메뉴 건너뛰기




Volumn 24, Issue 5, 2011, Pages 706-717

Synthetic approach to gain insight into antigenic determinants of cephalosporins: In vitro studies of chemical structure-IgE molecular recognition relationships

Author keywords

[No Author keywords available]

Indexed keywords

CARRIER PROTEIN; CEFACLOR; CEFADROXIL; CEFALEXIN; CEFALONIO; CEFALOTIN; CEFAMANDOLE; CEFEPIME; CEFONICID; CEFOTAXIME; CEFOZIDIME; CEFPROZILO; CEFTAZIDIME; CEFTRIAXONE; CEFUROXIME; CEPHALOSPORIN; CEPHALOSPORIN DERIVATIVE; EPITOPE; IMMUNOGLOBULIN E; LOW MOLECULAR WEIGHT HEPARIN; LYSINE; UNCLASSIFIED DRUG;

EID: 79956128371     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100446g     Document Type: Article
Times cited : (31)

References (37)
  • 1
    • 61849182463 scopus 로고    scopus 로고
    • Immune-mediated adverse drug reactions
    • Uetrecht, J. (2009) Immune-mediated adverse drug reactions Chem. Res. Toxicol. 22, 24-34
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 24-34
    • Uetrecht, J.1
  • 3
    • 84973718396 scopus 로고
    • Studies on the sensitization of animals with simple chemical compounds
    • Landsteiner, K. and Jacobs, J. (1935) Studies on the sensitization of animals with simple chemical compounds J. Exp. Med. 61, 643-656
    • (1935) J. Exp. Med. , vol.61 , pp. 643-656
    • Landsteiner, K.1    Jacobs, J.2
  • 4
    • 38949104743 scopus 로고    scopus 로고
    • Idiosyncratic drug reactions: Past, present, and future
    • DOI 10.1021/tx700186p
    • Uetrecht, J. (2008) Idiosyncratic drug reactions: past, present, and future Chem. Res. Toxicol. 21, 84-92 (Pubitemid 351219710)
    • (2008) Chemical Research in Toxicology , vol.21 , Issue.1 , pp. 84-92
    • Uetrecht, J.1
  • 6
    • 0035856014 scopus 로고    scopus 로고
    • Currents concepts: Cephalosporin allergy
    • Kelkar, P. S. and Li, J. T. (2001) Currents concepts: cephalosporin allergy N. Engl. J. Med. 345, 804-809
    • (2001) N. Engl. J. Med. , vol.345 , pp. 804-809
    • Kelkar, P.S.1    Li, J.T.2
  • 7
    • 66149128463 scopus 로고    scopus 로고
    • Evaluation of immediate allergic reactions to cephalosporins in non-penicillin-allergic patients
    • Somech, R., Weber, E. A., and Lavi, S. (2009) Evaluation of immediate allergic reactions to cephalosporins in non-penicillin-allergic patients Int. Arch. Allergy Immunol. 150, 205-209
    • (2009) Int. Arch. Allergy Immunol. , vol.150 , pp. 205-209
    • Somech, R.1    Weber, E.A.2    Lavi, S.3
  • 8
    • 0013871805 scopus 로고
    • The immunogenity of cephalosporins derivatives and their cross-reaction with penicillin
    • Batchelor, F. R., Dewdney, J. M., Weston, R. D., and Wheeler, A. W. (1966) The immunogenity of cephalosporins derivatives and their cross-reaction with penicillin Immunology 10, 21-33
    • (1966) Immunology , vol.10 , pp. 21-33
    • Batchelor, F.R.1    Dewdney, J.M.2    Weston, R.D.3    Wheeler, A.W.4
  • 9
    • 0008247789 scopus 로고
    • β-Lactam Antibiotics
    • in (, Eds.) pp - 320, Pergamon Press, Oxford, UK.
    • Lowe, G. (1979) β-Lactam Antibiotics, in Comprehensive Organic Chemistry (Barton, D. and Ollis, D., Eds.) pp 289 - 320, Pergamon Press, Oxford, UK.
    • (1979) Comprehensive Organic Chemistry , pp. 289
    • Lowe, G.1    Barton, D.2    Ollis, D.3
  • 10
    • 0015348423 scopus 로고
    • Correlation between hydrolysis of the -lactam bond of the cephalosporin nucleus and expulsion of the 3-substituent
    • O'Callaghan, C. H., Kirby, S. M., Morris, A., Waller, R. E., and Duncombe, R. E. (1972) Correlation between hydrolysis of the -lactam bond of the cephalosporin nucleus and expulsion of the 3-substituent J. Bacteriol. 110, 988-991
    • (1972) J. Bacteriol. , vol.110 , pp. 988-991
    • O'Callaghan, C.H.1    Kirby, S.M.2    Morris, A.3    Waller, R.E.4    Duncombe, R.E.5
  • 11
    • 0015640794 scopus 로고
    • A method for determining free azide ions by automatic analysis in the presence of a covalent cephalosporin azide
