Texaphyrin metal complexes having improved functionalization

Details Texaphyrin metal complexes having improved functionalization Texaphyrin metal complexes having improved functionalization

C - Chemistry, Metallurgy

07

D

C07D 487/22 (2006.01) A61K 41/00 (2006.01) A61K 47/48 (2006.01) A61K 49/00 (2006.01) A61K 51/04 (2006.01) C07F 5/00 (2006.01) C07H 15/26 (2006.01) C07H 21/00 (2006.01) C07J 43/00 (2006.01) C07K 2/00 (2006.01) C07K 14/435 (2006.01) C07K 16/00 (2006.01)

Patent

CA 2182960

Texaphyrin metal complexes of formula (I) having improved function- alization include the addition of elec- tron donating groups to positions 2, 7, 12, 15, 18 and/or 21 and/or the addi- tion of electron withdrawing groups to positions 15 or 18 of the macrocycle. Electron donating groups at positions 2, 7, 12, 15, 18 and/or 21 contribute elec- trons to the aromatic .pi. system of the macrocycle which stabilizes the metal complex to demetallation and the imine bonds to hydrolysis. These texaphyrin metal complexes having enhanced sta- bility are useful for localization, mag- netic resonance imaging, radiosensiti- zation, radiation therapy, fluorescence imaging, photodynamic tumor therapy and applications requiring singlet oxy- gen production for cytotoxicity. Elec- tron withdrawing groups at positions 15 or 18 render the macrocycle more readily reduced, i.e. the redox potential is lower and the macrocycle more readily gains an electron to form a radical. Such texaphyrins having a low redox potential are useful for radiosensitization applications.

Des complexes métalliques de texaphyrine selon la formule (I) présentent une fonctionnalisation améliorée après addition de groupes donneurs d'électrons en position 2, 7, 12, 15, 18 et/ou 21 et/ou addition de groupes capteurs d'électrons en position 15 ou 18 du macrocycle. Les groupes donneurs d'électrons en position 2, 7, 12, 15, 18 et/ou 21 cèdent des électrons au système .pi. aromatique du macrocycle, qui rend le complexe métallique stable à la démétallisation et les liaisons imines stables à l'hydrolyse. Ces complexes métalliques de texaphyrine à stabilité renforcée sont utiles pour la localisation, l'imagerie par résonance magnétique, l'imagerie par fluorescence, la thérapie photodynamique des tumeurs et les applications nécessitant la production d'oxygène singulet pour la cytotoxicité. Les groupes capteurs d'électrons en position 15 ou 18 accélèrent la réduction du macrocycle, c'est-à-dire que le potentiel d'oxydo-réduction devient plus faible et que le macrocycle capte plus rapidement un électron pour former un radical. Ces texaphyrines à faible potentiel d'oxydo-réduction sont utiles pour les applications de radiosensibilisation.

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