Collect. Czech. Chem. Commun.
1995, 60, 1213-1228
https://doi.org/10.1135/cccc19951213
Quantitative Relationships Between Structure, Aggregation Properties and Antimicrobial Activity of Quaternary Ammonium Bolaamphiphiles
Magdaléna Pavlíkováa, Ivan Lackoa, Ferdinand Devínskýa and Dušan Mlynarčíkb
a Department of Chemical Theory of Drugs, Comenius University, 832 32 Bratislava, Slovak Republic
b Department of Cellular and Molecular Biology, Comenius University, 832 32 Bratislava, Slovak Republic
Crossref Cited-by Linking
- Pisárčik Martin, Bajcura Martin, Lukáč Miloš, Devínsky Ferdinand, Bilková Andrea, Bilka František, Horváth Branislav: Self-aggregation of cationic gemini surfactants with amide groups in the spacer and variable alkyl chain length. Colloid Polym Sci 2023, 301, 1379. <https://doi.org/10.1007/s00396-023-05154-6>
- Gao Zhe, Kan Yu-Chen, Xie Yang-Hu, Guo Rui, Li Chuang, Asilebieke Ayakuzi, Xu Yang, Chu Jian-Jun: A review on non-leaching antibacterial bone cement for orthopedic surgery: From past to current insights. AIP Advances 2023, 13. <https://doi.org/10.1063/5.0174845>
- Zhou Chengcheng, Wang Yilin: Structure–activity relationship of cationic surfactants as antimicrobial agents. Current Opinion in Colloid & Interface Science 2020, 45, 28. <https://doi.org/10.1016/j.cocis.2019.11.009>
- Holínková Petra, Pekař Miloslav: Fluorescence Study of Aggregation Behaviour of Cationic Surfactant Carbethopendecinium Bromide and its Comparison with Cetyltrimethylammonium Bromide. Tenside Surfactants Detergents 2019, 56, 300. <https://doi.org/10.3139/113.110633>
- Zhu Wenbin, Liu Fang, He Jingwei: Effect of polymerizable quaternary ammonium monomer MEIM-x's alkyl chain length and content on bone cement's antibacterial activity and physicochemical properties. Journal of the Mechanical Behavior of Biomedical Materials 2018, 87, 279. <https://doi.org/10.1016/j.jmbbm.2018.08.004>
- Lukáč Miloš, Devínsky Ferdinand, Pisárčik Martin, Papapetropoulou Aspasia, Bukovský Marián, Horváth Branislav: Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity. J Surfact & Detergents 2017, 20, 159. <https://doi.org/10.1007/s11743-016-1908-6>
- Pisárčik Martin, Jampílek Josef, Lukáč Miloš, Horáková Renáta, Devínsky Ferdinand, Bukovský Marián, Kalina Michal, Tkacz Jakub, Opravil Tomáš: Silver Nanoparticles Stabilised by Cationic Gemini Surfactants with Variable Spacer Length. Molecules 2017, 22, 1794. <https://doi.org/10.3390/molecules22101794>
- Kumar Dileep, Neo Kian‐Eang, Rub Malik Abdul: Effect of Alkanediyl‐α,ω‐Type Cationic Dimeric (Gemini) Surfactants on the Reaction Rate of Ninhydrin with [Cu(II)‐Gly‐Tyr]+ Complex. J Surfact & Detergents 2016, 19, 101. <https://doi.org/10.1007/s11743-015-1754-y>
- Valente Artur J.M., Söderman Olle: The formation of host–guest complexes between surfactants and cyclodextrins. Advances in Colloid and Interface Science 2014, 205, 156. <https://doi.org/10.1016/j.cis.2013.08.001>
- Pérez Lourdes, Pinazo Aurora, Pons Ramon, Infante MRosa: Gemini surfactants from natural amino acids. Advances in Colloid and Interface Science 2014, 205, 134. <https://doi.org/10.1016/j.cis.2013.10.020>
- Kumar Naveen, Tyagi Rashmi: Industrial Applications of Dimeric Surfactants: A Review. Journal of Dispersion Science and Technology 2014, 35, 205. <https://doi.org/10.1080/01932691.2013.780243>
- Li Junsheng, Kleintschek Tanja, Rieder Annika, Cheng Yin, Baumbach Tilo, Obst Ursula, Schwartz Thomas, Levkin Pavel A.: Hydrophobic Liquid-Infused Porous Polymer Surfaces for Antibacterial Applications. ACS Appl. Mater. Interfaces 2013, 5, 6704. <https://doi.org/10.1021/am401532z>
- Ansari Wajid Husain, Noori Sahar, Naqvi Andleeb, ud - Din Kabir -: Interaction between Zwitterionic Surfactants and Amphiphilic Drug: A Tensiometric Study. Zeitschrift für Physikalische Chemie 2013, 227, 441. <https://doi.org/10.1524/zpch.2012.0340>
- Kumar Naveen, Tyagi Rashmi: Dimeric Surfactants: Promising Ingredients of Cosmetics and Toiletries. Cosmetics 2013, 1, 3. <https://doi.org/10.3390/cosmetics1010003>
- Kida W., Kozak M.: Structural Changes of DPPC Bilayers Induced by Gemini Surfactant. Acta Phys. Pol. A 2012, 121, 893. <https://doi.org/10.12693/APhysPolA.121.893>
- Lukáč M., Timko L., Mrva M., Ondriska F., Karlovská J., Valentová J., Lacko I.: Synthesis, aggregation properties, and antiprotozoal activity of heterocyclic heterogemini surfactants. Heteroatom Chemistry 2010, 21, 203. <https://doi.org/10.1002/hc.20587>
