Juliusz Pernak

Publications (21)71.13 Total impact

• Article: Cytotoxicity, acute and subchronic toxicity of ionic liquid, didecyldimethylammonium saccharinate, in rats.

  Jadwiga Jodynis-Liebert, Michal Nowicki, Marek Murias, Teresa Adamska, Małgorzata Ewertowska, Małgorzata Kujawska, Hanna Piotrowska, Aneta Konwerska, Danuta Ostalska-Nowicka, Juliusz Pernak
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  ABSTRACT: The aim of this study was to investigate cytotoxicity, acute and subchronic oral toxicity of an ionic liquid didecyldimethylammonium saccharinate [DDA][Sac] in rat. IC(50) values tested on six human cell lines varied from 1.44 microM to 5.47 microM. The compound tested was classified to the 4th toxicity class with a fixed LD(50) cut-off value 500 mg/kg. Organ pathology induced by [DDA][Sac] in an acute experiment included exfoliation of the surface layer of the colon and alveolar septa in lung parenchyma. In a subchronic experiment rats were administered 10, 30 and 100 mg/kg/day [DDA][Sac] for 28 days. Reduced body weight gain and slightly reduced food consumption was observed particularly in high-dose rats. Slight hematology changes were found only in mid-dose females. Statistically significant changes in clinical chemistry parameters included: increases in the ALT, SDH, ALP and GGT activities, and in glucose, blood urea nitrogen and creatinine concentrations. However, these changes did not occur in both sexes and were not dose-related with the exception of ALP in females. No treatment-related microscopic changes were observed in a subchronic experiment. Under the condition of this study the lowest-observed-adverse-effect level of [DDA][Sac] was considered to be 10 mg/kg/day.
  Regulatory Toxicology and Pharmacology 03/2010; 57(2-3):266-73. · 2.43 Impact Factor
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  Available from: Whitney Hough

  Article: Ionic liquids with dual biological function: sweet and anti-microbial, hydrophobic quaternary ammonium-based salts

  Whitney L Hough-Troutman, Marcin Smiglak, Scott Griffin, W Matthew Reichert, Ilona Mirska, Jadwiga Jodynis-Liebert, Teresa Adamska, Jan Nawrot, Monika Stasiewicz, Robin D Rogers, Juliusz Pernak
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  ABSTRACT: The dual nature of ionic liquids has been exploited to synthesize materials that contain two independent biological functions by combining anti-bacterial quaternary ammonium compounds with artificial sweetener anions. The synthesis and physical properties of eight new ionic liquids, didecyldimethylammonium saccharinate ([DDA][Sac]), didecyldimethylammonium acesulfamate ([DDA][Ace]), benzalkonium saccharinate ([BA][Sac]), benzalkonium acesulfamate ([BA][Ace]), hexadecylpyridinium saccharinate ([HEX][Sac]), hexadecylpyridinium acesulfamate ([HEX][Ace]), 3-hydroxy-1-octyloxymethylpyridinium saccharinate ([1-(OctOMe)-3-OH-Py][Sac]), and 3-hydroxy-1-octyloxymethylpyridinium acesulfamate ([1-(OctOMe)-3-OH-Py][Ace]), are reported, as well as the single crystal structures for [HEX][Ace] and [1-(OctOMe)-3-OH-Py][Sac]. Determination of anti-microbial activities is described for six of the ILs. While some exhibited decreased anti-microbial activity others showed a dramatic increase. For two of the ionic liquids, [DDA][Sac] and [DDA][ACE], oral toxicity, skin irritation, and deterrent activity was also established. Unfortunately, both ILs received a Category 4 (harmful) rating for oral toxicity and skin irritation. However, deterrent activity experiments point to use as an insect deterrent, as both ILs scored either ''very good'' or ''good'' against several types of insects.
  New Journal of Chemistry 01/2009; · 2.61 Impact Factor
• Article: Acute and subacute (28-day) toxicity studies of ionic liquid, didecyldimethyl ammonium acesulfamate, in rats.

