title: Phosphonium pillar[5]arenes as a new class of efficient biofilm inhibitors: importance of charge cooperativity and the pillar platform.
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.
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Roymon
authors: R
authors: Joseph
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Dana
authors: D
authors: Kaizerman
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Ido M
authors: IM
authors: Herzog
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Maya
authors: M
authors: Hadar
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Mark
authors: M
authors: Feldman
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Micha
authors: M
authors: Fridman
authors: School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel. ycohen@post.tau.ac.il.
authors: Yoram
authors: Y
authors: Cohen
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects*; D047250:Calixarenes; D013293:Enterococcus faecalis / Q000187:drug effects* / Q000502:physiology; D016908:Gram-Positive Bacterial Infections / Q000188:drug therapy; D006801:Humans; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000494:pharmacology*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry / Q000494:pharmacology*; D013203:Staphylococcal Infections / Q000188:drug therapy; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000502:physiology
chemical_list: D000900:Anti-Bacterial Agents; D009943:Organophosphorus Compounds; D000644:Quaternary Ammonium Compounds; C570642:pillar(5)arene; D047250:Calixarenes