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Synthesis and evaluation of a radioiodinated BODIPY derivative as a thiol‐labeling agent
Author(s) -
Watanabe Hiroyuki,
Itagaki Futa,
Shimizu Yoichi,
Iikuni Shimpei,
Ono Masahiro
Publication year - 2019
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.3809
Subject(s) - bodipy , chemistry , maleimide , thiol , covalent bond , fluorescence , cysteine , combinatorial chemistry , derivative (finance) , labelling , imaging agent , biochemistry , in vivo , organic chemistry , enzyme , physics , microbiology and biotechnology , quantum mechanics , financial economics , economics , biology
Labeling agents with radioisotopes or fluorescent dyes are useful for investigating the biodistributions of biologically active proteins and peptides. Compared with molecular imaging with a single modality, dual imaging probes provide complementary information for each modality. The development of a dual radioisotope/fluorescence agent for protein labeling would thus be valuable for both preclinical and clinical applications. In this study, we designed and synthesized a radioiodinated BODIPY derivative (BODIPY‐ML) with a maleimide group as a thiol‐labeling agent. In the presence of N ‐chlorosuccinimide and 1% acetic acid, [ 125 I]BODIPY‐ML was successfully obtained at a radiochemical yield of 42%. In conjugation studies, model proteins including RGD peptides and anti‐HER2 VHH were successfully labeled with BODIPY‐ML via covalent bonds. The results demonstrated the feasibility of the radioiodinated BODIPY as a dual‐labeling agent via thiol groups.