quaternary ammonium compounds


Summary: Derivatives of ammonium compounds, NH4+ Y-, in which all four of the hydrogens bonded to nitrogen have been replaced with hydrocarbyl groups. These are distinguished from IMINES which are RN=CR2.

Top Publications

  1. Furi L, Ciusa M, Knight D, Di Lorenzo V, Tocci N, Cirasola D, et al. Evaluation of reduced susceptibility to quaternary ammonium compounds and bisbiguanides in clinical isolates and laboratory-generated mutants of Staphylococcus aureus. Antimicrob Agents Chemother. 2013;57:3488-97 pubmed publisher
    ..In addition, current in vitro tests appear not to be suitable for predicting levels of resistance that are clinically relevant. ..
  2. Hyun H, Bordo M, Nasr K, Feith D, Lee J, Kim S, et al. cGMP-Compatible preparative scale synthesis of near-infrared fluorophores. Contrast Media Mol Imaging. 2012;7:516-24 pubmed publisher
    ..Finally, we report the unique in vivo properties of ZW800-1 in large animals approaching the size of humans, thus laying the foundation for rapid clinical translation of these methods...
  3. Zhi Q, Lo E, Lin H. Randomized clinical trial on effectiveness of silver diamine fluoride and glass ionomer in arresting dentine caries in preschool children. J Dent. 2012;40:962-7 pubmed publisher
  4. Warren C. Quaternary ammonium compounds can be abundant in some soils and are taken up as intact molecules by plants. New Phytol. 2013;198:476-85 pubmed publisher
    ..oblongifolia and mycorrhizal Triticum aestivum) have the ability to take up intact molecules of three quaternary ammonium compounds (betaine, carnitine and acetyl-carnitine)...
  5. Hong Y, Li M, Cao H, Gu J. Residence of habitat-specific anammox bacteria in the deep-sea subsurface sediments of the South China Sea: analyses of marker gene abundance with physical chemical parameters. Microb Ecol. 2011;62:36-47 pubmed publisher
  6. Liu B, Lo E, Chu C, Lin H. Randomized trial on fluorides and sealants for fissure caries prevention. J Dent Res. 2012;91:753-8 pubmed publisher
    ..gov number CT01446107). ..
  7. Buffet Bataillon S, Tattevin P, Bonnaure Mallet M, Jolivet Gougeon A. Emergence of resistance to antibacterial agents: the role of quaternary ammonium compounds--a critical review. Int J Antimicrob Agents. 2012;39:381-9 pubmed publisher
    b>Quaternary ammonium compounds (QACs) are widely distributed in hospitals, industry and cosmetics. Little attention has been focused on the potential impact of QACs on the emergence of antibiotic resistance in patients and the environment...
  8. Soumet C, Fourreau E, Legrandois P, Maris P. Resistance to phenicol compounds following adaptation to quaternary ammonium compounds in Escherichia coli. Vet Microbiol. 2012;158:147-52 pubmed publisher
    Bacterial adaptation to quaternary ammonium compounds (QACs) is mainly documented for benzalkonium chloride (BC) and few data are available for other QACs...
  9. Thompson J, Begenisich T. Selectivity filter gating in large-conductance Ca(2+)-activated K+ channels. J Gen Physiol. 2012;139:235-44 pubmed publisher
    ..Our results add significantly to the evidence against a cytoplasmic gate in BK channels and represent a positive test for selectivity filter gating. ..

More Information


  1. Gori F, Tringe S, Kartal B, Marchiori E, Machiori E, Jetten M. The metagenomic basis of anammox metabolism in Candidatus 'Brocadia fulgida'. Biochem Soc Trans. 2011;39:1799-804 pubmed publisher
    ..In the present article, we discuss the important genes of anammox metabolism in Candidatus 'Brocadia fulgida' that were retrieved via a metagenomic approach. ..
