Effects of (+)-, (-)- and (.+-.)-Indenestrols A and B on Microtubule Polymerization
| Autor: | Taiko Oda, Tadashi Hata, Yumiko Sakakibara, Hiroyuki Hanzawa, Yoshihiro Sato |
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| Rok vydání: | 1992 |
| Předmět: |
Magnetic Resonance Spectroscopy
Polymers Swine Stereochemistry Metabolite Microtubules Chemical synthesis Microtubule polymerization chemistry.chemical_compound X-Ray Diffraction Microtubule Drug Discovery Animals Molecule Estrogens Non-Steroidal Diethylstilbestrol Chromatography High Pressure Liquid Stereoisomerism General Chemistry General Medicine In vitro Indenes chemistry Microtubule Proteins Chromatography Thin Layer Turbidimetry Enantiomer |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 40:588-592 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.40.588 |
| Popis: | Indenestrol A (IA) is a metabolite of diethylstilbestrol (DES), and indenestrol B (IB) is an analog of IA. IA was simply obtained from E,E-dienestrol in the presence of dilute sulfuric acid, and a mixture of IA and IB was formed by thermal cyclization of E,E-dienestrol. In order to elucidate the effects of optically active IA and IB on microtubule assembly, the IA and IB enantiomers were separated to greater than 99% purity by high-pressure liquid chromatography using a chiral column. The di(4-bromobenzoate) of (-)-IB was analyzed by X-ray crystallography and its absolute structure was determined as C(3)-S. The (+)-, (-)-, and (+/-)-indenestrols A and B were shown to be inhibitors of microtubule assembly in vitro using microtubule proteins from porcine brain. (+/-)-IB is more active than (+/-)-IA, and the order of inhibitory activity of the enantiomers on microtubule assembly was (+)-IB greater than (+)-IA greater than (-)-IA greater than (-)-IB. |
| Databáze: | OpenAIRE |
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