메뉴 건너뛰기




Volumn 41, Issue 8, 1997, Pages 1649-1657

Structure-activity relationship of carbacephalosporins and cephalosporins: Antibacterial activity and interaction with the intestinal proton-dependent dipeptide transport carrier of caco-2 cells

Author keywords

[No Author keywords available]

Indexed keywords

CARBACEPHEM DERIVATIVE; CARRIER PROTEIN; CEFALEXIN; CEFAMANDOLE; CEFOTAXIME; CEPHALOSPORIN DERIVATIVE; CYCLACILLIN; LORACARBEF; PHENYLGLYCINE;

EID: 0030877222     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.8.1649     Document Type: Article
Times cited : (39)

References (49)
  • 1
    • 85008529803 scopus 로고
    • Studies on optically active amino acids. XVIII. Studies on α-methyl-α-amino acids. XIV. Several optical properties of α-methyl-α-amino acids
    • Achiwa, K., S. Terashima, H. Mizuno, N. Takamura, T. Kitagawa, K. Ishikawa, and S.-I. Yamada. 1970. Studies on optically active amino acids. XVIII. Studies on α-methyl-α-amino acids. XIV. Several optical properties of α-methyl-α-amino acids. Chem. Pharm. Bull. 18:61-74.
    • (1970) Chem. Pharm. Bull. , vol.18 , pp. 61-74
    • Achiwa, K.1    Terashima, S.2    Mizuno, H.3    Takamura, N.4    Kitagawa, T.5    Ishikawa, K.6    Yamada, S.-I.7
  • 3
    • 0028197288 scopus 로고
    • Absorption of peptide and peptidomimetic drugs
    • Amidon, G. L., and H. J. Lee. 1994. Absorption of peptide and peptidomimetic drugs. Annu. Rev. Pharmacol. Toxicol. 34:321-341.
    • (1994) Annu. Rev. Pharmacol. Toxicol. , vol.34 , pp. 321-341
    • Amidon, G.L.1    Lee, H.J.2
  • 4
    • 0025878066 scopus 로고
    • Structural requirements for the intestinal mucosal-cell peptide transporter: The need for N-terminal α-amino group
    • Bai, P., P. Subramanian, H. I. Mosberg, and G. L. Amidon. 1991. Structural requirements for the intestinal mucosal-cell peptide transporter: the need for N-terminal α-amino group. Pharm. Res. 8:593-599.
    • (1991) Pharm. Res. , vol.8 , pp. 593-599
    • Bai, P.1    Subramanian, P.2    Mosberg, H.I.3    Amidon, G.L.4
  • 6
    • 0001160137 scopus 로고
    • Pentavalent organobismuth reagents. Part VI. Comparative migratory aptitudes of aryl groups in the arylation of phenols and enols by pentavalent bismuth reagents
    • Barton, D. H. R., N. Y. Bhatnagar, J. Finet, and W. B. Motherwell. 1986. Pentavalent organobismuth reagents. Part VI. Comparative migratory aptitudes of aryl groups in the arylation of phenols and enols by pentavalent bismuth reagents. Tetrahedron 42:3111-3122.
    • (1986) Tetrahedron , vol.42 , pp. 3111-3122
    • Barton, D.H.R.1    Bhatnagar, N.Y.2    Finet, J.3    Motherwell, W.B.4
  • 7
  • 8
    • 0019823303 scopus 로고
    • Characteristics of dipeptide transport in normal and papain-treated brush border membrane vesicles from mouse intestine. II. Uptake of glycyl-L-leucine
    • Berteloot, A., A. H. Khan, and K. Ramaswamy. 1981. Characteristics of dipeptide transport in normal and papain-treated brush border membrane vesicles from mouse intestine. II. Uptake of glycyl-L-leucine. Biochim. Biophys. Acta 649:179-188.
