메뉴 건너뛰기




Volumn 78, Issue 1, 2011, Pages 33-41

Design, synthesis, and biological evaluation of β-lactam antibiotic-based imidazolium- and pyridinium-type ionic liquids

Author keywords

lactam; Antibacterial; Cetylpyridinium; Imidazolium; Ionic liquid; Quaternary ammonium compounds; Sodium ampicillin

Indexed keywords

1 HEXADECYL 2,3 DIMETHYLIMIDAZOLIUM AMPICILLIN; 1 HEXADECYL 3 METHYLIMIDAZOLIUM AMPICILLIN; AMPICILLIN; AMPICILLIN DERIVATIVE; BETA LACTAM ANTIBIOTIC; CETYLPYRIDINIUM AMPICILLIN; IMIDAZOLE DERIVATIVE; IONIC LIQUID; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 80955177472     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01114.x     Document Type: Article
Times cited : (91)

References (52)
  • 1
    • 80955178427 scopus 로고    scopus 로고
    • Combating antibiotic resistance in bacteria
    • Maheshwari R. (2007) Combating antibiotic resistance in bacteria. Indian J Microbiol;47:181-183.
    • (2007) Indian J Microbiol , vol.47 , pp. 181-183
    • Maheshwari, R.1
  • 3
    • 1542575746 scopus 로고    scopus 로고
    • Antibiotic development pipeline runs dry
    • Nelson R. (2003) Antibiotic development pipeline runs dry. Lancet;362:1726-1727.
    • (2003) Lancet , vol.362 , pp. 1726-1727
    • Nelson, R.1
  • 4
    • 80955180630 scopus 로고
    • Congress U.S. ed. Assessment, O.o.T. Washington, DC: U.S. Government Printing Office.
    • Congress U.S. (1995) Impacts of Antibiotic Resistant Bacteria ed. Assessment, O.o.T. Washington, DC: U.S. Government Printing Office.
    • (1995) Impacts of Antibiotic Resistant Bacteria
  • 7
    • 20744460085 scopus 로고    scopus 로고
    • Nosocomial infections due to methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci at a university hospital in taiwan from 1991 to 2003: resistance trends, antibiotic usage and in vitro activities of newer antimicrobial agents
    • Hsueh P.-R., Chenc W.-H., Teng L.-J., Luha K.-T. (2005) Nosocomial infections due to methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci at a university hospital in taiwan from 1991 to 2003: resistance trends, antibiotic usage and in vitro activities of newer antimicrobial agents. Int J Antimicrob Agents;26:43-49.
    • (2005) Int J Antimicrob Agents , vol.26 , pp. 43-49
    • Hsueh, P.-R.1    Chenc, W.-H.2    Teng, L.-J.3    Luha, K.-T.4
  • 9
    • 43149092918 scopus 로고    scopus 로고
    • Controllable formation of ionic liquid micro- and nanoparticles via melt-emulsion-quench approach
    • Tesfai A., El-Zahab B., Bwambok D., Baker G., Fakayode S., Lowry M., Warner I. (2008) Controllable formation of ionic liquid micro- and nanoparticles via melt-emulsion-quench approach. Nano Lett;8:897-901.
    • (2008) Nano Lett , vol.8 , pp. 897-901
    • Tesfai, A.1    El-Zahab, B.2    Bwambok, D.3    Baker, G.4    Fakayode, S.5    Lowry, M.6    Warner, I.7
  • 10
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids. Solvents for synthesis and catalysis
    • Welton T. (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev;99:2071-2083.
    • (1999) Chem Rev , vol.99 , pp. 2071-2083
    • Welton, T.1
  • 12
  • 14
    • 80955180627 scopus 로고    scopus 로고
    • Ionic liquids
    • Binnemans K. (2006) Ionic liquids. Chem Rev;105:4128-4204.
    • (2006) Chem Rev , vol.105 , pp. 4128-4204
    • Binnemans, K.1
  • 16
    • 17844367313 scopus 로고    scopus 로고
    • Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids
    • Docherty K.M., Kulpa C.F. (2005) Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem;7:185-189.
    • (2005) Green Chem , vol.7 , pp. 185-189
    • Docherty, K.M.1    Kulpa, C.F.2
  • 17
    • 1342279565 scopus 로고    scopus 로고
    • Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts
    • Demberelnyamba D., Seung P., Huen L., Chang K., Ick-Dong Y. (2004) Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. Bioorg Med Chem;12:853-857.
    • (2004) Bioorg Med Chem , vol.12 , pp. 853-857
    • Demberelnyamba, D.1    Seung, P.2    Huen, L.3    Chang, K.4    Ick-Dong, Y.5
  • 21
    • 43149112306 scopus 로고    scopus 로고
    • Cytotoxicity of selected imidazolium-derived ionic liquids in he human caco-2 cell line. Sub structural toxicological interpretation through a qsar study
    • Garcia-Lorenzo A., Tojo E., Tojo J., Teijeira M., Rodriguez-Berrocal F., Gonzalez M., Martinez-Zorzana V. (2008) Cytotoxicity of selected imidazolium-derived ionic liquids in he human caco-2 cell line. Sub structural toxicological interpretation through a qsar study. Green Chem;10:508-516.
    • (2008) Green Chem , vol.10 , pp. 508-516
    • Garcia-Lorenzo, A.1    Tojo, E.2    Tojo, J.3    Teijeira, M.4    Rodriguez-Berrocal, F.5    Gonzalez, M.6    Martinez-Zorzana, V.7
  • 23
    • 32244443852 scopus 로고    scopus 로고
    • Polymer architecture and drug delivery
    • Qiu L., Bae Y. (2006) Polymer architecture and drug delivery. Pharm Res;23:1-30.
    • (2006) Pharm Res , vol.23 , pp. 1-30
    • Qiu, L.1    Bae, Y.2
  • 24
    • 33845388144 scopus 로고    scopus 로고
    • Micellar nanocarriers: pharmaceutical perspectives
    • Torchilin V. (2007) Micellar nanocarriers: pharmaceutical perspectives. Pharm Res;24:1-16.
    • (2007) Pharm Res , vol.24 , pp. 1-16
    • Torchilin, V.1
  • 26
    • 0017235304 scopus 로고
    • Clinical study on the antifungal activity of griseofulvin in the presence of surfactants
    • Said S., Mahrous H., Kassem A. (1976) Clinical study on the antifungal activity of griseofulvin in the presence of surfactants. Infection;4:49-50.
    • (1976) Infection , vol.4 , pp. 49-50
    • Said, S.1    Mahrous, H.2    Kassem, A.3
  • 27
    • 0024337493 scopus 로고
    • Improved delivery through biological membranes xli. Brain-enhanced delivery of chlorambucil
    • Bodor N., Venkatraghavan V., Winwood D., Estes K., Brewster M.E. (1989) Improved delivery through biological membranes xli. Brain-enhanced delivery of chlorambucil. Int J Pharm;53:195-208.
    • (1989) Int J Pharm , vol.53 , pp. 195-208
    • Bodor, N.1    Venkatraghavan, V.2    Winwood, D.3    Estes, K.4    Brewster, M.E.5
  • 28
    • 0014330907 scopus 로고
    • Solubilization of chloramphenicol by benzalkonium chloride and study of their combined activity against pseudomonas aeruginosa
    • Yousef R.T., Ghobashy A.A. (1968) Solubilization of chloramphenicol by benzalkonium chloride and study of their combined activity against pseudomonas aeruginosa. Acta Pharm Suec;5:385-392.
    • (1968) Acta Pharm Suec , vol.5 , pp. 385-392
    • Yousef, R.T.1    Ghobashy, A.A.2
  • 29
    • 0028452895 scopus 로고
    • Targeting penicillins to the central nervous system: chemical delivery and redox analogs
    • Pop E. (1994) Targeting penicillins to the central nervous system: chemical delivery and redox analogs. Adv Drug Delivery Rev;14:211-226.
    • (1994) Adv Drug Delivery Rev , vol.14 , pp. 211-226
    • Pop, E.1
  • 30
    • 0036001403 scopus 로고    scopus 로고
    • High throughput screening of transdermal formulations
    • Krande P., Mitragotri S. (2002) High throughput screening of transdermal formulations. Pharm Res;19:655-660.
    • (2002) Pharm Res , vol.19 , pp. 655-660
    • Krande, P.1    Mitragotri, S.2
  • 31
    • 78049499869 scopus 로고    scopus 로고
    • New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs
    • Müllertz A., Ogbonna A., Ren S., Rades T. (2010) New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs. J Pharm Pharmacol;62:1622-1636.
    • (2010) J Pharm Pharmacol , vol.62 , pp. 1622-1636
    • Müllertz, A.1    Ogbonna, A.2    Ren, S.3    Rades, T.4
  • 32
    • 36248965667 scopus 로고    scopus 로고
    • Combination drugs, an emerging option for antibacterial therapy
    • Cottarel G., Wierzbowki J. (2007) Combination drugs, an emerging option for antibacterial therapy. Trends Biotechnol;25:547-555.
    • (2007) Trends Biotechnol , vol.25 , pp. 547-555
    • Cottarel, G.1    Wierzbowki, J.2
  • 34
    • 0016095487 scopus 로고
    • The spectrophotometric determination of ampicillin and cloxacillin in combined injections
    • Davidson A.G., Stenlake J.B. (1974) The spectrophotometric determination of ampicillin and cloxacillin in combined injections. Analyst;99:476-481.
    • (1974) Analyst , vol.99 , pp. 476-481
    • Davidson, A.G.1    Stenlake, J.B.2
  • 35
    • 33746862153 scopus 로고    scopus 로고
    • Dynamic stokes shift and excitation wavelength dependent fluorescence of dipolar molecules in room temperature ionic liquids
    • Samanta A. (2006) Dynamic stokes shift and excitation wavelength dependent fluorescence of dipolar molecules in room temperature ionic liquids. J Phys Chem B;110:13704-13716.
    • (2006) J Phys Chem B , vol.110 , pp. 13704-13716
    • Samanta, A.1
  • 36
    • 33747074311 scopus 로고    scopus 로고
    • Optical absorption and fluorescence studies on imidazolium ionic liquids comprising the bis(trifluoromethanesulphonyl)imide anion
    • Paul A., Samanta A. (2006) Optical absorption and fluorescence studies on imidazolium ionic liquids comprising the bis(trifluoromethanesulphonyl)imide anion. J Chem Sci;118:335-340.
    • (2006) J Chem Sci , vol.118 , pp. 335-340
    • Paul, A.1    Samanta, A.2
  • 37
    • 33746255616 scopus 로고    scopus 로고
    • Excitation wavelength dependent fluorescence behavior of the room temperature ionic liquids and dissolved dipolar solutes
    • Mandal P.K., Paul A., Samanta A. (2006) Excitation wavelength dependent fluorescence behavior of the room temperature ionic liquids and dissolved dipolar solutes. J Photochem Photobiol A: Chem;182:113-120.
    • (2006) J Photochem Photobiol A: Chem , vol.182 , pp. 113-120
    • Mandal, P.K.1    Paul, A.2    Samanta, A.3
  • 38
    • 0004296312 scopus 로고    scopus 로고
    • NCCLS, 8th edn. Approved standard. In M2-A8. Villanova, PA: National Committee on Clinical Laboratory Standards.
    • NCCLS (2006) Performance Standards for Antimicrobial Disk Susceptibility Tests, 8th edn. Approved standard. In M2-A8. Villanova, PA: National Committee on Clinical Laboratory Standards.
    • (2006) Performance Standards for Antimicrobial Disk Susceptibility Tests
  • 39
    • 0027392568 scopus 로고
    • Comparative analysis of using MTT and xtt in colorimetric assays for quantitating bovine neutrophil bactericidal activity
    • Stevens M.G., Olsen S.C. (1993) Comparative analysis of using MTT and xtt in colorimetric assays for quantitating bovine neutrophil bactericidal activity. J Immunol Meth;157:225-231.
    • (1993) J Immunol Meth , vol.157 , pp. 225-231
    • Stevens, M.G.1    Olsen, S.C.2
  • 40
    • 0029044999 scopus 로고
    • Nondestructive and continuous spectrophotometric measurement of cell respiration using a tetrazolium-formazan microemulsion
    • Stowe R.P., Koenig D.W., Mishra S.K., Pierson D.L. (1995) Nondestructive and continuous spectrophotometric measurement of cell respiration using a tetrazolium-formazan microemulsion. J Microbiol Meth;22:283-292.
    • (1995) J Microbiol Meth , vol.22 , pp. 283-292