  Jadwiga Jodynis-Liebert, Michał Nowicki, Teresa Adamska, Małgorzata Ewertowska, Małgorzata Kujawska, Ewelina Petzke, Aneta Konwerska, Danuta Ostalska-Nowicka, Juliusz Pernak
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  ABSTRACT: The aim of this study was to investigate acute and subacute oral toxicity of an ionic liquid, didecyldimethylammonium acesulfamate [DDA][Ace], in rats. The compound tested was classified to the fourth toxicity class with a fixed LD(50) cut-off value of 500 mg/kg. Organ pathology induced by [DDA][Ace] in acute experiments included exfoliation of the surface layer of the digestive tract and alveolar septa in lung parenchyma. In a subacute experiment, rats were administered 10, 50, and 100 mg/kg/day [DDA][Ace] for 28 days. Reduced body weight gain and reduced food consumption was observed in mid- and high-dose rats. Statistically significant hematology changes were found mostly in high-dose groups of both sexes: increases in hematocrit, mean corpuscular volume, and mean platelet volume. Statistically significant changes in clinical chemistry parameters included increases in the GGT, SDH, and LDH activity and bilirubin concentration, and decreases in triglycerides, glucose, and inorganic phosphorus concentration. No treatment-related microscopic changes were observed. Under the conditions of this study, the lowest-observed-adverse-effect level of [DDA][Ace] was considered to be 10 mg/kg/day.
  Drug and Chemical Toxicology 01/2009; 32(4):395-404. · 1.08 Impact Factor
• Article: Long-alkyl-chain quaternary ammonium lactate based ionic liquids.

  Jacek Cybulski, Anna Wiśniewska, Anna Kulig-Adamiak, Lidia Lewicka, Anna Cieniecka-Rosłonkiewicz, Kazimierz Kita, Andrzej Fojutowski, Jan Nawrot, Katarzyna Materna, Juliusz Pernak
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  ABSTRACT: A new group of quaternary ammonium lactate based ionic liquids have been prepared and characterized. Didecyldimethylammonium (DDA) and benzalkonium (BA) D,L- and L-lactates are air-stable, hydrophilic, surface-active salts. They are very effective antibacterial and antifungal agents, especially the DDA lactates, against Streptococcus mutants and Candida albicans. Their activities are comparable or more effective than the original benzalkonium chloride. In addition, they have been shown to be good insect-feeding deterrents. However, they are poor antifungal agents for wood preservation. The toxicity of the DDA and BA lactates has also been studied and the results are presented in this paper.
  Chemistry 09/2008; 14(30):9305-11. · 5.93 Impact Factor
• Article: Ionic liquids for the production of insecticidal and microbicidal extracts of the fungus Cantharellus cibarius.

  Anna Cieniecka-Rosłonkiewicz, Agnieszka Sas, Elzbieta Przybysz, Bolesław Morytz, Anna Syguda, Juliusz Pernak
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  ABSTRACT: Different ionic liquids were used as solvents for the effective extraction of the active metabolites of the fruit bodies of C. cibarius. The type of ionic liquid was found to play a significant role in this process. We found that the protic ionic liquid 1-[(nonyloxy)methyl]-1H-imidazol-3-ium salicylate (6) is a most-efficient extracting agent, being superior to classical solvents such as AcOEt or hexane. The obtained extracts generally revealed high insecticidal activities against both house fly and cockroach, with similar potencies as the standard pesticides bromfenvinphos or alphacypermethrin, as well as significant activities against bacteria, yeast, and moulds. Notably, the cidal activities against plant-pathogenic bacteria were stronger than against human bacterial strains.
  Chemistry & Biodiversity 10/2007; 4(9):2218-24. · 1.80 Impact Factor
• Article: Synthesis and properties of trigeminal tricationic ionic liquids.

