18F-labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins
In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled...
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| Veröffentlicht in: | Biochemistry (Easton) 1989-05, Vol.28 (11), p.4801-4806 |
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| container_end_page | 4806 |
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| container_issue | 11 |
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| container_title | Biochemistry (Easton) |
| container_volume | 28 |
| creator | SHAI, Y KIRK, K. L CHANNING, M. A DUNN, B. B LESNIAK, M. A EASTMAN, R. C FINN, R. D ROTH, J JACOBSON, K. A |
| description | In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled insulin retains the essential biological properties of native insulin, as measured in vitro by binding to insulin receptors on human cells and stimulation of glucose metabolism in rat adipocytes. The overall process can be carried out speedily to yield a product of sufficient purity to permit in vivo studies. The method appears to be applicable to a wide variety of peptides. |
| format | Article |
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L ; CHANNING, M. A ; DUNN, B. B ; LESNIAK, M. A ; EASTMAN, R. C ; FINN, R. D ; ROTH, J ; JACOBSON, K. A</creator><creatorcontrib>SHAI, Y ; KIRK, K. L ; CHANNING, M. A ; DUNN, B. B ; LESNIAK, M. A ; EASTMAN, R. C ; FINN, R. D ; ROTH, J ; JACOBSON, K. A</creatorcontrib><description>In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled insulin retains the essential biological properties of native insulin, as measured in vitro by binding to insulin receptors on human cells and stimulation of glucose metabolism in rat adipocytes. The overall process can be carried out speedily to yield a product of sufficient purity to permit in vivo studies. The method appears to be applicable to a wide variety of peptides.</description><identifier>ISSN: 0006-2960</identifier><identifier>EISSN: 1520-4995</identifier><identifier>PMID: 2669963</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Adipose Tissue - metabolism ; Analytical, structural and metabolic biochemistry ; Animals ; Biological and medical sciences ; Cell Line ; Fluorine Radioisotopes ; Fundamental and applied biological sciences. Psychology ; General aspects, investigation methods ; Glucose - metabolism ; Humans ; Insulin - analogs & derivatives ; Isotope Labeling - methods ; Peptides ; Proteins ; Rats ; Receptor, Insulin - metabolism ; Tomography, Emission-Computed - methods</subject><ispartof>Biochemistry (Easton), 1989-05, Vol.28 (11), p.4801-4806</ispartof><rights>1991 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19298725$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2669963$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SHAI, Y</creatorcontrib><creatorcontrib>KIRK, K. L</creatorcontrib><creatorcontrib>CHANNING, M. A</creatorcontrib><creatorcontrib>DUNN, B. B</creatorcontrib><creatorcontrib>LESNIAK, M. A</creatorcontrib><creatorcontrib>EASTMAN, R. C</creatorcontrib><creatorcontrib>FINN, R. D</creatorcontrib><creatorcontrib>ROTH, J</creatorcontrib><creatorcontrib>JACOBSON, K. A</creatorcontrib><title>18F-labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins</title><title>Biochemistry (Easton)</title><addtitle>Biochemistry</addtitle><description>In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled insulin retains the essential biological properties of native insulin, as measured in vitro by binding to insulin receptors on human cells and stimulation of glucose metabolism in rat adipocytes. The overall process can be carried out speedily to yield a product of sufficient purity to permit in vivo studies. The method appears to be applicable to a wide variety of peptides.</description><subject>Adipose Tissue - metabolism</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Fluorine Radioisotopes</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects, investigation methods</subject><subject>Glucose - metabolism</subject><subject>Humans</subject><subject>Insulin - analogs & derivatives</subject><subject>Isotope Labeling - methods</subject><subject>Peptides</subject><subject>Proteins</subject><subject>Rats</subject><subject>Receptor, Insulin - metabolism</subject><subject>Tomography, Emission-Computed - methods</subject><issn>0006-2960</issn><issn>1520-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpVkNFKwzAUhosoc04fQciN3hXSNEkTLwQZToWBN3pd0uZki6RNTdLB3t4Ox9Crw-H_zvfDOcvmBSM4p1Ky82yOMeY5kRxfZlcxfk0rxRWdZTPCuZS8nGe7QqxypxpwoJHt4-hs_4AUGoKPaQvJtmgT_DigDtLWa-_8Zo-MDxPb-jD4oJL1PfLmcOOjTWHaoLMpwYFJHg0wJKshItXrgzbBVHOdXRjlItwc5yL7XD1_LF_z9fvL2_JpnQ9FKUTOtJAgecMrakjDgQthSiYY5drgkjLMSMPaplGSghSaUdMITVtlFEhTYVYussdf7zA2HegW-hSUq4dgOxX2tVe2_p_0dltv_K4uKWG8FJPg_igI_nuEmOrOxhacUz34MdaVLJjgBZnA279Np4rjp6f87pir2CpngupbG09YIYkUFWHlD0kFi9w</recordid><startdate>19890530</startdate><enddate>19890530</enddate><creator>SHAI, Y</creator><creator>KIRK, K. 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Psychology</topic><topic>General aspects, investigation methods</topic><topic>Glucose - metabolism</topic><topic>Humans</topic><topic>Insulin - analogs & derivatives</topic><topic>Isotope Labeling - methods</topic><topic>Peptides</topic><topic>Proteins</topic><topic>Rats</topic><topic>Receptor, Insulin - metabolism</topic><topic>Tomography, Emission-Computed - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SHAI, Y</creatorcontrib><creatorcontrib>KIRK, K. L</creatorcontrib><creatorcontrib>CHANNING, M. A</creatorcontrib><creatorcontrib>DUNN, B. B</creatorcontrib><creatorcontrib>LESNIAK, M. A</creatorcontrib><creatorcontrib>EASTMAN, R. C</creatorcontrib><creatorcontrib>FINN, R. D</creatorcontrib><creatorcontrib>ROTH, J</creatorcontrib><creatorcontrib>JACOBSON, K. A</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Biochemistry (Easton)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SHAI, Y</au><au>KIRK, K. L</au><au>CHANNING, M. A</au><au>DUNN, B. B</au><au>LESNIAK, M. A</au><au>EASTMAN, R. C</au><au>FINN, R. D</au><au>ROTH, J</au><au>JACOBSON, K. A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>18F-labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins</atitle><jtitle>Biochemistry (Easton)</jtitle><addtitle>Biochemistry</addtitle><date>1989-05-30</date><risdate>1989</risdate><volume>28</volume><issue>11</issue><spage>4801</spage><epage>4806</epage><pages>4801-4806</pages><issn>0006-2960</issn><eissn>1520-4995</eissn><abstract>In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled insulin retains the essential biological properties of native insulin, as measured in vitro by binding to insulin receptors on human cells and stimulation of glucose metabolism in rat adipocytes. The overall process can be carried out speedily to yield a product of sufficient purity to permit in vivo studies. The method appears to be applicable to a wide variety of peptides.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>2669963</pmid><tpages>6</tpages></addata></record> |
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| ispartof | Biochemistry (Easton), 1989-05, Vol.28 (11), p.4801-4806 |
| issn | 0006-2960 1520-4995 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Adipose Tissue - metabolism Analytical, structural and metabolic biochemistry Animals Biological and medical sciences Cell Line Fluorine Radioisotopes Fundamental and applied biological sciences. Psychology General aspects, investigation methods Glucose - metabolism Humans Insulin - analogs & derivatives Isotope Labeling - methods Peptides Proteins Rats Receptor, Insulin - metabolism Tomography, Emission-Computed - methods |
| title | 18F-labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins |
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