Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers
Abstract Dual-modality imaging agents featuring both a radioactive complex for positron emission tomography (PET) and a fluorophore for optical fluorescence imaging (OFI) are crucial tools for reinforcing clinical diagnosis and intraoperative surgeries. We report the synthesis and characterisation o...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-06-01
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| Series: | Communications Chemistry |
| Online Access: | https://doi.org/10.1038/s42004-023-00906-5 |
| _version_ | 1797811634050170880 |
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| author | Faustine d’Orchymont Jason P. Holland |
| author_facet | Faustine d’Orchymont Jason P. Holland |
| author_sort | Faustine d’Orchymont |
| collection | DOAJ |
| description | Abstract Dual-modality imaging agents featuring both a radioactive complex for positron emission tomography (PET) and a fluorophore for optical fluorescence imaging (OFI) are crucial tools for reinforcing clinical diagnosis and intraoperative surgeries. We report the synthesis and characterisation of bimodal mechanically interlocked rotaxane-based imaging agents, constructed via the cucurbit[6]uril CB[6]-mediated alkyne-azide ‘click’ reaction. Two synthetic routes involving four- or six-component reactions are developed to access asymmetric rotaxanes. Furthermore, by using this rapid and versatile approach, a peptide-based rotaxane targeted toward the clinical prostate cancer biomarker, prostate-specific membrane antigen (PSMA), and bearing a 68Ga-radiometal ion complex for positron emission tomography and fluorescein as an optically active imaging agent, was synthesised. The chemical and radiochemical stability, and the cellular uptake profile of the radiolabelled and fluorescent rotaxane was evaluated in vitro where the experimental data demonstrate the viability of using an asymmetric rotaxane platform to produce dual-modality imaging agents that specifically target prostate cancer cells. |
| first_indexed | 2024-03-13T07:25:34Z |
| format | Article |
| id | doaj.art-9bfcfc8056154137bbdd111e7c0ab396 |
| institution | Directory Open Access Journal |
| issn | 2399-3669 |
| language | English |
| last_indexed | 2024-03-13T07:25:34Z |
| publishDate | 2023-06-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Communications Chemistry |
| spelling | doaj.art-9bfcfc8056154137bbdd111e7c0ab3962023-06-04T11:23:14ZengNature PortfolioCommunications Chemistry2399-36692023-06-016111010.1038/s42004-023-00906-5Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkersFaustine d’Orchymont0Jason P. Holland1University of Zurich, Department of ChemistryUniversity of Zurich, Department of ChemistryAbstract Dual-modality imaging agents featuring both a radioactive complex for positron emission tomography (PET) and a fluorophore for optical fluorescence imaging (OFI) are crucial tools for reinforcing clinical diagnosis and intraoperative surgeries. We report the synthesis and characterisation of bimodal mechanically interlocked rotaxane-based imaging agents, constructed via the cucurbit[6]uril CB[6]-mediated alkyne-azide ‘click’ reaction. Two synthetic routes involving four- or six-component reactions are developed to access asymmetric rotaxanes. Furthermore, by using this rapid and versatile approach, a peptide-based rotaxane targeted toward the clinical prostate cancer biomarker, prostate-specific membrane antigen (PSMA), and bearing a 68Ga-radiometal ion complex for positron emission tomography and fluorescein as an optically active imaging agent, was synthesised. The chemical and radiochemical stability, and the cellular uptake profile of the radiolabelled and fluorescent rotaxane was evaluated in vitro where the experimental data demonstrate the viability of using an asymmetric rotaxane platform to produce dual-modality imaging agents that specifically target prostate cancer cells.https://doi.org/10.1038/s42004-023-00906-5 |
| spellingShingle | Faustine d’Orchymont Jason P. Holland Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers Communications Chemistry |
| title | Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers |
| title_full | Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers |
| title_fullStr | Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers |
| title_full_unstemmed | Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers |
| title_short | Asymmetric rotaxanes as dual-modality supramolecular imaging agents for targeting cancer biomarkers |
| title_sort | asymmetric rotaxanes as dual modality supramolecular imaging agents for targeting cancer biomarkers |
| url | https://doi.org/10.1038/s42004-023-00906-5 |
| work_keys_str_mv | AT faustinedorchymont asymmetricrotaxanesasdualmodalitysupramolecularimagingagentsfortargetingcancerbiomarkers AT jasonpholland asymmetricrotaxanesasdualmodalitysupramolecularimagingagentsfortargetingcancerbiomarkers |