Effects of synthetic estrogens, (R,R)-(+)-, (S,S)-(-)-, dl- and meso-hexestrol stereoisomers on microtubule assembly

Yumiko Sakakibara, Kiyoshi Hasegawa, Taiko Oda, Hazime SaitÔ, Masahiko Kodama, Aiko Hirata, Michio Matsuhashi, Yoshihiro Sato

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Abstract

We previously reported on the inhibition of microtubule polymerization and the formation of ribbon structures by synthetic estrogens [Sato et al., J Biochem 101: 1247-1252, 1987]. The present investigation aimed to analyse these effects in vitro on stereochemical point of view, using hexestrol isomers ((R,R)-(+)-hexestrol, (S,S)-(-)-hexestrol and meso-hexestrol) and dl-hexestrol. Among hexestrols, dl-hexestrol showed the highest activity in ribbon formation from microtubule proteins at 100 μM. On the other hand, meso-hexestrol was distinguished from others by inhibition of microtubule assembly and formation of a large amount of aggregates from purified tubulin in the presence of MgCl2 and DMSO. These results were discussed with physico-chemical properties of hexestrols, e.g. absolute configurations as well as circular dichroism spectra and solid state carbon-13 nuclear magnetic resonance spectra.

Original languageEnglish
Pages (from-to)167-172
Number of pages6
JournalBiochemical Pharmacology
Volume39
Issue number1
DOIs
Publication statusPublished - 1990 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Pharmacology

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    Sakakibara, Y., Hasegawa, K., Oda, T., SaitÔ, H., Kodama, M., Hirata, A., Matsuhashi, M., & Sato, Y. (1990). Effects of synthetic estrogens, (R,R)-(+)-, (S,S)-(-)-, dl- and meso-hexestrol stereoisomers on microtubule assembly. Biochemical Pharmacology, 39(1), 167-172. https://doi.org/10.1016/0006-2952(90)90661-4