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Journal articles on the topic 'Quaternary Ammonium Compounds – metabolism'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Ancelin, Marie L., Michèle Calas, Anne Bonhoure, Serge Herbute, and Henri J. Vial. "In Vivo Antimalarial Activities of Mono- and Bis Quaternary Ammonium Salts Interfering with Plasmodium Phospholipid Metabolism." Antimicrobial Agents and Chemotherapy 47, no. 8 (August 2003): 2598–605. http://dx.doi.org/10.1128/aac.47.8.2598-2605.2003.

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ABSTRACT We previously showed that quaternary ammonium salts have potent antimalarial activities against the blood stage of drug-resistant Plasmodium falciparum. In the present study, 13 compounds of this series were comparatively assessed in murine in vivo malarial models. Mice infected with Plasmodium berghei were successfully treated with 11 quaternary ammonium salts in a 4-day suppressive test with a once-daily intraperitoneal administration. The dose required to decrease parasitemia by 50% (ED50) ranged from 0.04 to 4.5 mg/kg of body weight. For six mono- and three bis-quaternary ammonium salts, the therapeutic indices (i.e., 50% lethal dose and ED50) were higher than 5, and at best, around 20 to 30 for five of them (E6, E8, F4, G5, and G25), which is comparable to that of chloroquine under the same conditions. Plasmodium chabaudi was significantly more susceptible to G5, G15, and G25 compounds than P. berghei. Similar therapeutic indices were obtained, regardless of the administration mode or initial parasitemia (up to 11.2%). Parasitemia clearance was complete without recrudescence. Subcutaneously administered radioactive compounds had a short elimination half-life in mice (3.5 h) with low bioavailability (17.3%), which was likely due to the permanent cationic charge of the molecule. The high in vivo therapeutic index in the P. chabaudi-infected mouse model and the absence of recrudescence highlight the enormous potential of these quaternary ammonium salts for clinical malarial treatment.

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2

Rajasekaran, Lada R., D. Aspinall, G. P. Jones, and L. G. Paleg. "Stress metabolism. IX. Effect of salt stress on trigonelline accumulation in tomato." Canadian Journal of Plant Science 81, no. 3 (July 1, 2001): 487–98. http://dx.doi.org/10.4141/p00-079.

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The presence of quaternary ammonium compounds (QAC) and their accumulation in tomato (Lycopersicon esculentum Mill.) cv. Duke in response to different modes for causing NaCl stress were studied. Pre-germinated tomato seeds were grown in sand culture and 25-d-old seedlings were subjected to abrupt, progressive or prolonged salt stress using NaCl at various osmotic potentials. Plant water status was measured using psychrometry and quaternary ammonium compounds were visualized using thin-layer chromatography and then confirmed and quantified using nuclear magnetic resonance spectrometry. Leaf water potential and osmotic potential declined depending on the osmotic potential of the rooting medium and the mode of stress imposition. A greater decline in osmotic potential compared with the total water potential led to turgor maintenance in plants under progressive or prolonged NaCl stress. The QAC, trigonelline and choline were identified in tomato. Trigonelline, but not choline, accumulated rapidly in response to abrupt, progressive or prolonged NaCl stress. The threshold external water potential (ψext.) for trigonelline accumulation was –0.565 MPa. Trigonelline accumulation correlated with changes in ψL (r = –0.92***), ψS (r = –0.94***) and ψP (r = 0.85***). Trigonelline contributed only –0.035 MPa to the osmotic adjustment, suggesting that its role may also lie in areas other than osmoregulation. Key words: Bataines choline, growth, Lycopersicon esculentum, salt stress, trigonelline, water relations

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3

Ancelin, Marie L., Michèle Calas, Valérie Vidal-Sailhan, Serge Herbuté, Pascal Ringwald, and Henri J. Vial. "Potent Inhibitors of Plasmodium Phospholipid Metabolism with a Broad Spectrum of In Vitro Antimalarial Activities." Antimicrobial Agents and Chemotherapy 47, no. 8 (August 2003): 2590–97. http://dx.doi.org/10.1128/aac.47.8.2590-2597.2003.