    • (1981) Biochim. Biophys. Acta , vol.649 , pp. 179-188
    • Berteloot, A.1    Khan, A.H.2    Ramaswamy, K.3
  • 11
    • 0028273953 scopus 로고
    • Intestinal absorption of peptide drugs: Advances in our understanding and clinical implications
    • Catnach, S. M., P. D. Fairclough, and S. M. Hammond. 1994. Intestinal absorption of peptide drugs: advances in our understanding and clinical implications. Gut 35:441-444.
    • (1994) Gut , vol.35 , pp. 441-444
    • Catnach, S.M.1    Fairclough, P.D.2    Hammond, S.M.3
  • 12
    • 0028840804 scopus 로고
    • Stereoselective uptake of β-lactam antibiotics by the intestinal peptide transporter
    • Daniel, H., and D. T. Thwaites. 1995. Stereoselective uptake of β-lactam antibiotics by the intestinal peptide transporter. Br. J. Pharm. 116:3021-3027.
    • (1995) Br. J. Pharm. , vol.116 , pp. 3021-3027
    • Daniel, H.1    Thwaites, D.T.2
  • 13
    • 0025046860 scopus 로고
    • Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2
    • Dantzig, A. H., and L. Bergin. 1990. Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2. Biochim. Biophys. Acta 1027:211-217.
    • (1990) Biochim. Biophys. Acta , vol.1027 , pp. 211-217
    • Dantzig, A.H.1    Bergin, L.2
  • 14
    • 0028345208 scopus 로고
    • Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells
    • Dantzig, A. H., D. C. Duckworth, and L. B. Tabas. 1994. Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim. Biophys. Acta 1191:7-13.
    • (1994) Biochim. Biophys. Acta , vol.1191 , pp. 7-13
    • Dantzig, A.H.1    Duckworth, D.C.2    Tabas, L.B.3
  • 15
    • 0026496355 scopus 로고
    • Cefaclor uptake by the proton-dependent dipeptide transport carrier of human intestinal Caco-2 cells and comparison to cephalexin uptake
    • Dantzig, A. H., L. B. Tabas, and L. Bergin. 1992. Cefaclor uptake by the proton-dependent dipeptide transport carrier of human intestinal Caco-2 cells and comparison to cephalexin uptake. Biochim. Biophys. Acta 1112: 167-173.
    • (1992) Biochim. Biophys. Acta , vol.1112 , pp. 167-173
    • Dantzig, A.H.1    Tabas, L.B.2    Bergin, L.3
  • 16
    • 0026668442 scopus 로고
    • Pharmacokinetic profile of loracarbef
    • DeSante, K. A., and M. L. Zeckel. 1992. Pharmacokinetic profile of loracarbef. Am. J. Med. 92(Suppl. 6A):16S-19S.
    • (1992) Am. J. Med. , vol.92 , Issue.SUPPL. 6A
    • Desante, K.A.1    Zeckel, M.L.2
  • 17
    • 0021829848 scopus 로고
    • Peptide transport in rabbit intestinal brush-border membrane vesicles studies with a potential-sensitive dye
    • Ganapathy, V., G. Burckhardt, and F. H. Leibach. 1985. Peptide transport in rabbit intestinal brush-border membrane vesicles studies with a potential-sensitive dye. Biochim. Biophys. Acta 816:234-240.
    • (1985) Biochim. Biophys. Acta , vol.816 , pp. 234-240
    • Ganapathy, V.1    Burckhardt, G.2    Leibach, F.H.3
  • 18
    • 0021025978 scopus 로고
    • Role of pH gradient and membrane potential in dipeptide transport in intestinal and renal brush-border membrane vesicles from the rabbit. Studies with L-carnosine and glycyl-L-proline
    • Ganapathy, V., and F. H. Leibach. 1983. Role of pH gradient and membrane potential in dipeptide transport in intestinal and renal brush-border membrane vesicles from the rabbit. Studies with L-carnosine and glycyl-L-proline. J. Biol. Chem. 258:14189-14192.
