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Synthesis of Carboranes Containing an Azulene Framework and in Vitro Evaluation as Boron Carriers
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    Synthesis of Carboranes Containing an Azulene Framework and in Vitro Evaluation as Boron Carriers
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    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-77, Japan
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 1997, 40, 18, 2825–2830
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    https://doi.org/10.1021/jm970023x
    Published August 29, 1997
    Copyright © 1997 American Chemical Society

    Abstract

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    3-(o-Carboranylhydroxymethyl)-7-isopropylazulene sodium carboxylate (1) and 3-(o-carboranylmethyl)-7-isopropylazulene sodium sulfonate (2) were synthesized from the palladium-catalyzed addition reaction of 1-carboranyltributylstannnane (4) to azulene aldehydes (3 and 9). Although the water solubility of 1 was of the order of 10-6 M, that of 2 was of the order of 10-3 M and was enough for clinical use. The cytotoxicity of 1 (IC50) toward B-16 melanoma cells was of the order of 10-5 M, whereas that of 2 was of the order of 10-4 M. This value was close to that of BPA (∼9 × 10-3 M) which is utilized for clinical use. The boron uptake by B-16 cells was 0.17 μg of B/106 cells for 1 and 0.25 μg of B/106 cells for 2. It is clear that compound 2 accumulates in B-16 melanoma cells with a significantly high level although it is highly water soluble and its cytotoxicity is significantly low.

    Copyright © 1997 American Chemical Society

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     Abstract published in Advance ACS Abstracts, August 1, 1997.

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 1997, 40, 18, 2825–2830
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm970023x
    Published August 29, 1997
    Copyright © 1997 American Chemical Society

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