1. Academic Validation
  2. Synthesis of carboranes containing an azulene framework and in vitro evaluation as boron carriers

Synthesis of carboranes containing an azulene framework and in vitro evaluation as boron carriers

  • J Med Chem. 1997 Aug 29;40(18):2825-30. doi: 10.1021/jm970023x.
H Nakamura 1 M Sekido Y Yamamoto
Affiliations

Affiliation

  • 1 Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
Abstract

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-carboranyltributylstannane (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 (approximately 9 x 10(-3) M) which is utilized for clinical use. The boron uptake by B-16 cells was 0.17 microgram of B/10(6) cells for 1 and 0.25 microgram of B/10(6) 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.

Figures