  2. Li M, Cao H, Hong Y, Gu J. Seasonal dynamics of anammox bacteria in estuarial sediment of the Mai Po Nature Reserve revealed by analyzing the 16S rRNA and hydrazine oxidoreductase (hzo) genes. Microbes Environ. 2011;26:15-22 pubmed
  3. Chebli Y, Kaneda M, Zerzour R, Geitmann A. The cell wall of the Arabidopsis pollen tube--spatial distribution, recycling, and network formation of polysaccharides. Plant Physiol. 2012;160:1940-55 pubmed publisher
    ..A series of strategic enzymatic treatments also suggests that pectins, cellulose, and callose are highly cross linked to each other...
  4. van Niftrik L, Jetten M. Anaerobic ammonium-oxidizing bacteria: unique microorganisms with exceptional properties. Microbiol Mol Biol Rev. 2012;76:585-96 pubmed publisher
    ..With these unique properties, anammox bacteria are food for thought concerning the early evolution of the domains Bacteria, Archaea, and Eukarya. ..
  5. Mei M, Li Q, Chu C, Yiu C, Lo E. The inhibitory effects of silver diamine fluoride at different concentrations on matrix metalloproteinases. Dent Mater. 2012;28:903-8 pubmed publisher
    ..Greater inhibitory effect on MMPs was found with higher concentration of SDF solution. SDF had more inhibition on MMPs than solutions of NaF and AgNO(3) containing equivalent concentration of fluoride and silver ions, respectively. ..
  6. Zou N, Li B, Dong G, Kronzucker H, Shi W. Ammonium-induced loss of root gravitropism is related to auxin distribution and TRH1 function, and is uncoupled from the inhibition of root elongation in Arabidopsis. J Exp Bot. 2012;63:3777-88 pubmed publisher
    ..Together, the results demonstrate that the effects of NH(4)(+) on root gravitropism are related to delayed lateral auxin redistribution and the TRH1 pathway, and are largely independent of inhibitory effects on root elongation. ..
  7. Henriksen Lacey M, Devitt A, Perrie Y. The vesicle size of DDA:TDB liposomal adjuvants plays a role in the cell-mediated immune response but has no significant effect on antibody production. J Control Release. 2011;154:131-7 pubmed publisher
  8. Bassin J, Pronk M, Kraan R, Kleerebezem R, van Loosdrecht M. Ammonium adsorption in aerobic granular sludge, activated sludge and anammox granules. Water Res. 2011;45:5257-65 pubmed publisher
    ..The results indicate that adsorption or better ion exchange of ammonium should be incorporated into models for nitrification/denitrification, certainly when aerobic granular sludge is used. ..
  9. Chu C, Mei L, Seneviratne C, Lo E. Effects of silver diamine fluoride on dentine carious lesions induced by Streptococcus mutans and Actinomyces naeslundii biofilms. Int J Paediatr Dent. 2012;22:2-10 pubmed publisher
    ..mutans or A. naeslundii formed on dentine surfaces. SDF slowed down demineralization of dentine. This dual activity could be the reason behind clinical success of SDF...
  10. Jaroszynski L, Oleszkiewicz J. Autotrophic ammonium removal from reject water: partial nitrification and anammox in one-reactor versus two-reactor systems. Environ Technol. 2011;32:289-94 pubmed
    ..The impact of two process configurations on the operational stability and process performance was presented based on two cases--DEMON and the SHARON-ANAMMOX process. ..
  11. Oplatowska M, Donnelly R, Majithiya R, Glenn Kennedy D, Elliott C. The potential for human exposure, direct and indirect, to the suspected carcinogenic triphenylmethane dye Brilliant Green from green paper towels. Food Chem Toxicol. 2011;49:1870-6 pubmed publisher
  12. Kalvelage T, Jensen M, Contreras S, Revsbech N, Lam P, Günter M, et al. Oxygen sensitivity of anammox and coupled N-cycle processes in oxygen minimum zones. PLoS ONE. 2011;6:e29299 pubmed publisher
    ..Our study provides the first robust estimates of O(2) sensitivities for processes directly and indirectly connected with N-loss. These are essential to assess the effects of ocean de-oxygenation on oceanic N-cycling. ..
  13. Haraguchi N, Ahamed P, Parvez M, Itsuno S. Synthesis of main-chain chiral quaternary ammonium polymers for asymmetric catalysis using quaternization polymerization. Molecules. 2012;17:7569-83 pubmed publisher
    ..The catalytic activity of the polymeric chiral organocatalysts was investigated on the asymmetric benzylation of N-(diphenylmethylidene)glycine tert-butyl ester. ..
