Carboranylporphyrins and uses thereof

Wu, Haitao; Miura, Michiko

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Title: Carboranylporphyrins and uses thereof

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, 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.

Inventors:: Wu, Haitao; Miura, Michiko

Issue Date:: 2006-01-24

Research Org.:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1175633

Patent Number(s):: 6989443

Application Number:: 10/878,138

Assignee:: Brookhaven Science Associates, LLC (Upton, NY)

Patent Classifications (CPCs):: A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

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A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
A61K41/0071 - {PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines}
A61K41/0095 - {Boron neutron capture therapy, i.e. BNCT, e.g. using boronated porphyrins}
A61K49/106 - {the complex-forming compound being cyclic, e.g. DOTA}
A61K51/0485 - {Porphyrins, texaphyrins wherein the nitrogen atoms forming the central ring system complex the radioactive metal}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D487/22 - in which the condensed system contains four or more hetero rings

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DOE Contract Number:: AC02-98CH10886

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 60 APPLIED LIFE SCIENCES

Citation Formats


                    Wu, Haitao, and Miura, Michiko. Carboranylporphyrins and uses thereof.  United States: N. p., 2006. 
        Web.

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                    Wu, Haitao, & Miura, Michiko. Carboranylporphyrins and uses thereof.  United States.

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                    Wu, Haitao, and Miura, Michiko. Tue .  
        "Carboranylporphyrins and uses thereof".  United States.  https://www.osti.gov/servlets/purl/1175633.

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@article{osti_1175633,

  title        = {Carboranylporphyrins and uses thereof},

  author       = {Wu, Haitao and Miura, Michiko},

  abstractNote = {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, 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.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2006},

  month        = {1}

}

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Works referenced in this record:

The Effect of Macromolecular Architecture in Nanomaterials: A Comparison of Site Isolation in Porphyrin Core Dendrimers and Their Isomeric Linear Analogues
journal, April 2002

Harth, Eva M.; Hecht, Stefan; Helms, Brett
Journal of the American Chemical Society, Vol. 124, Issue 15
https://doi.org/10.1021/ja025536u

19F NMR Spectra and Structures of Halogenated Porphyrins
journal, July 1995

Birnbaum, Eva R.; Hodge, Julia A.; Grinstaff, Mark W.
Inorganic Chemistry, Vol. 34, Issue 14
https://doi.org/10.1021/ic00118a010

Synthesis of carboranyl derivatives of deuteroporphyrin IX
journal, December 1999

Zakharkin, L. I.; Ol'shevskaya, V. A.; Panfilova, S. Yu.
Russian Chemical Bulletin, Vol. 48, Issue 12
https://doi.org/10.1007/BF02498279

A Carboranyl Porphyrin for Boron Neutron Capture Therapy of Brain Tumors
book, January 1989

Kahl, S. B.; Joel, D. D.; Finkel, G. C.
Clinical Aspects of Neutron Capture Therapy
https://doi.org/10.1007/978-1-4684-5622-6_23

In vivo animal studies with gadolinium (III) texaphyrin as a radiation enhancer
journal, November 1999

Miller, Richard A.; Woodburn, Kathryn; Fan, Qing
International Journal of Radiation Oncology*Biology*Physics, Vol. 45, Issue 4
https://doi.org/10.1016/S0360-3016(99)00274-6

A Straightforward Synthesis of 3,4-Difluoropyrrole
journal, August 1998

Woller, Eric K.; Smirnov, Valeriy V.; DiMagno, Stephen G.
The Journal of Organic Chemistry, Vol. 63, Issue 16
https://doi.org/10.1021/jo9805798

Octabromotetraphenylporphyrin and its metal derivatives: Electronic structure and electrochemical properties
journal, January 1991

Bhyrappa, P.; Krishnan, V.
Inorganic Chemistry, Vol. 30, Issue 2
https://doi.org/10.1021/ic00002a018

Porphyrin-mediated boron neutron capture therapy: evaluation of the reactions of skin and central nervous system
journal, January 2003

Morris, G. M.; Coderre, J. A.; Hopewell, J. W.
International Journal of Radiation Biology, Vol. 79, Issue 3
https://doi.org/10.1080/0955300031000073392

New Metalloporphyrins with Extremely Altered Redox Properties: Synthesis, Structure, and Facile Reduction to Air-Stable π-Anion Radicals of Zinc and Nickel β-Heptanitroporphyrins
journal, July 1997

Ozette, Karine; Leduc, Philippe; Palacio, Magali
Journal of the American Chemical Society, Vol. 119, Issue 27
https://doi.org/10.1021/ja970882a

Synthesis of a porphyrin-labelled carboranyl phosphate diester: a potential new drug for boron neutron capture therapy of cancer
journal, July 2002

Maderna, Andreas; Huertas, Ramon; Hawthorne, M. Frederick
Chemical Communications, Issue 16
https://doi.org/10.1039/b203730k

Current status of 10B-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
journal, April 1985

Fairchild, R. G.; Bond, V. P.
International Journal of Radiation Oncology*Biology*Physics, Vol. 11, Issue 4
https://doi.org/10.1016/0360-3016(85)90318-9

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
journal, March 1997

Woller, Eric K.; DiMagno, Stephen G.
The Journal of Organic Chemistry, Vol. 62, Issue 6
https://doi.org/10.1021/jo962159t

Evaluation of carborane-containing porphyrins as tumour targeting agents for boron neutron capture therapy.
journal, July 1998