    • (1983) J. Biol. Chem. , vol.258 , pp. 14189-14192
    • Ganapathy, V.1    Leibach, F.H.2
  • 19
    • 0019822915 scopus 로고
    • Transport of glycyl-L-proline into intestinal and renal brush border vesicles from rabbit
    • Ganapathy, V., J. R. Mendicino, and F. H. Leibach. 1981. Transport of glycyl-L-proline into intestinal and renal brush border vesicles from rabbit. J. Biol. Chem. 256:116-124.
    • (1981) J. Biol. Chem. , vol.256 , pp. 116-124
    • Ganapathy, V.1    Mendicino, J.R.2    Leibach, F.H.3
  • 20
    • 0019605676 scopus 로고
    • The cluster tray method for rapid measurement of solute fluxes in adherent cultured cells
    • Gazzola, G. C., V. Dall'Asta, R. Franchi-Gazzola, and M. F. White. 1981. The cluster tray method for rapid measurement of solute fluxes in adherent cultured cells. Anal. Biochem. 115:368-374.
    • (1981) Anal. Biochem. , vol.115 , pp. 368-374
    • Gazzola, G.C.1    DalL'Asta, V.2    Franchi-Gazzola, R.3    White, M.F.4
  • 21
    • 0023546523 scopus 로고
    • Hydrophobicity and central nervous system agents: On the principle of minimal hydrophobicity in drug design
    • Hansch, C., J. P. Bjorkroth, and A. Leo. 1987. Hydrophobicity and central nervous system agents: on the principle of minimal hydrophobicity in drug design. J. Pharm. Sci. 79:663-687.
    • (1987) J. Pharm. Sci. , vol.79 , pp. 663-687
    • Hansch, C.1    Bjorkroth, J.P.2    Leo, A.3
  • 22
    • 0030054574 scopus 로고    scopus 로고
    • Molecular modeling study of structural requirements for the oligopeptide transporter
    • Hidalgo, J., and J. Li. 1996. Molecular modeling study of structural requirements for the oligopeptide transporter. J. Drug Targeting 4:9-17.
    • (1996) J. Drug Targeting , vol.4 , pp. 9-17
    • Hidalgo, J.1    Li, J.2
  • 23
    • 0029968911 scopus 로고    scopus 로고
    • Drug chirality: A consideration of the significance of the stereochemistry of antimicrobial agents
    • Hutt, A. J., and J. O'Grady. 1996. Drug chirality: a consideration of the significance of the stereochemistry of antimicrobial agents. J. Antimicrob. Chemother. 37:7-32.
    • (1996) J. Antimicrob. Chemother. , vol.37 , pp. 7-32
    • Hutt, A.J.1    O'Grady, J.2
  • 24
    • 0037533356 scopus 로고
    • 2-Chloro-4,6-disubstituted-1,3,5-triazines - A novel group of condensing reagents
    • Kaminski, Z. J. 1985. 2-Chloro-4,6-disubstituted-1,3,5-triazines - a novel group of condensing reagents. Tetrahedron Lett. 26:2901-2904.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2901-2904
    • Kaminski, Z.J.1
  • 25
    • 85004275726 scopus 로고
    • Pharmacokinetics of orally absorbed beta-lactam antibiotics LY228238 and LY257128 in laboratory animals
    • American Society for Microbiology, Washington, D.C.
    • Kasher, J. S., J. A. Eudaly, R. Johnson, and J. Shoufler. 1988. Pharmacokinetics of orally absorbed beta-lactam antibiotics LY228238 and LY257128 in laboratory animals, abstr. 535, p. 202. In Program and abstracts of the 28th Interscience Conference on Antimicrobial Agents and Chemotherapy. American Society for Microbiology, Washington, D.C.
