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j.bmc.2011.03.059.pdf | 238.37 kB | Adobe PDF | 見る/開く |
タイトル: | Concise site-specific synthesis of DTPA-peptide conjugates: application to imaging probes for the chemokine receptor CXCR4. |
著者: | Masuda, Ryo Oishi, Shinya https://orcid.org/0000-0002-3246-4809 (unconfirmed) Ohno, Hiroaki https://orcid.org/0000-0002-3246-4809 (unconfirmed) Kimura, Hiroyuki Saji, Hideo Fujii, Nobutaka |
著者名の別形: | 大石, 真也 |
キーワード: | CXCR4 DTPA Molecular imaging |
発行日: | 15-May-2011 |
出版者: | Elsevier BV |
誌名: | Bioorganic & medicinal chemistry |
巻: | 19 |
号: | 10 |
開始ページ: | 3216 |
終了ページ: | 3220 |
抄録: | Diethylenetriaminepentaacetic acid (DTPA) is a useful chelating agent for radionuclides such as (68)Ga, (99m)Tc and (111)In, which are applicable to nuclear medicine imaging. In this study, we established a facile synthetic protocol for the production of mono-DTPA-conjugated peptide probes. A novel monoreactive DTPA precursor reagent was synthesized in two steps using the chemistry of the o-nitrobenzenesulfonyl (Ns) protecting group, and under mild conditions this DTPA precursor was incorporated onto an N(ε)-bromoacetylated Lys of a protected peptide resin. The site-specific DTPA conjugation was facilitated by using a highly acid-labile 4-methyltrityl (Mtt) protecting group for the target site of the bioactive peptide during the solid-phase synthesis. A combination of both techniques yielded peptides with disulfide bonds, such as octreotide and polyphemusin II-derived CXCR4 antagonists. DTPA-peptide conjugates were purified in a single step following cleavage from the resin and disulfide bond formation. This site-specific on-resin construction strategy was used for the design and synthesis of a novel In-DTPA-labeled CXCR4 antagonist, which exhibited highly potent inhibitory activity against SDF-1-CXCR4 binding. |
著作権等: | © 2011 Elsevier Ltd. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/159701 |
DOI(出版社版): | 10.1016/j.bmc.2011.03.059 |
PubMed ID: | 21524584 |
出現コレクション: | 学術雑誌掲載論文等 |
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