Carboranylporphyrins and uses thereof

Details Carboranylporphyrins and uses thereof Carboranylporphyrins and uses thereof

2006-02-07

2006-02-07

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C534S015000, C514S185000, C514S410000, C424S009100, C424S009362, C424S009610

Reexamination Certificate

active

06995260

ABSTRACT:
The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity carborane-containing 5, 10, 15, 20-tetraphenylporphyrin compounds and methods for their use particularly in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for the treatment of tumors of the brain, head and neck, and surrounding tissue. The invention is also directed to using these carborane-containing tetraphenyl porphyrin compounds to methods of tumor imaging and/or diagnosis such as MRI, SPECT, or PET.

REFERENCES:
patent: 4783529 (1988-11-01), Lavallee et al.
patent: 4959356 (1990-09-01), Miura et al.
patent: 5149801 (1992-09-01), Kahl et al.
patent: 5162231 (1992-11-01), Cole et al.
patent: 5268371 (1993-12-01), Mauclaire et al.
patent: 5312896 (1994-05-01), Bhardwaj et al.
patent: 5563132 (1996-10-01), Bodaness
patent: 5648485 (1997-07-01), Dolphin et al.
patent: 5654423 (1997-08-01), Kahl et al.
patent: 5674467 (1997-10-01), Maier et al.
patent: 5877165 (1999-03-01), Miura et al.
patent: 5955586 (1999-09-01), Sessler et al.
patent: 6010805 (2000-01-01), Scanlon, Jr. et al.
patent: 6066628 (2000-05-01), Stojiljkovic et al.
patent: 6566517 (2003-05-01), Miura et al.
patent: 2004/0023942 (2004-02-01), Bart et al.
patent: WO 01/85736 (2001-11-01), None
patent: WO 2004030661 (2004-04-01), None
Frixa et al. (Org. Biomol. Chem., 2003, 1, 306-317.)
Foye et al. (Principles of Medicinal Chemistry, Fourth Edition., Williams & Wilkins 1995. pp. 902-907).
Frixa et al. Synthesis of meso-substituted porphyrins carrying carboranes and oligo(ethylene glycol) units for potential applications in boron neutron capture therapy.Org. Biomol. Chem., 2003, 1, 306-317.
Morris et al., “Porphyrin-mediated boron neutron capture therapy: evaluation of the reactions of skin and central nervous system,”Int. J. Radiat. Biol.,79(3): 149-158 (2003).
Vincente, et al., “Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra (4-nido-carboranylphenyl)prophyrin,”J. Photochem. Photobiol. B. Biology,68(2-3): 123-132 (2002).
Maderna et al., “Synthesis of a porphyrin-labelled carboranyl phosphate diester: a potential new drug for boron neutron capture therapy of cancer,”Chem. Commun.,16: 1784-1785 (2002).
Miura et al., “Boron Neutron Capture of a Murine Mammary Carcinoma using a Lipophilic Carboranyltetraphenylporphyrin,”Radiat. Res.,155(4): 603-610 (2001).
Miura et al., “Evaluation of carborane-containing porphyrins as tumor targeting agents for boron neutron capture therapy,”Br. J. Radiol.,71(847): 773-781 (1998).
Miura et al., “Synthesis of a Nickel Tetracarboranylphenylporphyrin for Boron Neutro-Capture Therapy: Biodistribution and Toxicity in Tumor-Bearing Mice,”Int. J. Cancer,68(1): 114-119 (1996).
Kahl et al., “A Carboranyl Porphyrin for Boron Neutron Capture Therapy of Brain Tumors,”Basic Life Sci.,50: 193-203 (1989).
Miura et al., “Biodistribution of copper carboranyltetraphenylporphyrins in rodents bearing an isogeneic or human neoplasm,”J. NeuroOncol,5: 111-117 (2001).
Berlin et al., “Are Porphyrin Mixtures Favorable Photodynamic Anticancer Drugs? A Model Study with Combinatorial Libraries of Tetraphenylporphyrins,”Combinatorial Chemistry,61(2): 107-118 (1998).
Miller et al., “In Vivo Animal Studies with Gadolinium (III) Texaphyrin As a Radiation Enhancer,”Int. J. Radiat. Oncol. Biol. Phys.,45(4): 981-989 (1999).
Bhyrappa et al., “Octabromotetraphenylporphyrin and Its Metal Derivatives: Electronic Structure and Electrochemical Properties,”Inorg. Chem., 30: 239-245 (1991).
Birnbaum et al., “19F NMR Spectra and Structures of Halogenated Porphyrins,”Inorg. Chem.,34(14): 3625-3632 (1995).
Fairchild et al., “Current Status of10B-Neutron Capture Therapy: Enhancement of Tumor Dose Via Beam Filtration and Dose Rate, and the Effects of These Parameters on Minimum Boron Content: a Theoretical Evaluation,”Int. J. Radiat. Oncol. Biol. Phys.,11(4): 831-840 (1985).
Woller et al., “2, 3, 7, 8, 12, 13, 17, 18-Octafluoro-5, 10, 15, 20-tetraarylporphyrins and Their Zinc Complexes: First Spectroscopic, Electrochemical, and Structural Characterization of a Perfluorinated Tetraarylmetalloporphyrin,”J. Org. Chem.,62(6): 1588-1593 (1997).
Woller et al., “A Straightforward Synthesis of 3,4-Difluoropyrrole,”J. Org. Chem.,63(16): 5706-5707 (1998).
Ozette et al., “New Metalloporphyrins with Extremely Altered Redox Properties: Synthesis, Structure, and Facile Reduction to Air-Stable n-Anion Radicals of Zinc and Nickel β-Heptanitroporphyrins,”J. Am. Chem. Soc.,119(27): 6442-6443 (1997).
Chanana et al., “Boron Neutron Capture Therapy for Glioblastoma Multiforme: Interim Results from the Phase I/II Dose-Escalation Studies,”Neurosurgery, 44(6): 1182-1193 (1999).
Vincente et al., “Syntheses of carbon—carbon linked carboranylated porphyrins for boron neutron capture therapy of cancer.”Tetrahedron Letters,41: 7623-7627 (2000).
Evstigneeva, “Synthesis of Carboranylporphyrins and the Perspectives of Their Use for Boron Neutron Capture Therapy,”Molecules,5: 1479-80 (2001).
Zakharkin et al., “Synthesis of carboranyl derivatives of deuteroporphyrin IX, ”Russian Chemical Bulletin,48(12): 2312-14 (1999).
“Brain Tumor Patients Offered New Hope with Expanded Trial of Promising Therapy,” Press Release, Brookhaven National Labs, Nov. 1998, <http://virtualtrials.com/bnct2.cfm.>.
Gomez, “Boron Neutron Capture Therapy (BNCT),” Dec. 1, 1998, Lawrence Berkeley National Laboratory, <http://www.virtualtrials.com/bnct.cfm>.

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