  14. McDonald T, Dietrich F, Lutzoni F. Multiple horizontal gene transfers of ammonium transporters/ammonia permeases from prokaryotes to eukaryotes: toward a new functional and evolutionary classification. Mol Biol Evol. 2012;29:51-60 pubmed publisher
    ..The clades as depicted in this phylogenetic study appear to correspond to functionally different groups, with AMTs and ammonia permeases forming two distinct and possibly monophyletic groups. ..
  15. Wu Y, Ma L, Cheley S, Bayley H, Cui Q, Chapman E. Permeation of styryl dyes through nanometer-scale pores in membranes. Biochemistry. 2011;50:7493-502 pubmed publisher
    ..Together, the data reported here help provide a framework for interpreting dye destaining rates from secretory vesicles. ..
  16. Bartolomé Martín D, Ramírez Franco J, Castro E, Sánchez Prieto J, Torres M. Efficient synaptic vesicle recycling after intense exocytosis concomitant with the accumulation of non-releasable endosomes at early developmental stages. J Cell Sci. 2012;125:422-34 pubmed publisher
    ..Furthermore, cell maturation in culture increased the proportion of synaptic boutons that were capable of an intense release response, whereas the chronic blockage of synaptic activity diminished the capacity of boutons to release dye. ..
  17. Rooks C, Schmid M, Mehsana W, Trimmer M. The depth-specific significance and relative abundance of anaerobic ammonium-oxidizing bacteria in estuarine sediments (Medway Estuary, UK). FEMS Microbiol Ecol. 2012;80:19-29 pubmed publisher
    ..Moreover, deficits detected in the retrieval of (15) N gas from denitrification in Survey 2 may imply potential links between dissimilatory nitrate reduction to ammonium and anammox in estuarine sediments. ..
  18. Melo L, Palombo R, Petri D, Bruns M, Pereira E, Carmona Ribeiro A. Structure-activity relationship for quaternary ammonium compounds hybridized with poly(methyl methacrylate). ACS Appl Mater Interfaces. 2011;3:1933-9 pubmed publisher
    ..DODAB sustained immobilization at the film surface killed bacteria upon contact. TPAB ability to diffuse was useless because of its unfavorable hydrophobic-hydrophilic balance for bioactivity. ..
  19. Holdsworth S, Law C. The major facilitator superfamily transporter MdtM contributes to the intrinsic resistance of Escherichia coli to quaternary ammonium compounds. J Antimicrob Chemother. 2013;68:831-9 pubmed publisher
    b>Quaternary ammonium compounds (QACs) are used extensively as biocides and their misuse may be contributing to the development of bacterial resistance...
  20. Kindaichi T, Awata T, Suzuki Y, Tanabe K, Hatamoto M, Ozaki N, et al. Enrichment using an up-flow column reactor and community structure of marine anammox bacteria from coastal sediment. Microbes Environ. 2011;26:67-73 pubmed
    ..The marine anammox bacteria enriched in this study have potential applications to the treatment of industrial wastewater containing high levels of ammonium and salt. ..
  21. Kartal B, Maalcke W, de Almeida N, Cirpus I, Gloerich J, Geerts W, et al. Molecular mechanism of anaerobic ammonium oxidation. Nature. 2011;479:127-30 pubmed publisher
    ..Furthermore, they reinforce the role of nitric oxide in the evolution of the nitrogen cycle. ..
  22. Pitcher A, Villanueva L, Hopmans E, Schouten S, Reichart G, Sinninghe Damsté J. Niche segregation of ammonia-oxidizing archaea and anammox bacteria in the Arabian Sea oxygen minimum zone. ISME J. 2011;5:1896-904 pubmed publisher
  23. Amano T, Yoshinaga I, Yamagishi T, Thuoc C, Thu P, Ueda S, et al. Contribution of anammox bacteria to benthic nitrogen cycling in a mangrove forest and shrimp ponds, Haiphong, Vietnam. Microbes Environ. 2011;26:1-6 pubmed
    ..Furthermore, this study provides new insight into the biogeography of anammox bacteria: 'Scalindua' and 'Kuenenia'-like species coexisted in the blackish sediment as in some temperate estuarine sediment. ..
