Journal of labelled compounds & radiopharmaceuticals最新文献_第8页

Open-source flow setup for rapid and efficient [18F]fluoride drying for automation of PET tracer syntheses 用于快速高效[18 F]氟化物干燥的开源流程设置，实现 PET 示踪剂合成自动化。

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-28 DOI: 10.1002/jlcr.4080

Florian Menzel, Jonathan Cotton, Thomas Ziegler, Andreas Maurer, Jochen M. Neumaier

{"title":"Open-source flow setup for rapid and efficient [18F]fluoride drying for automation of PET tracer syntheses","authors":"Florian Menzel, Jonathan Cotton, Thomas Ziegler, Andreas Maurer, Jochen M. Neumaier","doi":"10.1002/jlcr.4080","DOIUrl":"10.1002/jlcr.4080","url":null,"abstract":"One of the key strategies for radiochemical research facilities is the automation of synthesis processes. Unnecessary manual operations increase the radiation exposure of personnel, while simultaneously threatening the reliability of syntheses. We have previously reported an affordable open-source system comprising 3D-printed continuous flow reactors, a custom syringe pump, and a pressure regulator that can be used to perform radiofluorinations. In this paper, we address additional essential processes that are needed for radiotracer development and synthesis, with the aim of making laboratory work safer and research more efficient. We have designed and evaluated a fully automated system for rapidly and effectively processing and drying aqueous [18F]fluoride that can be directly connected to the cyclotron. This process relies on triflyl fluoride gas generation and allows nucleophilic [18F]fluoride to be prepared safely in a hotcell within 10 min and an activity recovery of 91.7 ± 1.6% (n = 5). Owing to the need for convenient radiofluorinated prosthetic ligands, we have adapted our continuous flow system to produce [18F]fluoroethyl tosylate (FEOTs) and [18F]fluoroethyl triflate (FEOTf), prosthetic groups that are widely used for late-stage fluoroethylation of PET tracers. The processes as well as the radiolabeling of different groups are compared and comprehensively discussed. Having a method providing [18F]fluoroethyl tosylate (FEOTs) as well as [18F]fluoroethyl triflate (FEOTf) quickly and highly efficiently is beneficial for radiochemical research.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"67 2","pages":"40-58"},"PeriodicalIF":0.9,"publicationDate":"2023-12-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jlcr.4080","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139058439","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Development of radiotracers for riboflavin transporter 3 imaging in diseases—A brief overview 用于核黄素转运体 3 在疾病中成像的放射性racers 的开发--简述。

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-22 DOI: 10.1002/jlcr.4076

Jindian Li, Xianzhong Zhang

引用次数: 0

Automated radiosynthesis of [18F]CETO, a PET radiotracer for imaging adrenal glands, on Synthra RNplus 用于肾上腺成像的 PET 放射性示踪剂 [18 F]CETO 在 Synthra RNplus 上的自动放射合成。

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-20 DOI: 10.1002/jlcr.4078

Matthew Hird, Joseph J. Russell, Lei Li Corrigan, Istvan Boros, Patrik Nordeman, Gunnar Antoni, Mark Gurnell, Franklin I. Aigbirhio

