Selective binding of methotrexate to monomeric, dimeric and polymeric cyclodextrins characterized by formation of more stable complexes with dimeric β-cyclodextrin.

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Reactions of 6-bromo-and 6-iodo-6-deoxy-β-cyclodextrin with organic amines of diverse nature afforded a series of monocationic derivatives with aminium groups located in the cyclodextrin scaffold on the side of the primary hydroxy groups. The structure and composition of the obtained cationic β-cyclodextrin derivatives were confirmed by 1 H and 13 C NMR data.Cationic cyclodextrin derivatives owing to the positive charge on the cyclodextrin matrix are capable of incorporation in biologic membranes and of penetration through biologic barriers [1-4]. They are potential objects of pharmacological studies as drug carriers and also as carriers for the DNA delivery (vectorization) in the gene therapy [3][4][5][6][7].The preparation of cationic derivatives commonly utilizes 6-azido-6-deoxy cyclodextrin derivatives that are converted into amines by treating with triphenylphosphine in aqueous ammonia [8,9]. However this method possesses a limitation since it is suitable only for the preparation of aminium cyclodextrin derivatives from primary amines.

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