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Review

Recent developments in reversing glycopeptide-resistant pathogens

Pages 1005-1019 | Published online: 25 Feb 2005

Bibliography

  • PARENTI F, CAVALLERI B: Novel glycopeptide antibiotics of the dalbaheptide group. Drugs Future (1990) 15:57–72.
  • NAGARAJAN R: Structure activity relationships of vancomycin-type glycopeptides antibiotics. J. Antibiot. (1993) 46:1181–1195.
  • NAGARAJAN R: Glycopeptide Antibiotics. Marcel Dekker, Inc. New York (1994).
  • WILLIAMS DH: Structural studies on some antibiotics ofthe vancomycin group, and on the antibiotic-receptor complexes, by 111 NMR. Acc. Chem. Res. (1984) 17:364–369.
  • COURVALIN P: Resistance of enterococci to glycopep-tides. Antimicrob. Agents Chemother. (1990) 34:2291–2296.
  • •Review of the genetics and mechanisms of glycopeptide resistance in enterococci.
  • WALSH CT, FISHER SL, PARK IS, PRAHALAD M, WU Z: Bacterial resistance to vancomycin: five genes and one missing hydrogen bond tell the story. Chem. Biol. (1996) 3:21–28.
  • ••Recent review of genetics and enzymology of glycopeptideresistance in enterococci.
  • SWARTZ MN: Hospital-acquired infections: diseases with increasingly limited therapies. Proc. Natl. Acad. ScL USA (1994) 91:2420–2427.
  • MALABARBA A, NICAS T I, THOMPSON RC: Structural modifications of glycopeptide antibiotics. Med. Res. Rev. (1997) 17:69–137.
  • •A survey of the most active semi-synthetic glycopeptides synthesised in Biosearch Italia SpA and Eli Lilly & Co.
  • SETTI EL, QUATTROCCHIO L, MICETICH RG: Current approaches to overcome bacterial resistance. Drugs Future (1997) 22:271–284.
  • NICCOLAI D, TARSI L, THOMAS RJ: The renewed challenge of antibacterial chemotherapy. J. Chem. Soc. Chem. Commun. (1997) 2333–2342.
  • MALABARBA A, CIABATTI, R, ROMANO G et al: BI-397: anew developmental semisynthetic glycopeptide antibiotic. 38th ICAAC. San Diego, USA (1998). Abstract A–107.
  • RODRIGUEZ MJ, SNYDER NJ, ZWEIFEL MJ et al.: Novel glycopeptide antibiotics: N-alkylated derivatives active against vancomycin-resistant enterococci. J. Antibiot. (1998) 51:560–569.
  • ZELENITSKY SA, KARLOWSKY JA, ZHANEL GG, HOBAN DJ, NICAS T: Time-kill curves for a semisynthetic glycopeptide, LY 333328, against vancomycin-susceptible and vancomycin-resistant enterococcus faecium strains. Antimicrob. Agents Chemother. (1997) 41:1407–1408.
  • HARLANDS S, TEBBS SE, ELLIOTT TS: Evaluation of the in-vitro activity of the glycopeptide antibiotic LY 333328 in comparison with vancomycin and teicoplanin. j Antimicrob. Chem other. (1998) 41:273–276.
  • MALABARBA A: New approaches to the treatment of vancomycin-resistant bacterial infections. Exp. Opin. Ther. Patents (1996) 6(7)627–644.
  • CHIEN J, ALLERHEILIGEN S, PHILLIPS D, CERIMELE B, THOMASSON HR: Safety and pharmacokinetics of single intravenous doses of LY 333328 diphosphate (glycopeptide) in healthy men. 38th ICAAC. San Diego, USA (1998). Abstract A–55.
  • BORGHI A, SPREAFICO F, BERETTA G et al.: Deacylation of the glycopeptide antibiotic A40926 by actinoplanes teichomyceticus ATCC 31121. J. Antibiot. (1996) 49:607–609.
  • PAVLOV AY, PREOBRAZHENSKAYA MN, MALABARBA A,CIABATTI R: Synthesis and antibacterial activity of derivatives of the glycopeptide antibiotic A-40926 N-alkylated at the aminoglucuronyl moiety. J. Antibiot. (1998) 51:525–527.