{"title":"Automated radiosynthesis of [18F]CETO, a PET radiotracer for imaging adrenal glands, on Synthra RNplus","authors":"Matthew Hird, Joseph J. Russell, Lei Li Corrigan, Istvan Boros, Patrik Nordeman, Gunnar Antoni, Mark Gurnell, Franklin I. Aigbirhio","doi":"10.1002/jlcr.4078","DOIUrl":"10.1002/jlcr.4078","url":null,"abstract":"Primary aldosteronism (PA) is the leading secondary cause of hypertension. Determining whether one (unilateral) or both (bilateral) adrenal glands are the source of PA in a patient remains challenging, and yet it is a critical step in the decision whether to recommend potentially curative surgery (adrenalectomy) or lifelong medical therapy (typically requiring multiple drugs). Recently, we have developed a fluorine-18 radiopharmaceutical [18F]CETO to permit greater access to PA molecular imaging. Herein, we report an automated synthesis of this radiotracer. To manufacture the radiopharmaceutical routinely for clinical PET studies, we implemented an automated radiosynthesis method on a Synthra RNplus© synthesiser for which Cl-tosyletomidate was used as the precursor for radiolabelling via nucleophilic [18F]fluorination. [18F]CETO was produced with 35 ± 1% (n = 7), decay corrected and 25 ± 4% (n = 7) non-decay corrected radiochemical yield with molar activities ranging from 150 to 400 GBq/μmol. The GMP compliant manufacturing process produces a sterile formulated [18F]CETO injectable solution for human use as demonstrated by the results of quality control. Automation of the radiosynthesis of [18F]CETO should facilitate uptake by other adrenal centres and increase access to molecular imaging in PA.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"67 2","pages":"67-75"},"PeriodicalIF":0.9,"publicationDate":"2023-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jlcr.4078","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138806677","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Validation of a good manufacturing practice procedure for the production of [11C]AZD4747, a CNS penetrant KRASG12c inhibitor 验证生产中枢神经系统穿透性 KRASG12c 抑制剂 [11C]AZD4747 的良好生产规范程序

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-20 DOI: 10.1002/jlcr.4079

Miguel A. Cortés González, Antonia A. Högnäsbacka, Christer Halldin, Magnus Schou

引用次数: 0

[11C]CO2 BOP fixation with amines to access 11C-labeled ureas for PET imaging 用胺固定[11C]CO2 BOP，获得用于 PET 成像的 11C 标记脲类

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-10 DOI: 10.1002/jlcr.4075

Coralie M. Bonnemaire, Albert D. Windhorst, Romano Orru, Eelco Ruijter, Danielle J. Vugts

{"title":"[11C]CO2 BOP fixation with amines to access 11C-labeled ureas for PET imaging","authors":"Coralie M. Bonnemaire, Albert D. Windhorst, Romano Orru, Eelco Ruijter, Danielle J. Vugts","doi":"10.1002/jlcr.4075","DOIUrl":"10.1002/jlcr.4075","url":null,"abstract":"Carbon-11 (11C) is a widely used radionuclide for positron emission tomography (PET) owing to the omnipresence of carbon atoms in organic molecules. While its half-life of 20.4 min is ideal for imaging and dosimetry, it also limits the synthetic possibilities. As such, the development of fast and easy, high-yielding synthesis methods is crucial for the application of 11C-labeled tracers in humans.In this study, we present a novel and efficient method for the reaction of [11C]CO2 with amine precursors using benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP) to access 11C-labeled ureas. Our method is extremely fast as it only requires transfer of [11C]CO2 into a solution with precursor and BOP at room temperature, where it reacts momentary into the desired 11C-labeled urea. This simple procedure makes it possible to radiolabel urea directly from [11C]CO2 without the need for advanced equipment, making the method applicable for all laboratories where [11C]CO2 is available. We synthesized a small series of aliphatic symmetrical and non-symmetrical 11C-labeled ureas using this method, and achieved good to excellent yields.The novelty of our study lies in the fact that peptide coupling reagent BOP is used for the first time in radiochemistry to activate [11C]CO2, facilitating its reaction with amines to obtain 11C-labeled ureas.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"67 6","pages":"201-210"},"PeriodicalIF":0.9,"publicationDate":"2023-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jlcr.4075","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138627896","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

14C-radiolabeling of a new steroidal antiandrogen with a C-18 angular methyl extension 对带有 C-18 角甲基延伸的新型甾体抗雄激素进行 14C 放射标记

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-08 DOI: 10.1002/jlcr.4074

Jean-Yves Sancéau

引用次数: 0

Synthesis and spectroscopic characterization of 13C4-labeled 4-cyano-2-oxobutyraldehyde semicarbazone: A metabolite of nitrofurazone 13 C4标记的4-氰基-2-氧丁醛缩氨基脲的合成和光谱表征:硝基呋喃酮的代谢物。

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-12-03 DOI: 10.1002/jlcr.4077

