Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

The Cu(I)-catalysed Huisgen cycloaddition, known as “click” reaction, has been applied to the synthesis of a range of triazole-linked porphyrin/corrole to DOTA/NOTA derivatives. Microwave irradiation significantly accelerates the reaction. The synthesis of heterobimetallic complexes was easily achie...

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Bibliographic Details
Main Authors: Nicolas Desbois, Sandrine Pacquelet, Adrien Dubois, Clément Michelin, Claude P. Gros
Format: Article
Language:English
Published: Beilstein-Institut 2015-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
click chemistry
corrole
DOTA
microwave
NOTA
porphyrin
Online Access:https://doi.org/10.3762/bjoc.11.239
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spelling doaj-55fa33321be74a428053be2a8fac4abe2021-03-02T10:12:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-11-011112202220810.3762/bjoc.11.2391860-5397-11-239Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloadditionNicolas Desbois0Sandrine Pacquelet1Adrien Dubois2Clément Michelin3Claude P. Gros4Université de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, FranceUniversité de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, FranceUniversité de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, FranceUniversité de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, FranceUniversité de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, FranceThe Cu(I)-catalysed Huisgen cycloaddition, known as “click” reaction, has been applied to the synthesis of a range of triazole-linked porphyrin/corrole to DOTA/NOTA derivatives. Microwave irradiation significantly accelerates the reaction. The synthesis of heterobimetallic complexes was easily achieved in up to 60% isolated yield. Heterobimetallic complexes were easily prepared as potential MRI/PET (SPECT) bimodal contrast agents incorporating one metal (Mn, Gd) for the enhancement of contrast for MRI applications and one “cold” metal (Cu, Ga, In) for future radionuclear imaging applications. Preliminary relaxivity measurements showed that the reported complexes are promising contrast agents (CA) in MRI.https://doi.org/10.3762/bjoc.11.239click chemistrycorroleDOTAmicrowaveNOTAporphyrin
collection DOAJ
language English
format Article
sources DOAJ
author Nicolas Desbois
Sandrine Pacquelet
Adrien Dubois
Clément Michelin
Claude P. Gros
spellingShingle Nicolas Desbois
Sandrine Pacquelet
Adrien Dubois
Clément Michelin
Claude P. Gros
Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
Beilstein Journal of Organic Chemistry
click chemistry
corrole
DOTA
microwave
NOTA
porphyrin
author_facet Nicolas Desbois
Sandrine Pacquelet
Adrien Dubois
Clément Michelin
Claude P. Gros
author_sort Nicolas Desbois
title Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
title_short Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
title_full Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
title_fullStr Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
title_full_unstemmed Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
title_sort easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2015-11-01
description The Cu(I)-catalysed Huisgen cycloaddition, known as “click” reaction, has been applied to the synthesis of a range of triazole-linked porphyrin/corrole to DOTA/NOTA derivatives. Microwave irradiation significantly accelerates the reaction. The synthesis of heterobimetallic complexes was easily achieved in up to 60% isolated yield. Heterobimetallic complexes were easily prepared as potential MRI/PET (SPECT) bimodal contrast agents incorporating one metal (Mn, Gd) for the enhancement of contrast for MRI applications and one “cold” metal (Cu, Ga, In) for future radionuclear imaging applications. Preliminary relaxivity measurements showed that the reported complexes are promising contrast agents (CA) in MRI.
topic click chemistry
corrole
DOTA
microwave
NOTA
porphyrin
url https://doi.org/10.3762/bjoc.11.239
work_keys_str_mv AT nicolasdesbois easyaccesstoheterobimetalliccomplexesformedicalimagingapplicationsviamicrowaveenhancedcycloaddition
AT sandrinepacquelet easyaccesstoheterobimetalliccomplexesformedicalimagingapplicationsviamicrowaveenhancedcycloaddition
AT adriendubois easyaccesstoheterobimetalliccomplexesformedicalimagingapplicationsviamicrowaveenhancedcycloaddition
AT clementmichelin easyaccesstoheterobimetalliccomplexesformedicalimagingapplicationsviamicrowaveenhancedcycloaddition
AT claudepgros easyaccesstoheterobimetalliccomplexesformedicalimagingapplicationsviamicrowaveenhancedcycloaddition
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