Syntheses and evaluation of a homologous series of aza-vesamicol as improved radioiodine-labeled probes for sigma-1 receptor imaging

Ogawa, Kenji; Masuda, Ryohei; Mishiro, Kenji; Wang, Mengfei; Kozaka, Takashi; Shiba, Kazuhiro; Kinuya, Seigo; Odani, Akira

doi:10.1016/j.bmc.2019.03.054

Cited by 5 publications

(18 citation statements)

References 27 publications

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“…We recently reported the simple one-step reaction of an 125 I-and 211 At-labeling method of a monomeric RGD peptide via a Pd-catalyzed stannylation reaction after deprotection [8], whereas, in this study, deprotection after the 125/131 I-labeling reaction, namely the two-step reaction, was performed because the Pd-catalyzed stannylation reaction failed after deprotection. The reason for this failure is not apparent; however, the yield of the stannylation reaction of the monomeric RGD peptide is lower (25%) than that of other stannylation reactions in previous studies (45-75%) [8,13,14]. We suppose that this difference might be derived from impeding the efficient stannylation reaction by functional groups of the amino acid residues of RGD peptides.…”

Section: Discussionmentioning

confidence: 71%

Synthesis and Evaluation of a Dimeric RGD Peptide as a Preliminary Study for Radiotheranostics with Radiohalogens

et al. 2021

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We recently developed 125I- and 211At-labeled monomer RGD peptides using a novel radiolabeling method. Both labeled peptides showed high accumulation in the tumor and exhibited similar biodistribution, demonstrating their usefulness for radiotheranostics. This study applied the labeling method to a dimer RGD peptide with the aim of gaining higher accumulation in tumor tissues based on improved affinity with αvβ3 integrin. We synthesized an iodine-introduced dimer RGD peptide, E[c(RGDfK)] (6), and an 125/131I-labeled dimer RGD peptide, E[c(RGDfK)]{[125/131I]c[RGDf(4-I)K]} ([125/131I]6), and evaluated them as a preliminary step to the synthesis of an 211At-labeled dimer RGD peptide. The affinity of 6 for αvβ3 integrin was higher than that of a monomer RGD peptide. In the biodistribution experiment at 4 h postinjection, the accumulation of [125I]6 (4.12 ± 0.42% ID/g) in the tumor was significantly increased compared with that of 125I-labeled monomer RGD peptide (2.93 ± 0.08% ID/g). Moreover, the accumulation of [125I]6 in the tumor was greatly inhibited by co-injection of an excess RGD peptide. However, a single injection of [131I]6 (11.1 MBq) did not inhibit tumor growth in tumor-bearing mice. We expect that the labeling method for targeted alpha therapy with 211At using a dimer RGD peptide could prove useful in future clinical applications.

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Section: Discussionmentioning

confidence: 71%

Synthesis and Evaluation of a Dimeric RGD Peptide as a Preliminary Study for Radiotheranostics with Radiohalogens

et al. 2021

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“…Radiotheranostics contributes to the concept of personalized precision medicine, and represents a tool for improving patient outcomes, enhancement of therapy efficacy, and predicting adverse effects. [184][185][186] σ1Rs are highly expressed in different types of tumors and several peer-reviewed studies show the therapeutic and diagnostic potential of σ1R ligands in cancer. 154,[187][188][189] Therefore, σ1R targeted radionuclide therapies are considered to be radiotheranostics.…”

Section: Radiotheranosticsmentioning

confidence: 99%

“…This information is used as a diagnostic biomarker that can determine the efficacy of the σ1R probe as a therapy and measure tumor shrinking. 186 Ogawa, K. introduced some σ1R radiolabelled probes as "a companion diagnostic test of therapeutic agents," 184 and reported the use of a radiolabelled σR ligand for receptor radionuclide therapy for the first time. 190 The iodinated vesamicol derivative (+)-2-[4-(4-iodophenyl)piperidino] cyclohexanol [(+)-pIV] is a σ1R ligand that showed high affinity (K i = 1.30 nM) at σ1Rs over VAChT (K i = 1260 nM).…”

Section: Radiotheranosticsmentioning

confidence: 99%

“…Compared to the parent compound, [ 125 I]1 showed better biodistribution as a σ1R imaging probe at 24 h postinjection. 184 Radiotheranostics could be also applied in pain management and [ 18 F]FTC-146 could be considered as a potential agent. The diagnostic agent [ 18 F]FTC-146 was able to accumulate at injured sciatic nerves created in a rat model and accurately detected the peripheral nerve injury and neuroinflammatory areas, which correlated to pain sensitivity, using PET/MR imaging and ex vivo…”

Section: Radiotheranosticsmentioning

confidence: 99%

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In vitroandin vivosigma 1 receptor imaging studies in different disease states

Agha

McCurdy

2021

RSC Med. Chem.

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“…5A) was prepared by a standard halogenation reaction using the corresponding tributylstannyl precursor and was evaluated. 57…”

Section: Sigma-1 Receptor Targeted Probesmentioning

confidence: 99%

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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Syntheses and evaluation of a homologous series of aza-vesamicol as improved radioiodine-labeled probes for sigma-1 receptor imaging

Cited by 5 publications

References 27 publications

Synthesis and Evaluation of a Dimeric RGD Peptide as a Preliminary Study for Radiotheranostics with Radiohalogens

Synthesis and Evaluation of a Dimeric RGD Peptide as a Preliminary Study for Radiotheranostics with Radiohalogens

In vitroandin vivosigma 1 receptor imaging studies in different disease states

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

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