  Juliusz Pernak, Andrzej Skrzypczak, Grzegorz Lota, Elzbieta Frackowiak
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  ABSTRACT: Novel trigeminal tricationic ionic liquids (TTILs) have been successfully synthesized in high yields by means of Menschutkin quaternization via an S(N)1 mechanism. This reaction presents a new convenient method for transforming glycerol into multifunctional compounds. The physical properties of a series of TTILs were characterized by using a variety of techniques. The prepared salts were tested for antimicrobial activity. Electrochemical characterization of TTILs was also performed, which allowed the estimation of the conductivity of these new compounds, to establish their electrochemical stability window and capacitance properties over a wide range of temperatures. A good correlation of the physical properties of TTILs with capacitance values was observed.
  Chemistry 02/2007; 13(11):3106-12. · 5.93 Impact Factor
• Article: Choline-derivative-based ionic liquids.

  Juliusz Pernak, Anna Syguda, Ilona Mirska, Anna Pernak, Jan Nawrot, Aleksandra Pradzyńska, Scott T Griffin, Robin D Rogers
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  ABSTRACT: A total of sixty-three choline derivative-based ionic liquids in the forms of chlorides, acesulfamates, and bis(trifluoromethylsulfonyl)imides have been prepared and their physical properties (density, viscosity, solubility, and thermal stability) have been determined. Thirteen of these salts are known chlorides: precursors to the 26 water-soluble acesulfamates, 12 acesulfamates only partially miscible with water, and 12 water-insoluble imides. The crystal structures for two of the chloride salts-(2-hydroxyethyl)dimethylundecyloxymethylammonium chloride and cyclododecyloxymethyl(2-hydroxyethyl)dimethylammonium chloride-were determined. The antimicrobial (cocci, rods, and fungi) activities of the new hydrophilic acesulfamate-based ILs were measured and 12 were found to be active. The alkoxymethyl(2-hydroxyethyl)dimethylammonium acesulfamates have been shown to be insect feeding deterrents and thus open up a new generation of synthetic deterrents based on ionic liquids. The alkoxymethyl(2-decanoyloxyethyl)dimethylammonium bis(trifluoromethylsulfonyl)imides have also been shown to act as fixatives for soft tissues and can furthermore be used as substitutes for formalin and also preservatives for blood.
  Chemistry 02/2007; 13(24):6817-27. · 5.93 Impact Factor
• Article: Wirkung neuer Iminiumverbindungen gegen ausgewählte Bakterien‐ und Pilzstämme, 9. Mitt. Synthese von 1,2‐Dimethyl‐ und 1‐Butyl‐3‐(n‐alkylthiomethyl)imidazoliumchloriden

  Juliusz Pernak, Andrzej Skrzypczak, Slawoj Kucharski, Jerzy Krysinski
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  ABSTRACT: Die Imidazolium-Verbindungen 1 und 2 wurden durch Reaktion von Chlormethyl-n-alkylsulfid mit 1,2-Dimethyl- und 1-Butylimidazol synthetisiert. Die biologische Aktivität der gewonnenen Verbindungen wurde gegenüber 13-Bakterien- und Pilzstämmen untersucht. Die höchste Wirksamkeit besitzen die Verbindungen mit Dodecyl- und Octylrest.Activities of New Iminium Compounds on Selected Strains of Bacteria and Fungi, IX: Synthesis of 1,2-Dimethyl- and 1-Butyl-3-(n-alkylthiomethyl)imidazolium ChloridesSyntheses of the imidazolium compounds 1 and 2 were performed by reaction of chloromethyl n-alkyl sulfide with 1,2-dimethyl- and 1-butylimidazole. Antimicrobial activities of the products were tested against 13 strains of bacteria and fungi. Compounds with a dodecyl or octyl chain showed the best antibacterial properties.
  Archiv der Pharmazie 09/2006; 317(5):430 - 434. · 1.71 Impact Factor
• Article: Wirkung neuer Iminiumverbindungen gegen ausgewählte Bakterien‐ und Pilzstämme, 24. Mitt.: Synthese von 1‐n‐Octyl‐2‐phenyl‐3‐(n‐alkylthiomethyl)‐ und 1‐n‐Octyl‐2‐phenyl‐3‐(n‐alkoxymethyl)imidazoliumchloriden Activities of New Iminium Compounds on Selected Strains of Bacteria and Fungi, XXIV: Synthesis of 1‐n‐Octyl‐2‐phenyl‐3‐(n‐alkylthiomethyl)‐ and 1‐n‐Octyl‐2‐phenyl‐3‐(n‐alkoxymethyl)imidazolium Chlorides

