Quaternary ammonium compounds, referred to as QACs, are cationic substances with a structure on the edge of organic and inorganic chemistry and unique physicochemical properties. The purpose of the present work is to introduce QACs and their wide application potential. Fundamental properties, methods of preparation, and utilization in organic synthesis are reviewed. Modern applications and the use of QACs as reactive substrates, reagents, phase-transfer catalysts, ionic liquids, electrolytes, frameworks, surfactants, herbicides, and antimicrobials are further covered. A brief discussion of the health and environmental impact of QACs is also provided. The emphasis is largely on tetraalkylammonium compounds bearing linear alkyl chains.
- MeSH
- Anti-Infective Agents chemical synthesis chemistry pharmacology MeSH
- Herbicides chemical synthesis chemistry pharmacology MeSH
- Quaternary Ammonium Compounds chemical synthesis chemistry pharmacology MeSH
- Surface-Active Agents chemical synthesis chemistry pharmacology MeSH
- Publication type
- Journal Article MeSH
- Review MeSH
Štúdia hodnotila rýchlosť a kinetiku enzýmovej hydrolýzy N-(2-benzoyloxyetyl)-alkyldimetylamó- niumbromidov – potenciálnych ľahko biodegradovateľných dezinficiencií „soft“ charakteru. Produk- tmi enzýmovej hydrolýzy sledovaných substrátov katalyzovanej mikrozómovou esterázou boli substituovaný cholín a kyselina benzoová, ktorá ako hydrolytický produkt bola stanovovaná metó- dou HPLC. Sledoval sa vplyv dĺžky alkylového reťazca jednotlivých homológov na rýchlosť enzýmo- vej hydrolýzy a na ich afinitu k mikrozómovej esteráze pečene a pľúc potkana in vitro. Zistilo sa, že štruktúrna modifikácia (rôzna dĺžka alifatického reťazca na amóniovom dusíku týchto zlúčenín) významne ovplyvňuje kinetiku enzýmovej hydrolýzy esterovej väzby. Z hľadiska rýchlosti enzýmo- vej hydrolýzy nebola zaznamenaná významná medziorgánová variabilita: V pečeni aj v pľúcach má závislosť rýchlosti enzýmovej hydrolýzy od dĺžky alifatického reťazca tvar klesajúcej hyperboly s maximami pre BCH2>BCH4>BCH8 = BCH10. Špecifická aktivita oboch esteráz sa pohybuje v rozsahu 0,2–3,5 nmol.min -1 .mg -1. Z hľadiska afinity sa výrazný medziorgánový rozdiel prejavil 10-násobne vyššou afinitou substrátov k pľúcnej mikrozómovej esteráze ako k pečeňovej. Vplyv dĺžky alkylu jednotlivých homológov na afinitu má aj v tomto prípade nelineárny charakter. V oboch orgánoch bola zistená určitá korelácia medzi rýchlosťou enzýmovej hydrolýzy a afinitou k mikrozó- movým esterázam.
The study evaluated the rate and kinetics of enzymatic hydrolysis of N-(2-benzoyloxyethyl)-alkyl- dimethylammonium bromides, potential easily biodegradable disinfectants of soft character. The products of enzymatic hydrolysis of the substrates under study, catalysed by microsomal esterase, included substituted substrates choline and benzoic acid which, as a hydrolytic product, was essayed by HPLC. The effect of the length of the alkyl chain of the individual homologues on the rate of enzymatic hydrolysis and their affinity to microsomal esterase of the rat liver and lung in vitro was examined. The structural modification (varying length of the aliphatic chain on the ammonium nitrogen of these compounds) was found to significantly influence the kinetics of enzymatic hydrolysis of the esteric bond. From the viewpoint of the rate of enzymatic hydrolysis no significant inter-organ variability was observed: in the liver as well as the lung the dependence of the rate of enzymatic hydrolysis on the length of the aliphatic chain possesses the shape of a falling hyperbole with the maxima for BCH2>BCH4>BCH8 = BCH10. The specific activity of both esterases ranges within 0.2–3.5 nmol.min -1 .mg -1. From the viewpoint of affinity, a marked inter-organ difference was manifested by 10 times higher affinity of the substrates to the lung microsomal esterase in comparison with the liver one. The effect of the length of the alkyl of the individual homologues on the affinity is of a non-linear character also in this case. In both organs, a certain correlation was found between the rate of enzymatic hydrolysis and affinity to microsomal esterases.
- MeSH
- Esterases analysis physiology MeSH
- Hydrolysis MeSH
- Microsomes, Liver enzymology MeSH
- Rats MeSH
- Quaternary Ammonium Compounds metabolism MeSH
- Lung enzymology MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Animals MeSH
- Publication type
- Comparative Study MeSH
Quaternary ammonium salts (QUATs) are compounds with wide use in organic synthesis, pharmacy or other fields of industry. Thanks to their specific physical and chemical properties resulting from their amphiphilic character they are already used as phase-transfer catalysts, ionic liquids, dyes, antimicrobial agents and disinfectants, antiarrhythmics, bronchodilators etc. There is still an effort to prepare new active compounds. Several organosynthetic methods are used to prepare QUATs: probably the best way is the Menshutkin reaction. Recently, also a microwave synthesis was introduced to prepare QUATs bringing better yields, shorter reaction times and a possibility of solvent-free reactions.
