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Radioiodination of BODIPY and its application to a nuclear and optical dual functional labeling agent for proteins and peptides.

ABSTRACT: In molecular imaging research, the development of multimodal imaging probes has recently attracted much attention. In the present study, we prepared radioiodinated BODIPY and applied it as a nuclear and optical dual functional labeling agent for proteins and peptides. We designed and synthesized [¹²⁵I]BODIPY with a N-hydroxysuccinimide (NHS) ester, and evaluated its utility as a nuclear and fluorescent dual labeling agent for proteins and peptides. In the radioiodination reaction of BODIPY-NHS with [¹²⁵I]NaI, [¹²⁵I]BODIPY-NHS was obtained at a 48% radiochemical yield. When we carried out the conjugation reaction of [¹²⁵I]BODIPY-NHS with bovine serum albumin (BSA) and RGD (Arg-Gly-Asp) peptide as a model protein and peptide, respectively, [¹²⁵I]BODIPY-BSA and [¹²⁵I]BODIPY-RGD peptide were successfully prepared at 98 and 82% radiochemical yields, respectively. Furthermore, we prepared [¹²³I]BODIPY-trastuzumab by this conjugation reaction and successfully applied it to single photon emission computed tomography (SPECT) imaging studies using tumor-bearing mice, suggesting that radioiodinated BODIPY-NHS serves as a dual functional labeling agent for proteins and peptides. Since iodine has various radioisotopes that can be used for SPECT and positron emission tomography (PET) imaging, biological research, and radiotherapy, the radioiodinated BODIPY may be extensively applicable from basic to clinical research.

SUBMITTER: Ono M

PROVIDER: S-EPMC5469783 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Radioiodination of BODIPY and its application to a nuclear and optical dual functional labeling agent for proteins and peptides.

Ono Masahiro M Watanabe Hiroyuki H Ikehata Yuki Y Ding Ning N Yoshimura Masashi M Sano Kohei K Saji Hideo H

Scientific reports 20170613 1

In molecular imaging research, the development of multimodal imaging probes has recently attracted much attention. In the present study, we prepared radioiodinated BODIPY and applied it as a nuclear and optical dual functional labeling agent for proteins and peptides. We designed and synthesized [<sup>125</sup>I]BODIPY with a N-hydroxysuccinimide (NHS) ester, and evaluated its utility as a nuclear and fluorescent dual labeling agent for proteins and peptides. In the radioiodination reaction of B ...[more]

PMID: 28611426

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Project description:Aliphatic polyesters are among materials most extensively used for producing biodegradable polymeric nanoparticles currently in development as delivery carriers and imaging agents for a range of biomedical applications. Their clinical translation requires robust particle labeling methodologies that allow reliably monitoring the fate of these formulations in complex biological environments. In the present study, a practical and versatile synthetic strategy providing conjugates of poly(D,L-lactide) representative of this class of polymers with BODIPY fluorophores varying in functional groups and excitation/emission maxima was investigated as a tool for making traceable nanoparticles. Polymer-probe conjugation was accomplished by carbodiimide-induced and 4-(dimethylamino)pyridinium 4-toluenesulfonate-catalyzed esterification of the polymer's terminal hydroxyl group, either directly with a carboxy-functionalized fluorophore or with amine-protected amino acids (Boc-glycine or Boc-6-aminohexanoic acid). In the latter case, the amino acid-derivatized polymeric precursors were reacted with amine-reactive BODIPY dyes after the removal of the protective group. Unlike nanoparticles encapsulating a strongly hydrophobic BODIPY505/515 (logPo/w = 4.3), nanoparticles labeled covalently with its carboxy-functionalized analogue (BODIPY FL) demonstrated stable particle-tracer association under perfect sink conditions. Furthermore, in contrast to the encapsulated dye rapidly partitioning from particles onto cell membranes but not stably retained by cultured cells, the internalization of the covalently attached probe was an irreversible process requiring the presence of serum, consistent with active nanoparticle uptake by endocytosis. In conclusion, the conjugation of particle-forming polymers with BODIPY fluorophores offers an effective and accessible labeling strategy for making traceable polyester-based biodegradable nanoparticles and is expected to facilitate their development and optimization as therapeutic carriers and diagnostic agents.

Dataset Information

Radioiodination of BODIPY and its application to a nuclear and optical dual functional labeling agent for proteins and peptides.

Publications

Radioiodination of BODIPY and its application to a nuclear and optical dual functional labeling agent for proteins and peptides.

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