{"title":"无催化剂的thia-Diels-Alder点击反应用于成像应用的肽标记","authors":"Timothé Maujean , Patrice Marchand , Patrick Wagner , Stéphanie Riché , Frédéric Boisson , Nicolas Girard , Julie Karpenko , Dominique Bonnet , Mihaela Gulea","doi":"10.1080/10426507.2023.2165659","DOIUrl":null,"url":null,"abstract":"<div><p>A thia-Diels-Alder reaction between a phosphonodithioester and a highly reactive exocyclic diene for the chemoselective labeling of peptides under catalyst-free mild conditions is described. An efficient method to introduce the dithioester function into a model tripeptide was first developed and then applied to two bioactive peptides, PSMA and apelin-13. The tripeptide-dithioester was used to optimize the cycloaddition with dienes bearing fluorine-18 or a fluorophore. Then, the cycloaddition of the PSMA-dithioester with the <sup>18</sup>F-diene led to a new PSMA-radiotracer, which was used for in vivo Positron Emission Tomography (PET) imaging. In the same way, a fluorescent apelin-13 probe was obtained from the apelin-dithioester and a squaraine-linked diene before beingused for in cellulo optical imaging.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Catalyst-free thia-Diels-Alder click reaction for the labeling of peptides for imaging applications\",\"authors\":\"Timothé Maujean , Patrice Marchand , Patrick Wagner , Stéphanie Riché , Frédéric Boisson , Nicolas Girard , Julie Karpenko , Dominique Bonnet , Mihaela Gulea\",\"doi\":\"10.1080/10426507.2023.2165659\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A thia-Diels-Alder reaction between a phosphonodithioester and a highly reactive exocyclic diene for the chemoselective labeling of peptides under catalyst-free mild conditions is described. An efficient method to introduce the dithioester function into a model tripeptide was first developed and then applied to two bioactive peptides, PSMA and apelin-13. The tripeptide-dithioester was used to optimize the cycloaddition with dienes bearing fluorine-18 or a fluorophore. Then, the cycloaddition of the PSMA-dithioester with the <sup>18</sup>F-diene led to a new PSMA-radiotracer, which was used for in vivo Positron Emission Tomography (PET) imaging. In the same way, a fluorescent apelin-13 probe was obtained from the apelin-dithioester and a squaraine-linked diene before beingused for in cellulo optical imaging.</p></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650723000126\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650723000126","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Catalyst-free thia-Diels-Alder click reaction for the labeling of peptides for imaging applications
A thia-Diels-Alder reaction between a phosphonodithioester and a highly reactive exocyclic diene for the chemoselective labeling of peptides under catalyst-free mild conditions is described. An efficient method to introduce the dithioester function into a model tripeptide was first developed and then applied to two bioactive peptides, PSMA and apelin-13. The tripeptide-dithioester was used to optimize the cycloaddition with dienes bearing fluorine-18 or a fluorophore. Then, the cycloaddition of the PSMA-dithioester with the 18F-diene led to a new PSMA-radiotracer, which was used for in vivo Positron Emission Tomography (PET) imaging. In the same way, a fluorescent apelin-13 probe was obtained from the apelin-dithioester and a squaraine-linked diene before beingused for in cellulo optical imaging.
期刊介绍：
Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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