Radiosynthesis of an 18 F-fluoroglycosylated aminoferrocene for in-vivo imaging of reactive oxygen species activity by PET
The imaging of reactive oxygen species (ROS) at the molecular level with high sensitivity and specificity by positron emission tomography (PET) could be of enormous interest to increase our knowledge about ROS activity and signalling, especially in tumours. The aim of this research was to optimise t...
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Published in | Journal of labelled compounds & radiopharmaceuticals Vol. 61; no. 14; pp. 1081 - 1088 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
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01.12.2018
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Abstract | The imaging of reactive oxygen species (ROS) at the molecular level with high sensitivity and specificity by positron emission tomography (PET) could be of enormous interest to increase our knowledge about ROS activity and signalling, especially in tumours. The aim of this research was to optimise the click chemistry-based radiosynthesis of an
F-labelled aminoferrocene glycoconjugate that was derived from an N-alkylaminoferrocene lead structure known to have anticancer activity in vitro. Applying the solvent system phosphate buffer/THF (12/5), Cu(OAc)
and sodium ascorbate as reducing agent at 60°C, the alkyne 1 reacted with the
F-labelled glycosyl azide [
F]2 in the presence of carrier 3 (47μM) to obtain carrier-added [
F]4 in a radiochemical yield of 85%. Interestingly, the addition of carrier was essential for sufficient radiochemical yield, because it suppressed the oxidation of no-carrier-added (n.c.a.) [
F]4. Future work will include the formulation of c.a. [
F]4 for studying its biodistribution in tumour-bearing mice. |
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AbstractList | The imaging of reactive oxygen species (ROS) at the molecular level with high sensitivity and specificity by positron emission tomography (PET) could be of enormous interest to increase our knowledge about ROS activity and signalling, especially in tumours. The aim of this research was to optimise the click chemistry-based radiosynthesis of an
F-labelled aminoferrocene glycoconjugate that was derived from an N-alkylaminoferrocene lead structure known to have anticancer activity in vitro. Applying the solvent system phosphate buffer/THF (12/5), Cu(OAc)
and sodium ascorbate as reducing agent at 60°C, the alkyne 1 reacted with the
F-labelled glycosyl azide [
F]2 in the presence of carrier 3 (47μM) to obtain carrier-added [
F]4 in a radiochemical yield of 85%. Interestingly, the addition of carrier was essential for sufficient radiochemical yield, because it suppressed the oxidation of no-carrier-added (n.c.a.) [
F]4. Future work will include the formulation of c.a. [
F]4 for studying its biodistribution in tumour-bearing mice. The imaging of reactive oxygen species (ROS) at the molecular level with high sensitivity and specificity by positron emission tomography (PET) could be of enormous interest to increase our knowledge about ROS activity and signalling, especially in tumours. The aim of this research was to optimise the click chemistry‐based radiosynthesis of an 18 F‐labelled aminoferrocene glycoconjugate that was derived from an N‐alkylaminoferrocene lead structure known to have anticancer activity in vitro. Applying the solvent system phosphate buffer/THF (12/5), Cu(OAc) 2 and sodium ascorbate as reducing agent at 60°C, the alkyne 1 reacted with the 18 F‐labelled glycosyl azide [ 18 F] 2 in the presence of carrier 3 (47μM) to obtain carrier‐added [ 18 F] 4 in a radiochemical yield of 85%. Interestingly, the addition of carrier was essential for sufficient radiochemical yield, because it suppressed the oxidation of no‐carrier‐added (n.c.a.) [ 18 F] 4 . Future work will include the formulation of c.a. [ 18 F] 4 for studying its biodistribution in tumour‐bearing mice. |
Author | Toms, Johannes Prante, Olaf Maschauer, Simone Mokhir, Andriy Reshetnikov, Viktor |
Author_xml | – sequence: 1 givenname: Johannes surname: Toms fullname: Toms, Johannes organization: Department of Nuclear Medicine, Molecular Imaging and Radiochemistry, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Erlangen, Germany – sequence: 2 givenname: Viktor surname: Reshetnikov fullname: Reshetnikov, Viktor organization: Department of Chemistry and Pharmacy, Organic Chemistry Chair II, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Erlangen, Germany – sequence: 3 givenname: Simone surname: Maschauer fullname: Maschauer, Simone organization: Department of Nuclear Medicine, Molecular Imaging and Radiochemistry, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Erlangen, Germany – sequence: 4 givenname: Andriy orcidid: 0000-0002-9079-5569 surname: Mokhir fullname: Mokhir, Andriy organization: Department of Chemistry and Pharmacy, Organic Chemistry Chair II, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Erlangen, Germany – sequence: 5 givenname: Olaf orcidid: 0000-0003-0247-3656 surname: Prante fullname: Prante, Olaf organization: Department of Nuclear Medicine, Molecular Imaging and Radiochemistry, Friedrich-Alexander University Erlangen-Nürnberg (FAU), Erlangen, Germany |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30303563$$D View this record in MEDLINE/PubMed |
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Keywords | click chemistry positron emission tomography F-18 reactive oxygen species |
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References | e_1_2_7_6_1 e_1_2_7_5_1 e_1_2_7_4_1 e_1_2_7_3_1 e_1_2_7_9_1 e_1_2_7_8_1 Daum S (e_1_2_7_19_1) 2018 e_1_2_7_17_1 Maschauer S (e_1_2_7_18_1) 2014 e_1_2_7_16_1 e_1_2_7_2_1 e_1_2_7_15_1 e_1_2_7_14_1 e_1_2_7_25_1 e_1_2_7_24_1 e_1_2_7_12_1 e_1_2_7_11_1 e_1_2_7_22_1 e_1_2_7_10_1 e_1_2_7_21_1 e_1_2_7_20_1 Sasaki T (e_1_2_7_7_1) 1996; 37 Reshetnikov MSV (e_1_2_7_13_1) 2018 Hall DG (e_1_2_7_23_1) 2006 |
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Title | Radiosynthesis of an 18 F-fluoroglycosylated aminoferrocene for in-vivo imaging of reactive oxygen species activity by PET |
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