    • (1988) 28th Interscience Conference on Antimicrobial Agents and Chemotherapy , pp. 202
    • Kasher, J.S.1    Eudaly, J.A.2    Johnson, R.3    Shoufler, J.4
  • 26
    • 0000817870 scopus 로고
    • A highly efficient and general N-monomethylation of functionalized primary amines via formylation - Borane:methyl sulfide reduction
    • Krishnamurthy, S. 1982. A highly efficient and general N-monomethylation of functionalized primary amines via formylation - borane:methyl sulfide reduction. Tetrahedron Lett. 23:3315-3318.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3315-3318
    • Krishnamurthy, S.1
  • 28
    • 0001166311 scopus 로고
    • Transmembrane transport of small peptides
    • Matthews, D. M., and J. W. Payne. 1980. Transmembrane transport of small peptides. Curr. Top. Membr. Transp. 14:331-425.
    • (1980) Curr. Top. Membr. Transp. , vol.14 , pp. 331-425
    • Matthews, D.M.1    Payne, J.W.2
  • 30
    • 0027436878 scopus 로고
    • Characterization of the oral absorption of some β-lactams: Effect of the α-amino side chain group
    • Oh, D., P. J. Sinko, and G. L. Amidon. 1993. Characterization of the oral absorption of some β-lactams: effect of the α-amino side chain group. J. Pharm. Sci. 82:897-900.
    • (1993) J. Pharm. Sci. , vol.82 , pp. 897-900
    • Oh, D.1    Sinko, P.J.2    Amidon, G.L.3
  • 32
    • 0023150737 scopus 로고
    • Characteristics of glycyl-L-proline transport in intestinal brush-border membrane vesicles
    • (Gastrointest. Liver Physiol. 15)
    • Rajendran, V., J. M. Harig, and K. Ramaswamy. 1987. Characteristics of glycyl-L-proline transport in intestinal brush-border membrane vesicles. Am. J. Physiol. 252(Gastrointest. Liver Physiol. 15):G281-G286.
    • (1987) Am. J. Physiol. , vol.252
    • Rajendran, V.1    Harig, J.M.2    Ramaswamy, K.3
  • 33
    • 0022391238 scopus 로고
    • Transport of glycyl-L-proline by mouse intestinal brush-border membrane vesicles
    • Rajendran, V. M., A. Berteloot, and K. Ramaswamy. 1985. Transport of glycyl-L-proline by mouse intestinal brush-border membrane vesicles. Am. J. Physiol. 248:G682-G686.
    • (1985) Am. J. Physiol. , vol.248
    • Rajendran, V.M.1    Berteloot, A.2    Ramaswamy, K.3
  • 34
    • 0023882467 scopus 로고
    • Transport of glycyl-L-proline in intestinal brush-border membrane vesicles of the suckling rat: Characteristics and maturation
    • Said, H. M., F. K. Ghishan, and R. Redha. 1988. Transport of glycyl-L-proline in intestinal brush-border membrane vesicles of the suckling rat: characteristics and maturation. Biochim. Biophys. Acta 941:232-240.
    • (1988) Biochim. Biophys. Acta , vol.941 , pp. 232-240
    • Said, H.M.1    Ghishan, F.K.2    Redha, R.3
  • 35
    • 0026655596 scopus 로고
    • A new oral cephem, cefdinir: Its structure-activity relationships and biological profile
    • Sakane, K., Y. Inamoto, and T. Takaya. 1992. A new oral cephem, cefdinir: its structure-activity relationships and biological profile. Jpn. J. Antibiot. 45:909-925.
    • (1992) Jpn. J. Antibiot. , vol.45 , pp. 909-925
    • Sakane, K.1    Inamoto, Y.2    Takaya, T.3
  • 36
    • 0342867714 scopus 로고
    • Carrier-mediated transport in drug absorption
    • D. D. Breimer and P. Speiser (ed.), Elsevier Science Publishers B.V., Amsterdam, The Netherlands
    • Sezaki, H., and T. Kimura. 1983. Carrier-mediated transport in drug absorption, p. 133-142. In D. D. Breimer and P. Speiser (ed.), Topics in pharmaceutical sciences. Elsevier Science Publishers B.V., Amsterdam, The Netherlands.