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ABSTRACT We characterized the potent in vitro antimalarial activity and biologic assessment of 13 phospholipid polar head analogs on a comparative basis. There was a positive relationship between the abilities of the drugs to inhibit parasite growth in culture and their abilities to specifically inhibit phosphatidylcholine biosynthesis of Plasmodium falciparum-infected erythrocytes. Maximal activity of G25 was observed for the trophozoite stage of the 48-h erythrocytic cycle (50% inhibitory concentration, 0.75 nM), whereas the schizont and ring stages were 12- and 213-fold less susceptible. The compounds exerted a rapid nonreversible cytotoxic effect, with complete clearance of parasitemia after 5 h of contact with the mature stages. The compounds were highly specific against P. falciparum, with much lower toxicity against three other mammalian cell lines, and the in vitro therapeutic indices ranged from 300 to 2,500,000. Finally, the monoquaternary ammonium E10 and two bis-ammonium salts, G5 and G25, were similarly active against multiresistant strains and fresh isolates of P. falciparum. This impressive selective in vitro toxicity against P. falciparum strongly highlights the clinical potential of these quaternary ammonium salts for malarial chemotherapy.

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4

Takenaka, Shinji, Takashi Tonoki, Kazuya Taira, Shuichiro Murakami, and Kenji Aoki. "Adaptation of Pseudomonas sp. Strain 7-6 to Quaternary Ammonium Compounds and Their Degradation via Dual Pathways." Applied and Environmental Microbiology 73, no. 6 (January 19, 2007): 1797–802. http://dx.doi.org/10.1128/aem.02426-06.

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ABSTRACT Pseudomonas sp. strain 7-6, isolated from active sludge obtained from a wastewater facility, utilized a quaternary ammonium surfactant, n-dodecyltrimethylammonium chloride (DTAC), as its sole carbon, nitrogen, and energy source. When initially grown in the presence of 10 mM DTAC medium, the isolate was unable to degrade DTAC. The strain was cultivated in gradually increasing concentrations of the surfactant until continuous exposure led to high tolerance and biodegradation of the compound. Based on the identification of five metabolites by gas chromatography-mass spectrometry analysis, two possible pathways for DTAC metabolism were proposed. In pathway 1, DTAC is converted to lauric acid via n-dodecanal with the release of trimethylamine; in pathway 2, DTAC is converted to lauric acid via n-dodecyldimethylamine and then n-dodecanal with the release of dimethylamine. Among the identified metabolites, the strain precultivated on DTAC medium could utilize n-dodecanal and lauric acid as sole carbon sources and trimethylamine and dimethylamine as sole nitrogen sources, but it could not efficiently utilize n-dodecyldimethylamine. These results indicated pathway 1 is the main pathway for the degradation of DTAC.

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5

Hernandez, Monica N., and Steven E. Lindow. "Contact-dependent traits in Pseudomonas syringae B728a." PLOS ONE 16, no. 2 (February 11, 2021): e0241655. http://dx.doi.org/10.1371/journal.pone.0241655.

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Production of the biosurfactant syringafactin by the plant pathogen Pseudomonas syringae B728a is a surface contact-dependent trait. Expression of syfA, as measured using a gfp reporter gene fusion was low in planktonic cells in liquid cultures but over 4-fold higher in cells immobilized on surfaces as varied as glass, plastic, paper, parafilm, agar, membrane filters, and leaves. Induction of syfA as measured by GFP fluorescence was rapid, occurring within two hours after immobilization of cells on surfaces. Comparison of the global transcriptome by RNA sequencing of planktonic cells in a nutrient medium with that of cells immobilized for 2 hours on filters placed on this solidified medium revealed that, in addition to syfA, 3156 other genes were differentially expressed. Genes repressed in immobilized cells included those involved in quaternary ammonium compound (QAC) metabolism and transport, compatible solute production, carbohydrate metabolism and transport, organic acid metabolism and transport, phytotoxin synthesis and transport, amino acid metabolism and transport, and secondary metabolism. Genes induced in immobilized cells included syfA plus those involved in translation, siderophore synthesis and transport, nucleotide metabolism and transport, flagellar synthesis and motility, lipopolysaccharide (LPS) synthesis and transport, energy generation, transcription, chemosensing and chemotaxis, replication and DNA repair, iron-sulfur proteins, peptidoglycan/cell wall polymers, terpenoid backbone synthesis, iron metabolism and transport, and cell division. That many genes are rapidly differentially expressed upon transfer of cells from a planktonic to an immobilized state suggests that cells experience the two environments differently. It seems possible that surface contact initiates anticipatory changes in P. syringae gene expression, which enables rapid and appropriate physiological responses to the different environmental conditions such as might occur in a biofilm. Such responses could help cells survive transitions from aquatic habitats fostering planktonic traits to attachment on surfaces, conditions that alternatively occur on leaves.

