H4picoopaRobust Chelate for 225Ac/111In Theranostics
The nuclear decay characteristics of 225Ac (E α = 5–8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t 1/2 = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. S...
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| Published in | Bioconjugate chemistry Vol. 33; no. 10; pp. 1900 - 1921 |
|---|---|
| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
19.10.2022
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1043-1802 1520-4812 1520-4812 |
| DOI | 10.1021/acs.bioconjchem.2c00364 |
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| Abstract | The nuclear decay characteristics of 225Ac (E α = 5–8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t 1/2 = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. Since 225Ac does not possess any suitable low-energy, high abundance γ-ray emissions for nuclear imaging, there is a clear need for the development of other companion radionuclides with similar coordination characteristics and comparable half-lives, which can be applied in diagnostics. H4picoopa was designed and executed as a high-denticity ligand for chelation of [225Ac]Ac3+, and the complexation characteristics have been explored through nuclear magnetic resonance (NMR) spectroscopy, solution thermodynamic stability studies, and radiolabeling. The ligand shows highly favorable complexation with La3+ (pM = 17.6), Lu3+ (pM = 21.3), and In3+ (pM = 31.2) and demonstrates effective radiolabeling of both [225Ac]Ac3+ and [111In]In3+ ions achieving quantitative radiochemical conversions (RCCs) under mild conditions (RT, 10 min), accompanied by high serum stability (>97% radiochemical purity (RCP) over 6 days). A bifunctional analogue of H4picoopa was synthesized and conjugated to the Pip-Nle-CycMSHhex peptide for targeting of MC1R positive melanoma tumors. In vivo single-photon emission computed tomography (SPECT) and biodistribution studies of the 111In-radiolabeled bioconjugate in mice bearing B16-F10 tumors showed good radiotracer stability, although improved tumor targeting could not be achieved for imaging purposes. This work highlights H4picoopa as a very promising platform for application of [225Ac]Ac3+ and [111In]In3+ as a theranostic pair and allows great versatility for the incorporation of other directing vectors. The logical synthetic approach reported here for bifunctional H4picoopa, involving an azide-functionalized covalent linker and CuI-catalyzed alkyne-azide cycloaddition, allows for ease of optimization of bioconjugate pharmacokinetics and will be valuable for further radiopharmaceutical applications moving forward. |
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| AbstractList | The nuclear decay characteristics of 225Ac (E α = 5–8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t 1/2 = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. Since 225Ac does not possess any suitable low-energy, high abundance γ-ray emissions for nuclear imaging, there is a clear need for the development of other companion radionuclides with similar coordination characteristics and comparable half-lives, which can be applied in diagnostics. H4picoopa was designed and executed as a high-denticity ligand for chelation of [225Ac]Ac3+, and the complexation characteristics have been explored through nuclear magnetic resonance (NMR) spectroscopy, solution thermodynamic stability studies, and radiolabeling. The ligand shows highly favorable complexation with La3+ (pM = 17.6), Lu3+ (pM = 21.3), and In3+ (pM = 31.2) and demonstrates effective radiolabeling of both [225Ac]Ac3+ and [111In]In3+ ions achieving quantitative radiochemical conversions (RCCs) under mild conditions (RT, 10 min), accompanied by high serum stability (>97% radiochemical purity (RCP) over 6 days). A bifunctional analogue of H4picoopa was synthesized and conjugated to the Pip-Nle-CycMSHhex peptide for targeting of MC1R positive melanoma tumors. In vivo single-photon emission computed tomography (SPECT) and biodistribution studies of the 111In-radiolabeled bioconjugate in mice bearing B16-F10 tumors showed good radiotracer stability, although improved tumor targeting could not be achieved for imaging purposes. This work highlights H4picoopa as a very promising platform for application of [225Ac]Ac3+ and [111In]In3+ as a theranostic pair and allows great versatility for the