    • (1983) Topics in Pharmaceutical Sciences , pp. 133-142
    • Sezaki, H.1    Kimura, T.2
  • 38
    • 0343302777 scopus 로고
    • Effect of β-lactam antibiotics on cephalexin transport via the proton dependent transport carrier of human intestinal Caco-2 cells. Part II. New synthesis and antibacterial activity
    • American Society for Microbiology, Washington, D.C.
    • Snyder, N. J., A. H. Dantzig, D. O. Spry, and L. B. Tabas. 1991. Effect of β-lactam antibiotics on cephalexin transport via the proton dependent transport carrier of human intestinal Caco-2 cells. Part II. New synthesis and antibacterial activity, abstr. 165, p. 126. In Program and abstracts of the 31st Interscience Conference on Antimicrobial Agents and Chemotherapy. American Society for Microbiology, Washington, D.C.
    • (1991) 31st Interscience Conference on Antimicrobial Agents and Chemotherapy , pp. 126
    • Snyder, N.J.1    Dantzig, A.H.2    Spry, D.O.3    Tabas, L.B.4
  • 39
    • 0343738301 scopus 로고
    • Structure-activity relationship of loracarbef: Antibacterial activity and interaction with the intestinal proton-dependent dipeptide transport carrier of Caco-2 cells
    • J. Einhorn (ed.), American Society for Microbiology, Washington, D.C.
    • Snyder, N. J., L. B. Tabas, D. M. Berry, D. C. Duckworth, D. O. Spry, and A. H. Dantzig. 1993. Structure-activity relationship of loracarbef: antibacterial activity and interaction with the intestinal proton-dependent dipeptide transport carrier of Caco-2 cells, p. 132-133. In J. Einhorn (ed.), Recent advances in chemotherapy. American Society for Microbiology, Washington, D.C.
    • (1993) Recent Advances in Chemotherapy , pp. 132-133
    • Snyder, N.J.1    Tabas, L.B.2    Berry, D.M.3    Duckworth, D.C.4    Spry, D.O.5    Dantzig, A.H.6
  • 40
    • 0343738300 scopus 로고
    • Uptake of β-lactam antibiotics into human intestinal Caco-2 cells via the proton-dependent dipeptide transport carrier
    • American Society for Microbiology, Washington, D.C.
    • Snyder, N. J., L. B. Tabas, D. M. Berry, D. O. Spry, and A. H. Dantzig. 1992. Uptake of β-lactam antibiotics into human intestinal Caco-2 cells via the proton-dependent dipeptide transport carrier, abstr. 1461, p. 354. In Program and abstracts of the 32nd Interscience Conference on Antimicrobial Agents and Chemotherapy. American Society for Microbiology, Washington, D.C.
    • (1992) 32nd Interscience Conference on Antimicrobial Agents and Chemotherapy , pp. 354
    • Snyder, N.J.1    Tabas, L.B.2    Berry, D.M.3    Spry, D.O.4    Dantzig, A.H.5
  • 41
    • 6844222490 scopus 로고
    • The reactions of aliphatic acid chlorides
    • Sonntag, N. O. V. 1953. The reactions of aliphatic acid chlorides. Chem. Rev. 52:237-416.
    • (1953) Chem. Rev. , vol.52 , pp. 237-416
    • Sonntag, N.O.V.1
  • 42
    • 0024355601 scopus 로고
    • C(3)-cyclopropyl cephems and carbacephems
    • Spry, D. O., J. S. Kasher, and N. J. Snyder. 1989. C(3)-cyclopropyl cephems and carbacephems. J. Antibiot. 42:1653-1660.
    • (1989) J. Antibiot. , vol.42 , pp. 1653-1660
    • Spry, D.O.1    Kasher, J.S.2    Snyder, N.J.3
  • 43
    • 0342867710 scopus 로고
    • Effect of β-lactam antibiotics on cephalexin transport via the proton-dependent dipeptide transport carrier of human intestinal Caco-2 cells. Part 1. Clinically used β-lactams
    • American Society for Microbiology, Washington, D.C.