Anuradha Singh, David J. Smith, Gary D. Strahan, Steven J. Lehotay

{"title":"Synthesis and spectroscopic characterization of 13C4-labeled 4-cyano-2-oxobutyraldehyde semicarbazone: A metabolite of nitrofurazone","authors":"Anuradha Singh, David J. Smith, Gary D. Strahan, Steven J. Lehotay","doi":"10.1002/jlcr.4077","DOIUrl":"10.1002/jlcr.4077","url":null,"abstract":"Nitrofurazone usage in food-producing animals is prohibited in most countries, including the United States. Regulatory agencies regularly monitor its use in domestic, export/import animals' food products by measuring the semicarbazide (SEM) metabolite as a biomarker of nitrofurazone exposure. However, the use of SEM is controversial because it is also produced in food naturally and thus gives false positive results. A cyano-metabolite, 4-cyano-2-oxobutyraldehyde semicarbazone (COBS), is proposed as an alternate specific marker of nitrofurazone to distinguish nitrofurazone from treated or untreated animals. A synthetic method was developed to produce COBS via metallic hydrogenation of nitrofurazone. The product was isolated and characterized by one- and two-dimensional nuclear magnetic spectroscopy (NMR) experiments, Fourier-transform infrared spectroscopy (FT-IR), and mass spectrometry. The developed synthetic procedure was further extended to synthesize isotopically labeled 4-[13C]-cyano-2-oxo- [2, 3, 4-13C3]-butyraldehyde semicarbazone. Labeled COBS is useful as an internal standard for its quantification in food-producing animals. Thus, the developed method provides a possibility for its commercial synthesis to procure COBS. This is the first synthesis of the alternate specific marker metabolite of nitrofurazone for possible usage in regulatory analysis to solve a real-world problem.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"67 1","pages":"18-24"},"PeriodicalIF":0.9,"publicationDate":"2023-12-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138477840","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis of trifold-labeled versatile reagent [3,5-13C2,4-15 N]4-phenyl-1,2,4-triazoline-3,5-dione 三价标记多用途试剂[3,5-13 C2,4-15 N]4-苯基-1,2,4-三唑啉-3,5-二酮的合成。

IF 1.8 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-11-20 DOI: 10.1002/jlcr.4067

Frederic Bourgeois, Ulrich Höller, Thomas Netscher

{"title":"Synthesis of trifold-labeled versatile reagent [3,5-13C2,4-15 N]4-phenyl-1,2,4-triazoline-3,5-dione","authors":"Frederic Bourgeois, Ulrich Höller, Thomas Netscher","doi":"10.1002/jlcr.4067","DOIUrl":"10.1002/jlcr.4067","url":null,"abstract":"Triazolinediones are an important class of derivatization agents that have found application in various research disciplines. Their unique reactivity often allows precise and selective tagging of relevant molecular scaffolds to facilitate structural elucidation, tracking in biological systems, and stabilization of labile compounds. Recent research efforts mainly focused on the development of novel fluorescent and ionizable or isotopically labeled tags improving the quantification and identification of the parent molecule by suitable analytical methods. However, these concepts often lack the ability to improve properties facilitating the analysis by nuclear magnetic resonance (NMR) spectroscopy. We herein describe the first synthesis of 13C and 15N labeled [3,5-13C2,4-15 N]4-phenyl-1,2,4-triazoline-3,5-dione utilizing the Cookson/Zinner–Deucker synthesis of urazoles. The introduced isotopic labels are ideally suited to support the structural elucidation of unknown and complex derivatization mixtures by NMR, thereby exploiting the increased sensitivity of detecting long-range JHC and additional JCC and JCN couplings within the derivatized compounds of interest.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"66 14","pages":"461-466"},"PeriodicalIF":1.8,"publicationDate":"2023-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138176387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Novel synthesis of 11C-labeled imidazolines via Pd(0)-mediated 11C-carbomethoxylation using [11C]CO and arylborons 用[11 C]CO和芳基硼经Pd(0)介导的11 C-碳甲氧基化合成11 C标记咪唑啉的新方法。

IF 0.9 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-11-13 DOI: 10.1002/jlcr.4072

Hideki Ishii, Katsuyuki Minegishi, Kotaro Nagatsu, Nobuki Nengaki, Ming-Rong Zhang

