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 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
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. |
|---|---|
| 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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| Cites_doi | 10.1021/mp4004817 10.1196/annals.1427.007 10.1038/jcbfm.1988.28 10.1021/ja509198w 10.1021/om00136a033 10.1002/chem.201604473 10.1021/acs.bioconjchem.6b00472 10.2967/jnumed.112.115436 10.1021/jm2014937 10.1016/j.nucmedbio.2017.05.011 10.1002/anie.200904137 10.1016/j.nucmedbio.2017.09.004 10.1016/j.carres.2009.02.001 10.1002/anie.201706585 10.1021/acs.jmedchem.6b00675 10.1602/neurorx.2.1.44 10.1089/ars.2015.6415 10.1039/C3OB42379D 10.1016/S0955-0674(03)00002-4 |
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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 |
| References_xml | – ident: e_1_2_7_20_1 doi: 10.1021/mp4004817 – ident: e_1_2_7_5_1 doi: 10.1196/annals.1427.007 – ident: e_1_2_7_6_1 doi: 10.1038/jcbfm.1988.28 – ident: e_1_2_7_10_1 doi: 10.1021/ja509198w – ident: e_1_2_7_24_1 doi: 10.1021/om00136a033 – ident: e_1_2_7_11_1 doi: 10.1002/chem.201604473 – ident: e_1_2_7_16_1 doi: 10.1021/acs.bioconjchem.6b00472 – year: 2018 ident: e_1_2_7_19_1 article-title: Identification of active species derived from anticancer N‐alkylaminoferrocene‐based prodrugs and their radiolabeling with 18F publication-title: Bioconjug Chem contributor: fullname: Daum S – ident: e_1_2_7_4_1 doi: 10.2967/jnumed.112.115436 – ident: e_1_2_7_25_1 doi: 10.1021/jm2014937 – ident: e_1_2_7_9_1 doi: 10.1016/j.nucmedbio.2017.05.011 – volume-title: Boronic acids: preparation, applications in organic synthesis and medicine year: 2006 ident: e_1_2_7_23_1 contributor: fullname: Hall DG – volume: 37 start-page: 1698 issue: 10 year: 1996 ident: e_1_2_7_7_1 article-title: Assessment of antioxidative ability in brain: technetium‐99m‐meso‐HMPAO as an imaging agent for glutathione localization publication-title: J Nucl Med contributor: fullname: Sasaki T – start-page: 16 year: 2014 ident: e_1_2_7_18_1 article-title: Sweetening pharmaceutical radiochemistry by 18F‐fluoroglycosylation: a short review publication-title: Biomed Res Int contributor: fullname: Maschauer S – ident: e_1_2_7_15_1 doi: 10.1002/anie.200904137 – ident: e_1_2_7_21_1 doi: 10.1016/j.nucmedbio.2017.09.004 – ident: e_1_2_7_22_1 doi: 10.1016/j.carres.2009.02.001 – ident: e_1_2_7_12_1 doi: 10.1002/anie.201706585 – volume-title: unpublished results year: 2018 ident: e_1_2_7_13_1 contributor: fullname: Reshetnikov MSV – ident: e_1_2_7_17_1 doi: 10.1021/acs.jmedchem.6b00675 – ident: e_1_2_7_14_1 doi: 10.1602/neurorx.2.1.44 – ident: e_1_2_7_3_1 doi: 10.1089/ars.2015.6415 – ident: e_1_2_7_8_1 doi: 10.1039/C3OB42379D – ident: e_1_2_7_2_1 doi: 10.1016/S0955-0674(03)00002-4 |
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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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