    • Waller, R. E. (1973) A method for determining free azide ions by automatic analysis in the presence of a covalent cephalosporin azide Analyst 98, 535-541
    • (1973) Analyst , vol.98 , pp. 535-541
    • Waller, R.E.1
  • 12
    • 41549124659 scopus 로고
    • Chemical studies related to cephalosporin allergy. I. Kinetics of aminolysis of cephalosporins and effect of C-3 substituents on β-lactam reactivity
    • Bundgaard, H. (1975) Chemical studies related to cephalosporin allergy. I. Kinetics of aminolysis of cephalosporins and effect of C-3 substituents on β-lactam reactivity Arch. Pharm. Chem., Sci. Ed. 3, 94-123
    • (1975) Arch. Pharm. Chem., Sci. Ed. , vol.3 , pp. 94-123
    • Bundgaard, H.1
  • 13
    • 0016607474 scopus 로고
    • Electronic structures of cephalosporins and penicillins. 4. Modeling acylation by the beta-lactam ring
    • Boyd, D. B., Hermann, R. B., Presti, D. E., and Marsh, M. M. (1975) Electronic structures of cephalosporins and penicillins. 4. Modeling acylation by the beta-lactam ring J. Med. Chem. 18, 408-417
    • (1975) J. Med. Chem. , vol.18 , pp. 408-417
    • Boyd, D.B.1    Hermann, R.B.2    Presti, D.E.3    Marsh, M.M.4
  • 14
    • 0018656310 scopus 로고
    • Electronic structures of cephalosporin and penicillins. 9. Departure of a leaving group in cephalosporins
    • DOI 10.1021/jm00193a006
    • Boyd, D. B. and Lunn, W. H. W. (1979) Electronic structures of cephalosporins and penicillins. 9. Departure of a leaving group in cephalosporins J. Med. Chem. 22, 778-784 (Pubitemid 10234135)
    • (1979) Journal of Medicinal Chemistry , vol.22 , Issue.7 , pp. 778-784
    • Boyd, D.B.1    Lunn, W.H.W.2
  • 15
    • 0021341894 scopus 로고
    • Elimination of a good leaving group from the 3'-position of a cephalosporin need not be concerted with β-lactam ring opening: TEM-2 β-lactamase-catalyzed hydrolysis of pyridine-2-azo-4'-(N',N'- dimethylaniline) cephalosporin (PADAC) and of cephaloridine
    • DOI 10.1021/ja00317a053
    • Faraci, W. S. and Pratt, R. F. (1984) Elimination of a good leaving group from the 30-position of a cephalosporin need not be concerted with b-lactam ring opening: TEM-2 β-lactamase-catalized hydrolysis of pyridine-2-azo-40-(N′,N′-dimethylaniline) cephalosporin (PADAC) and of cephaloridine J. Am. Chem. Soc. 106, 1489-1490 (Pubitemid 14169723)
    • (1984) Journal of the American Chemical Society , vol.106 , Issue.5 , pp. 1489-1490
    • Faraci, W.S.1    Pratt, R.F.2
  • 16
    • 0022481301 scopus 로고
    • 1H NMR of cephalosporoate intermediates in aqueous solution during the hydrazinolysis and β-lactamase-catalyzed hydrolysis of cephalosporins with 3' leaving groups: Kinetics and equilibria of the 3' elimination reaction
    • Pratt, R. F. and Faraci, W. S. (1986) Direct observation by 1H-NMR of cephalosporoate intermediates in aqueous solution during the hydrazinolysis and β-lactamasecatalized hydrolysis of cephalosporin with 3′ leaving groups: kinetics and equilibria of the 3′ elimination reaction J. Am. Chem. Soc. 108, 5328-5333 (Pubitemid 16041645)
    • (1986) Journal of the American Chemical Society , vol.108 , Issue.17 , pp. 5328-5333
    • Pratt, R.F.1    Faraci, W.S.2
  • 25
    • 33847182810 scopus 로고    scopus 로고
    • Safe use of selected cephalosporins in penicillin-allergic patients: A meta-analysis
    • Pichichero, M. E. and Casey, J. R. (2007) Safe use of selected cephalosporins in penicillin-allergic patients: A meta-analysis Otolaryngol., Head Neck Surg. 136, 340-347
    • (2007) Otolaryngol., Head Neck Surg. , vol.136 , pp. 340-347
    • Pichichero, M.E.1    Casey, J.R.2
  • 26
    • 23244454423 scopus 로고    scopus 로고
    • A review of evidence supporting the American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients
    • Pichichero, M. E. (2005) A review of evidence supporting the American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients Pediatrics 115, 1048-1057
