Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1993-07-28
1996-10-29
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
540145, 540465, 540474, 534 11, 534 15, 534 16, 5483027, 424 93, C07D48722
Patent
active
055697593
ABSTRACT:
The present invention involves water soluble hydroxy-substituted texaphyrins retaining lipophilicity, the synthesis of such compounds and their uses. These expanded porphyrin-like macrocycles are efficient chelators of divalent and trivalent metal ions. Various metal (e.g., transition, main group, and lanthanide) complexes of the hydroxy-substituted texaphyrin derivatives of the present invention have unusual water solubility and stability. They absorb light strongly in a physiologically important region (i.e. 690-880 nm). They have enhanced relaxivity and therefore are useful in magnetic resonance imaging. They form long-lived triplet states in high yield and act as photosensitizers for the generation of singlet oxygen. Thus, they are useful for inactivation or destruction of enveloped viruses, mononuclear or other cells infected with such viruses as well as tumor cells. They are water soluble, yet they retain sufficient lipophilicity so as to have greater affinity for lipid rich areas such as atheroma and tumors. They may be used for magnetic resonance imaging followed by photodynamic tumor therapy in the treatment of atheroma and tumors. These properties, coupled with their high chemical stability and appreciable solubility in water, add to their usefulness.
REFERENCES:
patent: 3920692 (1975-11-01), Wiersdorffetal
patent: 4878891 (1989-11-01), Judy et al.
patent: 4883790 (1989-11-01), Levy 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.
Abid et al., "Lanthanide Complexes of Some Macrocyclic Schiff Bases Derived from Pyridine-2, 6-dicarboxaldehyde and .alpha.,.omega.-Primary Diamines", Inorg. Chim. Acta, vol. 95, (1984) 119-125.
Acholla et al, "Binucleating Tetrapyrrole Macrocycles", J. Am. Chem. Soc. , vol. 107 (1985) 6902-6908.
Acholla et al., "A Binucleating `Accordian`Tetrapyrrole Macrocycle", Tetrahedron Lett., vol. 25 (1984) 3269-3270.
Ansell, "X-Ray Crystal Structure of the Pentagonal Bipyramidal Nickel (11) Complex [Ni.sup.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. (1982) 546-547.
Bauer et al., "Sapphyrins: Novel Aromatic Pentapyrrolic Macrocycles", J. Am. Chem. Soc., vol. 105, (1983) 6429-6436.
Broadhurst et al., "Preparation of Some Sulphur-containing Polypyrrolic Macrocycles. Sulphur Extrusion from a meso-Thiaphlorin", J. Chem. Soc., Chem. Commun. (1970) 807-809.
Broadhurst et al., "18-and 22-.pi.-Electron Macrocycles Containing Furan, Pyrrole, and Thiophen Rings", J. Chem. Soc. Commun. Chem. (1969) 1480-1482.
Broadhurst et al., "New Macrocyclic Aromatic Systems Related to Porphins", J. Chem. Soc., Chem. Commun. (1969) 23-24.
Broadhurst et al., "The Synthesis of 22 .pi.Electron Macrocycles. Sapphyrins and Related Compounds", J. Chem. Soc. Perkin Trans. 1 (1972) 2111-2116.
Cuellar et al., "Synthesis and Characterization of Metallo and Metal-Free Octaalkylphthalocyanines and Uranyl Decaalkysuperphthalocyanines", Inorg. Chem., vol. 20 (1981) 3766-3770.
Day et al., "Large Metal Ion-Centered Template Reactions. A Uranyl Complex of Cyclopentakis (2-iminoisoindoline)", J. Am. Chem. Soc., vol. 97 (1975) 4519-4527.
De Cola et al., "Hexaaza Macrocyclic Complexes of the Lanthanides", Inorg. Chem., vol. 25 (1986) 1729-1732.
Dougherty, "Photosensitizers: Therapy and Detection of Malignant Tumors", Photochem. Photobiol., vol. 45 (1987) 879-889.
Ser. No. 07/882,964 Jan. 21, 1992, Sessler et al.
Gosmann et al., "Synthesis of a Fourfold Enlarged Porphyrin with an Extremely Large, Diamagnetic Ring-Current Effect", Angew. Chem., Int. Ed. Engl., vol. 25 (1986) 1100-1101.
