Texaphyrin metal complexes having improved functionalization
First Claim
1. A texaphyrin having the structure:
- ##STR5## wherein M is H, a divalent metal cation selected from the group consisting of Ca+2, Mn+2, Co+2, Ni+2, Zn+2, Cd+2, Hg+2, Fe+2, Sm+2 and UO2+2 or a trivalent metal cation selected from the group consisting of Mn+3, Co+3, Ni+3, Fe+3, Ho+3, Ce+3, Y+3, In+3, Pr+3, Nd+3, Sm+3, Eu+3, Gd+3, Tb+3, Dy+3, Er+3, Tm+3, Yb+3, Lu+3, La+3, and U+3 ;
R1 -R4 and R6 -R9 are independently hydrogen, halide other than iodide, hydroxyl, alkyl, aryl, haloalkyl other than iodoalkyl, nitro, formyl, acyl, hydroxyalkyl, oxyalkyl, oxyhydroxyalkyl, carboxy, carboxyalkyl, carboxyamidealkyl, a sapphyrin molecule, or a linker to a sapphyrin molecule;
R5 and R10 are independently hydrogen, alkyl, aryl, hydroxyalkyl, oxyalkyl, oxyhydroxyalkyl, carboxyalkyl, carboxyamidealkyl or a linker to a sapphyrin molecule;
at least one of R5, R6, R9, and R10 is other than hydrogen; and
N is an integer less than or equal to 2.
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Abstract
Texaphyrin metal complexes having improved functionalization including the addition of electron donating groups to positions 12, 15, 18 and/or 21 and/or the addition of electron withdrawing groups to positions 15 or 18 of the macrocycle. Electron donating groups at positions 12, 15, 18 and/or 21 contribute electrons to the aromatic π system of the macrocycle which stabilizes the metal complex to demetallation and the imine bonds to hydrolysis, these texaphyrin metal complexes having enhanced stability are useful for localization, magnetic resonance imaging, radiosensitization, radiation therapy, fluorescence imaging, photodynamic tumor therapy and applications requiring singlet oxygen production for cytotoxicity. Electron 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.
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Citations
34 Claims
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1. A texaphyrin having the structure:
- ##STR5## wherein M is H, a divalent metal cation selected from the group consisting of Ca+2, Mn+2, Co+2, Ni+2, Zn+2, Cd+2, Hg+2, Fe+2, Sm+2 and UO2+2 or a trivalent metal cation selected from the group consisting of Mn+3, Co+3, Ni+3, Fe+3, Ho+3, Ce+3, Y+3, In+3, Pr+3, Nd+3, Sm+3, Eu+3, Gd+3, Tb+3, Dy+3, Er+3, Tm+3, Yb+3, Lu+3, La+3, and U+3 ;
R1 -R4 and R6 -R9 are independently hydrogen, halide other than iodide, hydroxyl, alkyl, aryl, haloalkyl other than iodoalkyl, nitro, formyl, acyl, hydroxyalkyl, oxyalkyl, oxyhydroxyalkyl, carboxy, carboxyalkyl, carboxyamidealkyl, a sapphyrin molecule, or a linker to a sapphyrin molecule; R5 and R10 are independently hydrogen, alkyl, aryl, hydroxyalkyl, oxyalkyl, oxyhydroxyalkyl, carboxyalkyl, carboxyamidealkyl or a linker to a sapphyrin molecule; at least one of R5, R6, R9, and R10 is other than hydrogen; and N is an integer less than or equal to 2. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34)
- ##STR5## wherein M is H, a divalent metal cation selected from the group consisting of Ca+2, Mn+2, Co+2, Ni+2, Zn+2, Cd+2, Hg+2, Fe+2, Sm+2 and UO2+2 or a trivalent metal cation selected from the group consisting of Mn+3, Co+3, Ni+3, Fe+3, Ho+3, Ce+3, Y+3, In+3, Pr+3, Nd+3, Sm+3, Eu+3, Gd+3, Tb+3, Dy+3, Er+3, Tm+3, Yb+3, Lu+3, La+3, and U+3 ;
Specification