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6

Inazu, Masato. "Functional Expression of Choline Transporters in the Blood–Brain Barrier." Nutrients 11, no. 10 (September 20, 2019): 2265. http://dx.doi.org/10.3390/nu11102265.

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Cholinergic neurons in the central nervous system play a vital role in higher brain functions, such as learning and memory. Choline is essential for the synthesis of the neurotransmitter acetylcholine by cholinergic neurons. The synthesis and metabolism of acetylcholine are important mechanisms for regulating neuronal activity. Choline is a positively charged quaternary ammonium compound that requires transporters to pass through the plasma membrane. Currently, there are three groups of choline transporters with different characteristics, such as affinity for choline, tissue distribution, and sodium dependence. They include (I) polyspecific organic cation transporters (OCT1-3: SLC22A1-3) with a low affinity for choline, (II) high-affinity choline transporter 1 (CHT1: SLC5A7), and (III) choline transporter-like proteins (CTL1-5: SLC44A1-5). Brain microvascular endothelial cells, which comprise part of the blood–brain barrier, take up extracellular choline via intermediate-affinity choline transporter-like protein 1 (CTL1) and low-affinity CTL2 transporters. CTL2 is responsible for excreting a high concentration of choline taken up by the brain microvascular endothelial cells on the brain side of the blood–brain barrier. CTL2 is also highly expressed in mitochondria and may be involved in the oxidative pathway of choline metabolism. Therefore, CTL1- and CTL2-mediated choline transport to the brain through the blood–brain barrier plays an essential role in various functions of the central nervous system by acting as the rate-limiting step of cholinergic neuronal activity.

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7

Sabapathy, Nadana N. "Chapter 14 Quaternary ammonium compounds." Toxicology 91, no. 1 (June 1994): 93–98. http://dx.doi.org/10.1016/0300-483x(94)90247-x.

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8

Meini, S., A. Lecci, F. Carini, M. Tramontana, S. Giuliani, C. A. Maggi, R. Ricci, et al. "In vitro and in vivo activity of analogues of the kinin B2 receptor antagonist MEN11270." Canadian Journal of Physiology and Pharmacology 80, no. 4 (April 1, 2002): 293–302. http://dx.doi.org/10.1139/y02-022.

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In this study, we describe the in vitro and in vivo activities of a series of cyclic peptide analogues of the selective kinin B2 receptor antagonist MEN11270 on Chinese hamster ovary cells expressing the human B2 receptor (hB2R), the human isolated umbilical vein (hUV), the isolated guinea pig ileum (gpI), and bradykinin (BK) induced bronchoconstriction (BC) and hypotension in anaesthetized guinea pigs. Substitutions in the backbone of MEN11270 (H-DArg-Arg-Pro-Hyp-Gly-Thi-c(Dab-DTic-Oic-Arg)c(7γ-10α)) aimed to increase the potency in inhibiting bronchospasm versus hypotension following the topical (intratracheal (i.t.)) or systemic (intravenous (i.v.)) application of these antagonists. A series of analogues were left unprotected from N-terminal cleavage by aminopeptidases (MEN12739, MEN13052, MEN13346, and MEN13371): these compounds maintained sizeable affinities for the hB2R (pKi = 9.4, 9.6, 9.7, and 8.6, respectively) and antagonist activities toward BK in the hUV (pA2 = 7.9, 8.3, 8.2, and 7.5) and gpI assays (pKB = 7.4, 7.8, 7.9, and 7.9), but the inhibition of BK-induced BC and hypotension in vivo was negligible following either i.v. or i.t. administration. Two analogues (MEN12388 and MEN13405) could be potential substrates of angiotensin-converting enzyme: these have good activity in the hB2R (pKi = 9.5 and 8.9, respectively), hUV (pA2 = 8.2 for MEN12388), and gpI assays (pKB = 8.4 and 8.0) but an in vivo activity 10- to 30-fold lower than the parent compound MEN11270 (pKi = 9.4, pA2 = 8.1, pKB = 8.3) when given by either the i.v. or the i.t. route. Other analogues were functionalized with a quaternary ammonium Lys derivative (MEN13031, MEN12374, and the previously mentioned MEN13052) or with an ethyl group on Arg (MEN13655 and the previously mentioned MEN13346 and MEN13405) in order to hinder or facilitate local absorption. MEN13346 and MEN13031 (pKi = 9.7and 9.5, pA2 = 8.2 and 7.9, pKB = 7.9 and 8.5, respectively) were 10- to 30-fold less active in vivo than MEN11270, without improving the discrimination between BK-induced BC and hypotension after either systemic or topical administration. It is concluded that the decreased in vivo activities of cyclic analogues of MEN11270 on BK-induced BC and hypotension following either their intratracheal or their intravenous routes of administration might be due in large part to metabolic degradation.Key words: bradykinin, asthma, blood pressure, guinea pig, metabolism.