  • PANZONE G, FERRARI P, KURZ M, TRANI A: A novel glycopeptide carrying a 3-oxazolin-5-one ring obtained by intra-molecular cyclization. J. Antibiot. (1998) 51:872–879.
  • PAVLOV AY, LAZHKO El, PREOBRAZHENSKAYA MN: Anew type of chemical modification of glycopeptides antibiotics: aminomethylated derivatives of eremomy-cin and their antibacterial activity. J. Antibiot (1997) 50:509–513.
  • PAVLOV AY, PREOBRAZHENSKAYA MN, MALABARBA A,CIABATTI R, COLOMBO L: Mono and double modified teicoplanin aglycon derivatives on the amino acid No. 7: structure-activity relationship. J. Antibiot. (1998) 51:73–78.
  • SHI, Z, GRIFFIH JH: Catalysis of carbamate hydrolysisby vancomycin and semisynthetic derivatives. J. Am. Chem. Soc. (1993) 115:6482–6486.
  • SUNDRAM UN, GRIFFIH JH: General and efficientmethod for the solution- and solid-phase synthesis of vancomycin carboxamide derivatives. J. Org. Chem. (1995) 60:1102–1103.
  • RAO J, COLTON IJ, WHITESIDES GM: Using capillaryelectrophoresis to study the electrostatic interaction involved in the association of El-Ala-El-Ala with vancomycin. J. Am. Chem. Soc. (1997) 119:9336–9340.
  • SYNDER NJ, COOPER RDG, BRIGGS BS et al: Enzymaticdeacylation of teicoplanin followed by reductive alkylation: synthesis and antibacterial activity of new glycopeptides. j Antibiot. (1998) 51:945–951.
  • MALABARBA A, CIABATTI R: Reductive Hydrolysis of the59,60-amide bond of tricoplanin antibiotics: a key step from natural to synthetic glycopeptides. J. Med. Chem. (1994) 37:2988–2990.
  • MALABARBA A, CIABATTI R, KETTENRING J et al.: Structure modification of the active site in teicoplanin and related glycopeptides. 1. Reductive hydrolysis of the 1,2- and 2,3-peptide bonds. J. Org. Chem. (1996) 61:2137–2150.
  • ••Methodology for the highly regioselective reductivecleavage of 1,2 and 2,3-amide bonds was detailed. Synthesis of teicoplanin derivatives with enlarged F-O-G ring was included.
  • MALABARBA A, CIABATTI R, MAGGINI M, FERRARI P, COLOMBO L, DENARO M: Structure modification of the active site in teicoplanin and related glycopeptides. 2. Deglucoteicoplanin-derived tetrapeptide. J. Org. Chem. (1996) 61:2151–2157.
  • ••Detailed synthesis of deglucoteicoplanin-derived tetrapep-tide via reductive hydrolysis of specific amide bond followed by double Edman degradation.
  • MALABARBA A, CIABATTI R, GERLI E et al.: Substitution of amino acids 1 and 3 in teicoplanin aglycon: synthesis and antibacterial activity of three first non-natural dalbaheptides. J. Antibiot. (1997) 50:70–81.
  • •Synthetic glycopeptides derived from the substitution of amino acid 1 of deglucoteicoplanin with D-lysine or D-N-methyl leucine and of its amino acid 3 with L-phenylalanine or L-lysine were investigated.
  • WILLIAMS DH: The glycopeptide story-how to kill the deadly `superbugs'. Nat. Prod. Rep. (1996) 13:469–477.
  • ••Recent review on the structures and mode of action ofvancomycin group glycopeptides. Contribution of dimerisa-tion and membrane anchoring effect to the overall antibac-terial activities of glycopeptides was discussed.
  • SHARMAN GJ, TRY AC, DANCER R et al: The role of dimerization and membrane anchoring in activity of glycopeptide antibiotics against vancomycin-resistant bacteria. J. Am. Chem. Soc. (1997) 119:12041–12047.
  • LOLL PJ, BEVIVINO AE, KORTY BD, AXELSEN PH: Simultaneous recognition of a carboxylate-containing ligand and an intramolecular surrogate ligand in the crystal structure of an asymmetric vancomycin dimer. J. Am. Chem. Soc. (1997) 119:1516–1522.
  • •First crystal structure of vancomycin.
