메뉴 건너뛰기




Volumn 49, Issue 7, 2015, Pages 4218-4225

Cu(II)-catalyzed transformation of benzylpenicillin revisited: The overlooked oxidation

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; CATALYSIS; HYDROLYSIS; METAL IONS; OXIDATION; OXYGEN; SEWAGE TREATMENT PLANTS;

EID: 84926443126     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es505114u     Document Type: Article
Times cited : (59)

References (53)
  • 1
    • 0343522919 scopus 로고
    • The mechanisms of reactions of β-lactam antibiotics
    • Page, M. I. The mechanisms of reactions of β-lactam antibiotics Acc. Chem. Res. 1984, 17 (4) 144-151
    • (1984) Acc. Chem. Res. , vol.17 , Issue.4 , pp. 144-151
    • Page, M.I.1
  • 2
    • 84882775778 scopus 로고    scopus 로고
    • FDA. U.S. Food and Drug Administration: Washington, DC
    • FDA. Drugs Use Review; U.S. Food and Drug Administration: Washington, DC, 2012.
    • (2012) Drugs Use Review
  • 4
    • 0017169928 scopus 로고
    • Pharmacokinetics of the penicillins in man
    • Barza, M.; Weinstein, L. Pharmacokinetics of the penicillins in man Clin. Pharmacokinet. 1976, 1 (4) 297-308
    • (1976) Clin. Pharmacokinet. , vol.1 , Issue.4 , pp. 297-308
    • Barza, M.1    Weinstein, L.2
  • 6
    • 10644265358 scopus 로고    scopus 로고
    • Antibiotics in the environment: Occurrence in Italian STPs, fate, and preliminary assessment on algal toxicity of amoxicillin
    • Andreozzi, R.; Caprio, V.; Ciniglia, C.; De Champdoré, M.; Lo Giudice, R.; Marotta, R.; Zuccato, E. Antibiotics in the environment: Occurrence in Italian STPs, fate, and preliminary assessment on algal toxicity of amoxicillin Environ. Sci. Technol. 2004, 38 (24) 6832-6838
    • (2004) Environ. Sci. Technol. , vol.38 , Issue.24 , pp. 6832-6838
    • Andreozzi, R.1    Caprio, V.2    Ciniglia, C.3    De Champdoré, M.4    Lo Giudice, R.5    Marotta, R.6    Zuccato, E.7
  • 7
    • 34548687233 scopus 로고    scopus 로고
    • Removal of antibiotics in conventional and advanced wastewater treatment: Implications for environmental discharge and wastewater recycling
    • Watkinson, A. J.; Murby, E. J.; Costanzo, S. D. Removal of antibiotics in conventional and advanced wastewater treatment: Implications for environmental discharge and wastewater recycling Water Res. 2007, 41 (18) 4164-4176
    • (2007) Water Res. , vol.41 , Issue.18 , pp. 4164-4176
    • Watkinson, A.J.1    Murby, E.J.2    Costanzo, S.D.3
  • 8
    • 33646157485 scopus 로고    scopus 로고
    • Trace determination of β-lactam antibiotics in surface water and urban wastewater using liquid chromatography combined with electrospray tandem mass spectrometry
    • Cha, J. M.; Yang, S.; Carlson, K. H. Trace determination of β-lactam antibiotics in surface water and urban wastewater using liquid chromatography combined with electrospray tandem mass spectrometry J. Chromatogr., A 2006, 1115 (1-2) 46-57
    • (2006) J. Chromatogr., A , vol.1115 , Issue.12 , pp. 46-57
    • Cha, J.M.1    Yang, S.2    Carlson, K.H.3
  • 10
    • 4444241488 scopus 로고    scopus 로고
    • Resistance in the environment