incorporation of other directing vectors. The logical synthetic approach reported here for bifunctional H4picoopa, involving an azide-functionalized covalent linker and CuI-catalyzed alkyne-azide cycloaddition, allows for ease of optimization of bioconjugate pharmacokinetics and will be valuable for further radiopharmaceutical applications moving forward. The nuclear decay characteristics of 225Ac (Eα = 5–8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t1/2 = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. Since 225Ac does not possess any suitable low-energy, high abundance γ-ray emissions for nuclear imaging, there is a clear need for the development of other companion radionuclides with similar coordination characteristics and comparable half-lives, which can be applied in diagnostics. H4picoopa was designed and executed as a high-denticity ligand for chelation of [225Ac]Ac3+, and the complexation characteristics have been explored through nuclear magnetic resonance (NMR) spectroscopy, solution thermodynamic stability studies, and radiolabeling. The ligand shows highly favorable complexation with La3+ (pM = 17.6), Lu3+ (pM = 21.3), and In3+ (pM = 31.2) and demonstrates effective radiolabeling of both [225Ac]Ac3+ and [111In]In3+ ions achieving quantitative radiochemical conversions (RCCs) under mild conditions (RT, 10 min), accompanied by high serum stability (>97% radiochemical purity (RCP) over 6 days). A bifunctional analogue of H4picoopa was synthesized and conjugated to the Pip-Nle-CycMSHhex peptide for targeting of MC1R positive melanoma tumors. In vivo single-photon emission computed tomography (SPECT) and biodistribution studies of the 111In-radiolabeled bioconjugate in mice bearing B16-F10 tumors showed good radiotracer stability, although improved tumor targeting could not be achieved for imaging purposes. This work highlights H4picoopa as a very promising platform for application of [225Ac]Ac3+ and [111In]In3+ as a theranostic pair and allows great versatility for the incorporation of other directing vectors. The logical synthetic approach reported here for bifunctional H4picoopa, involving an azide-functionalized covalent linker and CuI-catalyzed alkyne-azide cycloaddition, allows for ease of optimization of bioconjugate pharmacokinetics and will be valuable for further radiopharmaceutical applications moving forward. The nuclear decay characteristics of Ac-225 (E-alpha = 5- 8 MeV, linear energy transfer (LET) = similar to 100 keV/mu m, t(1/2) = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. Since Ac-225 does not possess any suitable low-energy, high abundance gamma-ray emissions for nuclear imaging, there is a clear need for the development of other companion radionuclides with similar coordination characteristics and comparable half-lives, which can be applied in diagnostics. H4picoopa was designed and executed as a high-denticity ligand for chelation of [Ac-225]Ac3+, and the complexation characteristics have been explored through nuclear magnetic resonance (NMR) spectroscopy, solution thermodynamic stability studies, and radiolabeling. The ligand shows highly favorable complexation with La3+ (pM = 17.6), Lu3+ (pM = 21.3), and In3+ (pM = 31.2) and demonstrates effective radiolabeling of both [Ac-225]Ac3+ and [In-111]In3+ ions achieving quantitative radiochemical conversions (RCCs) under mild conditions (RT, 10 min), accompanied by high serum stability (> 97% radiochemical purity (RCP) over 6 days). A bifunctional analogue of H4picoopa was synthesized and conjugated to the Pip-Nle-CycMSHhex peptide for targeting of MC1R positive melanoma tumors. In vivo single-photon emission computed tomography (SPECT) and biodistribution studies of the( 111)In-radiolabeled bioconjugate in mice bearing B16-F10 tumors showed good radiotracer stability, although improved tumor targeting could not be achieved for imaging purposes. This work highlights H(4)picoopa as a very promising platform for application of [Ac-225]Ac3+ and [In-111]In(3+ )as a theranostic pair and allows great versatility for the incorporation of other directing vectors. The logical synthetic approach reported here for bifunctional H(4)picoopa, involving an azide-functionalized covalent linker and CuIcatalyzed alkyne-azide cycloaddition, allows for ease of optimization of bioconjugate pharmacokinetics and will be valuable for further