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9

DOCKX, Jozef. "Quaternary Ammonium Compounds in Organic Synthesis." Synthesis 1973, no. 08 (September 12, 2002): 441–56. http://dx.doi.org/10.1055/s-1973-22233.

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10

McLean, William F. H., Gerald Blunden, and Kenneth Jewers. "Quaternary ammonium compounds in the Capparaceae." Biochemical Systematics and Ecology 24, no. 5 (July 1996): 427–34. http://dx.doi.org/10.1016/0305-1978(96)00044-0.

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11

Purohit, A., M. C. Kopferschmitt-Kubler, C. Moreau, E. Popin, M. Blaumeiser, and G. Pauli. "Quaternary ammonium compounds and occupational asthma." International Archives of Occupational and Environmental Health 73, no. 6 (August 18, 2000): 423–27. http://dx.doi.org/10.1007/s004200000162.

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12

Zubris, Deanna, Kevin Minbiole, and William Wuest. "Polymeric Quaternary Ammonium Compounds: Versatile Antimicrobial Materials." Current Topics in Medicinal Chemistry 17, no. 3 (November 24, 2016): 305–18. http://dx.doi.org/10.2174/1568026616666160829155805.

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13

Detmers, Frank J. M., Bert L. de Groot, E. Matthias Müller, Andrew Hinton, Irene B. M. Konings, Mozes Sze, Sabine L. Flitsch, Helmut Grubmüller, and Peter M. T. Deen. "Quaternary Ammonium Compounds as Water Channel Blockers." Journal of Biological Chemistry 281, no. 20 (March 21, 2006): 14207–14. http://dx.doi.org/10.1074/jbc.m513072200.

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14

ZHANG, Yu, Yinyan CHEN, Yuntong HU, Fang HUANG, and Yuhong XIAO. "Quaternary ammonium compounds in dental restorative materials." Dental Materials Journal 37, no. 2 (2018): 183–91. http://dx.doi.org/10.4012/dmj.2017-096.

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15

Harrowfield, Jack M., William R. Richmond, and Alexander N. Sobolev. "Inclusion of quaternary ammonium compounds by calixarenes." Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 19, no. 1-4 (1994): 257–76. http://dx.doi.org/10.1007/bf00708986.

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16

Kennedy, MA, VS Mellon, G. Caldwell, and LN Potgieter. "Virucidal efficacy of the newer quaternary ammonium compounds." Journal of the American Animal Hospital Association 31, no. 3 (May 1, 1995): 254–58. http://dx.doi.org/10.5326/15473317-31-3-254.

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The virucidal activity of several disinfectants containing newer generation quaternary ammonium compounds (QACs) as their active ingredients was evaluated. Disinfectants were used at the manufacturers' recommended dilutions with isolates of feline herpesvirus, feline calicivirus, and canine parvovirus, and a contact time of 10 minutes at room temperature. Detoxification of virus/disinfectant solutions was done by dialysis prior to virus assay in cell cultures. Two of four disinfectants completely inactivated feline herpesvirus, and two significantly reduced the titer of this virus. None of the disinfectants that were tested completely inactivated feline calicivirus. Canine parvovirus was not inactivated significantly by any of the QAC disinfectants. Sodium hypochlorite completely inactivated all viruses.