{"title":"Novel synthesis of 11C-labeled imidazolines via Pd(0)-mediated 11C-carbomethoxylation using [11C]CO and arylborons","authors":"Hideki Ishii, Katsuyuki Minegishi, Kotaro Nagatsu, Nobuki Nengaki, Ming-Rong Zhang","doi":"10.1002/jlcr.4072","DOIUrl":"10.1002/jlcr.4072","url":null,"abstract":"A labeling technique was developed for the imidazoline I2 receptor ligand 2-(3-fluoro-tolyl)-4, 5-dihydro-1H-imidazole (FTIMD) using Pd(0)-mediated 11C-carbomethoxylation with [11C]CO, followed by imidazoline ring formation with ethylenediamine-trimethylaluminium (EDA-AlMe3). To achieve this, [11C]CO was passed through a methanol (MeOH) solution containing 3-fluoro-4-methylphenylboronic acid (1), palladium (II) acetate (Pd [OAc]2), triphenylphosphine (PPh3), and p-benzoquinone (PBQ). The mixture was then heated at 65°C for 5 min. EDA was introduced into the reaction mixture, and MeOH was completely evaporated at temperatures exceeding 100°C. The dried reaction mixture was combined with an EDA-AlMe (1:1) toluene solution and heated at 145°C for 10 min. Portions of the reaction mixture were analyzed through high-performance liquid chromatography, resulting in [11C]FTIMD with 26% (n = 2) decay-corrected radiochemical yield (RCY). This method could be utilized for various arylborons to produce [2-11C]imidazolines 4a–h with RCYs ranging from low to moderate. Notably, [2-11C]benazoline was obtained with a moderate RCY of 65%. The proposed technique serves as an alternative to the Grignard method, which uses [11C]CO to generate a [2-11C]-labeled imidazoline ring.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"67 6","pages":"227-234"},"PeriodicalIF":0.9,"publicationDate":"2023-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"92154763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Facile synthesis of 14C-nitrofurazone from 14C-urea 用14C-尿素催化合成14C-硝基呋喃酮。

IF 1.8 4区医学

Journal of labelled compounds & radiopharmaceuticals Pub Date : 2023-11-08 DOI: 10.1002/jlcr.4068

Anuradha Singh, David J. Smith

{"title":"Facile synthesis of 14C-nitrofurazone from 14C-urea","authors":"Anuradha Singh, David J. Smith","doi":"10.1002/jlcr.4068","DOIUrl":"10.1002/jlcr.4068","url":null,"abstract":"The veterinary drug nitrofurazone (5-nitro-2-furaldehyde semicarbazone) exhibits excellent antimicrobial properties but its application in food-producing animals is prohibited. The illegal use of nitrofurazone is regularly monitored by food regulatory agencies. Currently, semicarbazide (SEM) is used as a marker of nitrofurazone exposure. However, the use of SEM as a marker of nitrofurazone is under scrutiny after evidence of a high incidence of false positive tests. To overcome the current dilemma, it is necessary to identify a nitrofurazone-specific marker analyte which requires conducting nitrofurazone metabolism studies in food-producing animals. The use of carbon-14 labeled nitrofurazone would facilitate metabolism studies and structural elucidation of nitrofurazone metabolites of possible utility as a marker compound. In the present work, a synthetic method is described to procure radiolabeled nitrofurazone that incorporates 14C- carbon at the semicarbazide moiety. The method incorporates 14C-carbon via employing readily available and more economically affordable [14C]-urea compared with [14C]-semicarbazide. To the best of our knowledge, there is no report on the synthesis of 5-nitro-2-furaldehyde [14C]-semicarbazone from 14C-urea. The developed method involves monoamination of [14C]-urea followed by a condensation reaction with 5-nitro-2-furaldehyde to produce 5-nitro-2-furaldehyde [14C]-semicarbazone in 85% yield with greater than 98% radiochemical purity.","PeriodicalId":16288,"journal":{"name":"Journal of labelled compounds & radiopharmaceuticals","volume":"66 14","pages":"467-472"},"PeriodicalIF":1.8,"publicationDate":"2023-11-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"71521761","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0