Comparison of Radioiodine- or Radiobromine-Labeled RGD Peptides between Direct and Indirect Labeling Methods

Ogawa, Kenji; Takeda, Takuya; Yokokawa, Masaru; Yu, Jing; Makino, Akihiro; Kiyono, Yasushi; Shiba, Kazuhiro; Kinuya, Seigo; Odani, Akira

doi:10.1248/cpb.c18-00081

Cited by 26 publications

(27 citation statements)

References 27 publications

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“…It has been reported that major non-collagenous bone proteins, such as osteopontin and bone sialoprotein, contain many acidic amino acids (aspartic acid (Asp) or glutamic acid (Glu)) in their amino acid sequences, whose offers HA binding ability, [26][27][28] and polyglutamic acid peptides and polyaspartic acid peptides could be carriers of drugs to bone because of their high affinity for HA. [29][30][31] To evaluate acidic amino acid peptides as a carriers of radiometals to bone lesions, I designed [ 67 . 32,33) An attractive radionuclide for PET clinically is 68 Ga (T 1/2 = 67.7 min) because of its radiophysical properties.…”

Section: Biographymentioning

confidence: 99%

“…34) Since it is a 68 Ge/ 68 Ga generator-produced radionuclide, an on-site cyclotron is not required. Although I am interested in 68 Ga, 67 Ga (T 1/2 = 3.26 d) was used in these acidic amino acid peptide carrier studies as an alternative radionuclide because of its long half-life. An excellent chelator for radiotheranostics is the DOTA ligand because it forms stable complexes with trivalent metals, such as 67/68 Not only clinically used [ 99 m Tc] Tc-bisphosphonate complexes but also my synthesized probes can accumulate in metastatic osteoblastic lesions well, however it is difficult to accumulate in metastatic osteolytic lesions, because the bone accumulation mechanism of these probes is based on a high affinity for HA.…”

Section: Biographymentioning

confidence: 99%

“…63) Radiolabeled RGD peptides have been investigated for not only imaging and determination of α v β 3 integrin expression but also for radionuclide therapy. [64][65][66][67] However, 211 At-labeled RGD peptides have never to date been reported. Thus, I aimed in this study to determine their radiotheranostics potential by coupling 211 At-labeled and 123 I-labeled RGD peptides.…”

Section: Rgd Peptidementioning

confidence: 99%

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Development of Diagnostic and Therapeutic Probes with Controlled Pharmacokinetics for Use in Radiotheranostics

Ogawa

2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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The word "theranostics," a portmanteau word made by combining "therapeutics" and "diagnostics," refers to a personalized medicine concept. Recently, the word, "radiotheranostics," has also been used in nuclear medicine as a term that refer to the use of radioisotopes for combined imaging and therapy. For radiotheranostics, a diagnostic probe and a corresponding therapeutic probe can be prepared by introducing diagnostic and therapeutic radioisotopes into the same precursor. These diagnostic and therapeutic probes can be designed to show equivalent pharmacokinetics, which is important for radiotheranostics. As imaging can predict the absorbed radiation dose and thus the therapeutic and side effects, radiotheranostics can help achieve the goal of personalized medicine. In this review, I discuss the use of radiolabeled probes targeting bone metastases, sigma-1 receptor, and α V β 3 integrin for radiotheranostics.

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Section: Biographymentioning

confidence: 99%

Section: Biographymentioning

confidence: 99%

Section: Rgd Peptidementioning

confidence: 99%

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Development of Diagnostic and Therapeutic Probes with Controlled Pharmacokinetics for Use in Radiotheranostics

Ogawa

2019

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…I-124 is an attractive radionuclide for the development of mAbs as potential immunoPET imaging pharmaceuticals due to its physical properties (decay characteristics and half-life), easy and routine production by cyclotrons [ 21 ], and well-established methodologies for radioiodination [ 22 , 23 , 24 ]. For example, 124 I has been used to label small molecules, peptides, mAbs, proteins, and antibody fragments for tumor imaging [ 25 , 26 , 27 , 28 ], in thyroid and parathyroid cancer imaging [ 29 , 30 , 31 ], to label single molecules like meta-iodobenzylguanidine (MIBG), amino acids, and fatty acids among others for investigation of several heart and brain diseases, as well as functional studies of neurotransmitter receptors [ 32 , 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

Radiochemistry, Production Processes, Labeling Methods, and ImmunoPET Imaging Pharmaceuticals of Iodine-124

