PT  - JOURNAL ARTICLE
AU  - Lin, Wei-Yu
AU  - Liu, Kan
AU  - Olma, Sebastian
AU  - Sirk, Shannon
AU  - Lepin, Eric
AU  - Olafsen, Tove
AU  - Wu, Anna
AU  - Shen, Clifton Kwang-Fu
TI  - Synthesis of 4-[18F]fluorophenyl-4'-nitrophenylcarbamate ([18F]FPNPC) and N-(4-[18F]fluorophenyl)-N-(2-maleimidoethyl)urea ([18F]FPMEU) for fluorine-18 labeling biomolecules
DP  - 2009 May 01
TA  - Journal of Nuclear Medicine
PG  - 1115--1115
VI  - 50
IP  - supplement 2
4099  - http://jnm.snmjournals.org/content/50/supplement_2/1115.short
4100  - http://jnm.snmjournals.org/content/50/supplement_2/1115.full
SO  - J Nucl Med2009 May 01; 50
AB  - 1115 Learning Objectives We developed two different 18F-tags, [18F]FPNPC and [18F]FPMEU, for radiolabeling of biomolecules. [18F]FPNPC can be used to react randomly with primary amines of lysines, while [18F]FPMEU can conjugate site-specifically to a thiol group of a cysteine. Summary: A radiosynthesis of [18F]FPNPC following a described synthesis was carried out. Starting with the radiofluorination of dinitrobenzene to get 4-[18F]fluoronitrobenzene, reduction of the remaining nitro group using H3PO3 and Pd black resulted in 4-[18F]fluoroaniline. It was activated with 4-nitrophenylchloroformate to give a radiochemically pure [18F]FPNPC after three solid phase extraction (SPE) purifications. The RCY is up to 60% referred to [18F]F- after 65 min of synthesis. The novel thiophilic 18F-tag, [18F]FPMEU, can be obtained one step from [18F]FPNPC after reaction with N-(2-aminoethyl)maleimide. Within an additional 35 min, the final RCY is 40 % (n>10) after SPE purification. A HER2 targeting peptide (KGSGKCCYSL) was chosen as a model compound to be radiolabeled with [18F]FPNPC. After 15 min, high RCY can be achieved (70%). [18F]FPMEU conjugation also give high labeling yield (85%), with freshly prepared HER2-targeting peptide using TCEP as reducant agent for thiol group in 30 min. We are optimizing the entire reaction sequences so that it can be adaptable for automation and microfluidic-based radiolabeling. The biological evaluations are well under progress.