TMEDA-derived biscationic amphiphiles: An economical preparation of potent antibacterial agents

Bioorganic & Medicinal Chemistry Letters
Jacob W BlackKevin P C Minbiole

Abstract

Bis-alkylated derivatives of N,N,N',N'-tetramethylethylenediamine (TMEDA) represent a well-known class of versatile biscationic amphiphiles, owing to their low cost and ease of preparation. Asymmetric TMEDA derivatives, however, have been studied significantly less, particularly in regards to their antimicrobial properties. We have thus prepared a series of 36 mono- and bis-alkylated TMEDA derivatives to evaluate their inhibition of bacterial growth. This series of compounds showed low micromolar activity against a panel of four bacteria. Optimal inhibition was observed when the biscationic amphiphiles possessed modest asymmetry and were composed of between 20 and 24 total carbon atoms in the side chains. These amphiphiles were prepared in a simple two-step procedure, utilizing inexpensive materials and atom-economical reactions, making them practical for further development.

References

Mar 26, 2004·Nature Reviews. Microbiology·Christopher Walsh
Oct 1, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Avinash Bhadani, Sukhprit Singh
Aug 11, 2010·Antimicrobial Agents and Chemotherapy·Brandon FindlayFrank Schweizer
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Nov 13, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Xudong WangZhihong Li

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Citations

Jul 10, 2015·ACS Infectious Diseases·Megan C JenningsWilliam M Wuest
Apr 11, 2017·Bioorganic & Medicinal Chemistry Letters·Ryan A AllenKevin P C Minbiole
Dec 30, 2016·ChemMedChem·Saleh E Al-KhalifaKevin P C Minbiole
Aug 26, 2014·Chembiochem : a European Journal of Chemical Biology·Megan C JenningsWilliam M Wuest
Oct 26, 2018·ChemMedChem·Renee C KontosKevin P C Minbiole
Sep 1, 2015·Chembiochem : a European Journal of Chemical Biology·Myles A MitchellKevin P C Minbiole
Jun 24, 2017·Colloids and Surfaces. B, Biointerfaces·Tara M GallagherKevin L Caran
May 8, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Abdullah O Ba-Salem, Jean Duhamel
Jul 3, 2021·International Journal of Molecular Sciences·Anatoly N VereshchaginValentine P Ananikov
Nov 19, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Abdullah O Ba-Salem, Jean Duhamel

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