scholarly journals Self‐Propagated para ‐Fluoro‐Thiol Reaction

2019 ◽  
Vol 25 (43) ◽  
pp. 10049-10053 ◽  
Author(s):  
Federica Cavalli ◽  
Fabian R. Bloesser ◽  
Christopher Barner‐Kowollik ◽  
Leonie Barner
Keyword(s):  
2019 ◽  
Vol 10 (22) ◽  
pp. 2781-2791 ◽  
Author(s):  
Federica Cavalli ◽  
Lies De Keer ◽  
Birgit Huber ◽  
Paul H. M. Van Steenberge ◽  
Dagmar R. D'hooge ◽  
...  

A detailed kinetic study on the para-fluoro-thiol reaction (PFTR) using experimental analysis and kinetic Monte Carlo modeling is introduced, covering the difference in reactivity of a selected variety of structurally different thiols, uniquely including polymeric thiols.


2018 ◽  
Vol 9 (20) ◽  
pp. 2679-2684 ◽  
Author(s):  
Guillaume Delaittre ◽  
Leonie Barner

The current literature describing the application of the para-fluoro–thiol reaction in the realm of macromolecular chemistry and the future of this coupling strategy are discussed.


2002 ◽  
Vol 307 (1) ◽  
pp. 76-83 ◽  
Author(s):  
Talia Miron ◽  
Irina Shin ◽  
Guy Feigenblat ◽  
Lev Weiner ◽  
David Mirelman ◽  
...  

2015 ◽  
Vol 54 (30) ◽  
pp. 8732-8735 ◽  
Author(s):  
Wenqian Feng ◽  
Linxian Li ◽  
Chengwu Yang ◽  
Alexander Welle ◽  
Oliver Trapp ◽  
...  

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1562
Author(s):  
Chiara Da Pieve ◽  
Ata Makarem ◽  
Stephen Turnock ◽  
Justyna Maczynska ◽  
Graham Smith ◽  
...  

Site-selective bioconjugation of cysteine-containing peptides and proteins is currently achieved via a maleimide–thiol reaction (Michael addition). When maleimide-functionalized chelators are used and the resulting bioconjugates are subsequently radiolabeled, instability has been observed both during radiosynthesis and post-injection in vivo, reducing radiochemical yield and negatively impacting performance. Recently, a phenyloxadiazolyl methylsulfone derivative (PODS) was proposed as an alternative to maleimide for the site-selective conjugation and radiolabeling of proteins, demonstrating improved in vitro stability and in vivo performance. Therefore, we have synthesized two novel PODS-bearing bifunctional chelators (NOTA-PODS and NODAGA-PODS) and attached them to the EGFR-targeting affibody molecule ZEGFR:03115. After radiolabeling with the aluminum fluoride complex ([18F]AlF), both conjugates showed good stability in murine serum. When injected in high EGFR-expressing tumor-bearing mice, [18F]AlF-NOTA-PODS-ZEGFR:03115 and [18F]AlF-NODAGA-PODS-ZEGFR:03115 showed similar pharmacokinetics and a specific tumor uptake of 14.1 ± 5.3% and 16.7 ± 4.5% ID/g at 1 h post-injection, respectively. The current results are encouraging for using PODS as an alternative to maleimide-based thiol-selective bioconjugation reactions.


2017 ◽  
Vol 8 (25) ◽  
pp. 3778-3782 ◽  
Author(s):  
Federica Cavalli ◽  
Hatice Mutlu ◽  
Sven O. Steinmueller ◽  
Leonie Barner

We introduce the regioselective para-fluoro-thiol reaction (PFTR) as a novel strategy for precision network formation evidenced by XPS and ToF-SIMS.


2020 ◽  
Vol 56 (95) ◽  
pp. 14996-14999
Author(s):  
Fabian R. Bloesser ◽  
Federica Cavalli ◽  
Sarah L. Walden ◽  
Leonie Barner ◽  
Christopher Barner-Kowollik
Keyword(s):  

We exploit the fluoride that is released via the para-fluoro-thiol reaction (PFTR) to cleave silyl ethers, turning the PFTR into an effective self-reporting chemiluminescence (CL) probe.


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