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17

Hu, Mingming, Chong Chen, Hao Yuan, Xiaofang Zhao, ,Yahong Li, and Weizhen Wang. "Biofouling control method based on quaternary ammonium compounds." DESALINATION AND WATER TREATMENT 119 (2018): 118–24. http://dx.doi.org/10.5004/dwt.2018.22425.

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18

Sundheim, G., S. Langsrud, E. Heir, and A. L. Holck. "Bacterial resistance to disinfectants containing quaternary ammonium compounds." International Biodeterioration & Biodegradation 41, no. 3-4 (January 1998): 235–39. http://dx.doi.org/10.1016/s0964-8305(98)00027-4.

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19

LO, S. L., and S. F. SHIUE. "RECOVERY OF Cr(VI) BY QUATERNARY AMMONIUM COMPOUNDS." Water Research 32, no. 1 (January 1998): 174–78. http://dx.doi.org/10.1016/s0043-1354(97)00193-0.

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20

Druvari, Denisa, Nikos Koromilas, Vlasoula Bekiari, Georgios Bokias, and Joannis Kallitsis. "Polymeric Antimicrobial Coatings Based on Quaternary Ammonium Compounds." Coatings 8, no. 1 (December 23, 2017): 8. http://dx.doi.org/10.3390/coatings8010008.

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21

Gilbert, Elangeni A., Javier F. Guastavino, Rocío A. Nicollier, María Verónica Lancelle, Karen Russell-White, and Marcelo C. Murguía. "Synthesis and Properties of Cleavable Quaternary Ammonium Compounds." Journal of Oleo Science 70, no. 1 (2021): 59–65. http://dx.doi.org/10.5650/jos.ess20216.

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22

Ren, Rong, Dongfang Liu, Kexun Li, Jie Sun, and Chong Zhang. "Adsorption of Quaternary Ammonium Compounds onto Activated Sludge." Journal of Water Resource and Protection 03, no. 02 (2011): 105–13. http://dx.doi.org/10.4236/jwarp.2011.32012.

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23

Wang, Yang, Rui Chen, Ting Li, Piming Ma, Hongji Zhang, Mingliang Du, Mingqing Chen, and Weifu Dong. "Antimicrobial Waterborne Polyurethanes Based on Quaternary Ammonium Compounds." Industrial & Engineering Chemistry Research 59, no. 1 (December 12, 2019): 458–63. http://dx.doi.org/10.1021/acs.iecr.9b04828.

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24

Ismail, Zainab Z., Ulas Tezel, and Spyros G. Pavlostathis. "Sorption of quaternary ammonium compounds to municipal sludge." Water Research 44, no. 7 (April 2010): 2303–13. http://dx.doi.org/10.1016/j.watres.2009.12.029.

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25

Fisher, Dixie L., M. Arthur Moseley, James O. Mullis, Daniel L. Norwood, and Thomas A. Baillie. "Recognition of quaternary ammonium compounds using mass spectrometry." Rapid Communications in Mass Spectrometry 8, no. 1 (January 1994): 65–70. http://dx.doi.org/10.1002/rcm.1290080113.

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26

Zerdoum, A., M. Libera, M. Crismaru, J. A. Loontjens, H. van der Mei, and H. Busscher. "Morphological Effects of Quaternary Ammonium Compounds on Staphylococcal Biofilms." Microscopy and Microanalysis 18, S2 (July 2012): 22–23. http://dx.doi.org/10.1017/s1431927612001961.

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27

Larsen, Søren T., Henrik Verder, and Gunnar D. Nielsen. "Airway Effects of Inhaled Quaternary Ammonium Compounds in Mice." Basic & Clinical Pharmacology & Toxicology 110, no. 6 (January 18, 2012): 537–43. http://dx.doi.org/10.1111/j.1742-7843.2011.00851.x.

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28

Ioannou, Christopher J., Geoff W. Hanlon, and Stephen P. Denyer. "Action of Disinfectant Quaternary Ammonium Compounds against Staphylococcus aureus." Antimicrobial Agents and Chemotherapy 51, no. 1 (October 23, 2006): 296–306. http://dx.doi.org/10.1128/aac.00375-06.