    • Kümmerer, K. Resistance in the environment J. Antimicrob. Chemoth. 2004, 54 (2) 311-320
    • (2004) J. Antimicrob. Chemoth. , vol.54 , Issue.2 , pp. 311-320
    • Kümmerer, K.1
  • 11
    • 0020691813 scopus 로고
    • β-lactam antibiotics: Geometrical requirements for antibacterial activities
    • Cohen, N. C. β-lactam antibiotics: Geometrical requirements for antibacterial activities J. Med. Chem. 1983, 26 (2) 259-264
    • (1983) J. Med. Chem. , vol.26 , Issue.2 , pp. 259-264
    • Cohen, N.C.1
  • 12
    • 22544463102 scopus 로고    scopus 로고
    • Degradation of β-lactam antibiotics
    • Deshpande, A. D.; Baheti, K. G.; Chatterjee, N. R. Degradation of β-lactam antibiotics Curr. Sci. 2004, 87 (12) 1684-1695
    • (2004) Curr. Sci. , vol.87 , Issue.12 , pp. 1684-1695
    • Deshpande, A.D.1    Baheti, K.G.2    Chatterjee, N.R.3
  • 14
    • 0032717888 scopus 로고    scopus 로고
    • The combined effects of pH and temperature on penicillin G decomposition and its stability modeling
    • Kheirolomoom, A.; Kazemi-Vaysari, A.; Ardjmand, M.; Baradar-Khoshfetrat, A. The combined effects of pH and temperature on penicillin G decomposition and its stability modeling Process Biochem. 1999, 35 (1-2) 205-211
    • (1999) Process Biochem. , vol.35 , Issue.12 , pp. 205-211
    • Kheirolomoom, A.1    Kazemi-Vaysari, A.2    Ardjmand, M.3    Baradar-Khoshfetrat, A.4
  • 16
    • 0015039834 scopus 로고
    • β-lactam antibiotics: Their physicochemical properties and biological activities in relation to structure
    • Hou, J.; Poole, J. β-lactam antibiotics: Their physicochemical properties and biological activities in relation to structure J. Pharm. Sci. 1971, 60 (4) 503-532
    • (1971) J. Pharm. Sci. , vol.60 , Issue.4 , pp. 503-532
    • Hou, J.1    Poole, J.2
  • 17
    • 37049091643 scopus 로고
    • Investigation of a proposed penicillin G acidic degradation scheme using high-pressure liquid chromatography and optimization techniques and mechanistic considerations
    • Kessler, D. P.; Cushman, M.; Ghebre-Sellassie, I.; Knevel, A. M.; Hem, S. L. Investigation of a proposed penicillin G acidic degradation scheme using high-pressure liquid chromatography and optimization techniques and mechanistic considerations J. Chem. Soc., Perkin Trans. 2 1983, 9) 1699-1703
    • (1983) J. Chem. Soc., Perkin Trans. 2 , Issue.9 , pp. 1699-1703
    • Kessler, D.P.1    Cushman, M.2    Ghebre-Sellassie, I.3    Knevel, A.M.4    Hem, S.L.5
  • 19
    • 0017069282 scopus 로고
    • Kinetic analysis of penicillin degradation in acidic media
    • Blaha, J. M.; Knevel, A. M.; Kessler, D. P.; Mincy, J. W.; Hem, S. L. Kinetic analysis of penicillin degradation in acidic media J. Pharm. Sci. 1976, 65 (8) 1165-1170
    • (1976) J. Pharm. Sci. , vol.65 , Issue.8 , pp. 1165-1170
    • Blaha, J.M.1    Knevel, A.M.2    Kessler, D.P.3    Mincy, J.W.4    Hem, S.L.5
  • 20
    • 37049093551 scopus 로고
    • A kinetic analysis of the acidic degradation of penicillin G and confirmation of penicillamine as a degradation product