Gossauer, "Syntheses of Some Unusual Polypyrrole Macrocycles", Bull. Soc. Chim. Belg., vol. 92 (1983) 793-795.
Knubel et al., "Biomimetic Synthesis of an Octavinylogous Porphyrin with an Aromatic [34] Annulene System", Angew. Chem., Int. Ed. Engl., vol. 27 (1988) 1170-1172.
Lauffer, "Paramagnetic Metal Complexes as Water Proton Relaxation Agents for NMR Imaging: Theory and Design", Chem. Rev. vol. 87 (1987) 901-927.
LeGoff et al., "Synthesis of a [1, 5, 1, 5] Platyrin, a 26 .pi.-Electron Tetrapyrrolic Annulene", J. Org. Chem. vol. 52 (1987) 710-711.
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., vol. 100 (1978) 1695-1705.
Rexhausen et al., "The Synthesis of a New 22 .pi.-Electron Macrocycle: Pentaphyrin", J. Chem. Soc., Chem. Commun. (1983) 275.
Sessler et al., "Synthesis and Crystal Structure of a Novel Tripyrrane-containing Porphyrinogen-like Macrocycle"J. Org. Chem., vol. 52 (1987) 4394-4397.
Sessler et al., "The Coordination Chemistry of Planar Pentadentate `Porphyrin-Like`Ligands", Comm. Inorg. Chem., vol. 7 (1988) 333-350.
Sessler et al., "An `Expanded Porphyrin`: The Synthesis and Structure of a New Aromatic Pentadentate Ligand", J. Am. Chem. Soc., vol. 110 (1988) 5586-5588.
Tweedle et al., "Principles of Contrast-Enhanced MRI", in "magnetic Resonance Imaging,"2nd ed. Partain, et al, Eds., W. B. Saunders: Philadelphia, vol. I (1988) 793-809.
Vogel et al., "Porphycene -a Novel Porphin Isomer", Angew. Chem., Int. Ed. Engl., vol. 25 (1986) 257-259.
Vogel et al., "2,7,12,17-Tetrapropylporphycene -Counterpart of Octaethylporphyrin in the Porphycene Series", Angew. Chem., Int. Ed. Engl., vol. 26 (1987) 928-931.
Sessler et al., "A Water-Stable Gadolinium (III) Complex Derived from a New Pentadentate `Expanded Porphyrin`Ligand", Inorg. Chem., vol. 28 (1989) 3390-3393.
Sessler et al., "Binding of Pyridine and Benzimidazole to a Cadmium `Expanded Porphyrin`: Solution and X-ray Structural Studies", Inorg. Chem., vol. 28 (1989) 1333-1341.
Harriman et al., "Metallotexaphyrins: A New Family of Photosensitisers for Efficient Generation of Singlet Oxygen", J. Chem. Soc., Chem. Commun., (1989) 314-316.
Sessler et al., "Expanded Porphyrins: The synthesis and Metal Binding Properties of Novel Tripyrrane-Containing Macrocycles", J. Coord. Chem., vol. 18 (1988) 99-104.
Sessler et al., "A Water-Stable Gadolinium (III) Complex Derived from a New Pentadentate", Chem. Absts., vol. 111:125716e (2 Oct. 1989) p. 720.
Sessler et al., "The Synthesis and Structure of a Novel 22 .pi.-Electron Aromatic Pentadentate Macrocyclic Ligand: An Expanded Porphyrin", Toronto ACS Meeting, Jun. 1988.
Sessler et al., "`Texaphyrin`: A Novel 22 .pi.-Electron Aromatic Pentadentate Macrocyclic Ligand", ACS meeting, Los Angeles, Sep. 1988.
Stinson, "Unusual Porphyrin Analog Promises Many Applications", Chemical and Engineering News, Aug. 8, 1988, pp. 26-27.
Sessler et al., "Tripyrroledimethine-derived (`Texaphyrin`-type ) Macrocycles: Potential Photosensitizers Which Absorb in the Far-red Spectral Region", SPIE, vol. 1426, Optical Methods for Tumor Treatment and Early Diagnosis: Mechanism and Technique (1991) 318-329.
Hemmi Gregory W.
Mody Tarak D.
Sessler Jonathan L.
Board of Regents University of Texas System
Shah Mukund J.
Sripada Pavanaram K.
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