification and/or formulation processes. In vitro binding assay and in vivo PET molecular imaging study using the (18)F-labeled cRGD peptide also demonstrated a successful application of our (18)F-labeling protocol.
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| Authors | Kalme Sachin, Vinod H Jadhav, Eun-Mi Kim, Hye Lan Kim, Sang Bong Lee, Hwan-Jeong Jeong, Seok Tae Lim, Myung-Hee Sohn, Dong Wook Kim |
| Journal | Bioconjugate chemistry (Bioconjug Chem) Vol. 23 Issue 8 Pg. 1680-6 (Aug 15 2012) ISSN: 1520-4812 [Electronic] United States |
| PMID | 22770524 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't) |
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