  Juliusz Pernak, Jerzy Krysinski, Andrzej Skrzypczak, Lucyna Michalak
  Archiv der Pharmazie 09/2006; 323(5):307 - 310. · 1.71 Impact Factor
• Source

  Available from: Whitney Hough

  Article: Long alkyl chain quaternary ammonium-based ionic liquids and potential applications

  Juliusz Pernak, Marcin Smiglak, Scott T Griffin, Whitney L Hough, Timothy B Wilson, Anna Pernak, Jadwiga Zabielska-Matejuk, Andrzej Fojutowski, Kazimierz Kita, Robin D Rogers
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  ABSTRACT: Due to the high interest in the applications of ionic liquids, new, cheaper, multifunctional ionic liquids which are easy to prepare are highly desired. Here, we present a new group of air-and moisture-stable, hydrophobic ammonium-based ionic liquids and their properties, including the single-crystal X-ray structure of benzethonium nitrate. These salts have utility as anti-bacterial, anti-fungal agents. Additionally, the potential application of these ionic liquids for wood preservation was tested with positive results. The toxicity of benzalkonium and didecyldimethylammonium nitrates were studied and are presented herein.
  Green Chemistry 01/2006; · 6.32 Impact Factor
• Article: Synthesis and properties of chiral ammonium-based ionic liquids.

  Juliusz Pernak, Joanna Feder-Kubis
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  ABSTRACT: New chiral ammonium-based ionic liquids containing the (1R,2S,5R)-(-)-menthyl group can be easily and efficiently prepared under ambient conditions. The preparation and characterization of trialkyl[(1R,2S,5R)-(-)-menthoxymethyl]ammonium salts is reported. The salts have been demonstrated to be air- and moisture-stable under ambient conditions and can be readily used in a variety of standard experimental procedures. The single-crystal X-ray structure of butyldimethyl[(1R,2S,5R)-(-)-menthoxymethyl]ammonium chloride has been determined. The chiral, room-temperature ionic liquids have been characterized by physical properties such as specific rotation, density, viscosity, thermal degradation, and glass transition temperature. Trialkyl[(1R,2S,5R)-(-)-menthoxymethyl]ammonium chloride prototype ionic liquids have also been found to exhibit strong antimicrobial and high antielectrostatic activities.
  Chemistry 08/2005; 11(15):4441-9. · 5.93 Impact Factor
• Article: Synthesis and properties of new cationic surfactants: 1-Alkylthiomethyl-3-carbamoylpyridinium chlorides

  Juliusz Pernak, Małgorzata Zygadło, Anna Cieniecka-Rosłonkiewicz
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  ABSTRACT: 1-Alkylthiomethyl-3-carbamoylpyridinium and 1-alkylthiomethyl-4-carbamoylpyridinium chlorides were prepared by the reaction of nicotinamide or isonicotinamide with chloromethyl alkyl sulfides. The obtained chlorides were examined for their antimicrobial activities. 4-Carbamoyl-1-dodecylthiomethylpyridinium chloride exhibited strong antimicrobial activity, similar to the activity of benzalkonium chloride. All synthesized chlorides underwent hydrolysis in aqueous solutions at temperatures higher than 70–75°C. In aqueous solution 1-alkylthiomethyl-3-carbamoylpyridinium chlorides reacted with ozone. A new generation of cationic surfactants that were hydrolyzed and ozone-reactive in an aqueous solution was synthesized during this study.
  Journal of Surfactants and Detergents 06/2005; 8(3):233-239. · 1.54 Impact Factor
• Article: Room-temperature phosphonium ionic liquids for supercapacitor application

