Synthesis, Fluorine-18 Radiolabeling, and In Vivo PET Imaging of a Hydrophilic Fluorosulfotetrazine
The development of 18F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performa...
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| Published in | Pharmaceuticals (Basel, Switzerland) Vol. 16; no. 5; p. 636 |
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| Abstract | The development of 18F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic 18F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with 18/19F-fluoride. Propargylic 18/19F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the 18F-fluorosulfotetrazine in 29–35% DCY, within 90–95 min. The experimental LogP and LogD7.4 values of −1.27 ± 0.02 and −1.70 ± 0.02, respectively, confirmed the hydrophilicity of the 18F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the 18F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. |
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| AbstractList | The development of
18
F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic
18
F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with
18/19
F-fluoride. Propargylic
18/19
F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the
18
F-fluorosulfotetrazine in 29–35% DCY, within 90–95 min. The experimental LogP and LogD
7.4
values of −1.27 ± 0.02 and −1.70 ± 0.02, respectively, confirmed the hydrophilicity of the
18
F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the
18
F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. The development of 18 F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pretargeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic 18 F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with 18/19 F-fluoride. Propargylic 18/19 F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the 18 F-fluorosulfotetrazine in 29-35% DCY, within 90-95 min. The experimental LogP and LogD 7.4 values of −1.27 ± 0.02 and −1.70 ± 0.02, respectively, confirmed the hydrophilicity of the 18 F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the 18 Ffluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. The development of 18F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic 18F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with 18/19F-fluoride. Propargylic 18/19F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the 18F-fluorosulfotetrazine in 29–35% DCY, within 90–95 min. The experimental LogP and LogD7.4 values of −1.27 ± 0.02 and −1.70 ± 0.02, respectively, confirmed the hydrophilicity of the 18F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the 18F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. The development of [sup.18] F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic [sup.18] F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with [sup.18/19] F-fluoride. Propargylic [sup.18/19] F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the [sup.18] F-fluorosulfotetrazine in 29–35% DCY, within 90–95 min. The experimental LogP and LogD[sub.7.4] values of −1.27 ± 0.02 and −1.70 ± 0.02, respectively, confirmed the hydrophilicity of the [sup.18] F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the [sup.18] F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. The development of 18F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic 18F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with 18/19F-fluoride. Propargylic 18/19F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the 18F-fluorosulfotetrazine in 29-35% DCY, within 90-95 min. The experimental LogP and LogD7.4 values of -1.27 ± 0.02 and -1.70 ± 0.02, respectively, confirmed the hydrophilicity of the 18F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the 18F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications.The development of 18F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic 18F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with 18/19F-fluoride. Propargylic 18/19F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the 18F-fluorosulfotetrazine in 29-35% DCY, within 90-95 min. The experimental LogP and LogD7.4 values of -1.27 ± 0.02 and -1.70 ± 0.02, respectively, confirmed the hydrophilicity of the 18F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the 18F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. The development of F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major challenge, especially for pre-targeting applications. The hydrophilicity of the tetrazine has clearly become a crucial parameter for the performance of in vivo chemistry. In this study, we present the design, the synthesis, the radiosynthesis, the physicochemical characterization, the in vitro and in vivo stability, as well as the pharmacokinetics and the biodistribution determined by PET imaging in healthy animals of an original hydrophilic F-fluorosulfotetrazine. This tetrazine was prepared and radiolabelled with fluorine-18 according to a three-step procedure, starting from propargylic butanesultone as the precursor. The propargylic sultone was converted into the corresponding propargylic fluorosulfonate by a ring-opening reaction with F-fluoride. Propargylic F-fluorosulfonate was then subject to a CuACC reaction with an azidotetrazine, followed by oxidation. The overall automated radiosynthesis afforded the F-fluorosulfotetrazine in 29-35% DCY, within 90-95 min. The experimental LogP and LogD values of -1.27 ± 0.02 and -1.70 ± 0.02, respectively, confirmed the hydrophilicity of the F-fluorosulfotetrazine. In vitro and in vivo studies displayed a total stability of the F-fluorosulfotetrazine without any traces of metabolization, the absence of non-specific retention in all organs, and the appropriate pharmacokinetics for pre-targeting applications. |
| Audience | Academic |
| Author | Guillouet, Stéphane Seimbille, Yann Perrio, Cécile Beaufrez, Jason |
| AuthorAffiliation | 1 UAR 3408, CNRS, CEA, Unicaen, Cyceron, Bd Henri Becquerel, 14074 Caen, France 2 Department of Radiology & Nuclear Medicine, Erasmus MC, University Medical Center Rotterdam, Wytemaweg 80, 3015 CN Rotterdam, The Netherlands |
| AuthorAffiliation_xml | – name: 1 UAR 3408, CNRS, CEA, Unicaen, Cyceron, Bd Henri Becquerel, 14074 Caen, France – name: 2 Department of Radiology & Nuclear Medicine, Erasmus MC, University Medical Center Rotterdam, Wytemaweg 80, 3015 CN Rotterdam, The Netherlands |
| Author_xml | – sequence: 1 givenname: Jason surname: Beaufrez fullname: Beaufrez, Jason – sequence: 2 givenname: Stéphane surname: Guillouet fullname: Guillouet, Stéphane – sequence: 3 givenname: Yann orcidid: 0000-0002-9736-5318 surname: Seimbille fullname: Seimbille, Yann – sequence: 4 givenname: Cécile surname: Perrio fullname: Perrio, Cécile |
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| Keywords | bioconjugation fluorine-18 pre-targeting PET imaging sultone sulfonic acid salt tetrazine hydrophilicity |
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| Snippet | The development of 18F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major... The development of F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major... The development of [sup.18] F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a... The development of 18 F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major... The development of 18 F-fluorotetrazines, suitable for the radiolabeling of biologics such as proteins and antibodies by IEDDA ligation, represents a major... |
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| SubjectTerms | Acids bioconjugation Chemical properties Chemical Sciences Fluorides Fluorine Fluorine compounds fluorine-18 hydrophilicity Life Sciences Medicinal Chemistry Methods PET imaging Pharmaceutical sciences Pharmacokinetics Pharmacology Potassium pre-targeting Radioactive tracers Reagents Sodium Structure Temperature tetrazine |
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| Title | Synthesis, Fluorine-18 Radiolabeling, and In Vivo PET Imaging of a Hydrophilic Fluorosulfotetrazine |
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