    • (2005) Pediatrics , vol.115 , pp. 1048-1057
    • Pichichero, M.E.1
  • 27
    • 0033039237 scopus 로고    scopus 로고
    • Penicillins and cephalosporins as allergens - Structural aspects of recognition and cross-reactions
    • DOI 10.1046/j.1365-2222.1999.00575.x
    • Baldo, B. A. (1999) Penicillins and cephalosporins as allergens: structural aspects of recognition and cross-reactions Clin. Exp. Allergy 29, 744-749 (Pubitemid 29268461)
    • (1999) Clinical and Experimental Allergy , vol.29 , Issue.6 , pp. 744-749
    • Baldo, B.A.1
  • 30
    • 0032474717 scopus 로고    scopus 로고
    • A chemoselective, acid mediated conversion of amide acetal to oxazole: The key step in the synthesis of cardiovascular drug, ifetroban sodium
    • DOI 10.1016/S0040-4039(98)00904-6, PII S0040403998009046
    • Swaminathan, S., Singh, A. K., Li, W.-S., Venit, J. J., Natalie, K. J., Jr., Simpson, J. H., Weaver, R. E., and Siverberg, L. J. (1998) A chemoselective, acid mediated conversion of amide acetal to oxazole: the key step in the synthesis of cardiovascular drug, ifetroban sodium Tetrahedron Lett. 39, 4769-4772 (Pubitemid 28267306)
    • (1998) Tetrahedron Letters , vol.39 , Issue.27 , pp. 4769-4772
    • Swaminathan, S.1    Singh, A.K.2    Li, W.-S.3    Venit, J.J.4    Natalie Jr., K.J.5    Simpson, J.H.6    Weaver, R.E.7    Silverberg, L.J.8
  • 31
    • 10744223860 scopus 로고    scopus 로고
    • Diagnosis of immediate allergic reactions to beta-lactam antibiotics
    • ENDA and EAACI Interest Group on Drug Hypersensititvy., - 972.
    • Torres, M. J., Blanca, M., Fernandez, J., Romano, A., de Weck, A., Aberer, W., Brockow, K., Pichler, W. J., and Demoly, P., ENDA and EAACI Interest Group on Drug Hypersensititvy (2003) Diagnosis of immediate allergic reactions to beta-lactam antibiotics. Allergy, 58, 961 - 972.
    • (2003) Allergy , vol.58 , pp. 961
    • Torres, M.J.1    Blanca, M.2    Fernandez, J.3    Romano, A.4    De Weck, A.5    Aberer, W.6    Brockow, K.7    Pichler, W.J.8    Demoly, P.9
  • 32
    • 0025934227 scopus 로고
    • Differences in serum IgE antibody activity to benzylpenicillin and amoxicillin measured by RAST in a group of penicillin allergic patients
    • Blanca, M., Mayorga, C., Sanchez, F., Vega, J. M., Fernandez, J., Juarez, C., Suau, R., and Perez, E. (1991) Differences in serum IgE antibody activity to benzylpenicillin and amoxicillin measured by RAST in a group of penicillin allergic patients Allergy 46, 632-638
    • (1991) Allergy , vol.46 , pp. 632-638
    • Blanca, M.1    Mayorga, C.2    Sanchez, F.3    Vega, J.M.4    Fernandez, J.5    Juarez, C.6    Suau, R.7    Perez, E.8
  • 35
    • 0040357383 scopus 로고    scopus 로고
    • Synthesis of characteristic H-ras lipopeptides by employing noble-metal-, acid-, and reduction-labile blocking groups
    • Kadereit, D. and Waldmann, H. (2000) Synthesis of characteristic H-ras lipopeptides by employing noble-metal-, acid-, and reduction-labile blocking groups ChemBioChem 1, 200-203
    • (2000) ChemBioChem , vol.1 , pp. 200-203
    • Kadereit, D.1    Waldmann, H.2
  • 36
    • 0025134861 scopus 로고
    • Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy
    • DOI 10.1016/0161-5890(90)90094-G
    • Baldo, B. A. and Harle, D. G. (1990) Identification of penicillin allergenic determinants that bind IgE in the sera of patients with penicillin allergy Mol. Immunol. 27, 1063-1071 (Pubitemid 20382043)
    • (1990) Molecular Immunology , vol.27 , Issue.11 , pp. 1063-1071
    • Harle, D.G.1    Baldo, B.A.2
  • 37
    • 64349093749 scopus 로고    scopus 로고
    • Covalent modifiers: An orthogonal approach to drug design
    • Potashman, M. H. and Duggan, M. E. (2009) Covalent modifiers: an orthogonal approach to drug design J. Med. Chem. 52, 1231-1246
    • (2009) J. Med. Chem. , vol.52 , pp. 1231-1246
    • Potashman, M.H.1    Duggan, M.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.