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ABSTRACT Mode-of-action studies concluded that alkyldimethylbenzylammonium chloride (ADBAC) (a blend of C12, C14 and C16 alkyl homologues) and didecyldimethylammonium chloride (DDAC) are both membrane-active agents, possessing subtly different modes of action reflecting early cell interactions against Staphylococcus aureus. ADBAC and DDAC exhibited similar MIC behaviors from 0.4 ppm to 1.8 ppm over an inoculum range of 1 × 105 to 1 × 109 CFU/ml at 35°C. For ADBAC and DDAC, an increased rapidity of killing against S. aureus (final concentration, 2 × 109 CFU/ml) was observed at 35°C compared to 25°C. Concentration exponents (η) for killing were <2.5 for both agents, and temperature influenced the η value. Examination of leakage and kill data suggested that a single leakage marker was not indicative of cell death. ADBAC and DDAC possessed Langmuir (L4) and high-affinity (H3/4) uptake isotherms, respectively. ADBAC molecules formed a single monolayer of coverage of cells at the end of primary uptake, and DDAC formed a double monolayer. Rapid cell leakage occurred at bactericidal concentrations, with total depletion of the intracellular potassium and 260-nm-absorbing pools released in this strict order. Autolysis was observed for ADBAC and DDAC at concentrations of 9 μg/ml (0.0278 mM and 0.0276 mM, respectively) and above, together with the depletion of approximately 30% of the internal potassium pool. Autolysis contributed to ADBAC and DDAC lethality, although high biocide concentrations may have inhibited autolytic enzyme activity.

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29

Rhodes, D., and A. D. Hanson. "Quaternary Ammonium and Tertiary Sulfonium Compounds in Higher Plants." Annual Review of Plant Physiology and Plant Molecular Biology 44, no. 1 (June 1993): 357–84. http://dx.doi.org/10.1146/annurev.pp.44.060193.002041.

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30

Mereghetti, L., R. Quentin, N. Marquet-Van Der Mee, and A. Audurier. "Low Sensitivity of Listeria monocytogenes to Quaternary Ammonium Compounds." Applied and Environmental Microbiology 66, no. 11 (November 1, 2000): 5083–86. http://dx.doi.org/10.1128/aem.66.11.5083-5086.2000.

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ABSTRACT Ninety-seven epidemiologically unrelated strains of Listeria monocytogenes were investigated for their sensitivities to quaternary ammonium compounds (benzalkonium chloride and cetrimide). The MICs for seven serogroup 1/2 strains were high. Three came from the environment and four came from food; none were isolated from human or animal samples. All 97 strains carried the mdrL gene, which encodes a multidrug efflux pump, and the orfA gene, a putative transcriptional repressor of mdrL. The absence of plasmids in four of the seven resistant strains and the conservation of resistance after plasmid curing suggested that the resistance genes are not plasmid borne. Moreover, PCR amplification and Southern blot hybridization experiments failed to find genes phylogenetically related to the qacA and smr genes, encoding multidrug efflux systems previously described for the genusStaphylococcus. The high association between nontypeability by phages and the loss of sensitivity to quaternary ammonium compounds are suggestive of an intrinsic resistance due to modifications in the cell wall.

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Blaustein, Robert O. "Kinetics of Tethering Quaternary Ammonium Compounds to K+ Channels." Journal of General Physiology 120, no. 2 (July 30, 2002): 203–16. http://dx.doi.org/10.1085/jgp.20028613.

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Polymeric maleimido–quaternary ammonium (QA) compounds have been shown to function as molecular tape measures when covalently tethered to external cysteine residues of a Shaker K+ channel (Blaustein R.O., P.A. Cole, C. Williams, and C. Miller. 2000. Nat. Struct. Biol. 7:309–311). For sufficiently long compounds, the cysteine–maleimide tethering reaction creates a high concentration, at the channel's pore, of a TEA-like moiety that irreversibly blocks current. This paper investigates a striking feature of the maleimide–cysteine tethering kinetics. Strong blockers—those that induce substantial levels (>80%) of irreversible inhibition of current—react with channel cysteines much more rapidly than weak blockers and, when delivered to channels with four cysteine targets, react with multiexponential kinetics. This behavior is shown to arise from the ability of a strong blocker to concentrate its maleimide end near a channel's cysteine target by exploiting the reversible pore-blocking affinity of its QA headgroup.