  24. Buffet Bataillon S, Branger B, Cormier M, Bonnaure Mallet M, Jolivet Gougeon A. Effect of higher minimum inhibitory concentrations of quaternary ammonium compounds in clinical E. coli isolates on antibiotic susceptibilities and clinical outcomes. J Hosp Infect. 2011;79:141-6 pubmed publisher
    b>Quaternary ammonium compounds (QACs) are cationic surfactants used as preservatives and environmental disinfectants. Limited data are available regarding the effect of QACs in the clinical setting...
  25. Harhangi H, Le Roy M, van Alen T, Hu B, Groen J, Kartal B, et al. Hydrazine synthase, a unique phylomarker with which to study the presence and biodiversity of anammox bacteria. Appl Environ Microbiol. 2012;78:752-8 pubmed publisher
  26. Hu B, Shen L, Xu X, Zheng P. Anaerobic ammonium oxidation (anammox) in different natural ecosystems. Biochem Soc Trans. 2011;39:1811-6 pubmed publisher
  27. Piechotta P, Rapedius M, Stansfeld P, Bollepalli M, Ehrlich G, Erhlich G, et al. The pore structure and gating mechanism of K2P channels. EMBO J. 2011;30:3607-19 pubmed publisher
    ..These results demonstrate that the primary activation mechanisms in TREK-1 reside close to, or within the selectivity filter and do not involve gating at the cytoplasmic bundle crossing. ..
  28. Waser M, Gratzer K, Herchl R, Muller N. Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts. Org Biomol Chem. 2012;10:251-4 pubmed publisher
    ..These compounds were found to catalyse the asymmetric ?-alkylation of glycine Schiff bases with high enantioselectivities and in good yields...
  29. Jensen M, Lam P, Revsbech N, Nagel B, Gaye B, Jetten M, et al. Intensive nitrogen loss over the Omani Shelf due to anammox coupled with dissimilatory nitrite reduction to ammonium. ISME J. 2011;5:1660-70 pubmed publisher
    ..The close reliance of anammox on DNRA also highlights the need to take into account the effects of coupling N-transformations on oceanic N-loss and subsequent N-balance estimates. ..
  30. Cydzik M, Rudowska M, Stefanowicz P, Szewczuk Z. The competition of charge remote and charge directed fragmentation mechanisms in quaternary ammonium salt derivatized peptides--an isotopic exchange study. J Am Soc Mass Spectrom. 2011;22:2103-7 pubmed publisher
    ..The isotopic labeling allows differentiation of fragments formed according to ChR and ChD mechanisms. ..
  31. Inácio Ã, Domingues N, Nunes A, Martins P, Moreno M, Estronca L, et al. Quaternary ammonium surfactant structure determines selective toxicity towards bacteria: mechanisms of action and clinical implications in antibacterial prophylaxis. J Antimicrob Chemother. 2016;71:641-54 pubmed publisher
    ..Our data show that short chain (C12) n-alkyl pyridinium bromides have a sufficiently large therapeutic window to be good microbicide candidates. ..
  32. Aliabadi M, Dastjerdi R, Kabiri K. HTCC-modified nanoclay for tissue engineering applications: a synergistic cell growth and antibacterial efficiency. Biomed Res Int. 2013;2013:749240 pubmed publisher
  33. Amand L, Carlsson B. The optimal dissolved oxygen profile in a nitrifying activated sludge process - comparisons with ammonium feedback control. Water Sci Technol. 2013;68:641-9 pubmed publisher
    ..5% savings in the air flow rate, while the optimal solution can achieve a 3-7% saving. Energy savings are larger when operating at higher DO concentrations. ..
  34. Xu H, Chang Q, Jia W, Jiang H, Sun P, Xie J. Iron status and lipopolysaccharide regulate Ndfip1 by activation of nuclear factor-kappa B. Biometals. 2013;26:981-8 pubmed publisher
    ..We speculate that iron status and LPS may contribute to the changes of Ndfip1 expression by activation of nuclear factor-kappa B. ..