radiopharmaceutical applications moving forward. The nuclear decay characteristics of 225Ac (Eα = 5-8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t1/2 = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. Since 225Ac does not possess any suitable low-energy, high abundance γ-ray emissions for nuclear imaging, there is a clear need for the development of other companion radionuclides with similar coordination characteristics and comparable half-lives, which can be applied in diagnostics. H4picoopa was designed and executed as a high-denticity ligand for chelation of [225Ac]Ac3+, and the complexation characteristics have been explored through nuclear magnetic resonance (NMR) spectroscopy, solution thermodynamic stability studies, and radiolabeling. The ligand shows highly favorable complexation with La3+ (pM = 17.6), Lu3+ (pM = 21.3), and In3+ (pM = 31.2) and demonstrates effective radiolabeling of both [225Ac]Ac3+ and [111In]In3+ ions achieving quantitative radiochemical conversions (RCCs) under mild conditions (RT, 10 min), accompanied by high serum stability (>97% radiochemical purity (RCP) over 6 days). A bifunctional analogue of H4picoopa was synthesized and conjugated to the Pip-Nle-CycMSHhex peptide for targeting of MC1R positive melanoma tumors. In vivo single-photon emission computed tomography (SPECT) and biodistribution studies of the 111In-radiolabeled bioconjugate in mice bearing B16-F10 tumors showed good radiotracer stability, although improved tumor targeting could not be achieved for imaging purposes. This work highlights H4picoopa as a very promising platform for application of [225Ac]Ac3+ and [111In]In3+ as a theranostic pair and allows great versatility for the incorporation of other directing vectors. The logical synthetic approach reported here for bifunctional H4picoopa, involving an azide-functionalized covalent linker and CuI-catalyzed alkyne-azide cycloaddition, allows for ease of optimization of bioconjugate pharmacokinetics and will be valuable for further radiopharmaceutical applications moving forward.The nuclear decay characteristics of 225Ac (Eα = 5-8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t1/2 = 9.92 days) are well recognized as advantageous for the treatment of primary and metastatic tumors; however, suitable chelation systems are required, which can accommodate this radiometal. Since 225Ac does not possess any suitable low-energy, high abundance γ-ray emissions for nuclear imaging, there is a clear need for the development of other companion radionuclides with similar coordination characteristics and comparable half-lives, which can be applied in diagnostics. H4picoopa was designed and executed as a high-denticity ligand for chelation of [225Ac]Ac3+, and the complexation characteristics have been explored through nuclear magnetic resonance (NMR) spectroscopy, solution thermodynamic stability studies, and radiolabeling. The ligand shows highly favorable complexation with La3+ (pM = 17.6), Lu3+ (pM = 21.3), and In3+ (pM = 31.2) and demonstrates effective radiolabeling of both [225Ac]Ac3+ and [111In]In3+ ions achieving quantitative radiochemical conversions (RCCs) under mild conditions (RT, 10 min), accompanied by high serum stability (>97% radiochemical purity (RCP) over 6 days). A bifunctional analogue of H4picoopa was synthesized and conjugated to the Pip-Nle-CycMSHhex peptide for targeting of MC1R positive melanoma tumors. In vivo single-photon emission computed tomography (SPECT) and biodistribution studies of the 111In-radiolabeled bioconjugate in mice bearing B16-F10 tumors showed good radiotracer stability, although improved tumor targeting could not be achieved for imaging purposes. This work highlights H4picoopa as a very promising platform for application of [225Ac]Ac3+ and [111In]In3+ as a theranostic pair and allows great versatility for the incorporation of other directing vectors. The logical synthetic approach reported here for bifunctional H4picoopa, involving an azide-functionalized covalent linker and CuI-catalyzed alkyne-azide cycloaddition, allows for ease of optimization of bioconjugate pharmacokinetics and will be valuable for further radiopharmaceutical applications moving forward. |
| Author | Rodríguez-Rodríguez, Cristina Zhang, Chengcheng Zeisler, Jutta Osooly, Maryam Radchenko, Valery Wharton, Luke Yang, Hua Lin, Kuo-Shyan Schaffer, Paul Jaraquemada-Peláez, María de Guadalupe Bénard, François Orvig, Chris |