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32

Hind, A. R., S. K. Bhargava, and P. G. Cullis. "Quantitation of quaternary ammonium compounds using electrospray mass spectrometry." Analytica Chimica Acta 377, no. 1 (December 1998): 39–45. http://dx.doi.org/10.1016/s0003-2670(98)00599-6.

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33

Hora, Priya I., and William A. Arnold. "Photochemical fate of quaternary ammonium compounds in river water." Environmental Science: Processes & Impacts 22, no. 6 (2020): 1368–81. http://dx.doi.org/10.1039/d0em00086h.

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34

Klimonda, Aleksandra, and Izabela Kowalska. "Removal of quaternary ammonium compounds in ion exchange process." E3S Web of Conferences 116 (2019): 00034. http://dx.doi.org/10.1051/e3sconf/201911600034.

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The study attempted to evaluate the effectiveness of ion exchange process in cationic surfactant (benzalkonium chloride, BAC) removal from model solutions. Four commercial cation-exchange resins were chosen for the batch tests in four doses (2.5–20 mL L-1). The experiments included evaluation of the following parameters on ion exchange efficiency: resin characteristics and dose, presence of inorganic salt and pH of treated solution. The ion exchange process was found to be very effective in cationic surfactant removal – two of tested resins allowed to remove up to 80% of contaminant after contact time of 40 minutes, the last two – after 60 minutes of mixing in all range of doses. The presence of electrolyte neither pH change has no essential effect on surfactant removal efficiency. The analysis of the ion exchange isotherms showed that the strongly-acidic macroporous resin C150 H was characterized by the highest BAC ion exchange capacity (153.8 mg mL-1), while the weakly-acidic gel resin C104 showed the best affinity of the exchanged ions to the resin matrix.

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35

Ventullo, Roy M., and Robert J. Larson. "Adaptation of Aquatic Microbial Communities to Quaternary Ammonium Compounds." Applied and Environmental Microbiology 51, no. 2 (1986): 356–61. http://dx.doi.org/10.1128/aem.51.2.356-361.1986.

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36

Sidhu, Maan Singh, Henning Sørum, and Askild Holck. "Resistance to Quaternary Ammonium Compounds in Food-Related Bacteria." Microbial Drug Resistance 8, no. 4 (December 2002): 393–99. http://dx.doi.org/10.1089/10766290260469679.

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37

Barney, Rocky, Joseph Carroll, and Dru Delaet. "Surfactant studies of quaternary ammonium compounds: Critical surfactant concentration." Journal of Surfactants and Detergents 9, no. 2 (June 2006): 137–40. http://dx.doi.org/10.1007/s11743-006-0382-y.

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38

Yang, Yuan, Ke Li, Yun-Xia Yang, and Qi Li. "Crystalline Inclusion Compounds: Thiourea and Bis-quaternary Ammonium Salts." Journal of Chemical Crystallography 45, no. 3 (March 2015): 120–27. http://dx.doi.org/10.1007/s10870-015-0571-5.

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39

Piecuch, Agata, Ewa Obłąk, and Katarzyna Guz-Regner. "Antibacterial Activity of Alanine-Derived Gemini Quaternary Ammonium Compounds." Journal of Surfactants and Detergents 19, no. 2 (December 30, 2015): 275–82. http://dx.doi.org/10.1007/s11743-015-1778-3.

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Cumming, Janet, Darryl William Hawker, Heather Chapman, and Kerry Nugent. "Sorption of Polymeric Quaternary Ammonium Compounds to Humic Acid." Water, Air, & Soil Pollution 214, no. 1-4 (April 21, 2010): 5–11. http://dx.doi.org/10.1007/s11270-010-0435-8.

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Al-Ahmad, A., M. Wiedmann-Al-Ahmad, G. Schön, F. D. Daschner, and K. Kümmerer. "Role of Acinetobacter for Biodegradability of Quaternary Ammonium Compounds." Bulletin of Environmental Contamination and Toxicology 64, no. 6 (June 2000): 764–70. http://dx.doi.org/10.1007/s001280000069.

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Van de Voorde, Antoine, Catherine Lorgeoux, Marie-Christine Gromaire, and Ghassan Chebbo. "Analysis of quaternary ammonium compounds in urban stormwater samples." Environmental Pollution 164 (May 2012): 150–57. http://dx.doi.org/10.1016/j.envpol.2012.01.037.

