Phosphonium pillar[5]arenes as a new class of efficient biofilm inhibitors: Importance of charge cooperativity and the pillar platform

Roymon Joseph, Dana Kaizerman, Ido M. Herzog, Maya Hadar, Mark Feldman, Micha Fridman, Yoram Cohen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

Biofilm formation, which frequently occurs in microbial infections and often reduces the efficacy of antibiotics, also perturbs many industrial and domestic processes. We found that a new class of water soluble pillar[5]arenes bearing phosphonium moieties (1, 2) and their respective ammonium analogues (3, 4) inhibit biofilm formation with IC50 values in the range of 0.67-1.66 μM. These compounds have no antimicrobial activity, do not damage red blood cell membranes, and do not affect mammalian cell viability in culture. Comparison of the antibiofilm activities of the phosphonium-decorated pillar[5]arene derivatives 1 and 2 with their respective ammonium counterparts 3 and 4 and their monomers 5 and 6, demonstrate that while positive charges, charge cooperativity and the pillararene platform are essential for the observed antibiofilm activity the nature of the charges is not.

Original languageAmerican English
Pages (from-to)10656-10659
Number of pages4
JournalChemical Communications
Volume52
Issue number70
DOIs
StatePublished - 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2016 The Royal Society of Chemistry.

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