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

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Hexestrol
Estradiol Congeners
Stereoisomerism
Microtubules
Microtubule Proteins
Magnesium Chloride
Dichroism
Tubulin
Circular Dichroism
Dimethyl Sulfoxide
Polymerization
Isomers
Chemical properties
Magnetic Resonance Spectroscopy
Carbon

ASJC Scopus subject areas

  • Pharmacology

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Effects of synthetic estrogens, (R,R)-(+)-, (S,S)-(-)-, dl- and meso-hexestrol stereoisomers on microtubule assembly. / Sakakibara, Yumiko; Hasegawa, Kiyoshi; Oda, Taiko; SaitÔ, Hazime; Kodama, Masahiko; Hirata, Aiko; Matsuhashi, Michio; Sato, Yoshihiro.

In: Biochemical Pharmacology, Vol. 39, No. 1, 01.01.1990, p. 167-172.

Research output: Contribution to journalArticle

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, vol. 39, no. 1, pp. 167-172. https://doi.org/10.1016/0006-2952(90)90661-4
Sakakibara, Yumiko ; Hasegawa, Kiyoshi ; Oda, Taiko ; SaitÔ, Hazime ; Kodama, Masahiko ; Hirata, Aiko ; Matsuhashi, Michio ; Sato, Yoshihiro. / Effects of synthetic estrogens, (R,R)-(+)-, (S,S)-(-)-, dl- and meso-hexestrol stereoisomers on microtubule assembly. In: Biochemical Pharmacology. 1990 ; Vol. 39, No. 1. pp. 167-172.
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