Kumar

Ghosh

2021

Molecules

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Target-specific biomolecules, monoclonal antibodies (mAb), proteins, and protein fragments are known to have high specificity and affinity for receptors associated with tumors and other pathological conditions. However, the large biomolecules have relatively intermediate to long circulation half-lives (>day) and tumor localization times. Combining superior target specificity of mAbs and high sensitivity and resolution of the PET (Positron Emission Tomography) imaging technique has created a paradigm-shifting imaging modality, ImmunoPET. In addition to metallic PET radionuclides, 124I is an attractive radionuclide for radiolabeling of mAbs as potential immunoPET imaging pharmaceuticals due to its physical properties (decay characteristics and half-life), easy and routine production by cyclotrons, and well-established methodologies for radioiodination. The objective of this report is to provide a comprehensive review of the physical properties of iodine and iodine radionuclides, production processes of 124I, various 124I-labeling methodologies for large biomolecules, mAbs, and the development of 124I-labeled immunoPET imaging pharmaceuticals for various cancer targets in preclinical and clinical environments. A summary of several production processes, including 123Te(d,n)124I, 124Te(d,2n)124I, 121Sb(α,n)124I, 123Sb(α,3n)124I, 123Sb(3He,2n)124I, natSb(α, xn)124I, natSb(3He,n)124I reactions, a detailed overview of the 124Te(p,n)124I reaction (including target selection, preparation, processing, and recovery of 124I), and a fully automated process that can be scaled up for GMP (Good Manufacturing Practices) production of large quantities of 124I is provided. Direct, using inorganic and organic oxidizing agents and enzyme catalysis, and indirect, using prosthetic groups, 124I-labeling techniques have been discussed. Significant research has been conducted, in more than the last two decades, in the development of 124I-labeled immunoPET imaging pharmaceuticals for target-specific cancer detection. Details of preclinical and clinical evaluations of the potential 124I-labeled immunoPET imaging pharmaceuticals are described here.

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“…In this study, we describe the development of novel radiobrominated probes for PDGFRβ imaging. The strategy of these probes are similer to that of our previous developed radioiodine-labeled probes 12 , but differece between iodine and boromine should alter their characteristics and biodistribution of the probes 25 – 27 , and the difference of radionuclides may give much impact in clinical nuclear medicine. Two brominated 1 derivatives, 1-{5-bromo-2-[5-(2-methoxyethoxy)-1 H -benzo[ d ]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine ( 2 ) and N -3-bromobenzoyl-1-{2-[5-(2-methoxyethoxy)-1 H -benzo[ d ]imidazol-1-yl]quinolin-8-yl}-piperidin-4-amine ( 3 ), were designed and synthesized.…”

Section: Introductionmentioning

confidence: 99%

Radiobrominated benzimidazole-quinoline derivatives as Platelet-derived growth factor receptor beta (PDGFRβ) imaging probes

Effendi

Mishiro

Takarada

et al. 2018

Sci Rep

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Platelet-derived growth factor receptor beta (PDGFRβ) affects in numerous human cancers and has been recognized as a promising molecular target for cancer therapies. The overexpression of PDGFRβ could be a biomarker for cancer diagnosis. Radiolabeled ligands having high affinity for the molecular target could be useful tools for the imaging of overexpressed receptors in tumors. In this study, we aimed to develop radiobrominated PDGFRβ ligands and evaluate their effectiveness as PDGFRβ imaging probes. The radiolabeled ligands were designed by modification of 1-{2-[5-(2-methoxyethoxy)-1H- benzo[d]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine (1), which shows selective inhibition profile toward PDGFRβ. The bromine atom was introduced directly into C-5 of the quinoline group of 1, or indirectly by the conjugation of 1 with the 3-bromo benzoyl group. [77Br]1-{5-Bromo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinoline-8-yl}piperidin-4-amine ([77Br]2) and [77Br]-N-3-bromobenzoyl-1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}-piperidin-4-amine ([77Br]3) were prepared using a bromodestannylation reaction. In a cellular uptake study, [77Br]2 and [77Br]3 more highly accumulatd in BxPC3-luc cells (PDGFRβ-positive) than in MCF7 cells (PDGFRβ-negative), and their accumulation was significantly reduced by pretreatment with inhibitors. In biodistribution experiments, [77Br]2 accumulation was higher than [77Br]3 accumulation at 1 h postinjection. These findings suggest that [76Br]2 is more promising for positron emission tomography (PET) imaging of PDGFRβ than [76Br]3.

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Comparison of Radioiodine- or Radiobromine-Labeled RGD Peptides between Direct and Indirect Labeling Methods

Cited by 26 publications

References 27 publications

Development of Diagnostic and Therapeutic Probes with Controlled Pharmacokinetics for Use in Radiotheranostics

Development of Diagnostic and Therapeutic Probes with Controlled Pharmacokinetics for Use in Radiotheranostics

Radiochemistry, Production Processes, Labeling Methods, and ImmunoPET Imaging Pharmaceuticals of Iodine-124

Radiobrominated benzimidazole-quinoline derivatives as Platelet-derived growth factor receptor beta (PDGFRβ) imaging probes

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