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Title: Porphyrin Based neuton capture agents for cancer therapy

Patent ·
OSTI ID:1175809

The invention describes the synthesis of a panel of novel carbon-carbon linked carboranyl-containing 5,10,15,20-tetraphenylporphyrins bearing 25–44% boron by weight. In certain embodiments, a phenyl porphyrin compound has a carboranyl group attached to the phenyl group by a carbon-carbon linkage, wherein the phenyl group corresponds to the following formula where R7 through R11 are hydrogen, a carboranyl group, or are selected from the group consisting of hydroxyl, NMe3+, PMePh2+, PO(OH)2, SO3H, COOH, and NH2. In this embodiment, the carboranyl group is attached to the phenyl group by a carbon-carbon linkage, either one or two of R7 through R11 are other than hydrogen; and the phenyl porphyrin compound contains at least one phenyl group having at least one of said carboranyl groups.

Research Organization:
Univ. of California, Oakland, CA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
98ER62633
Assignee:
The Regents of the University of California (Oakland, CA)
Patent Number(s):
7,067,653
Application Number:
10/258,948
OSTI ID:
1175809
Country of Publication:
United States
Language:
English

References (16)

Synthesis of carboranyl porphyrins: Potential drugs for boron neutron capture therapy journal March 1993
Synthesis of carboranyl derivatives of deuteroporphyrin IX journal December 1999
Plasma Pharmacokinetics and Tissue Biodistribution of Boron Following Administration of a Boronated Porphyrin in Dogs journal April 2000
The first alkylation of o-carboranes under essentially neutral conditions. Application to the synthesis of boron-10 carriers journal December 1990
Porphyrin-based Sensitizers in the Detection and Treatment of Cancer: Recent Progress journal August 2001
A comparative study on the pharmacokinetics and biodistribution of boronated porphyrin (BOPP) and sulfhydryl boron hydride (BSH) in the RG2 rat glioma model journal July 1995
Toxicology of a Boronated Porphyrin in Dogs journal May 1999
Preparation of carboranyl porphyrins for boron neutron capture therapy journal January 1990
Chapter 25. Cell Cycle Control and Cancer book January 1996
Synthesis of Carboranyl Amino Acids, Hydantoins, and Barbiturates journal January 1996
Boronated protoporphyrin (BOPP): localization in lysosomes of the human glioma cell line SF-767 with uptake modulated by lipoprotein levels journal October 1999
Selective tumor kill of cerebral glioma by photodynamic therapy using a boronated porphyrin photosensitizer. journal December 1995
An in vitro study of boronated porphyrins for potential use in boron neutron capture therapy journal October 1993
Evaluation of carborane-containing porphyrins as tumour targeting agents for boron neutron capture therapy. journal July 1998
A new boronated porphyrin (STA-BX909) for neutron capture therapy: an in vitro survival assay and in vivo tissue uptake study journal July 1999
Mitochondria are the functional intracellular target for a photosensitizing boronated porphyrin journal March 1996

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