Micellar and antimicrobial properties of a series of bis-quaternary ammonium compounds based on dabco derivatives

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Abstract

Self-assembly of bisquaternary ammonium compounds, long-chain derivatives of 1,4-diazabicyclo[2.2.2]octane containing a hydroxyethyl group was investigated using methods (tensiometry, conductometry, dynamic light scattering, spectroscopy, and fluorimetry). The values of critical micelle concentration, adsorption characteristics at the air–water interface, solubilization capacity toward the poorly water-soluble OrangeOT probe, aggregation numbers, and sizes were determined. The influence of the structure of the compounds under study (alkyl chain length and head group charge) on micelle-forming, antimicrobial properties, and hemolytic activity was established.

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Z. M. Shaihutdinova

Институт органической и физической химии им. А.Е. Арбузова, ФИЦ Казанский научный центр РАН; Казанский (Приволжский) федеральный университет

Email: tatyana_pashirova@mail.ru
Russian Federation, Казань; Казань

A. S. Sapunova

Институт органической и физической химии им. А.Е. Арбузова, ФИЦ Казанский научный центр РАН

Email: tatyana_pashirova@mail.ru
Russian Federation, Казань

D. V. Salakhieva

Казанский (Приволжский) федеральный университет

Email: tatyana_pashirova@mail.ru
Russian Federation, Казань

T. N. Pashirova

Институт органической и физической химии им. А.Е. Арбузова, ФИЦ Казанский научный центр РАН

Author for correspondence.
Email: tatyana_pashirova@mail.ru
Russian Federation, Казань

A. D. Voloshina

Институт органической и физической химии им. А.Е. Арбузова, ФИЦ Казанский научный центр РАН

Email: tatyana_pashirova@mail.ru
Russian Federation, Казань

A. V. Bogdanov

Институт органической и физической химии им. А.Е. Арбузова, ФИЦ Казанский научный центр РАН

Email: tatyana_pashirova@mail.ru
Russian Federation, Казань

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Supplementary files

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2. Fig. 1. Structure of dicationic surfactants bis-DABCO-n, where R = CnH2n+1 with n = 12, 14, 16, 18, 20; R`=C2H4OH.

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3. Fig. 2. Surface tension isotherms of aqueous solutions of bis-DABCO-n, where n = 14 (1), 16 (2), 18 (3), 20 (4), 25°C.

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4. Fig. 3. Dependences of specific electrical conductivity of aqueous solutions of bis-DABCO-n, where n = 14 (1), 16 (2), 18 (3), 20 (4), 25°C.

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5. Fig. 4. Dependence of log CMC, MIC in relation to Staphylococcus aureus ATCC 209p (Sa) and Candida albicans NCTC885–653 (Ca), HC50 on the number of carbon atoms (n) of the alkyl chain for bis-DABCO-n.

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6. Fig. 5. Change in absorption of saturated aqueous solutions of OrangeOT depending on the concentration of bis-DABCO-n, where n = 14 (1), 16 (2), 18 (3), 20 (4), λ = 495 nm; L = 1 cm; 25°C.

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7. Fig. 6. Fluorescence spectra of pyrene in bis-DABCO-14 solutions (a) and dependences of the intensity ratio of the first and third peaks of pyrene (I1/I3) in bis-DABCO-n solutions, where n = 14 (1), 16 (2), 18 (3), 20 (4), on their concentration (b), 25°C.

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8. Fig. 7. Dependence of ln (I0/I) in bis-DABCO-n solutions, where n = 14 (1), 16 (2), 18 (3), 20 (4), on the concentration of CPB at Cbis-Dabco-14 = 0.02 M (1), Cbis-Dabco-16 = 0.005 M (2), Cbis-Dabco-18 = 0.005 M (3), Cbis-Dabco-20 = 0.004 M (4), λ = 394 nm.

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