    • Kessler, D. P.; Ghebre-Sellassie, I.; Knevel, A. M.; Hem, S. L. A kinetic analysis of the acidic degradation of penicillin G and confirmation of penicillamine as a degradation product J. Chem. Soc., Perkin Trans. 2 1981, 9) 1247-1251
    • (1981) J. Chem. Soc., Perkin Trans. 2 , Issue.9 , pp. 1247-1251
    • Kessler, D.P.1    Ghebre-Sellassie, I.2    Knevel, A.M.3    Hem, S.L.4
  • 21
    • 0021338080 scopus 로고
    • β-Lactamases
    • Medeiros, A. A. β-Lactamases Br. Med. Bull. 1984, 40 (1) 18-27
    • (1984) Br. Med. Bull. , vol.40 , Issue.1 , pp. 18-27
    • Medeiros, A.A.1
  • 22
    • 0015456725 scopus 로고
    • Zinc and copper(II) ion catalyses of penicillins in alcohols
    • Ayim, J. S.; Rapson, H. D. Zinc and copper(II) ion catalyses of penicillins in alcohols J. Pharm. Pharmacol. 1972, 24 (Suppl) 172-173
    • (1972) J. Pharm. Pharmacol. , vol.24 , pp. 172-173
    • Ayim, J.S.1    Rapson, H.D.2
  • 23
    • 0023750248 scopus 로고
    • Degradation of some aqueous semisynthetic penicillin solutions in presence of copper(II) ions
    • Chatterjee, N. R.; Degani, M. S.; Singh, C. B. Degradation of some aqueous semisynthetic penicillin solutions in presence of copper(II) ions Indian J. Pharm. Sci. 1988, 50 (2) 128-30
    • (1988) Indian J. Pharm. Sci. , vol.50 , Issue.2 , pp. 128-130
    • Chatterjee, N.R.1    Degani, M.S.2    Singh, C.B.3
  • 24
    • 0014618607 scopus 로고
    • Cupric ion-catalyzed hydrolysis of penicillins: Mechanism and site of complexation
    • Cressman, W. A.; Sugita, E. T.; Doluisio, J. T.; Niebergall, P. J. Cupric ion-catalyzed hydrolysis of penicillins: Mechanism and site of complexation J. Pharm. Sci. 1969, 58 (12) 1471-1476
    • (1969) J. Pharm. Sci. , vol.58 , Issue.12 , pp. 1471-1476
    • Cressman, W.A.1    Sugita, E.T.2    Doluisio, J.T.3    Niebergall, P.J.4
  • 25
    • 0032079304 scopus 로고    scopus 로고
    • Degradation of ampicillin in the presence of cadmium(II) ions
    • García, A. M.; Navarro, P. G.; de las Parras, P. J. M. Degradation of ampicillin in the presence of cadmium(II) ions Talanta 1998, 46 (1) 101-109
    • (1998) Talanta , vol.46 , Issue.1 , pp. 101-109
    • García, A.M.1    Navarro, P.G.2    De Las Parras, P.J.M.3
  • 27
    • 0017066350 scopus 로고
    • The determination of penicillins by titrations with mercury(II) solution
    • Karlberg, B.; Forsman, U. The determination of penicillins by titrations with mercury(II) solution Anal. Chim. Acta 1976, 83, 309-316
    • (1976) Anal. Chim. Acta , vol.83 , pp. 309-316
    • Karlberg, B.1    Forsman, U.2
  • 28
    • 0015026379 scopus 로고
    • Spectrophotometric assay of ampicillin (alpha-Aminobenzylpenicillin) involving initial benzoylation of side chain alpha-Amino group
    • Tutt, D. E.; Schwartz, M. A. Spectrophotometric assay of ampicillin (alpha-Aminobenzylpenicillin) involving initial benzoylation of side chain alpha-Amino group Anal. Chem. 1971, 43 (3) 338-342
    • (1971) Anal. Chem. , vol.43 , Issue.3 , pp. 338-342
    • Tutt, D.E.1    Schwartz, M.A.2
  • 30
    • 0038417056 scopus 로고    scopus 로고
    • Transformation of the plant growth regulator daminozide (Alar) and structurally related compounds with Cu-II ions: Oxidation versus hydrolysis