- Lukáč Miloš, Pisárčik Martin, Lacko Ivan, Devínsky Ferdinand: Surface-active properties of nitrogen heterocyclic and dialkylamino derivates of hexadecylphosphocholine and cetyltrimethylammonium bromide. Journal of Colloid and Interface Science 2010, 347, 233. <https://doi.org/10.1016/j.jcis.2010.03.041>
- Tew Gregory N., Scott Richard W., Klein Michael L., DeGrado William F.: De Novo Design of Antimicrobial Polymers, Foldamers, and Small Molecules: From Discovery to Practical Applications. Acc. Chem. Res. 2010, 43, 30. <https://doi.org/10.1021/ar900036b>
- Lukáč Miloš, Lacko Ivan, Bukovský Marián, Kyselová Zuzana, Karlovská Janka, Horváth Branislav, Devínsky Ferdinand: Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine. Open Chemistry 2010, 8. <https://doi.org/10.2478/s11532-009-0126-8>
- Mohamed M. Z., Mohamed A. S.: Synthesis and Some Properties of Fluorinated Cationic Surfactants. J Surfact & Detergents 2009, 12, 345. <https://doi.org/10.1007/s11743-009-1126-6>
- Lukáč Miloš, Mojžiš Ján, Mojžišová Gabriela, Mrva Martin, Ondriska František, Valentová Jindra, Lacko Ivan, Bukovský Marián, Devínsky Ferdinand, Karlovská Janka: Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: Effect of phosphate group and environment of the ammonium cation on their biological activity. European Journal of Medicinal Chemistry 2009, 44, 4970. <https://doi.org/10.1016/j.ejmech.2009.08.011>
- Demberelnyamba D., Kim Ki-Sub, Choi Sukjeong, Park Seung-Yeob, Lee Huen, Kim Chang-Jin, Yoo Ick-Dong: Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. Bioorganic & Medicinal Chemistry 2004, 12, 853. <https://doi.org/10.1016/j.bmc.2004.01.003>
- Sharma Vikas, Borse Mahendra, Aswal V.K., Pokhriyal N.K., Joshi J.V., Goyal P.S., Devi Surekha: Synthesis, characterization, and SANS studies of novel alkanediyl-α,ω-bis(hydroxyethylmethylhexadecylammonium bromide) cationic gemini surfactants. Journal of Colloid and Interface Science 2004, 277, 450. <https://doi.org/10.1016/j.jcis.2004.04.032>
- Ilker M. Firat, Nüsslein Klaus, Tew Gregory N., Coughlin E. Bryan: Tuning the Hemolytic and Antibacterial Activities of Amphiphilic Polynorbornene Derivatives. J. Am. Chem. Soc. 2004, 126, 15870. <https://doi.org/10.1021/ja045664d>
- Massi L, Guittard F, Géribaldi S, Levy R, Duccini Y: Antimicrobial properties of highly fluorinated bis-ammonium salts. International Journal of Antimicrobial Agents 2003, 21, 20. <https://doi.org/10.1016/S0924-8579(02)00271-6>
- Bhattacharya Santanu, Haldar Jayanta: Molecular design of surfactants to tailor its aggregation properties. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2002, 205, 119. <https://doi.org/10.1016/S0927-7757(01)01147-5>
- Ryhänen Samppa J., Pakkanen Antti L., Säily Matti J., Bello Cristiano, Mancini Giovanna, Kinnunen Paavo K. J.: Impact of the Stereochemical Structure on the Thermal Phase Behavior of a Cationic Gemini Surfactant. J. Phys. Chem. B 2002, 106, 11694. <https://doi.org/10.1021/jp015623t>
- Guittard F., Geribaldi S.: Highly fluorinated molecular organised systems: strategy and concept. Journal of Fluorine Chemistry 2001, 107, 363. <https://doi.org/10.1016/S0022-1139(00)00380-8>
- Pisárčik Martin, Imae Toyoko, Devı́nsky Ferdinand, Lacko Ivan: Aggregates of sodium hyaluronate with cationic and aminoxide surfactants in aqueous solution — light scattering study. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2001, 183-185, 555. <https://doi.org/10.1016/S0927-7757(01)00512-X>
- Menger Fredric M., Mbadugha Bessie N. A.: Gemini Surfactants with a Disaccharide Spacer. J. Am. Chem. Soc. 2001, 123, 875. <https://doi.org/10.1021/ja0033178>
- Menger Fredric M., Keiper Jason S.: Gemini-Tenside. Angew Chem 2000, 112, 1980. <https://doi.org/10.1002/1521-3757(20000602)112:11<1980::AID-ANGE1980>3.0.CO;2-D>
- Menger Fredric M., Keiper Jason S.: Gemini-Tenside. Angewandte Chemie 2000, 112, 1980. <https://doi.org/10.1002/1521-3757(20000602)112:11<1980::AID-ANGE1980>3.0.CO;2-D>
- Cserháti Tibor, Forgács Esther: Influence of salt and pH on the hydrophobicity parameters of antisense nucleosides studied by reversed-phase thin-layer chromatography and multivariate mathematical–statistical methods. Journal of Biochemical and Biophysical Methods 1999, 41, 21. <https://doi.org/10.1016/S0165-022X(99)00029-9>
- Peresypkin Andrey V., Menger Fredric M.: Zwitterionic Geminis. Coacervate Formation from a Single Organic Compound. Org. Lett. 1999, 1, 1347. <https://doi.org/10.1021/ol990205g>
- Pérez Lourdes, Torres Josep Lluis, Manresa Angeles, Solans Conxita, Infante M Rosa: Synthesis, Aggregation, and Biological Properties of a New Class of Gemini Cationic Amphiphilic Compounds from Arginine, bis(Args). Langmuir 1996, 12, 5296. <https://doi.org/10.1021/la960301f>