PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2014 | 63 | 2 |
Tytuł artykułu

Dibasic esters of ortho-/meta-alkoxyphenylcarbamic acid containing 1-dipropylamino-3-piperidinopropan-1-yl and their antimicrobial activity

Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
In Europe, the presence of microorganisms that have become resistant to antimicrobials as the most significant disease threat has remained. The aim of the current research was to screen the in vitro susceptibility of Staphylococcus aureus, Escherichia coli and Candida albicans to the series of dibasic esters of ortho-/meta-alkoxyphenylcarbamic acid previously known for their local anaesthetic effectiveness and to contribute for the structure – antimicrobial potency relationships study within that class of the compounds. The antimicrobial activity investigation involved determination of the minimum inhibitory concentration (MIC) by applying the microdilution method; quantitative screening was performed on a blood agar (S. aureus), Endo agar (E. coli) or on Sabouraud’s agar (C. albicans). The activity against all the microorganisms tested was primarily influenced by the position of alkoxy side chain attached to lipophilic aromatic ring and by its length as well. Inspected meta-alkoxy substituted derivatives have shown higher efficiency against all chosen microorganisms than their ortho-alkoxy positional isomers. The most promising results were observed when investigating the activity of meta-alkoxy substituted molecules against E. coli with the estimated MICs in the range of 12–49 μg/ml. Furthermore, such potency was found to be quasi parabolically dependent on alkoxy chain length achieving a maximum for meta-hexyloxy derivative which has shown MIC = 12 μg/ml. Considered compound was also regarded as the most effective against S. aureus with MIC = 98 μg/ml. Evaluating the potency against C. albicans, it was revealed that no molecule within the tested set displayed MIC < 100 μg/ml.
Słowa kluczowe
EN
Wydawca
-
Rocznik
Tom
63
Numer
2
Opis fizyczny
p.231-236,fig.,ref.
Twórcy
autor
  • Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, SK-832 32 Bratislava, Slovak Republic
  • Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno, Czech Republic
autor
  • Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, SK-832 32 Bratislava, Slovak Republic
autor
  • Department of Cell and Molecular Biology of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, Slovak Republic
autor
  • Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, SK-832 32 Bratislava, Slovak Republic
Bibliografia
  • Andrasevic A.T. and M.J. Dowzicky. 2012. In vitro activity of tigecycline and comparators against Gram-negative pathogens isolated from blood in Europe (2004–2009). Int. J. Antimicrob. Agents 39: 115–123.
  • Andrews J.M. 2001. Determination of minimum inhibitory concentrations. J. Antimicrob. Chemother. 48: 5–16.
  • Balgavý P. and F. Devínsky. 1996. Cut-off effects in biological activities of surfactants. Adv. Colloid Interface Sci. 66: 23–63.
  • Csöllei J., Ľ. Búčiová, J. Čižmárik and L. Kopáčová. 1993. Studies of local anaesthetics CXII. Preparation and activity of dibasic alkylesters of 2-, and 3-alkoxy-substituted phenylcarbamic acids (In Slovak). Českoslov. Farm. 42: 127–129.
  • Čižmárik J., J. Trupl and M. Pešák. 1983. Korrelation zwischen der antimikrobiellen Aktivität quartärer Ammoniumsalze des Heptacains gegenüber Staphylococcus aureus der Extraktionskonstante der Ionenpaare (In German). Pharmazie 38: 789–790.
  • Čižmárik J., J. Trupl and M. Pešák. 1986. Beziehung zwischen antimikrobieller Wirkung auf Staphylococcus aureus und den Konstanten σ und π einiger p-substituierter Derivate der Phenylcarbamidsäure (In German). Pharmazie 41: 442–443.
  • Čižmárik J., J. Trupl and M. Pešák. 1987. A correlation between the antimicrobial activity to Staphylococcus aureus and selected physico-chemical parameters in the series of hydrochlorides piperidinoethylesters alkoxy-substituted phenyl-carbamic acids (In Slovak). Českoslov. Farm. 36: 345–348.
  • Dmitriev B.A., F.V. Toukach, O. Holst, E.T. Rietschel and S. Ehlers.2004. Tertiary structure of Staphylococcus aureus cell wall murein. J. Bacteriol. 186: 7141–7148.
  • Endl J., H.P. Seidl, F. Fiedler and K.H. Schleifer. 1983. Chemical composition and structure of cell wall teichoic acids of staphylococci. Arch. Microbiol. 35: 215–223.
