Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18 F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents
The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and i...
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| Veröffentlicht in: | Journal of medicinal chemistry 2020-10, Vol.63 (20), p.12008-12022 |
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| container_title | Journal of medicinal chemistry |
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| creator | Pickel, Thomas C Voll, Ronald J Yu, Weiping Wang, Zhaobin Nye, Jonathon A Bacsa, John Olson, Jeffrey J Liebeskind, Lanny S Goodman, Mark M |
| description | The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and in greater than 99% radiochemical purity. Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection. |
| doi_str_mv | 10.1021/acs.jmedchem.0c01302 |
| format | Article |
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Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/acs.jmedchem.0c01302</identifier><identifier>PMID: 32946235</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Carboxylic Acids - chemical synthesis ; Carboxylic Acids - chemistry ; Cyclopentanes - chemical synthesis ; Cyclopentanes - chemistry ; Dose-Response Relationship, Drug ; Fluorine Radioisotopes ; Glioblastoma - diagnostic imaging ; Humans ; Male ; Molecular Conformation ; Molecular Structure ; Positron-Emission Tomography ; Prostatic Neoplasms - diagnostic imaging ; Radiopharmaceuticals - chemical synthesis ; Radiopharmaceuticals - chemistry ; Radiopharmaceuticals - pharmacokinetics ; Rats ; Stereoisomerism ; Structure-Activity Relationship ; Tissue Distribution ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 2020-10, Vol.63 (20), p.12008-12022</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a263t-8eec77ffa9b54f261a869eefa07c7081b26dc6e9b7dbc4e4304d47bd49ca10a73</citedby><cites>FETCH-LOGICAL-a263t-8eec77ffa9b54f261a869eefa07c7081b26dc6e9b7dbc4e4304d47bd49ca10a73</cites><orcidid>0000-0002-2223-6618 ; 0000-0002-3438-1185 ; 0000-0001-5681-4458</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.0c01302$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jmedchem.0c01302$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32946235$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pickel, Thomas C</creatorcontrib><creatorcontrib>Voll, Ronald J</creatorcontrib><creatorcontrib>Yu, Weiping</creatorcontrib><creatorcontrib>Wang, Zhaobin</creatorcontrib><creatorcontrib>Nye, Jonathon A</creatorcontrib><creatorcontrib>Bacsa, John</creatorcontrib><creatorcontrib>Olson, Jeffrey J</creatorcontrib><creatorcontrib>Liebeskind, Lanny S</creatorcontrib><creatorcontrib>Goodman, Mark M</creatorcontrib><title>Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18 F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and in greater than 99% radiochemical purity. Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection.</description><subject>Animals</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - chemistry</subject><subject>Cyclopentanes - chemical synthesis</subject><subject>Cyclopentanes - chemistry</subject><subject>Dose-Response Relationship, Drug</subject><subject>Fluorine Radioisotopes</subject><subject>Glioblastoma - diagnostic imaging</subject><subject>Humans</subject><subject>Male</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Positron-Emission Tomography</subject><subject>Prostatic Neoplasms - diagnostic imaging</subject><subject>Radiopharmaceuticals - chemical synthesis</subject><subject>Radiopharmaceuticals - chemistry</subject><subject>Radiopharmaceuticals - pharmacokinetics</subject><subject>Rats</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Tissue Distribution</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kNtOGzEQhq0KVALlDRDyJZVwGB-yh8sQJRQJqVWB69WsdzYY7a4je4Oa9-mD1hDoJVczmvm_kf0xdiZhKkHJK7Rx-txTY5-on4IFqUF9YRM5UyBMAeaATQCUEipT-ogdx_gMAFoq_ZUdaVWaNJ5N2N_73TA-UXTxkv_GxvkOa-rcsL7kODT8Og382lns-PIFuy2Ozg_ctzwx3LrI70cK5F30PYX4upBi3rvBCy1W3dYHL4y4aPedLPjq-2JnO7-hYcSBhBQLDLX_s-uc5XPrGo6R_1o-8Nse1-kRfL5OyfiNHbbYRTp9ryfscbV8WPwQdz9vbhfzO4Eq06MoiGyety2W9cy0KpNYZCVRi5DbHApZq6yxGZV13tTWkNFgGpPXjSktSsBcnzCzv2uDjzFQW22C6zHsKgnVq_QqSa8-pFfv0hN2vsc22zrt_kMfllMA9oE33G_DkH7x-c1_SH6Snw</recordid><startdate>20201022</startdate><enddate>20201022</enddate><creator>Pickel, Thomas