    • Tabas, L. B., L. Bergin, and A. H. Dantzig. 1991. Effect of β-lactam antibiotics on cephalexin transport via the proton-dependent dipeptide transport carrier of human intestinal Caco-2 cells. Part 1. Clinically used β-lactams, abstr. 164, p. 126. In Program and abstracts of the 31st Interscience Conference on Antimicrobial Agents and Chemotherapy. American Society for Microbiology, Washington, D.C.
    • (1991) 31st Interscience Conference on Antimicrobial Agents and Chemotherapy , pp. 126
    • Tabas, L.B.1    Bergin, L.2    Dantzig, A.H.3
  • 45
    • 0029776737 scopus 로고    scopus 로고
    • Metabolism, uptake, and transepithelial transport of the diastereomers of Val-Val in the human intestinal cell line, Caco-2
    • Tamura, K., P. K. Bhatnagar, J. S. Takata, C.-P. Lee, P. L. Smith, and R. T. Borchardt. 1996. Metabolism, uptake, and transepithelial transport of the diastereomers of Val-Val in the human intestinal cell line, Caco-2. Pharm. Res. 13:1213-1218.
    • (1996) Pharm. Res. , vol.13 , pp. 1213-1218
    • Tamura, K.1    Bhatnagar, P.K.2    Takata, J.S.3    Lee, C.-P.4    Smith, P.L.5    Borchardt, R.T.6
  • 46
    • 0030455379 scopus 로고    scopus 로고
    • Metabolism, uptake, and transepithelial transport of the stereoisomers of Val-Val-Val in the human intestinal cell line, Caco-2
    • Tamura, K., C.-P. Lee, P. L. Smith, and R. T. Borchardt. 1996. Metabolism, uptake, and transepithelial transport of the stereoisomers of Val-Val-Val in the human intestinal cell line, Caco-2. Pharm. Res. 13:1663-1667.
    • (1996) Pharm. Res. , vol.13 , pp. 1663-1667
    • Tamura, K.1    Lee, C.-P.2    Smith, P.L.3    Borchardt, R.T.4
  • 47
    • 0002711352 scopus 로고
    • Dilution susceptibility test: Agar and macro-broth dilution procedure
    • E. H. Lennette, A. Balows, W. J. Hausler, Jr., and J. P. Truant (ed.), American Society for Microbiology, Washington, D.C.
    • Washington, J. A., and V. L. Sutter. 1980. Dilution susceptibility test: agar and macro-broth dilution procedure, p. 453-458. In E. H. Lennette, A. Balows, W. J. Hausler, Jr., and J. P. Truant (ed.), Manual of clinical microbiology, 3rd ed. American Society for Microbiology, Washington, D.C.
    • (1980) Manual of Clinical Microbiology, 3rd Ed. , pp. 453-458
    • Washington, J.A.1    Sutter, V.L.2
  • 48
    • 0024433160 scopus 로고
    • Characteristics of tripeptide transport in human jejunal brush-border membrane vesicles
    • Wilson, D., J. A. Barry, and K. Ramaswamy. 1989. Characteristics of tripeptide transport in human jejunal brush-border membrane vesicles. Biochim. Biophys. Acta 986:123-129.
    • (1989) Biochim. Biophys. Acta , vol.986 , pp. 123-129
    • Wilson, D.1    Barry, J.A.2    Ramaswamy, K.3
  • 49
    • 0024307467 scopus 로고
    • Transport characteristics of ceftibuten, a new oral cephem, in rat intestinal BBMV: Proton coupled and stereospecific transport of ceftibuten
    • Yoshikawa, T., N. Muranashi, M. Yoshida, T. Oguma, K. Hirano, and H. Yamada. 1989. Transport characteristics of ceftibuten, a new oral cephem, in rat intestinal BBMV: proton coupled and stereospecific transport of ceftibuten. Pharm. Res. 6:302-307.
    • (1989) Pharm. Res. , vol.6 , pp. 302-307
    • Yoshikawa, T.1    Muranashi, N.2    Yoshida, M.3    Oguma, T.4    Hirano, K.5    Yamada, H.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.