Literature DB >> 26086295

Novel Method for Radiolabeling and Dimerizing Thiolated Peptides Using (18)F-Hexafluorobenzene.

Orit Jacobson1, Xuefeng Yan1, Ying Ma1, Gang Niu1, Dale O Kiesewetter1, Xiaoyuan Chen1.   

Abstract

Hexafluorobenzene (HFB) reacts with free thiols to produce a unique and selective perfluoroaromatic linkage between two sulfurs. We modified this chemical reaction to produce dimeric (18)F-RGD-tetrafluorobenzene (TFB)-RGD, an integrin αvβ3 receptor ligand. (18)F-HFB was prepared by a fluorine exchange reaction using K(18)F/K2.2.2 at room temperature. The automated radiofluorination was optimized to minimize the amount of HFB precursor and, thus, maximize the specific activity. (18)F-HFB was isolated by distillation and subsequently reacted with thiolated c(RGDfk) peptide under basic and reducing conditions. The resulting (18)F-RGD-TFB-RGD demonstrated integrin receptor specific binding, cellular uptake, and in vivo tumor accumulation.(18)F-HFB can be efficiently incorporated into thiol-containing peptides at room temperature to provide novel imaging agents.

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Year:  2015        PMID： 26086295      PMCID： PMC5218596          DOI： 10.1021/acs.bioconjchem.5b00278

Source DB:  PubMed          Journal:  Bioconjug Chem        ISSN： 1043-1802            Impact factor:   4.774


  21 in total

1.  Quantitative PET imaging of tumor integrin alphavbeta3 expression with 18F-FRGD2.

Authors:  Xianzhong Zhang; Zhengming Xiong; Yun Wu; Weibo Cai; Jeffery R Tseng; Sanjiv S Gambhir; Xiaoyuan Chen
Journal:  J Nucl Med       Date:  2006-01       Impact factor: 10.057

2.  18F-labeling of peptides by means of an organosilicon-based fluoride acceptor.

Authors:  Ralf Schirrmacher; Gerrit Bradtmöller; Esther Schirrmacher; Oliver Thews; Julia Tillmanns; Thomas Siessmeier; Hans G Buchholz; Peter Bartenstein; Björn Wängler; Christof M Niemeyer; Klaus Jurkschat
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

3.  In vivo binding of [68Ga]-DOTATOC to somatostatin receptors in neuroendocrine tumours--impact of peptide mass.

Authors:  Irina Velikyan; Anders Sundin; Barbro Eriksson; Hans Lundqvist; Jens Sörensen; Mats Bergström; Bengt Långström
Journal:  Nucl Med Biol       Date:  2010-01-15       Impact factor: 2.408

4.  Stoichiometric leverage: rapid 18F-aryltrifluoroborate radiosynthesis at high specific activity for click conjugation.

Authors:  Zhibo Liu; Ying Li; Jerome Lozada; Paul Schaffer; Michael J Adam; Thomas J Ruth; David M Perrin
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-11       Impact factor: 15.336

5.  PET of tumor CXCR4 expression with 4-18F-T140.

Authors:  Orit Jacobson; Ido D Weiss; Dale O Kiesewetter; Joshua M Farber; Xiaoyuan Chen
Journal:  J Nucl Med       Date:  2010-10-18       Impact factor: 10.057

6.  Single step 18F-labeling of dimeric cycloRGD for functional PET imaging of tumors in mice.

Authors:  Ying Li; Zhibo Liu; Jerome Lozada; May Q Wong; Kuo-Shyan Lin; Donald Yapp; David M Perrin
Journal:  Nucl Med Biol       Date:  2013-10-03       Impact factor: 2.408

7.  Comparison of three dimeric 18F-AlF-NOTA-RGD tracers.

Authors:  Jinxia Guo; Lixin Lang; Shuo Hu; Ning Guo; Lei Zhu; Zhongchan Sun; Ying Ma; Dale O Kiesewetter; Gang Niu; Qingguo Xie; Xiaoyuan Chen
Journal:  Mol Imaging Biol       Date:  2014-04       Impact factor: 3.488

8.  First experience of 18F-alfatide in lung cancer patients using a new lyophilized kit for rapid radiofluorination.

Authors:  Weixing Wan; Ning Guo; Donghui Pan; Chunjing Yu; Yuan Weng; Shineng Luo; Hong Ding; Yuping Xu; Lizhen Wang; Lixin Lang; Qingguo Xie; Min Yang; Xiaoyuan Chen
Journal:  J Nucl Med       Date:  2013-04-03       Impact factor: 10.057

9.  A perfluoroaryl-cysteine S(N)Ar chemistry approach to unprotected peptide stapling.

Authors:  Alexander M Spokoyny; Yekui Zou; Jingjing J Ling; Hongtao Yu; Yu-Shan Lin; Bradley L Pentelute
Journal:  J Am Chem Soc       Date:  2013-04-16       Impact factor: 15.419

Review 10.  Cross-coupling reactions as valuable tool for the preparation of PET radiotracers.

Authors:  Marc Pretze; Philipp Grosse-Gehling; Constantin Mamat
Journal:  Molecules       Date:  2011-01-26       Impact factor: 4.411
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  6 in total

Review 1.  Arylation Chemistry for Bioconjugation.

Authors:  Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

Review 2.  18 F-Labeling of Sensitive Biomolecules for Positron Emission Tomography.

Authors:  Hema S Krishnan; Longle Ma; Neil Vasdev; Steven H Liang
Journal:  Chemistry       Date:  2017-09-01       Impact factor: 5.236

3.  Direct 11CN-Labeling of Unprotected Peptides via Palladium-Mediated Sequential Cross-Coupling Reactions.

Authors:  Wenjun Zhao; Hong Geun Lee; Stephen L Buchwald; Jacob M Hooker
Journal:  J Am Chem Soc       Date:  2017-05-17       Impact factor: 15.419

Review 4.  Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

Authors:  William D G Brittain; Christopher R Coxon
Journal:  Chemistry       Date:  2021-12-02       Impact factor: 5.020

5.  18F-Trifluoromethanesulfinate Enables Direct C-H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides.

Authors:  Choon Wee Kee; Osman Tack; Florian Guibbal; Thomas C Wilson; Patrick G Isenegger; Mateusz Imiołek; Stefan Verhoog; Michael Tilby; Giulia Boscutti; Sharon Ashworth; Juliette Chupin; Roxana Kashani; Adeline W J Poh; Jane K Sosabowski; Sven Macholl; Christophe Plisson; Bart Cornelissen; Michael C Willis; Jan Passchier; Benjamin G Davis; Véronique Gouverneur
Journal:  J Am Chem Soc       Date:  2020-01-13       Impact factor: 15.419

6.  Fully automated peptide radiolabeling from [18F]fluoride.

Authors:  Ryan A Davis; Chris Drake; Robin C Ippisch; Melissa Moore; Julie L Sutcliffe
Journal:  RSC Adv       Date:  2019-03-15       Impact factor: 4.036
  6 in total

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