    • Stowe, R.P.1    Koenig, D.W.2    Mishra, S.K.3    Pierson, D.L.4
  • 41
    • 33845994428 scopus 로고    scopus 로고
    • Action of disinfectant quaternary ammonium compounds against Staphylococcus aureus
    • Ioannou C.J., Hanlon G.W., Denyer S.P. (2007) Action of disinfectant quaternary ammonium compounds against Staphylococcus aureus. Antimicrob Agents Chemother;51:296-306.
    • (2007) Antimicrob Agents Chemother , vol.51 , pp. 296-306
    • Ioannou, C.J.1    Hanlon, G.W.2    Denyer, S.P.3
  • 42
    • 0032914892 scopus 로고    scopus 로고
    • The effect of hydrocarbon chain length, ph, and temperature on the binding and bactericidal effect of amphiphilic betaine esters on Salmonella typhimurium
    • Ahlstrom B., Thompson R.A., Edebo L. (1999) The effect of hydrocarbon chain length, ph, and temperature on the binding and bactericidal effect of amphiphilic betaine esters on Salmonella typhimurium. APMIS;107:318-324.
    • (1999) APMIS , vol.107 , pp. 318-324
    • Ahlstrom, B.1    Thompson, R.A.2    Edebo, L.3
  • 43
    • 34249702368 scopus 로고    scopus 로고
    • A novel group contribution method in the development of a qsar for predicting the toxicity (Vibrio fischeri ec50) of ionic liquids
    • Luis P., Ortiz I., Aldaco R., Irabien A. (2007) A novel group contribution method in the development of a qsar for predicting the toxicity (Vibrio fischeri ec50) of ionic liquids. Ecotoxicol Environ Saf;67:423-429.
    • (2007) Ecotoxicol Environ Saf , vol.67 , pp. 423-429
    • Luis, P.1    Ortiz, I.2    Aldaco, R.3    Irabien, A.4
  • 44
    • 3042680082 scopus 로고    scopus 로고
    • Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and wst-1 cell viability assays
    • Ranke J., Molter K., Stock F., Bottin-Weber U., Poczobutt J., Hoffmann J., Ondruschka B. (2004) Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and wst-1 cell viability assays. Ecotoxicol Environ Saf;58:396-404.
    • (2004) Ecotoxicol Environ Saf , vol.58 , pp. 396-404
    • Ranke, J.1    Molter, K.2    Stock, F.3    Bottin-Weber, U.4    Poczobutt, J.5    Hoffmann, J.6    Ondruschka, B.7
  • 45
    • 33645389717 scopus 로고    scopus 로고
    • Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modelling
    • Couling D.J., Bernot R.J., Docherty K.M., Dixon J.K., Maginn E.J. (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modelling. Green Chem;8:82-90.
    • (2006) Green Chem , vol.8 , pp. 82-90
    • Couling, D.J.1    Bernot, R.J.2    Docherty, K.M.3    Dixon, J.K.4    Maginn, E.J.5
  • 49
    • 0013808622 scopus 로고
    • Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-d-alanyl-d-alanine
    • Tipper D.J., Strominger J.L. (1965) Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-d-alanyl-d-alanine. Proc Natl Acad Sci USA;54:1133-1141.
    • (1965) Proc Natl Acad Sci USA , vol.54 , pp. 1133-1141
    • Tipper, D.J.1    Strominger, J.L.2
  • 50
    • 0029116103 scopus 로고
    • Application of the rough sets theory to the analysis of structure-activity-relationships of antimicrobial pyridinium compounds
    • Krysinkski J. (1995) Application of the rough sets theory to the analysis of structure-activity-relationships of antimicrobial pyridinium compounds. Pharmazie;50:593-597.
    • (1995) Pharmazie , vol.50 , pp. 593-597
    • Krysinkski, J.1
  • 51
    • 0141686034 scopus 로고    scopus 로고
    • Anti-microbial activities of ionic liquids
    • Pernak J., Sobaszkiewicz K., Mirska I. (2003) Anti-microbial activities of ionic liquids. Green Chem;5:52-56.
    • (2003) Green Chem , vol.5 , pp. 52-56
    • Pernak, J.1    Sobaszkiewicz, K.2    Mirska, I.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.