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Synthesis of 18 F‐radiolabeled organophosphine fluorides for thiol‐chemoselective peptide conjugation
Author(s) -
Zhuang Huanglan,
Guo Zhide,
Zhuang Rongqiang,
Zhang Xianzhong
Publication year - 2020
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3882
Subject(s) - chemistry , thiol , peptide , peptide synthesis , combinatorial chemistry , radiochemistry , stereochemistry , organic chemistry , biochemistry
Two 18 F‐radiolabeled organofluorophosphine fluorides ([ 18 F] 4 and [ 18 F] 7 ) for chemoselective thiol‐conjugation were designed and synthesized via 18 F– 19 F isotopic exchange reaction. This simple and rapid radiofluorination produced both 18 F‐radiolabeled fluorides in excellent radiochemical yields (>94%) and radiochemical purity. The optimal reaction conditions are 0.05‐mg substrate, 0.69 mg of potassium carbonate, and dried [ 18 F]F − were mixed in 100‐μl anhydrous acetonitrile at room temperature for 5 min. Both of [ 18 F] 4 and [ 18 F] 7 showed specificity for thiol‐conjugation with cysteine and have been used in the radiosynthesis of c (RGDfC). The [ 18 F] 7 with an adamantanyl‐hindered substituent displayed superior in vitro and in vivo stability.