  35. Kimura Y, Itokawa H, Noto K, Murakami T, Isaka K. Stability of autotrophic nitrogen removal system under four non-steady operations. Bioresour Technol. 2013;137:196-201 pubmed publisher
    ..Finally, the maximum capacity of each reactor was evaluated, and the nitritation rate was found to be 2.3 kg-N/m(3)/d at a DO of 4.0mg/L, and the nitrogen-conversion rate was 9.0 kg-N/m(3)/d. ..
  36. Cheng Y, Cai H, Yin B, Yao P. Cholic acid modified N-(2-hydroxy)-propyl-3-trimethylammonium chitosan chloride for superoxide dismutase delivery. Int J Pharm. 2013;454:425-34 pubmed publisher
    ..The results demonstrate that free HTCC-CA is effective to scavenge superoxide radicals in the blood circulation and SOD/HTCC-CA nanoparticles have better antioxidant efficiency than free SOD as well as free HTCC-CA. ..
  37. Park S, Lee S, Lee Y, Seo Y. CO2 capture from simulated fuel gas mixtures using semiclathrate hydrates formed by quaternary ammonium salts. Environ Sci Technol. 2013;47:7571-7 pubmed publisher
  38. Haroon M, Hu S, Shi Y, Imelfort M, Keller J, Hugenholtz P, et al. Anaerobic oxidation of methane coupled to nitrate reduction in a novel archaeal lineage. Nature. 2013;500:567-70 pubmed publisher
    ..We predict that 'M. nitroreducens' and other members of the 'Methanoperedenaceae' have an important role in linking the global carbon and nitrogen cycles in anoxic environments. ..
  39. Chen Z, Zhang C, Li X, Ma H, Wan C, Li K, et al. Aptasensor for electrochemical sensing of angiogenin based on electrode modified by cationic polyelectrolyte-functionalized graphene/gold nanoparticles composites. Biosens Bioelectron. 2015;65:232-7 pubmed publisher
    ..1pM to 5nM with a detection limit of 0.064pM. The developed sensor provides a promising strategy for the cancer diagnosis in medical application in the future. ..
  40. Chauhan V, Singh S, Kamboj R, Mishra R, Kaur G. Self-assembly, DNA binding and cytotoxicity trends of ether functionalized gemini pyridinium amphiphiles. J Colloid Interface Sci. 2014;417:385-95 pubmed publisher
    ..Further, thermal stability of these amphiphiles has been evaluated by thermogravimetric analysis (TGA). The dependence of self-assembly behavior and other properties on spacer as well as alkyl chain length has been established. ..
  41. Zhu Z, Su M, Ma L, Ma L, Liu D, Wang Z. Preparation of graphene oxide-silver nanoparticle nanohybrids with highly antibacterial capability. Talanta. 2013;117:449-55 pubmed publisher
  42. Stoffolano J, Danai L, Chambers J. Effect of channel blockers on the smooth muscle of the adult crop of the queen blowfly, Phormia regina. J Insect Sci. 2013;13:97 pubmed publisher
    ..Benzyltrimethylammonium chloride, never before reported for its effect on insect muscle, was as effective in suppressing crop muscle contraction as benzethonium chloride, which is a reported agonist of dromyosuppressin. ..
  43. Rodrigues C, Graça C, Maçôas E, Fedorov A, Afonso C, Martinho J. Excited-state proton transfer of fluorescein anion as an ionic liquid component. J Phys Chem B. 2013;117:14108-14 pubmed publisher
    ..The FILs have completely different spectroscopic properties from solvated fluorescein in Quat(+)Cl(-), where the prototropic equilibrium is shifted toward the neutral forms. ..
  44. Damián Chanique G, Heraldo Arévalo A, Alicia Zon M, Fernandez H. Eletrochemical reduction of patulin and 5-hydroxymethylfurfural in both neutral and acid non-aqueous media. Their electroanalytical determination in apple juices. Talanta. 2013;111:85-92 pubmed publisher
    ..This electroanalytical methodology appears as a good screening method for the determination of patulin in apple juices. ..
