Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-02-15
1997-02-04
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540465, 540472, C07D48722
Patent
active
055999239
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 .pi. 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.
REFERENCES:
patent: 4647447 (1987-03-01), Gries et al.
patent: 4878891 (1989-11-01), Judy et al.
patent: 4880008 (1989-11-01), Lauffer et al.
patent: 4883790 (1989-11-01), Levy et al.
patent: 4899755 (1990-02-01), Lauffer et al.
patent: 4915683 (1990-04-01), Sieber
patent: 4935498 (1990-06-01), Sessler et al.
patent: 4959363 (1990-09-01), Wentland
patent: 4977177 (1990-12-01), Bommer et al.
patent: 5021236 (1991-06-01), Gries et al.
patent: 5030200 (1991-07-01), Judy et al.
patent: 5041078 (1991-08-01), Matthews et al.
patent: 5162509 (1992-11-01), Sessler et al.
patent: 5252720 (1993-10-01), Sessler et al.
patent: 5256399 (1993-10-01), Sessler et al.
patent: 5272142 (1993-12-01), Sessler et al.
patent: 5292414 (1984-03-01), Sessler et al.
Akhtar et al., "Pharmaceutical Aspects of the Biological Stability and Membrane Transport Characteristics of Antisense Oligonucleotides," Gene Regulation: Biology of Antisense RNA and DNA, 133-145, 1992.
Acholla et al., "Binucleating Tetrapyrrole Macrocycles", J. Am. Chem. Soc., 107:6902-6908, 1985.
Acholla et al., "A Binucleating `Accordian` Tetrapyrrole Macrocycle", Tetrahedron Lett., 25:3269-3270, 1984.
Agrawal et al., "Cellular Uptake and Anti-HIV Activity of Oligonucleotides and Their Analogs," Gene Regulation: Biology of Antisense RNA and DNA, 273-283, 1992.
Agrawal and Tang, "Efficient Synthesis of Oligoribonucleotide and Its Phosphorothioate Analogue Using H-Phosphonate Approach," Tetrahedron Letters, 31(52):7541-7544, 1990.
Abid et al., "Lanthanide Complexes of Some Macrocyclic Schiff Bases Derived from Pyridine-2,6-dicarboxaldehyde and .alpha.,.omega.-Primary diamines", Inorg. Chim. Acta, 95:119-125, 1984.
Ansell, "X-Ray Crystal Structure of the Pentagonal Bipyramidal Nickel (11) Complex [Ni.sub.11 (L) (H.sub.2 O).sub.2 ] (BF.sub.4).sub.2 and the Selective Stabilisation of the Nickel (1) Oxidation State by a Quinquedentate Macrocyclic Ligand", J. Chem. Soc., Chem. Commun., 546-547, 1982.
Abid et al., "Lanthanide Complexes of Some Macrocyclic Schiff Bases Derived from Pyridine-2,6-dicarboxaldehyde and .alpha.,.omega.-Primary diamines", Inorg. Chim. Acta, 95:119-125, 1984.
Basile et al., "Metal-Activated Hydrolytic Cleavage of DNA," J. Am. Chem. Soc., 109:7550-7551, 1987.
Bauer et al., "Sapphyrins: Novel Aromatic Pentapyrrolic Macrocycles", J. Am. Chem. Soc., 105:6429-6436, 1983.
Bradley et al., "Antisense Therapeutics," Gene Regulation: Biology of Antisense RNA and DNA, 285-293, 1992.
Breslow et al., "Effects of Metal Ions, Including Mg.sup.2+ and Lanthanides, on the Cleavage of Ribonucleotides and RNA Model Compounds," Proc. Natl. Acad. Sci. USA, 88:4080-4083, 1991.
Broadhurst et al., "Preparation of Some Sulphur-containing Polypyrrolic Macrocycles. Sulphur Extrusion from a meso-Thiaphlorin", J. Chem. Soc., Chem. Commun., 807-809, 1970.
Abid et al., "Lanthanide Complexes of Some Macrocyclic Schiff Bases Derived from Pyridine-2,6-dicarboxaldehyde and .alpha.,.omega.-Primary diamines", Inorg. Chim. Acta, 95:119-125, 1984.
Broadhurst et al., "18-and 22-.pi.-Electron Macrocycles Containing Furan, Pyrrole, and Thiophene Rings", J. Chem. Soc., Chem. Commun., 1480-1482, 1969.
Broadhurst et al., "New Macrocyclic Aromatic Systems Related to Porphins", J. Chem. Soc., Chem. Commun., 23-24, 1969.
Broadhurst et al., "The Synthesis of 22 .pi.-Electron Macrocycles. Sapphyrins and Related Compounds", J. Chem. Soc. Perkin Trans. 1:2111-2116, 1972.
Browne and Bruice, "Chemistry of Phosphodiesters, DNA and Models. 2. The Hydrolysis of Bis(8-hydroxyquinoline) Phosphate in the Absence and Presence of Metal Ions," Journal of the American Chemical Society, 114(13):4951-4958, 1992.