| AuthorAffiliation | Department of Chemistry Life Sciences Division Faculty of Pharmaceutical Sciences Medicinal Inorganic Chemistry Group, Department of Chemistry Department of Physics and Astronomy Department of Molecular Oncology Simon Fraser University Department of Radiology |
| AuthorAffiliation_xml | – name: Department of Radiology – name: Department of Chemistry – name: Department of Molecular Oncology – name: Department of Physics and Astronomy – name: Faculty of Pharmaceutical Sciences – name: Medicinal Inorganic Chemistry Group, Department of Chemistry – name: Simon Fraser University – name: Life Sciences Division |
| Author_xml | – sequence: 1 givenname: Luke orcidid: 0000-0002-0636-8741 surname: Wharton fullname: Wharton, Luke organization: Life Sciences Division – sequence: 2 givenname: María de Guadalupe orcidid: 0000-0002-6204-707X surname: Jaraquemada-Peláez fullname: Jaraquemada-Peláez, María de Guadalupe organization: Medicinal Inorganic Chemistry Group, Department of Chemistry – sequence: 3 givenname: Chengcheng orcidid: 0000-0001-5786-4748 surname: Zhang fullname: Zhang, Chengcheng organization: Department of Molecular Oncology – sequence: 4 givenname: Jutta surname: Zeisler fullname: Zeisler, Jutta organization: Department of Molecular Oncology – sequence: 5 givenname: Cristina orcidid: 0000-0002-3313-4422 surname: Rodríguez-Rodríguez fullname: Rodríguez-Rodríguez, Cristina organization: Department of Physics and Astronomy – sequence: 6 givenname: Maryam surname: Osooly fullname: Osooly, Maryam organization: Faculty of Pharmaceutical Sciences – sequence: 7 givenname: Valery surname: Radchenko fullname: Radchenko, Valery organization: Department of Chemistry – sequence: 8 givenname: Hua orcidid: 0000-0003-1833-9515 surname: Yang fullname: Yang, Hua organization: Simon Fraser University – sequence: 9 givenname: Kuo-Shyan orcidid: 0000-0002-0739-0780 surname: Lin fullname: Lin, Kuo-Shyan organization: Department of Radiology – sequence: 10 givenname: François orcidid: 0000-0001-7995-3581 surname: Bénard fullname: Bénard, François organization: Department of Radiology – sequence: 11 givenname: Paul orcidid: 0000-0002-6392-8792 surname: Schaffer fullname: Schaffer, Paul organization: Department of Radiology – sequence: 12 givenname: Chris orcidid: 0000-0002-2830-5493 surname: Orvig fullname: Orvig, Chris email: orvig@chem.ubc.ca organization: Medicinal Inorganic Chemistry Group, Department of Chemistry |
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| Keywords | EQUILIBRIUM-CONSTANTS MELANOCYTE-STIMULATING HORMONE STABILITY MELANOCORTIN-1 RECEPTOR IN-111 LIGAND HOCTAPA DERIVATIVES RELEVANT |
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| PublicationTitle | Bioconjugate chemistry |
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| Snippet | The nuclear decay characteristics of 225Ac (E α = 5–8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t 1/2 = 9.92 days) are well recognized as advantageous... The nuclear decay characteristics of Ac-225 (E-alpha = 5- 8 MeV, linear energy transfer (LET) = similar to 100 keV/mu m, t(1/2) = 9.92 days) are well... The nuclear decay characteristics of 225Ac (Eα = 5–8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t1/2 = 9.92 days) are well recognized as advantageous for... The nuclear decay characteristics of 225Ac (Eα = 5-8 MeV, linear energy transfer (LET) = ∼100 keV/μm, t1/2 = 9.92 days) are well recognized as advantageous for... |
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| SubjectTerms | Alkynes Biochemical Research Methods Biochemistry & Molecular Biology Chelation Chemistry Chemistry, Multidisciplinary Chemistry, Organic Complexation Computed tomography Cycloaddition Emission analysis Emissions Energy transfer Gamma emission In vivo methods and tests Life Sciences & Biomedicine Ligands Linear energy transfer (LET) Medical imaging Melanoma Metastases NMR NMR spectroscopy Nuclear magnetic resonance Optimization Pharmaceuticals Pharmacokinetics Photon emission Physical Sciences Precision medicine Radioactive tracers Radiochemistry Radioisotopes Radiolabelling Science & Technology Single photon emission computed tomography Spectroscopy Stability Tumors |
| Title | H4picoopaRobust Chelate for 225Ac/111In Theranostics |
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