    • Huang, C. H.; Stone, A. T. Transformation of the plant growth regulator daminozide (Alar) and structurally related compounds with Cu-II ions: Oxidation versus hydrolysis Environ. Sci. Technol. 2003, 37 (9) 1829-1837
    • (2003) Environ. Sci. Technol. , vol.37 , Issue.9 , pp. 1829-1837
    • Huang, C.H.1    Stone, A.T.2
  • 31
    • 0002275350 scopus 로고    scopus 로고
    • Hydrolysis of phosphate esters catalyzed by copper(II)-triamine complexes. The effect of triamine ligands on the reactivity of the copper(II) catalysts
    • Itoh, T.; Hisada, H.; Usui, Y.; Fujii, Y. Hydrolysis of phosphate esters catalyzed by copper(II)-triamine complexes. The effect of triamine ligands on the reactivity of the copper(II) catalysts Inorg. Chim. Acta 1998, 283 (1) 51-60
    • (1998) Inorg. Chim. Acta , vol.283 , Issue.1 , pp. 51-60
    • Itoh, T.1    Hisada, H.2    Usui, Y.3    Fujii, Y.4
  • 32
    • 62749101234 scopus 로고    scopus 로고
    • Transformation of tetracyclines mediated by Mn(II) and Cu(II) ions in the presence of oxygen
    • Chen, W. R.; Huang, C. H. Transformation of tetracyclines mediated by Mn(II) and Cu(II) ions in the presence of oxygen Environ. Sci. Technol. 2009, 43 (2) 401-407
    • (2009) Environ. Sci. Technol. , vol.43 , Issue.2 , pp. 401-407
    • Chen, W.R.1    Huang, C.H.2
  • 33
    • 0034286436 scopus 로고    scopus 로고
    • Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media
    • Jungbluth, G.; Ruhling, I.; Ternes, W. Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media J. Chem. Soc., Perkin Trans. 2 2000, 9) 1946-1952
    • (2000) J. Chem. Soc., Perkin Trans. 2 , Issue.9 , pp. 1946-1952
    • Jungbluth, G.1    Ruhling, I.2    Ternes, W.3
  • 34
    • 0037124399 scopus 로고    scopus 로고
    • Kinetic Study of the oxidation of catechol by aqueous copper(II)
    • Kamau, P.; Jordan, R. B. Kinetic Study of the oxidation of catechol by aqueous copper(II) Inorg. Chem. 2002, 41 (12) 3076-3083
    • (2002) Inorg. Chem. , vol.41 , Issue.12 , pp. 3076-3083
    • Kamau, P.1    Jordan, R.B.2
  • 35
    • 0000514541 scopus 로고
    • Oxidation of 1,1-dimethylhydrazine by cupric halides. Isolation of a complex of 1,1-dimethyldiazene and a salt containing the 1,1,5,5-tetramethylformazanium ion
    • Boehm, J. R.; Balch, A. L.; Bizot, K. F.; Enemark, J. H. Oxidation of 1,1-dimethylhydrazine by cupric halides. Isolation of a complex of 1,1-dimethyldiazene and a salt containing the 1,1,5,5-tetramethylformazanium ion J. Am. Chem. Soc. 1975, 97 (3) 501-508
    • (1975) J. Am. Chem. Soc. , vol.97 , Issue.3 , pp. 501-508
    • Boehm, J.R.1    Balch, A.L.2    Bizot, K.F.3    Enemark, J.H.4
  • 36
    • 84862858567 scopus 로고    scopus 로고
    • Kinetics of Cu(II) reduction by natural organic matter
    • Pham, A. N.; Rose, A. L.; Waite, T. D. Kinetics of Cu(II) reduction by natural organic matter J. Phys. Chem. A 2012, 116 (25) 6590-6599
    • (2012) J. Phys. Chem. A , vol.116 , Issue.25 , pp. 6590-6599
    • Pham, A.N.1    Rose, A.L.2    Waite, T.D.3
  • 37
    • 84856750023 scopus 로고    scopus 로고
