Collect. Czech. Chem. Commun. 2004, 69, 384-396

Inclusion Complexation of Carbethopendecinium Bromide with Some α- and β-Cyclodextrins Studied by Potentiometry with Membrane Electrodes

František Kopecký*, Mária Vojteková, Silvia Kováčová and Monika Juríčeková

Faculty of Pharmacy, Comenius University, 832 32 Bratislava, Slovak Republic


Inclusion complexation of an antimicrobial quaternary ammonium salt, carbethopendecinium bromide (SBr, Septonex), with five cyclodextrins was investigated potentiometrically using the prepared membrane electrodes selective to the surface-active carbethopendecinium cations (S+). Relatively strong complexation of the S+ cations with native α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), and their random-substituted derivatives, namely hydroxypropyl-α-cyclodextrin (HP-α-CD), methyl-β-cyclodextrin (M-β-CD), and hydroxypropyl-β-cyclodextrin (HP-β-CD), was evidenced in dilute aqueous solution. In the region where the potentiometrically determined concentration of the free S+ cations remained lower than the critical micelle concentration (cmc) of SBr by a factor of ca ten, formation of the 1:1 complexes with the complexation constants K11 ≈ 104-105 was evaluated by two respective methods, based on a modified linear and a non-linear regression. Deviations from the 1:1 complexation were observed when concentration of the free S+ cations approached cmc of SBr more closely and also in solutions with large excess of α-CD. Comparison of K11 values corroborated the inclusion of the n-C14H29 alkyl chain of the carbethopendecinium cation as the mechanism of its complexation with cyclodextrins. The well-soluble native α-CD with good complex-forming capability towards S+ cations may be especially suitable for possible blocking the undesirable residues of carbethopendecinium bromide.

Keywords: Quaternary ammonium salt; Cationic surfactant; Antimicrobial activity; Septonex; α-Cyclodextrins; β-Cyclodextrins; Inclusion complexes; Potentiometry; Membrane electrodes.

References: 27 live references.