C</creator><creator>Voll, Ronald J</creator><creator>Yu, Weiping</creator><creator>Wang, Zhaobin</creator><creator>Nye, Jonathon A</creator><creator>Bacsa, John</creator><creator>Olson, Jeffrey J</creator><creator>Liebeskind, Lanny S</creator><creator>Goodman, Mark M</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2223-6618</orcidid><orcidid>https://orcid.org/0000-0002-3438-1185</orcidid><orcidid>https://orcid.org/0000-0001-5681-4458</orcidid></search><sort><creationdate>20201022</creationdate><title>Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18 F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents</title><author>Pickel, Thomas C ; Voll, Ronald J ; Yu, Weiping ; Wang, Zhaobin ; Nye, Jonathon A ; Bacsa, John ; Olson, Jeffrey J ; Liebeskind, Lanny S ; Goodman, Mark M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a263t-8eec77ffa9b54f261a869eefa07c7081b26dc6e9b7dbc4e4304d47bd49ca10a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Animals</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - chemistry</topic><topic>Cyclopentanes - chemical synthesis</topic><topic>Cyclopentanes - chemistry</topic><topic>Dose-Response Relationship, Drug</topic><topic>Fluorine Radioisotopes</topic><topic>Glioblastoma - diagnostic imaging</topic><topic>Humans</topic><topic>Male</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Positron-Emission Tomography</topic><topic>Prostatic Neoplasms - diagnostic imaging</topic><topic>Radiopharmaceuticals - chemical synthesis</topic><topic>Radiopharmaceuticals - chemistry</topic><topic>Radiopharmaceuticals - pharmacokinetics</topic><topic>Rats</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Tissue Distribution</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pickel, Thomas C</creatorcontrib><creatorcontrib>Voll, Ronald J</creatorcontrib><creatorcontrib>Yu, Weiping</creatorcontrib><creatorcontrib>Wang, Zhaobin</creatorcontrib><creatorcontrib>Nye, Jonathon A</creatorcontrib><creatorcontrib>Bacsa, John</creatorcontrib><creatorcontrib>Olson, Jeffrey J</creatorcontrib><creatorcontrib>Liebeskind, Lanny S</creatorcontrib><creatorcontrib>Goodman, Mark M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pickel, Thomas C</au><au>Voll, Ronald J</au><au>Yu, Weiping</au><au>Wang, Zhaobin</au><au>Nye, Jonathon A</au><au>Bacsa, John</au><au>Olson, Jeffrey J</au><au>Liebeskind, Lanny S</au><au>Goodman, Mark M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18 F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2020-10-22</date><risdate>2020</risdate><volume>63</volume><issue>20</issue><spage>12008</spage><epage>12022</epage><pages>12008-12022</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and in greater than 99% radiochemical purity. Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>32946235</pmid><doi>10.1021/acs.jmedchem.0c01302</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0002-2223-6618</orcidid><orcidid>https://orcid.org/0000-0002-3438-1185</orcidid><orcidid>https://orcid.org/0000-0001-5681-4458</orcidid></addata></record> |
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| subjects | Animals Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Cyclopentanes - chemical synthesis Cyclopentanes - chemistry Dose-Response Relationship, Drug Fluorine Radioisotopes Glioblastoma - diagnostic imaging Humans Male Molecular Conformation Molecular Structure Positron-Emission Tomography Prostatic Neoplasms - diagnostic imaging Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - chemistry Radiopharmaceuticals - pharmacokinetics Rats Stereoisomerism Structure-Activity Relationship Tissue Distribution Tumor Cells, Cultured |
| title | Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18 F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents |
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