Amphiphilic 1-alkyl-1,3-diazaadamantan-1-azonia bromides: A journey into self-organization and interaction with the lipid bilayer
Full article
| Journal |
Journal of Molecular Structure
ISSN: 0022-2860
, E-ISSN: 1872-8014
|
| Output data |
Year: 2026,
Volume: 1351,
Article number
: 144157,
Pages count
:
DOI:
10.1016/j.molstruc.2025.144157
|
| Authors |
Gaynanova G.A.
1,2
,
Vasileva L.A.
1
,
Romanova E.A.
1,2
,
Valeeva F.G.
1
,
Lyubina A.P.
1
,
Voloshina A.D.
1
,
Zadubrovskaya E.A.
3,4
,
Medved’ko A.V.
3
,
Vatsadze S.Z.
3
,
Zakharova L.Ya.
1
,
Sinyashin O.G.
1
|
| Affiliations |
| 1 |
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzov str., 420088 Kazan, Russia
|
| 2 |
Alexander Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlevskaya str., 420008 Kazan, Russia
|
| 3 |
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia
|
| 4 |
D. I. Mendeleev Russian University of Chemical Technology, 9, building 1 Miusskaya Ploshchad, 125047 Moscow, Russia
|
|
Funding (1)
A novel homologous series of amphiphilic bispidine derivatives, 1-alkyl-1,3-diazaadamantan-1-azonia bromides (CnAD, where n = 10, 12, 14, 16, 18), was synthesized, and their structure was characterized by X-ray diffraction, 13C and 1H NMR-spectroscopy. The Krafft point of CnAD was determined using conductometry. In homologous series, the critical micelle concentration (cmс) decreases from 7.9 mM to 2.7 mM as the tail length increases from the decyl to the tetradecyl homologue, with a high correlation coefficient (R² = 0.98). Spectrophotometry was employed to confirm the aggregation thresholds of these amphiphiles and to determine their solubilization capacity toward Orange OT, which ranged from 0.03 to 0.04 molOOT/molCnAD. Turbidimetry and electrophoretic light scattering demonstrated the ability of CnAD to integrate into the lipid bilayer of 1,2-dipalmitoyl-sn‑glycero-3-phosphocholine. It was established that long-tail homologues exhibited significantly higher antibacterial activity compared to the reference drugs chloramphenicol and norfloxacin. Additionally, their ability to influence the integrity of the cell membrane and cell wall of S. aureus, as well as to change its membrane potential, was assessed. Hemotoxicity assays revealed that C14AD possesses selective antimicrobial activity.