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Title

Symmetry Complementarity-Guided Design of Anthrax Toxin Inhibitors Based on β-Cyclodextrin: Synthesis and Relative Activities of Face-Selective Functionalized Polycationic Clusters

AuthorsDíaz Moscoso, Alejandro ; Méndez-Ardoy, Alejandro ; Ortega-Caballero, Fernando; Benito, Juan M. ; Ortiz-Mellet, Carmen; Defaye, Jacques; Robinson, Tanisha M.; Yohannes, Adiamseged; Karginov, Vladimir A.; García-Fernández, José Manuel
KeywordsAnthrax
Click chemistry
Cyclodextrins
Symmetry complementary
Toxin inhibitors
Issue Date7-Dec-2010
PublisherWiley-VCH
CitationChemMedChem 6(1): 181-192 (2011)
AbstractThree new series of potential anthrax toxin inhibitors based on the β-cyclodextrin (βCD) scaffold were developed by exploiting face-selective CuI-catalyzed azide–alkyne 1,3-cycloadditions, amine–isothiocyanate coupling, and allyl group hydroboration–oxidation/hydroxy → amine replacement reactions. The molecular design follows the “symmetry–complementarity” concept between homogeneously functionalized polycationic βCD derivatives and protective antigen (PA), a component of anthrax toxin known to form C7-symmetric pores on the cell membrane used by lethal and edema factors to gain access to the cytosol. The synthesis and antitoxin activity of a collection of βCD derivatives differing in the number, arrangement, and face location of the cationic elements are reported herein. These results set the basis for a structure–activity relationship development program of new candidates to combat the anthrax threat.
Description12 páginas, 3 figuras, 1 tabla, 4 esquemas.
Publisher version (URL)http://dx.doi.org/10.1002/cmdc.201000419
URIhttp://hdl.handle.net/10261/37025
DOI10.1002/cmdc.201000419
ISSN1860-7179
E-ISSN1860-7187
Appears in Collections:(IIQ) Artículos
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