Organické amóniové soli typu N-(2-benzyloxyetyl)-alkyldimetylamónium bromidov (BCHn-1) sútvorené homologickým radom Ar-COO(CH2)2-N+(CH3)2CnH2n+1·Br-, ktorý vo svojej štruktúre obsahujebiodegradačne labilnú esterovú väzbu, na základe ktorej patria medzi dezinficienciá a antiseptikásoft charakteru. Biotransformujú sa prednostne hydrolyticky na kyselinu benzoovúa substituovaný cholín. Rýchlosť enzýmovej hydrolýzy je závislá od chemickej štruktúry (dĺžkyalifatického reťazca na amóniovom dusíku), stúpa do počtu uhlíkov 10 alifatického reťazca a ďalšímpredĺžovaním rapídne klesá. Cieľom práce bol dôkaz katalytickej aktivity butyrylcholínesterázy naenzýmovej hydrolýze vybraných organických amóniových solí v prostredí mikrozómovej frakciepečene potkana, na základe inhibičných kinetických štúdií s fyzostigmínom – inhibítorom cholínesteráz.Produkt enzýmovej hydrolýzy BCHn-1, kyselina benzoová sa stanovila po extrakcii chloroformomz kyslého prostredia HPLC analýzou za použitia interného štandardu p-jódbenzoovej kyselinypri vlnovej dĺžke 228 nm. Kinetické parametre KM a VMAX sa vyhodnotili podľa Lineweavera-Burkametódou lineárnej regresnej analýzy. Špecifická aktivita butyrylcholínesterázy (E.C.3.1.1.8) v enzýmovomhydrolytickomproceseBCHn-1 bola významne ovplyvnená prítomnosťou fyzostigmínu, čo saprejavilo vzostupom KM, KI a IC50 hodnôt v študovanom enzýmovom procese vybraných substrátovhomologického radu BCHn-1 a poklesom Vmax a rýchlostných konštánt.
Organicammoniumsalts of N-(2-benzoyloxyethyl)-alkyldimethylammonium bromide (BCHn-1) typeare formed by the homological seriesAr-COO(CH2)2-N+(CH3)2CnH2a+1·Br-,whose structure containsa biodegradably labile ester bond, on the basis of which they rank among disinfectants andantiseptics of soft character. They are preferentially biotransformed hydrolytically to producebenzoic acid and substituted choline. The rapidity of enzymatic hydrolysis depends on the chemicalstructure (the length of the aliphatic chain on theammoniumnitrogen), it increases up to thenumberof 10 nitrogens of the aliphatic chain, and it rapidly decreases with further prolongation. The paperaimed to demonstrate the catalytic activity of butyrylcholinesterase on the enzymatic hydrolysis ofselected organic ammonium salts in the medium of the microsomal fraction of the rat liver on thebasis of inhibitory kinetic studies with physostigmine, a cholinesterase inhibitor. The product ofenzymatic hydrolysis of BCHn-1, benzoic acid,was determined after extraction with chloroform fromthe acid medium by means of HPLC analysis with the use of the internal standard p-iodobenzoicacid at the wavelength of 228 nm. Kinetic parameters KM and VMAX were evaluated followingLineweaver-Burke using the method of linear regression analysis. The specific activity of butyrylcholinesterase(E.C.3.1.1.8) in the enzymatic hydrolytic process of BCHn-1 was significantly influencedby the presence of physostigmine, which was manifested by increased KM, KI, and IC50 valuesin the investigated enzymatic process of selected substrates of the homological series BCHn-1, andby decreased VMAX and rate constants.
- MeSH
- Biodegradation, Environmental MeSH
- Butyrylcholinesterase pharmacokinetics MeSH
- Disinfectants chemistry metabolism MeSH
- Research Support as Topic MeSH
- Physostigmine MeSH
- Hydrolysis physiology MeSH
- Rats MeSH
- Quaternary Ammonium Compounds chemistry metabolism MeSH
- Benzoic Acid MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Animals MeSH
- Publication type
- Review MeSH
- Comparative Study MeSH
Since the discovery of antimicrobial agents, the misuse of antibiotics has led to the emergence of bacterial strains resistant to both antibiotics and common disinfectants like quaternary ammonium compounds (QACs). A new class, 'gemini' QACs, which contain two polar heads, has shown promise. Octenidine (OCT), a representative of this group, is effective against resistant microorganisms but has limitations such as low solubility and high cytotoxicity. In this study, we developed 16 novel OCT derivatives. These compounds were subjected to in silico screening to predict their membrane permeation. Testing against nosocomial bacterial strains (G+ and G-) and their biofilms revealed that most compounds were highly effective against G+ bacteria, while compounds 7, 8, and 10-12 were effective against G- bacteria. Notably, compounds 6-8 were significantly more effective than OCT and BAC standards across the bacterial panel. Compound 12 stood out due to its low cytotoxicity and broad-spectrum antimicrobial activity, comparable to OCT. It also demonstrated impressive antifungal activity. Compound 1 was highly selective to fungi and four times more effective than OCT without its cytotoxicity. Several compounds, including 4, 6, 8, 9, 10, and 12, showed strong virucidal activity against murine cytomegalovirus and herpes simplex virus 1. In conclusion, these gemini QACs, especially compound 12, offer a promising alternative to current disinfectants, addressing emerging resistances with their enhanced antimicrobial, antifungal, and virucidal properties.
- MeSH
- Anti-Bacterial Agents * pharmacology chemical synthesis chemistry MeSH
- Antifungal Agents pharmacology chemical synthesis chemistry MeSH
- Antiviral Agents pharmacology chemical synthesis chemistry MeSH
- Bacteria drug effects MeSH
- Biofilms drug effects MeSH
- Fungi drug effects MeSH
- Imines MeSH
- Quaternary Ammonium Compounds * pharmacology chemical synthesis chemistry MeSH
- Humans MeSH
- Microbial Sensitivity Tests * MeSH
- Molecular Structure MeSH
- Mice MeSH
- Pyridinium Compounds pharmacology chemical synthesis chemistry MeSH
- Pyridines pharmacology chemistry chemical synthesis MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