Miura, M.; Micca, P. L.; Fisher, C. D.
The British Journal of Radiology, Vol. 71, Issue 847
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Boron Neutron Capture Therapy for Glioblastoma Multiforme: Interim Results from the Phase I/II Dose-Escalation Studies
journal, June 1999

Chanana, Arjun D.; Capala,, Jacek; Chadha, Manjeet
Neurosurgery, Vol. 44, Issue 6
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Syntheses of carboncarbon linked carboranylated porphyrins for boron neutron capture therapy of cancer
journal, September 2000

Vicente, M. Graça H.; Shetty, Shankar J.; Wickramasinghe, Anura
Tetrahedron Letters, Vol. 41, Issue 40
https://doi.org/10.1016/S0040-4039(00)01346-0

Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra(4-nido-carboranylphenyl)porphyrin
journal, November 2002

Vicente, M. G. H.; Nurco, D. J.; Shetty, S. J.
Journal of Photochemistry and Photobiology B: Biology, Vol. 68, Issue 2-3
https://doi.org/10.1016/S1011-1344(02)00383-4

Biodistribution of Copper Carboranyltetraphenylporphyrins in Rodents Bearing an Isogeneic or Human Neoplasm
journal, January 2001

Miura, Michiko; Joel, Darrel D.; Smilowitz, Henry M.
Journal of Neuro-Oncology, Vol. 52, Issue 2, p. 111-117
https://doi.org/10.1023/A:1010622319892

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Similar Records

Title: Carboranylporphyrins and uses thereof

Abstract

Citation Formats

The Effect of Macromolecular Architecture in Nanomaterials: A Comparison of Site Isolation in Porphyrin Core Dendrimers and Their Isomeric Linear Analogues journal, April 2002

19F NMR Spectra and Structures of Halogenated Porphyrins journal, July 1995

Synthesis of carboranyl derivatives of deuteroporphyrin IX journal, December 1999

A Carboranyl Porphyrin for Boron Neutron Capture Therapy of Brain Tumors book, January 1989

In vivo animal studies with gadolinium (III) texaphyrin as a radiation enhancer journal, November 1999

A Straightforward Synthesis of 3,4-Difluoropyrrole journal, August 1998

Octabromotetraphenylporphyrin and its metal derivatives: Electronic structure and electrochemical properties journal, January 1991

Porphyrin-mediated boron neutron capture therapy: evaluation of the reactions of skin and central nervous system journal, January 2003

New Metalloporphyrins with Extremely Altered Redox Properties: Synthesis, Structure, and Facile Reduction to Air-Stable π-Anion Radicals of Zinc and Nickel β-Heptanitroporphyrins journal, July 1997

Synthesis of a porphyrin-labelled carboranyl phosphate diester: a potential new drug for boron neutron capture therapy of cancer journal, July 2002

Current status of 10B-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 journal, April 1985

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 journal, March 1997

Evaluation of carborane-containing porphyrins as tumour targeting agents for boron neutron capture therapy. journal, July 1998

Boron Neutron Capture Therapy for Glioblastoma Multiforme: Interim Results from the Phase I/II Dose-Escalation Studies journal, June 1999

Syntheses of carboncarbon linked carboranylated porphyrins for boron neutron capture therapy of cancer journal, September 2000

Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra(4-nido-carboranylphenyl)porphyrin journal, November 2002

Biodistribution of Copper Carboranyltetraphenylporphyrins in Rodents Bearing an Isogeneic or Human Neoplasm journal, January 2001

The Effect of Macromolecular Architecture in Nanomaterials: A Comparison of Site Isolation in Porphyrin Core Dendrimers and Their Isomeric Linear Analogues
journal, April 2002

19F NMR Spectra and Structures of Halogenated Porphyrins
journal, July 1995

Synthesis of carboranyl derivatives of deuteroporphyrin IX
journal, December 1999

A Carboranyl Porphyrin for Boron Neutron Capture Therapy of Brain Tumors
book, January 1989

In vivo animal studies with gadolinium (III) texaphyrin as a radiation enhancer
journal, November 1999

A Straightforward Synthesis of 3,4-Difluoropyrrole
journal, August 1998

Octabromotetraphenylporphyrin and its metal derivatives: Electronic structure and electrochemical properties
journal, January 1991

Porphyrin-mediated boron neutron capture therapy: evaluation of the reactions of skin and central nervous system
journal, January 2003

New Metalloporphyrins with Extremely Altered Redox Properties: Synthesis, Structure, and Facile Reduction to Air-Stable π-Anion Radicals of Zinc and Nickel β-Heptanitroporphyrins
journal, July 1997

Synthesis of a porphyrin-labelled carboranyl phosphate diester: a potential new drug for boron neutron capture therapy of cancer
journal, July 2002

Current status of 10B-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
journal, April 1985

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
journal, March 1997

Evaluation of carborane-containing porphyrins as tumour targeting agents for boron neutron capture therapy.
journal, July 1998

Boron Neutron Capture Therapy for Glioblastoma Multiforme: Interim Results from the Phase I/II Dose-Escalation Studies
journal, June 1999

Syntheses of carboncarbon linked carboranylated porphyrins for boron neutron capture therapy of cancer
journal, September 2000

Synthesis, dark toxicity and induction of in vitro DNA photodamage by a tetra(4-nido-carboranylphenyl)porphyrin
journal, November 2002

Biodistribution of Copper Carboranyltetraphenylporphyrins in Rodents Bearing an Isogeneic or Human Neoplasm
journal, January 2001