    • Effects of pH, chloride, and bicarbonate on Cu(I) oxidation kinetics at circumneutral pH
    • Yuan, X.; Pham, A. N.; Xing, G. W.; Rose, A. L.; Waite, T. D. Effects of pH, chloride, and bicarbonate on Cu(I) oxidation kinetics at circumneutral pH Environ. Sci. Technol. 2011, 46 (3) 1527-1535
    • (2011) Environ. Sci. Technol. , vol.46 , Issue.3 , pp. 1527-1535
    • Yuan, X.1    Pham, A.N.2    Xing, G.W.3    Rose, A.L.4    Waite, T.D.5
  • 39
    • 0024191809 scopus 로고
    • Measurement of copper(I) in surface waters of the subtropical Atlantic and Gulf of Mexico
    • Moffett, J. W.; Zika, R. G. Measurement of copper(I) in surface waters of the subtropical Atlantic and Gulf of Mexico Geochim. Cosmochim. Acta 1988, 52 (7) 1849-1857
    • (1988) Geochim. Cosmochim. Acta , vol.52 , Issue.7 , pp. 1849-1857
    • Moffett, J.W.1    Zika, R.G.2
  • 40
    • 84881464170 scopus 로고    scopus 로고
    • Copper-catalyzed hydroquinone oxidation and associated redox cycling of copper under conditions typical of natural saline waters
    • Yuan, X.; Pham, A. N.; Miller, C. J.; Waite, T. D. Copper-catalyzed hydroquinone oxidation and associated redox cycling of copper under conditions typical of natural saline waters Environ. Sci. Technol. 2013, 47 (15) 8355-8364
    • (2013) Environ. Sci. Technol. , vol.47 , Issue.15 , pp. 8355-8364
    • Yuan, X.1    Pham, A.N.2    Miller, C.J.3    Waite, T.D.4
  • 42
    • 33947455632 scopus 로고
    • Simultaneous determination of penicillin and penicilloic acid in fermentation samples by colorimetric method
    • Pan, S. C. Simultaneous determination of penicillin and penicilloic acid in fermentation samples by colorimetric method Anal. Chem. 1954, 26 (9) 1438-1444
    • (1954) Anal. Chem. , vol.26 , Issue.9 , pp. 1438-1444
    • Pan, S.C.1
  • 43
    • 0015048103 scopus 로고
    • Studies on the stability of drugs in biological media. III. Effect of cupric ion on the stability and antibacterial activity of penicillins in culture medium
    • Kakemi, K.; Sezaki, H.; Iwamoto, K.; Kobayashi, H.; Inui, K. Studies on the stability of drugs in biological media. III. Effect of cupric ion on the stability and antibacterial activity of penicillins in culture medium Chem. Pharm. Bull. 1971, 19 (4) 730-736
    • (1971) Chem. Pharm. Bull. , vol.19 , Issue.4 , pp. 730-736
    • Kakemi, K.1    Sezaki, H.2    Iwamoto, K.3    Kobayashi, H.4    Inui, K.5
  • 44
    • 77049326684 scopus 로고
    • The disintegration of penicillin in the presence of heavy metals
    • Gunther, G. The disintegration of penicillin in the presence of heavy metals Pharmazie 1950, 5 (12) 577
    • (1950) Pharmazie , vol.5 , Issue.12 , pp. 577
    • Gunther, G.1
  • 45
    • 18144421552 scopus 로고    scopus 로고
    • Insights into the reaction of β-lactam antibiotics with copper(II) ions in aqueous and micellar media: Kinetic and spectrometric studies
    • Fernández-González, A.; Badía, R.; Díaz-García, M. E. Insights into the reaction of β-lactam antibiotics with copper(II) ions in aqueous and micellar media: Kinetic and spectrometric studies Anal. Biochem. 2005, 341 (1) 113-121
