Preparation of Meta -Carboranylpropyl-2-Nitroimidazole Derivatives for Application to BNCT

Wilbur, D. Scott; Hamlin, Donald K.; Livesey, John C.; Srivastava, Rajiv Ranjan; Laramore, George E.; Griffin, Thomas W.

doi:10.1007/978-1-4615-2978-1_65

Cited by 3 publications

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“…However, knowledge of the behavior of the parent compound is instructive for estimating the behavior of the adduct. Similar rationales likely underly the design and synthesis of previously reported boron-containing hypoxia-affinic radiosensitizers as carriers of 10 B for neutron capture. − …”

Section: Introductionmentioning

confidence: 99%

“…Similar rationales likely underly the design and synthesis of previously reported boron-containing hypoxia-affinic radiosensitizers as carriers of 10 B for neutron capture. [13][14][15] BNCT could be extended from a binary treatment protocol to a ternary protocol by application of hyperthermia between drug administration and irradiation. Hyperthermia can selectively collapse the neovascular- ization of a tumor, trapping the nitroimidazole by bioreduction in the tumor 16 in a process that may be causative of the known synergy of nitroimidazoles on hyperthermia.…”

Section: Introductionmentioning

confidence: 99%

“…Subsequent clearance of unbound drug from surrounding tissues could provide a relatively 10 Bfree environment outside the target tumor. The use of boronated nitroimidazoles for BNCT has been previously described in reports from other laboratories [13][14][15] and in a preliminary report from our group. 17 The compound described in this report is representative of agents which can be prepared by simple coupling reactions to yield a large series of agents for experimental BNCT.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Evaluation of a Boronated Nitroimidazole for Boron Neutron Capture Therapy

1996

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We postulated that nitroimidazoles, previously used for radiosensitizing solid tumors, may be interesting templates as carriers of 10B for boron neutron capture therapy. To test this hypothesis, we synthesized a 10B-enriched nitroimidazole, 1-2[(undecahydro-closo-dodecaborato)thio]ethyl]-2- methyl-5-nitroimidazole (imidocaptate), by coupling the Cs salt of BSH (Cs2-10B12H11SH) with 1-(2-bromoethyl)-2-methyl-5-nitroimidazole followed by purification of the adduct. Imidocaptate was taken up by V-79 cells in culture and showed no inherent toxicity under euoxic conditions up to 1.05 mM (126 micrograms of 10B/mL of culture medium). Imidocaptate showed a dose-dependent decrease in D0 when the treated cells were irradiated with a thermal neutron beam. At the highest dose tested (126 micrograms of 10B/mL of culture medium), the ratio of control to sample D0 values was 2.6 for both linear quadratic and single-hit multitarget models. At 33 micrograms of 10B/mL, imidocaptate showed a control/treated D0 ration (1.5) equal to that observed with the disulfide form of BSH at 28 micrograms of 10B/mL. Compared to BSH and its disulfide, the reduced toxicity and equipotency of imidocaptate suggest that this agent may be useful for boron neutron capture therapy of cancer.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Evaluation of a Boronated Nitroimidazole for Boron Neutron Capture Therapy

1996

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Azanonaboranes Containing Imidazole Derivatives for Boron Neutron Capture Therapy: Synthesis, Characterization, and In Vitro Toxicity Evaluation

El‐Zaria

Genady

Gabel

2006

Chemistry A European J

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A number of azanonaboranes containing imidazole derivatives have been synthesized by a ligand-exchange reaction. The exo-NH(2)R group of the azanonaborane of the type [(RH(2)N)B(8)H(11)NHR] can be exchanged by one hetero-nitrogen atom of the imidazole ring. In the case of histamine, the exchange takes place on the aliphatic amino group, the hetero-nitrogen atom of the imidazole ring or both of them. The products were confirmed by NMR, IR spectroscopy, elemental analysis, and mass spectrometry. The electron-withdrawing effect of the nitro group in 2-nitroimidazole is the main hindrance to achieve the exchange reaction. In vitro experiments were performed with B16 melanoma cells. A comparison of the biological properties of the products in which the B(8)N cluster is connected to the hetero-nitrogen atom of imidazole ring or the aliphatic NH(2) group showed that incorporation of B(8)N cluster unit into primary amino group increases the compound's toxicity. In contrast, this specificity for cytotoxicity effect was not observed in the case of histamine containing two B(8)N clusters which was relatively nontoxic and did not inhibit colony formation up to concentrations of 2 mM.

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Metal Complexes as Photo- and Radiosensitizers

1999

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Preparation of Meta -Carboranylpropyl-2-Nitroimidazole Derivatives for Application to BNCT

Cited by 3 publications

References 10 publications

Synthesis and Evaluation of a Boronated Nitroimidazole for Boron Neutron Capture Therapy

Synthesis and Evaluation of a Boronated Nitroimidazole for Boron Neutron Capture Therapy

Azanonaboranes Containing Imidazole Derivatives for Boron Neutron Capture Therapy: Synthesis, Characterization, and In Vitro Toxicity Evaluation

Metal Complexes as Photo- and Radiosensitizers

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