Bicephalic amphiphile architecture affects antibacterial activity

作者: Jade E. LaDow , David C. Warnock , Kristina M. Hamill , Kaitlin L. Simmons , Robert W. Davis

DOI: 10.1016/J.EJMECH.2011.06.026

关键词:

摘要: A series of cationic amphiphiles, each with an aromatic core, was prepared and investigated for antimicrobial properties. The synthesized amphiphiles in this study are bicephalic (double-headed) that they possess two trimethylammonium head groups a single linear alkoxy tail. Minimum inhibitory minimum bactericidal concentrations these were the low micromolar range. Antimicrobial activities highly sensitive to chain length hydrophobic region, modestly reliant on relative positioning core. These trends more pronounced time kill assays, wherein longer compounds required significantly shorter times completely bacteria. Microscopy suggested mode cell death lysis. Strong inhibition observed both biscationic monocationic comparisons against Gram-positive bacteria; only maintained good activity versus Gram-negative bacteria tested. observations provide direction future structural investigations.

参考文章(32)
P. Johnson, J. D. Coombes, Anti-infective agents Foreign Compound Metabolism in Mammals. pp. 369- 386 ,(2003) , 10.1039/9781847556080-00369
Barbara E. Murray, Problems and Dilemmas of Antimicrobial Resistance Pharmacotherapy. ,vol. 12, ,(1992) , 10.1002/J.1875-9114.1992.TB04501.X
R HANCOCK, The bacterial outer membrane as a drug barrier Trends in Microbiology. ,vol. 5, pp. 37- 42 ,(1997) , 10.1016/S0966-842X(97)81773-8
Annette Meister, Alfred Blume, Self-assembly of bipolar amphiphiles Current Opinion in Colloid & Interface Science. ,vol. 12, pp. 138- 147 ,(2007) , 10.1016/J.COCIS.2007.05.003
G W Kaatz, S M Seo, C A Ruble, Efflux-mediated fluoroquinolone resistance in Staphylococcus aureus. Antimicrobial Agents and Chemotherapy. ,vol. 37, pp. 1086- 1094 ,(1993) , 10.1128/AAC.37.5.1086
Jayanta Haldar, Paturu Kondaiah, Santanu Bhattacharya, Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles. Incorporation of multiple head groups leads to impressive antibacterial activity. Journal of Medicinal Chemistry. ,vol. 48, pp. 3823- 3831 ,(2005) , 10.1021/JM049106L
Sisir Debnath, Anshupriya Shome, Dibyendu Das, Prasanta Kumar Das, Hydrogelation through self-assembly of fmoc-peptide functionalized cationic amphiphiles: potent antibacterial agent. Journal of Physical Chemistry B. ,vol. 114, pp. 4407- 4415 ,(2010) , 10.1021/JP909520W
Santanu Bhattacharya, Avinash Bajaj, Advances in gene delivery through molecular design of cationic lipids Chemical Communications. pp. 4632- 4656 ,(2009) , 10.1039/B900666B