Synthesis and Preliminary Biological Evaluation of (3-Iodobenzoyl)norbiotinamide and ((5-Iodo-3-pyridinyl)carbonyl)norbiotinamide: Two Radioiodinated Biotin Conjugates with Improved Stability
A new class of radioiodinated biotin conjugates is described in which the amido bond between biotin and the labeled prosthetic group is reversed. One conjugate, (3-[125I]iodobenzoyl)norbiotinamide (4c, [125I]IBB) was labeled with Na125I in one step from (3-(tributylstannyl)benzoyl)norbiotinamide (4b...
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| Veröffentlicht in: | Bioconjugate chemistry 1997-03, Vol.8 (2), p.179-186 |
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| container_title | Bioconjugate chemistry |
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| creator | Foulon, Catherine F Alston, Kevin L Zalutsky, Michael R |
| description | A new class of radioiodinated biotin conjugates is described in which the amido bond between biotin and the labeled prosthetic group is reversed. One conjugate, (3-[125I]iodobenzoyl)norbiotinamide (4c, [125I]IBB) was labeled with Na125I in one step from (3-(tributylstannyl)benzoyl)norbiotinamide (4b, TBB) via a demetalation reaction. However, the analogous reaction with ((5-(tributylstannyl)-3-pyridinyl)carbonyl)norbiotinamide (6b, TPB) failed to yield ((5-[131I]iodo-3-pyridinyl)carbonyl)norbiotinamide (6c, [131I]IPB), necessitating a two-step approach for synthesizing [131I]IPB. The binding of [125I]IBB and [131I]IPB to streptavidin in vitro was identical to that of biotinyl-3-[125I]iodoanilide, a conjugate with an amido bond with normal configuration. Both [125I]IBB and [131I]IPB were stable in serum while the first-generation compound was rapidly degraded. The biodistribution patterns of [125I]IBB and [131I]IPB in mice are consistent with limited degradation of these conjugates by biotinidase and deiodinases. |
| doi_str_mv | 10.1021/bc970006m |
| format | Article |
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One conjugate, (3-[125I]iodobenzoyl)norbiotinamide (4c, [125I]IBB) was labeled with Na125I in one step from (3-(tributylstannyl)benzoyl)norbiotinamide (4b, TBB) via a demetalation reaction. However, the analogous reaction with ((5-(tributylstannyl)-3-pyridinyl)carbonyl)norbiotinamide (6b, TPB) failed to yield ((5-[131I]iodo-3-pyridinyl)carbonyl)norbiotinamide (6c, [131I]IPB), necessitating a two-step approach for synthesizing [131I]IPB. The binding of [125I]IBB and [131I]IPB to streptavidin in vitro was identical to that of biotinyl-3-[125I]iodoanilide, a conjugate with an amido bond with normal configuration. Both [125I]IBB and [131I]IPB were stable in serum while the first-generation compound was rapidly degraded. The biodistribution patterns of [125I]IBB and [131I]IPB in mice are consistent with limited degradation of these conjugates by biotinidase and deiodinases.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc970006m</identifier><identifier>PMID: 9095358</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Bacterial Proteins - metabolism ; Biotin - analogs & derivatives ; Biotin - chemical synthesis ; Biotin - chemistry ; Drug Stability ; In Vitro Techniques ; Iodine Radioisotopes - pharmacokinetics ; Mice ; Mice, Inbred BALB C ; Molecular Structure ; Radiopharmaceuticals - chemical synthesis ; Radiopharmaceuticals - pharmacokinetics ; Streptavidin ; Tissue Distribution</subject><ispartof>Bioconjugate chemistry, 1997-03, Vol.8 (2), p.179-186</ispartof><rights>Copyright © 1997 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-6b79bc1b7286f8fc951330f8b64c21811d600bb8acefb7c8ac759d5d296a784f3</citedby><cites>FETCH-LOGICAL-a348t-6b79bc1b7286f8fc951330f8b64c21811d600bb8acefb7c8ac759d5d296a784f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc970006m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc970006m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2756,27067,27915,27916,56729,56779</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9095358$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Foulon, Catherine F</creatorcontrib><creatorcontrib>Alston, Kevin L</creatorcontrib><creatorcontrib>Zalutsky, Michael R</creatorcontrib><title>Synthesis and Preliminary Biological Evaluation of (3-Iodobenzoyl)norbiotinamide and ((5-Iodo-3-pyridinyl)carbonyl)norbiotinamide: Two Radioiodinated Biotin Conjugates with Improved Stability</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>A new class of radioiodinated biotin conjugates is described in which the amido bond between biotin and the labeled prosthetic group is reversed. One conjugate, (3-[125I]iodobenzoyl)norbiotinamide (4c, [125I]IBB) was labeled with Na125I in one step from (3-(tributylstannyl)benzoyl)norbiotinamide (4b, TBB) via a demetalation reaction. However, the analogous reaction with ((5-(tributylstannyl)-3-pyridinyl)carbonyl)norbiotinamide (6b, TPB) failed to yield ((5-[131I]iodo-3-pyridinyl)carbonyl)norbiotinamide (6c, [131I]IPB), necessitating a two-step approach for synthesizing [131I]IPB. The binding of [125I]IBB and [131I]IPB to streptavidin in vitro was identical to that of biotinyl-3-[125I]iodoanilide, a conjugate with an amido bond with normal configuration. Both [125I]IBB and [131I]IPB were stable in serum while the first-generation compound was rapidly degraded. The biodistribution patterns of [125I]IBB and [131I]IPB in mice are consistent with limited degradation of these conjugates by biotinidase and deiodinases.