title: F-18 labeling protocol of peptides based on chemically orthogonal strain-promoted cycloaddition under physiologically friendly reaction conditions.
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.
authors: Department of Nuclear Medicine, Cyclotron Research Center, Research Institute of Clinical Medicine, Chonbuk National University Medical School, Jeonju, Jeonbuk 561-712, Korea.
authors: Kalme
authors: K
authors: Sachin
authors: Vinod H
authors: VH
authors: Jadhav
authors: Eun-Mi
authors: EM
authors: Kim
authors: Hye Lan
authors: HL
authors: Kim
authors: Sang Bong
authors: SB
authors: Lee
authors: Hwan-Jeong
authors: HJ
authors: Jeong
authors: Seok Tae
authors: ST
authors: Lim
authors: Myung-Hee
authors: MH
authors: Sohn
authors: Dong Wook
authors: DW
authors: Kim
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000818:Animals; D001372:Aza Compounds / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D061565:Cycloaddition Reaction / Q000379:methods*; D005260:Female; D007457:Iodine Radioisotopes / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods*; D051379:Mice; D010455:Peptides / Q000737:chemistry* / Q000493:pharmacokinetics; D049268:Positron-Emission Tomography; D011849:Radioactive Tracers
chemical_list: D000480:Alkynes; D001372:Aza Compounds; D001386:Azides; D007457:Iodine Radioisotopes; D010455:Peptides; D011849:Radioactive Tracers