| 5-O-(4-[(125)I]Iodobenzyl)-L-ascorbic Acid: Electrophilic Radioiodination and Biodistribution in Mice. | |
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MedLine Citation:
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PMID: 22293483 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
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As a part of our efforts to develop potential imaging agents for ascorbate bioactivity, 5-O-(4-[(125)I]iodobenzyl)-L-ascorbic acid ([(125)I]1) was prepared through a two-step sequence which involved radioiodo-destannylation of a protected tributylstannyl precursor 6, followed by hydrolysis in acidic methanol of the protecting groups in 61% overall radiochemical yield, with a radiochemical purity of over 98% and a specific activity of more than 15.4 GBq/μmol. Tissue distribution of [(125)I]1 in tumor-bearing mice showed signs of distribution profiles similar to the reported results for 6-deoxy-6-[(18)F]fluoro-L-ascorbic (6-(18)FAsA) acid and 6-deoxy-6-[(131)I]iodo-L-ascorbic acid (6-(131)IAsA) but with notable differences in the adrenal glands, in which considerably lower uptake of radioactivity and rapid clearance with time were observed. Pretreatment of mice with a known inhibitor of ascorbate transport, sulfinpyrazone, did not produce any significant change in the adrenal uptake of radioactivity after injection of [(125)I]1 compared to the control, suggesting that uptake in the adrenal glands is independent of the sodium-dependent vitamin C transporter 2 transport mechanism. Introduction of a bulky substituent at C-5 on AsA, such as an iodobenzyloxy group, may not be suitable for the design of analogs that may still be able to maintain characteristic distribution properties in vivo seen with AsA itself. |
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Authors:
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Jintaek Kim; Tomohiro Kino; Hiroharu Kato; Fumihiko Yamamoto; Kohei Sano; Takahiro Mukai; Minoru Maeda |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chemical & pharmaceutical bulletin Volume: 60 ISSN: 1347-5223 ISO Abbreviation: Chem. Pharm. Bull. Publication Date: 2012 |
Date Detail:
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Created Date: 2012-02-01 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0377775 Medline TA: Chem Pharm Bull (Tokyo) Country: Japan |
Other Details:
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Languages: eng Pagination: 235-40 Citation Subset: IM |
Affiliation:
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Graduate School of Pharmaceutical Sciences, Kyushu University. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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