  • Enquist P.-A., A. Gylfe, U. Hägglund, P. Lindström, H. Norberg-Scherman, Ch. Sundin and M. Elofsson. 2012. Derivatives of 8-hydroxyquinoline – antibacterial agents that target intra- and extracellular Gram-negative pathogens. Bioorg. Med. Chem. Lett. 22: 3550–3553.
  • Gould I.M., R. Cauda, S. Esposito, F. Gudiol, T. Mazzei and J. Garau. 2011. Management of serious methicillin-resistant Staphylococcus aureus infections: what are the limits? Int. J. Antimicrob. Agents 37: 202–209.
  • Hsu D.I., L.K. Hidayat, R. Quist, J. Hindler, A. Karlsson, A. Yusof and A. Wong-Beringer. 2008. Comparison of method-specific vancomycin minimum inhibitory concentration values and their predictability for treatment outcome of methicillin-resistant Staphylococcus aureus (MRSA) infections. Int. J. Antimicrob. Agents 32: 378–385.
  • Králová K., H. Bujdáková and J. Čižmárik. 1995. Antifungal and antialgal activity of piperidinopropyl esters of alkoxy substituted phenylcarbamic acids. Pharmazie 50: 440–441.
  • Livermore D.M. 2011. Discovery research: the scientific challenge of finding new antibiotics. J. Antimicrob. Chemother. 66: 1941–1944.
  • Malík I., M. Bukovský, F. Andriamaity and J. Gališinová. 2012. Antimicrobial activity of meta-alkoxyphenylcarbamates containing substituted N-phenylpiperazine. Braz. J. Microbiol. 43: 959–965.
  • Malík I., E. Sedlárová, J. Csöllei, F. Andriamainty and J. Čižmárik. 2007. Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid. Chem. Papers 61: 206–213.
  • Mlynarčík D., J. Bittererová, J. Čižmárik and L. Masárová. 1991. The effect of piperidinoethylesters of n-alkoxyphenyl-carbamic acids on bacterial cells (In Slovak). Česk. Farm. 40: 25–28.
  • Mlynarčík D. and J. Čižmárik. 1976. Antimicrobial efficiency of ω-piperidinoethyl esters of n-alkoxy-phenylcarbamic acids. Folia Microbiol. 21: 75–76.
  • Mlynarčík D. and J. Čižmárik. 1979. Antimikrobielle Eigenschaften einiger basischer Ethylester von Alkoxyphenylcarbaminsäuren (In German). Pharmazie 34: 575.
  • Okele I.N. 2009. The tragedy of antimicrobial resistance: achieving a recognition of necessity. Curr. Sci. 97: 1564–1572.
  • Perez F., R.A. Salata and R.A. Bonomo. 2008. Current and novel antibiotics against resistant Gram-positive bacteria. Infect. Drug Resist. 1: 27–44.
  • Pokorná M. 1998. Relationship of the structure and local anaesthetic effect in the group of esters of alkoxy-substituted phenylcarbamic acid (In Czech). Čes. a Slov. Farm. 47: 14–20.
  • Poon H., M.H. Chang and H.B. Fung. 2012. Ceftaroline fosamil:A cephalosporin with activity against methicillin-resistant Staphylococcus aureus. Clin. Ther. 34: 743–765.
  • Putnam S.D., H.S. Sader, G.J. Moet, R.E. Mendes and R.N. Jones. 2007. Worldwide summary of telavacin spectrum and potency against Gram-positive pathogens: 2007 to 2008 surveillance results. Diagn. Microbiol. Infect. Dis. 67: 359–368.
  • Remko M., K.R. Liedl and B.M. Rode. 1997. Theoretical study on the local anaesthetic-receptor interaction. Chem. Papers 51: 234–241.
  • Remko M. and P.T. Van Duijnen. 1983. Ab initio investigations of local anesthetic-phospholipid model membrane interactions. Theochem, J. Mol. Struct. 104: 451-457.
  • Schneewind O., A. Fowler and K.F. Faull. 1995. Structure of the cell wall anchor of surface proteins in Staphylococcus aureus. Science 268: 103–106.
  • Sharma D., B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clerq and J. Balzarini. 2009. Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. Eur. J. Med. Chem. 44: 2347–2353.
  • Wise R. 2008. The worldwide threat of antimicrobial resistance. Curr. Sci. 95, 181-187.
  • Ziemska J., A. Rajnisz and J. Solecka. 2013. New perspectives on antibacterial drug research. Cent. Eur. J. Biol. 8: 943–957.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.agro-701b1540-68eb-4f12-815e-95d5157b709f
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.