TY - JOUR
T1 - Effects of synthetic estrogens, (R,R)-(+)-, (S,S)-(-)-, dl- and meso-hexestrol stereoisomers on microtubule assembly
AU - Sakakibara, Yumiko
AU - Hasegawa, Kiyoshi
AU - Oda, Taiko
AU - SaitÔ, Hazime
AU - Kodama, Masahiko
AU - Hirata, Aiko
AU - Matsuhashi, Michio
AU - Sato, Yoshihiro
N1 - Funding Information:
* This study was supported in part by Grant-in-Aid for Scientific Research from the Ministry of Education, Science and Culture of Japan (No. 61571064), by The Science Research Promotion Fund from Japan Private School Promotion Foundation (1986). and by Haraguchi Memorial Cancer Research Fund (T.O.). 1)T o whom correspondence should be addressed. 1 Abbreviations: DES, diethylstilbestrol; DMSO, dimethyl sulfoxide; MES, 2-(morpholino)ethanesulfonic acid; EGTA, ethyleneglycol-bis(2-aminoethylether)-N,N.N’.N’-tetraacetic . acid:. EDT& ethylenediamine tetraacetate; DMF. N.N-dimethvlformamide: MAPS. microtubule-associated proteins; CD, circular dichroism; CP-MAS. cross polarization-magic angle spinning.
PY - 1990/1/1
Y1 - 1990/1/1
N2 - 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.
AB - 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.
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U2 - 10.1016/0006-2952(90)90661-4
DO - 10.1016/0006-2952(90)90661-4
M3 - Article
C2 - 2153376
AN - SCOPUS:0025174977
SN - 0006-2952
VL - 39
SP - 167
EP - 172
JO - Biochemical Pharmacology
JF - Biochemical Pharmacology
IS - 1
ER -