Chin et al., "Co(III) Complex Promoted Hydrolysis of Phosphate Diesters: Comparison in Reactivity of Rigid cis-Diaquotetraazacobalt (III) Complexes," J. Am. Chem. Soc., 111:186-190, 1989.
Chin and Banaszczyk, "Rate-Determining Complexation in Catalytic Hydrolysis of Unactivated Esters in Neutral Water," J. Am. Chem. Soc., 111:2724-2726, 1989.
Chin and Banaszczyk, "Highly Efficient Hydrolytic Cleavage of Adenosine Monophosphate Resulting in a Binuclear Co(III) Complex with a Novel Doubly Bidentate .mu..sup.4 -Phosphato Bridge," J. Am. Chem. Soc., 111:4103-4104, 1989.
Chin and Zou, "Catalytic Hydrolysis of cAMP," Can. J. Chem., 65:1882-1884, 1987.
Chung et al., "Synthesis and Characterization of a Reactive Binuclear Co(III) Complex. Cooperative Promotion of Phosphodiester Hydrolysis," Tetrahedron Letters, 31(38):5413-5146, 1990.
Cohen, Jack S., "Chemically Modified Oligodeoxynucleotide Analogs as Regulators of Viral and Cellular Gene Expression," Gene Regulation: Biology of Antisense RNA and DNA, 247-259, 1992.
Cuellar et al., "Synthesis and Characterization of Metallo and Metal-Free Octaalkylphthalocyanines and Uranyl Decaalkysuperphthalocyanines", Inorg. Chem., 20:3766-3770, 1981.
Day et al., "Large Metal Ion-Centered Template Reactions. A Uranyl Complex of Cyclopentakis (2-iminoisoindoline)", J. Am. Chem. Soc., 97:4519-4527, 1975.
De Cola et al., "Hexaaza Macrocyclic Complexes of the Lanthanides", Inorg. Chem., 25:1729-1732, 1986.
Dougherty, "Photosensitizers: Therapy and Detection of Malignant Tumors", Photochem. Photobiol., 45:879-889, 1987.
Furuta et al., "Phosphate Anion Binding: Enhanced Transport of Nucleotide Monophosphate Using a Sapphyrin Carrier, " J. Am. Chem. Soc., 113:6677-6678, 1991.
Gosmann et al., "Synthesis of a Fourfold Enlarged Porphyrin with an Extremely Large, Diamagnetic Ring-Current Effect", Angew. Chem., Int. Ed Engl., 25:1100-1101, 1986.
Gossauer, "Syntheses of Some Unusual Polypyrrole Macrocycles", Bull. Soc. Chim. Belg., 92:793-795, 1983.
Hanvey et al., "Antisense and Antigene Properties of Peptide Nucleic Acids," Science, 258:1481-1485, 1992.
Harriman et al., "Metallotexaphyrins: A New Family of Photosensitisers for Efficient Generation of Singlet Oxygen", J. Chem. Soc., Chem. Commun., 314-316, 1989.
Hendry and Sargeson, "Metal Ion Promoted Phosphate Ester Hydrolysis. Intramolecular Attack of Coordinated Hydroxide Ion," J. Am. Chem. Soc., 111:2521-2527, 1989.
Kim and Chin, "Dimethyl Phosphate Hydrolysis at Neutral pH," J. Am. Chem. Soc., 114:9792-9795, 1992.
Knubel et al., "Biomimitic Synthesis of an Octavinylogous Porphyrin with an Aromatic [34] Annulene System", Angew. Chem., Int. Ed. Engl., 27:1170-1172, 1988.
Komiyama et al., "Unprecedentedly Fast Hydrolysis of the RNA Dinucleoside Monophosphates ApA and UpU by Rare Earth Metal Ions," J. Chem. Soc. Chem. Commun., 640-641, 1992.
Lauffer, "Paramagnetic Metal Complexes as Water Proton Relaxation Agents for NMR Imaging: Theory and Design", Chem. Rev. 87:901-927, 1987.
LeGoff et al., "Synthesis of a [1, 5, 1, 5,] Platyrin, a 26 .pi.-Electron Tetrapyrrolic Annulene", J. Org. Chem. 52:710-711, 1987.
Marks et al., "Large Metal Ion-Centered Template Reactions. Chemical and Spectral Studies of the Superphthalocyanine Dioxocyclopentakis (1-iminoisoindolinato) uranium (VI) and Its Derivatives", J. Am. Chem. Soc., 100:1695-1705, 1978.
Menger et al., "Phosphate Ester Hydrolysis Catalyzed by Metallomicelles," J
Hemmi Gregory W.
Mody Tarak D.
Sessler Jonathan L.
Board of Regents, University of TX
Pharmacyclics Inc.
Shah Mukund J.
Sripada Pavanaram K.
LandOfFree
Texaphyrin metal complexes having improved functionalization does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Texaphyrin metal complexes having improved functionalization, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Texaphyrin metal complexes having improved functionalization will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-679843