    • (2005) Anal. Biochem. , vol.341 , Issue.1 , pp. 113-121
    • Fernández-González, A.1    Badía, R.2    Díaz-García, M.E.3
  • 46
    • 11844283941 scopus 로고    scopus 로고
    • Speciation of Chromium(III) and Cobalt(III) (Amino)carboxylate complexes using capillary electrophoresis
    • Carbonaro, R. F.; Stone, A. T. Speciation of Chromium(III) and Cobalt(III) (Amino)carboxylate complexes using capillary electrophoresis Anal. Chem. 2004, 77 (1) 155-164
    • (2004) Anal. Chem. , vol.77 , Issue.1 , pp. 155-164
    • Carbonaro, R.F.1    Stone, A.T.2
  • 47
    • 0001569587 scopus 로고
    • Evaluation of bathocuproine for the spectro-photometric determination of copper(I) in copper redox studies with applications in studies of natural waters
    • Moffett, J. W.; Zika, R. G.; Petasne, R. G. Evaluation of bathocuproine for the spectro-photometric determination of copper(I) in copper redox studies with applications in studies of natural waters Anal. Chim. Acta 1985, 175, 171-179
    • (1985) Anal. Chim. Acta , vol.175 , pp. 171-179
    • Moffett, J.W.1    Zika, R.G.2    Petasne, R.G.3
  • 48
    • 85027953341 scopus 로고    scopus 로고
    • Metal complexes of penicillins and cephalosporins (Review)
    • Alekseev, V. G. Metal complexes of penicillins and cephalosporins (Review) Pharm. Chem. J. 2012, 45 (11) 679-697
    • (2012) Pharm. Chem. J. , vol.45 , Issue.11 , pp. 679-697
    • Alekseev, V.G.1
  • 50
    • 48749148898 scopus 로고
    • Oxidation kinetics of Cu(I) in seawater: Implications for its existence in the marine environment
    • Moffett, J. W.; Zika, R. G. Oxidation kinetics of Cu(I) in seawater: Implications for its existence in the marine environment Mar. Chem. 1983, 13 (3) 239-251
    • (1983) Mar. Chem. , vol.13 , Issue.3 , pp. 239-251
    • Moffett, J.W.1    Zika, R.G.2
  • 51
    • 0012078415 scopus 로고
    • Degradation of benzylpenicillin at pH 7.5 to d -benzylpenicilloic acid
    • Levine, B. B. Degradation of benzylpenicillin at pH 7.5 to d -benzylpenicilloic acid Nature 1960, 187 (4741) 939-940
    • (1960) Nature , vol.187 , Issue.4741 , pp. 939-940
    • Levine, B.B.1
  • 52
    • 49549138114 scopus 로고
    • Metal ion coordination by some penicillin and cephalosporin antibiotics
    • Fazakerley, G. V.; Jackson, G. E. Metal ion coordination by some penicillin and cephalosporin antibiotics J. Inorg. Nucl. Chem. 1975, 37 (11) 2371-2375
    • (1975) J. Inorg. Nucl. Chem. , vol.37 , Issue.11 , pp. 2371-2375
    • Fazakerley, G.V.1    Jackson, G.E.2
  • 53
    • 0012050888 scopus 로고
    • The copper(II) promoted hydrolysis of benzylpenicillin. Evidence for the participation of a Cu-OH species in the hydrolysis of the β-lactam ring
    • Hay, R. W.; Basak, A. K.; Pujari, M. P.; Perotti, A. The copper(II) promoted hydrolysis of benzylpenicillin. Evidence for the participation of a Cu-OH species in the hydrolysis of the β-lactam ring J. Chem. Soc. Dalton 1989, 2, 197-201
    • (1989) J. Chem. Soc. Dalton , vol.2 , pp. 197-201
    • Hay, R.W.1    Basak, A.K.2    Pujari, M.P.3    Perotti, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.