The importance of the phenyl-tropolone ‘aS’ configuration in colchicine's binding to tubulin
- 29 February 1988
- journal article
- Published by Wiley in FEBS Letters
- Vol. 229 (1) , 82-86
- https://doi.org/10.1016/0014-5793(88)80802-0
Abstract
Measuring ellipticities of (±)-colchicine and (±)-deacetamidocolchicine in the presence of tubulin afforded net positive CD bands with maxima at 340 nm resulting from reduction of the negative ellipticities upon binding of (−) enantiomers to the protein. Results of optical studies together with earlier NMR conformational analysis of these molecules substantiate the hypothesis that colchicinoids bind to tubulin with the phenyl-tropolone moiety in the ‘aS’ configuration. Natural colchicine which binds to tubulin, therefore, should be referred to as (−)-(aS, 7S)-colchicineKeywords
This publication has 20 references indexed in Scilit:
- Colchicine and its analogues: Recent findingsMedicinal Research Reviews, 1988
- Facile conversion of natural colchicine into (.+-.)-congeners and (+)-enantiomers including 2-demethyl analogsThe Journal of Organic Chemistry, 1986
- MicrotubulesPublished by Springer Nature ,1984
- Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicinesJournal of Medicinal Chemistry, 1981
- 13C‐ and 1H‐NMR. Assignments for colchicine derivativesHelvetica Chimica Acta, 1980
- A Controlled Trial of Colchicine in Preventing Attacks of Familial Mediterranean FeverNew England Journal of Medicine, 1974
- Colchicine-binding protein of mammalian brain and its relation to microtubulesBiochemistry, 1968
- Specification of Molecular ChiralityAngewandte Chemie International Edition in English, 1966
- Synthese des ColchicinsHelvetica Chimica Acta, 1961
- Beitrag zur Wirkung des ColchicinsNaunyn-Schmiedebergs Archiv für experimentelle Pathologie und Pharmakologie, 1932