</description><subject>Animals</subject><subject>Bacterial Proteins - metabolism</subject><subject>Biotin - analogs & derivatives</subject><subject>Biotin - chemical synthesis</subject><subject>Biotin - chemistry</subject><subject>Drug Stability</subject><subject>In Vitro Techniques</subject><subject>Iodine Radioisotopes - pharmacokinetics</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Molecular Structure</subject><subject>Radiopharmaceuticals - chemical synthesis</subject><subject>Radiopharmaceuticals - pharmacokinetics</subject><subject>Streptavidin</subject><subject>Tissue Distribution</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1uEzEUhUcIVEphwQMgeQNKFwP2eGZsd0ejFoIqETVBYmf5b1qHGTvYnrZhxZbX4lF4EtwmygZW1_L57rlX9xTFSwTfIlihd1IxAiFsh0fFIWoqWNYUVY_zG9a4RBRWT4tnMa4ywhCtDooDBlmDG3pY_F5sXLo20UYgnAbzYHo7WCfCBpxa3_srq0QPzm5EP4pkvQO-AxNczrz20rgfftMfOx-k9Sk3DVabB5vJpHlASlyuN8Fq6zKnRJDe_dNw8ufnL7C89eBSaOutz7BIRt-PzwiYercar_JPBLc2XYPZsA7-JuuLJKTtbdo8L550oo_mxa4eFV_Oz5bTj-XF5w-z6fuLUuCaprKVhEmFJKlo29FOsQZhDDsq21pViCKkWwilpEKZThKVK2mYbnTFWkFo3eGj4s3WNy_wfTQx8cFGZfpeOOPHyAlliJGKZfB4C6rgYwym4-tgh3xSjiC_z4vv88rsq53pKAej9-QuoKyXW93GZO72sgjfeEswafhyvuD1p0s6nX895Tjzr7e8UJGv_BhcPsl_5v4F_o6wyg</recordid><startdate>19970301</startdate><enddate>19970301</enddate><creator>Foulon, Catherine F</creator><creator>Alston, Kevin L</creator><creator>Zalutsky, Michael R</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19970301</creationdate><title>Synthesis and Preliminary Biological Evaluation of (3-Iodobenzoyl)norbiotinamide and ((5-Iodo-3-pyridinyl)carbonyl)norbiotinamide: Two Radioiodinated Biotin Conjugates with Improved Stability</title><author>Foulon, Catherine F ; Alston, Kevin L ; Zalutsky, Michael R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-6b79bc1b7286f8fc951330f8b64c21811d600bb8acefb7c8ac759d5d296a784f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Animals</topic><topic>Bacterial Proteins - metabolism</topic><topic>Biotin - analogs & derivatives</topic><topic>Biotin - chemical synthesis</topic><topic>Biotin - chemistry</topic><topic>Drug Stability</topic><topic>In Vitro Techniques</topic><topic>Iodine Radioisotopes - pharmacokinetics</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Molecular Structure</topic><topic>Radiopharmaceuticals - chemical synthesis</topic><topic>Radiopharmaceuticals - pharmacokinetics</topic><topic>Streptavidin</topic><topic>Tissue Distribution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Foulon, Catherine F</creatorcontrib><creatorcontrib>Alston, Kevin L</creatorcontrib><creatorcontrib>Zalutsky, Michael R</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Foulon, Catherine F</au><au>Alston, Kevin L</au><au>Zalutsky, Michael R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Preliminary Biological Evaluation of (3-Iodobenzoyl)norbiotinamide and ((5-Iodo-3-pyridinyl)carbonyl)norbiotinamide: Two Radioiodinated Biotin Conjugates with Improved Stability</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>1997-03-01</date><risdate>1997</risdate><volume>8</volume><issue>2</issue><spage>179</spage><epage>186</epage><pages>179-186</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>A new class of radioiodinated biotin conjugates is described in which the amido bond between biotin and the labeled prosthetic group is reversed. One conjugate, (3-[125I]iodobenzoyl)norbiotinamide (4c, [125I]IBB) was labeled with Na125I in one step from (3-(tributylstannyl)benzoyl)norbiotinamide (4b, TBB) via a demetalation reaction. However, the analogous reaction with ((5-(tributylstannyl)-3-pyridinyl)carbonyl)norbiotinamide (6b, TPB) failed to yield ((5-[131I]iodo-3-pyridinyl)carbonyl)norbiotinamide (6c, [131I]IPB), necessitating a two-step approach for synthesizing [131I]IPB. The binding of [125I]IBB and [131I]IPB to streptavidin in vitro was identical to that of biotinyl-3-[125I]iodoanilide, a conjugate with an amido bond with normal configuration. Both [125I]IBB and [131I]IPB were stable in serum while the first-generation compound was rapidly degraded. The biodistribution patterns of [125I]IBB and [131I]IPB in mice are consistent with limited degradation of these conjugates by biotinidase and deiodinases.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>9095358</pmid><doi>10.1021/bc970006m</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1043-1802 |
| ispartof | Bioconjugate chemistry, 1997-03, Vol.8 (2), p.179-186 |
| issn | 1043-1802 1520-4812 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_78919729 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Bacterial Proteins - metabolism Biotin - analogs & derivatives Biotin - chemical synthesis Biotin - chemistry Drug Stability In Vitro Techniques Iodine Radioisotopes - pharmacokinetics Mice Mice, Inbred BALB C Molecular Structure Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - pharmacokinetics Streptavidin Tissue Distribution |
| title | Synthesis and Preliminary Biological Evaluation of (3-Iodobenzoyl)norbiotinamide and ((5-Iodo-3-pyridinyl)carbonyl)norbiotinamide: Two Radioiodinated Biotin Conjugates with Improved Stability |
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