  Elzbieta Frackowiak, Grzegorz Lota, Juliusz Pernak
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  ABSTRACT: Ionic liquids (ILs) have been used as electrolytes for supercapacitors. Two phosphonium salts such as trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (IL1) and trihexyl(tetradecyl) phosphonium dicyanamide (IL2) have been selected for this target. To decrease the viscosity of ILs, a small amount of acetonitrile (from 5 to 25 wt %) was added. Supercapacitor based on activated carbon (AC) as electrodes and IL1 with 25 wt % of acetonitrile supplied capacitance values of 100 F / g at a high operating voltage of 3.4 V. Such a supercapacitor reached a high energy of ∼40 Wh / kg and a good cyclability.
  Applied Physics Letters 05/2005; · 3.84 Impact Factor
• Article: Phosphonium Acesulfamate Based Ionic Liquids

  Juliusz Pernak, Filip Stefaniak, Józef Węglewski
  Annalen der Chemie und Pharmacie 02/2005; 2005(4):650 - 652. · 3.10 Impact Factor
• Article: Ionic liquids as an alternative to formalin in histopathological diagnosis.

  Agnieszka Pernak, Katarzyna Iwanik, Przemysław Majewski, Marian Grzymisławski, Juliusz Pernak
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  ABSTRACT: Asymmetry of cations and the type of anions play a key role in the properties of ionic liquids (ILs) as fixatives for tissue preservation. 1-Methyl-3-octyloxymethylimidazolium tetrafluoroborate has proven to be a very good fixative, with similar effects as formalin. Our study shows that it is applicable for both histological and immunohistochemical purposes. After treatment with 1-methyl-3-octyloxymethylimidazolium tetrafluoroborate, tissue sections are more intensely stained. With respect to expression patterns and staining intensity, immunohistochemical staining is comparable in tissues fixed in formalin and the selected ILs. The present study demonstrates the properties of 1-methyl-3-octyloxymethylimidazolium tetrafluoroborate for tissue preservation in histopathological procedures, eliminating the requirement of formalin.
  Acta Histochemica 02/2005; 107(2):149-56. · 1.83 Impact Factor
• Article: Preparation and characterization of functionalized precipitated silica SYLOID® 244 using ionic liquids as modifiers

  Teofil Jesionowski, Monika Pokora, Kinga Sobaszkiewicz, Juliusz Pernak
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  ABSTRACT: Studies were performed on the chemical modification of SYLOID® 244 (Grace) precipitated silica using ionic liquids. The unmodified and ionic-liquid-functionalized silica were subjected to a comprehensive physicochemical and dispersive evaluation. Particle size, polydispersity and specific surface area (BET) and porous structure were examined. Moreover, stability of the colloids obtained was evaluated by estimation of isoelectric points. The extent of modification and its type were defined using fourier transform infrared spectroscopy and 29Si-cross-polarization/magic angle spinning/nuclear magnetic resonance techniques.The modification was not observed to deteriorate the dispersive properties of the silica. The silicas obtained exhibited a restricted tendency to form larger accumulations of particles, i.e. aggregates and agglomerates. Moreover, application of ionic liquids with a heptyloxymethyl or octyloxymethyl substituent resulted in complete hydrophobization of the silica surface. Tested powders manifested the highest stability within a pH range of 10–12. Copyright © 2004 John Wiley & Sons, Ltd.
  Surface and Interface Analysis 10/2004; 36(11):1491 - 1496. · 1.18 Impact Factor
• Article: Ionic liquids with symmetrical dialkoxymethyl-substituted imidazolium cations.