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43

Stefańska, Justyna, Anna Pietruczuk-Padzik, Marta Struga, Maciej Borkowski, and Stefan Tyski. "Biological Evaluation of Quaternary bis Ammonium Salt and Cetylpyridinum Bromide Against S. epidermidis biofilm." Polish Journal of Microbiology 62, no. 4 (2013): 359–64. http://dx.doi.org/10.33073/pjm-2013-049.

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Abstract:

Quaternary ammonium compounds are broad-spectrum bacteriocides widely used as antiseptics, disinfection and preservation agents. The aim of this study was to examine the activity of two quaternary ammonium salts, cetylpyridinum bromide and a newly synthesized quaternary bis ammonium salt, against S. epidermidis biofilm. The average values of killing efficiency for cetylpyridinum bromide ranged from 26.6% to 64.1% for all tested concentrations (0.125 to 8.0 microg x mL(-1)) and for quaternary bis ammonium salt the percentage of killing efficiency ranged from 59.7% to 88.4% for tested concentrations (from 2.0 to 128.0 microg x mL(-1)). Both tested compounds significantly affect staphylococcal biofilms, but any of used concentrations caused a total eradication of bacterial biofilm.

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Dimitrov, A., W. Radeck, St Rüdiger, and O. Bechstein. "On the electrochemical fluorination of quaternary ammonium compounds. Part 1. Tetraalkyl ammonium salts." Journal of Fluorine Chemistry 60, no. 1 (January 1993): 57–60. http://dx.doi.org/10.1016/s0022-1139(00)82195-8.

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Wang, Hongning, Wenjin Liu, Wei Yao, Ke Zhang, Jing Zhong, and Ruoyu Chen. "Quaternary ammonium salts intercalated α-ZrP compounds for adsorption of phenolic compounds." Applied Surface Science 268 (March 2013): 179–87. http://dx.doi.org/10.1016/j.apsusc.2012.12.054.

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ZHU, Yun-Peng, Keita ISHIHARA, Araki MASUYAMA, Yohji NAKATSUJI, and Mitsuo OKAHARA. "Preparation and Properties of Double-chain Bis (quaternary ammonium) Compounds." Journal of Japan Oil Chemists' Society 42, no. 3 (1993): 161–67. http://dx.doi.org/10.5650/jos1956.42.161.

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Okeke, Ugochukwu C., Chad R. Snyder, and Stanislav A. Frukhtbeyn. "Synthesis, Purification and Characterization of Polymerizable Multifunctional Quaternary Ammonium Compounds." Molecules 24, no. 8 (April 13, 2019): 1464. http://dx.doi.org/10.3390/molecules24081464.

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Methacrylate analogs of quaternary ammonium salts functionalized with carboxylic (AMadh1 68.8% yield, AMadh2 53.2% yield) and methoxysilane (AMsil1 94.8% yield, AMsil2 36.0% yield) groups were synthesized via Menschutkin reaction. Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (1H, 13C and 2D 1H-13C heteronuclear single quantum coherence (HSQC) NMR), mass spectrometry, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) were utilized to validate structures and characterize thermal properties of the novel multifunctional quaternary ammonium salts synthesized. The potential adhesive, coupling and antimicrobial properties of these multifunctional monomers encourage their further comprehensive evaluation in conventional and experimental copolymers and composites.

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Yagci, M. B., S. Bolca, J. P. A. Heuts, W. Ming, and G. de With. "Antimicrobial polyurethane coatings based on ionic liquid quaternary ammonium compounds." Progress in Organic Coatings 72, no. 3 (November 2011): 343–47. http://dx.doi.org/10.1016/j.porgcoat.2011.05.006.

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LARSEN, S. "Adjuvant effect of quaternary ammonium compounds in a murine model." Toxicology Letters 151, no. 2 (July 2004): 389–98. http://dx.doi.org/10.1016/j.toxlet.2004.03.008.

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Novoselova, N. V., A. A. Bobyleva, E. V. Lukovskaya, E. A. Sumtsova, V. N. Matveenko, A. V. Anisimov, and V. I. Terenin. "Synthesis and colloid-chemical properties of new quaternary ammonium compounds." Theoretical Foundations of Chemical Engineering 41, no. 5 (October 2007): 649–59. http://dx.doi.org/10.1134/s004057950705034x.

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