Design and Synthesis of Pironetin Analogue/Colchicine Hybrids and Study of Their Cytotoxic Activity and Mechanisms of Interaction with Tubulin
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Title
Design and Synthesis of Pironetin Analogue/Colchicine Hybrids and Study of Their Cytotoxic Activity and Mechanisms of Interaction with TubulinAuthor (s)
Date
2014-11Publisher
American Chemical SocietyBibliographic citation
VILANOVA, Concepción, et al. Design and Synthesis of Pironetin Analogue/Colchicine Hybrids and Study of Their Cytotoxic Activity and Mechanisms of Interaction with Tubulin. Journal of medicinal chemistry, 2014, 57.24: 10391-10403.Type
info:eu-repo/semantics/articlePublisher version
http://pubs.acs.org/doi/abs/10.1021/jm501112qSubject
Abstract
We here report the synthesis of a series of 12 hybrid molecules composed of a colchicine moiety and a pironetin analogue fragment. The two fragments are connected through an ester–amide spacer of variable length. The ... [+]
We here report the synthesis of a series of 12 hybrid molecules composed of a colchicine moiety and a pironetin analogue fragment. The two fragments are connected through an ester–amide spacer of variable length. The cytotoxic activities of these compounds and their interactions with tubulin have been investigated. Relations between the structure and activity are discussed. Since the spacer is not long enough to permit a simultaneous binding of the hybrid molecules to the colchicine and pironetin sites on tubulin, a further feature investigated was whether these molecules would interact with the latter through the pironetin end (irreversible covalent binding) or through the colchicine end (reversible noncovalent binding). It has been found that binding to tubulin may take place preferentially at either of these ends depending on the length of the connecting spacer. [-]
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J. Med. Chem., 2014, 57 (24)Rights
Copyright © 2014 American Chemical Society
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