  45. Ling Y, Chen T, Jing Y, Fan L, Wan Y, Lin J. ?-Aminobutyric acid (GABA) homeostasis regulates pollen germination and polarized growth in Picea wilsonii. Planta. 2013;238:831-43 pubmed publisher
    ..wilsonii by affecting actin filament patterns, vesicle trafficking, and the configuration and distribution of cell wall components. ..
  46. Wang Q, Zhao Y, Luo W, Li R, He Q, Fang X, et al. Single-particle analysis reveals shutoff control of the Arabidopsis ammonium transporter AMT1;3 by clustering and internalization. Proc Natl Acad Sci U S A. 2013;110:13204-9 pubmed publisher
    ..Our results revealed that the clustering and endocytosis of AMT1;3 provides an effective mechanism by which plant cells can avoid accumulation of toxic levels of ammonium by eliminating active AMT1;3 from the plasma membrane. ..
  47. Cameron D, Donahue D, Costin G, Kaufman L, Avalos J, Downey M, et al. Confirmation of in vitro and clinical safety assessment of behentrimonium chloride-containing leave-on body lotions using post-marketing adverse event data. Toxicol In Vitro. 2013;27:2203-12 pubmed publisher
    ..Therefore, if formulated in appropriate conditions at 1-5%, BTC will not cause dermal irritation or delayed contact sensitization when used in a whole-body, leave-on product. ..
  48. Kumar M, Bauddh K, Kumar S, Sainger M, Sainger P, Singh R. Increase in growth, productivity and nutritional status of wheat (Triticum aestivum L. cv. WH-711) and enrichment in soil fertility applied with organic matrix entrapped urea. J Environ Biol. 2013;34:1-9 pubmed
    ..Our data indicate that OMEU which are low cost, biodegradable and non-toxic can be used to replace the expensive chemical fertilizers for wheat cultivation in semi-arid, subtropical climate. ..
  49. Tavlieva M, Genieva S, Georgieva V, Vlaev L. Kinetic study of brilliant green adsorption from aqueous solution onto white rice husk ash. J Colloid Interface Sci. 2013;409:112-22 pubmed publisher
    ..04 kJ mol(-1)), the change of entropy (-318.31 J mol(-1) K(-1)), enthalpy (-47.50 kJ mol(-1)), and Gibbs free energy (range 44.81-54.36 kJ mol(-1)) for the formation of activated complex from the reagents. ..
  50. Bragg R, Jansen A, Coetzee M, van der Westhuizen W, Boucher C. Bacterial resistance to Quaternary Ammonium Compounds (QAC) disinfectants. Adv Exp Med Biol. 2014;808:1-13 pubmed publisher
    ..Our main focus is on the control of bacterial and viral diseases in the poultry industry in a post-antibiotic era, but the principles remain similar for disease control in any veterinary field as well as in human medicine. ..
  51. Paudyal R, Jamaluddin A, Warren J, Doyle S, Robert S, Warriner S, et al. Trafficking modulator TENin1 inhibits endocytosis, causes endomembrane protein accumulation at the pre-vacuolar compartment and impairs gravitropic response in Arabidopsis thaliana. Biochem J. 2014;460:177-85 pubmed publisher
    ..This compound and the resistant Arabidopsis accessions may be used as a resource in future studies to better understand endomembrane trafficking in plants. ..
  52. Hong Y, Chen S, Leung C, Lam J, Tang B. Water-soluble tetraphenylethene derivatives as fluorescent "light-up" probes for nucleic acid detection and their applications in cell imaging. Chem Asian J. 2013;8:1806-12 pubmed publisher
    ..Owing to their AIE characteristics, the dye molecules aggregate in DNA-rich regions and exert appreciable quantum efficiency as well as superior photostability. ..
  53. Xiang Z, Liu J, Sun H, Wen X. Discovery of Novel Potent Muscarinic M3 Receptor Antagonists with Proper Plasma Stability by Structural Recombination of Marketed M3 Antagonists. ChemMedChem. 2017;12:1173-1182 pubmed publisher
    ..In addition, structure-activity relationship studies revealed that the R configuration of the pyrrolidinyl C3 atom was clearly better than the S configuration. ..