  Juliusz Pernak, Kinga Sobaszkiewicz, Joanna Foksowicz-Flaczyk
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  ABSTRACT: A new one-step procedure is described for the synthesis of disubstituted imidazolium chlorides. 1,3-Dialkoxymethylimidazolium chlorides thus obtained can be employed as synthetic precursors of symmetrical ILs. The salts have been found to exhibit antimicrobial activity and an antielectrostatic effect. Their densities and viscosities have been determined and are reported herein. It has also been demonstrated that the ILs can be decomposed using an aqueous solution of KMnO(4). For each IL, the permanganate index (I(Mn)) has been estimated, which varies with the structure of cation. The only limitation of I(Mn) is the degree to which the IL dissolves in water.
  Chemistry 08/2004; 10(14):3479-85. · 5.93 Impact Factor
• Article: Suppression of deleterious effects of free silanols in liquid chromatography by imidazolium tetrafluoroborate ionic liquids.

  Roman Kaliszan, Michał Piotr Marszałł, Michał Jan Markuszewski, Tomasz Baczek, Juliusz Pernak
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  ABSTRACT: Silica-based stationary phases are commonly used in liquid chromatography, but their surface acidity causes known problems, especially when separating basic compounds. Deleterious effects of free silanols are not fully removed by standard prevention procedures consisting in adding alkylamines or other amino quenchers to the eluents. We found that ionic liquids of the imidazolium tetrafluoroborate class, added to mobile phases at concentrations of 0.5-1.5% (v/v), blocked silanols and provided excellent thin-layer chromatographic separations of strongly basic drugs which were otherwise not eluted, even with neat acetonitrile as the mobile phase. The silanol suppressing potency of imidazolium tetrafluoroborates was demonstrated to markedly exceed that of the standard mobile phase additives, like triethylamine, dimethyloctylamine and ammonia. The proposed new mobile phase additives were also demonstrated to provide reliable lipophilicity parameters of base drug analytes as determined by gradient mode of high-performance liquid chromatography. By applying the readily available and environmentally friendly imidazolium tetrafluoroborate ionic liquids, simple and efficient means of improvement of liquid chromatographic analysis of organic bases were elaborated.
  Journal of Chromatography 04/2004; 1030(1-2):263-71. · 4.53 Impact Factor
• Article: Ionic liquids in embalming and tissue preservation. Can traditional formalin-fixation be replaced safely?

  Przemysław Majewski, Agnieszka Pernak, Marian Grzymisławski, Katarzyna Iwanik, Juliusz Pernak
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  ABSTRACT: Ionic liquids (ILs) can be used for embalming and tissue preservation. ILs does not cause tissue damage and the tissue colour remains unaltered after treatment. Microscopical morphology of tissues fixed in ILs is of better quality than that of tissues fixed in formalin. Tissue preservation depends on the type of ILs. Best results were obtained with 1-methyl-3-octyloxymethylimidazolium tetrafluoroborate, the density of which resembles that of water. The salt is nonvaporous and when used as a formalin substitute, it eliminates health hazards in the pathological laboratory.
  Acta Histochemica 02/2003; 105(2):135-42. · 1.83 Impact Factor
• Article: Synthesis and anti-microbial activities of choline-like quaternary ammonium chlorides.

  Juliusz Pernak, Przemysław Chwała
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  ABSTRACT: New choline-like quaternary ammonium chlorides were obtained. The work-up procedure of synthesis was quick and efficient. The obtained chlorides showed anti-microbial activities. Quaternary ammonium chlorides derivatives of deanol esters exhibited strong activity and wide anti-bacterial spectra, similar to the activity of benzalkonium chloride. The relationship between chemical structure and anti-microbial activity was analyzed by the QSAR method.
  European Journal of Medicinal Chemistry 38(11-12):1035-42. · 3.35 Impact Factor