  • SUNDRAM UN, GRIFFIN JH, NICAS TI: Novel vancomycindimers with activity against vancomycin-resistant enterococci. J. Am. Chem. Soc. (1996) 118:13107–13108.
  • ••Novel covalently linked head-to-head dimers were synthe-sised and anti-VRE activities were reported.
  • RAO J, WHITESIDES GM: Tight binding of a dimeric derivative of vancomycin with dimeric I.-Lys-El-Ala-El-Ala. J. Am. Chem. Soc. (1997) 119:10286–10290.
  • RAO JH, LAHIRI J, ISAACS L, WEISS RM, WHITESIDES GM:A trivalent system from vancomycin-D-Ala-D-Ala with higher affinity than avidin-biotin. Science (1998) 280:708–711.
  • STAROSKE T, WILLIAMS DH: Synthesis of covalent head-to-tail dimers of vancomycin. Tetrahedron Lett. (1998) 39:4917–4920.
  • ••Novel covalently linked head-to-tail dimers weresynthesised.
  • WILLIAMS DH, BARDSLEY B: The vancomycin group of antibiotics and the fight against resistant bacteria. Angew. Chem. Int. Ed. Engl. (1999) 38:1173–1193.
  • ••An overview of the structure and mode of action of thevancomycin family glycopeptides.
  • GE M, CHEN Z, ONISHI HR et al.: Vancomycin deriva- tives that inhibit peptidoglycan biosynthesis without binding El-Ala-El-Ala. Science (1999) 284:507–511.
  • ••New insight on the mode of action of LY 333328. Inhibitionof transglycosylation independent of peptide binding was proposed as principal mechanism of LY 333328 against VRE.
  • BARRIERE JC, BOUANCHAUD DH, PARIS JM, ROLIN O, HARRIS NV, SMITH C: Antimicrobial activity against staphylococcus aureus of semisynthetic injectable streptogramins: RP59500 and related compounds. J. Antimicrob. Chemother. (1992) 30:1–8.
  • COCITO C, GIAMBATTISTA MD, NYSSEN E, VANNUFFELP: Inhibition of protein synthesis by streptogramins and related antibiotics. J. Antimicrob. Chemother. (1997) 39(Suppl. A7–13).
  • •Mode of action of RP-59500.
  • MAHAYNI R, PERRI MB, DEMBRY LM, ZERVOS MJ Comparative in-vitro and bactericidal activity of RP-59500 (quinupristin/dalfopristin), against multi- drug resistant E. faecium. 34th ICAAC. Orlando, USA (1994). Abstract E3.
  • ELIOPOULOS GM, WENNERSTEN CB, GOLD HS et al: Characterization of vancomycin-resistant enterococci faecium in vitro isolates from the United States and their susceptibility to dalfopristin-quinupristin. Antimicrob. Agents Chemother. (1998) 42:1088–1092.
  • PECHERE JC: In-vitro activity of RP-59500, a semisyn-thetic streptogramin, against staphylococci and streptococci. j Antimicrob. Chemother. (1992) 30:15–18.
  • LINDEN P, PASCULLE AW, MCDEVITT D, DOTTERWEICH L: Emergence of superinfection with enterococcus faecalis during RP-59500 treatment of vancomycin-resistant enterococcus faecium infection (VREF). 36th ICAAC. New Orleans, USA (1996). Abstract LM32.
  • HANG SL, RYBAK MJ: In vitro bactericidal activity of RP-59500 (quinupristin/dalfopristin; RP) alone and in combination against resistant strains of enterococcus species and staphylococcus aureus (SA). 35th ICAAC. Sans Francisco, USA (1995). Abstract E–121.
  • GANGULY AK, MCCORMICK JL, SAKSENA AK, DAS RP, CHAN TM: Chemical modifications and structure activity studies of ziracin and related everninomicin antibiotics. Bioorg. Med. Chem. Lett. (1999) 9:1209–1214.
  • MURAKAMI H, HANAKI H, SASAKI K, INABA Y, HORI N, HIRAMATSU K: In vitro activity of Everninomicin (EVNM, ziracin), a new injectable antibiotic, against clinically isolated strains including vancomycin low-resistant staphylococcus and VRE. 38th ICAAC. San Diego, USA (1998). Abstract E–120.
  • BLACK TA, ZHAO W, SHAW KJ, HARE S: Physiological investigation on the mechanism of action of SCH 27899 (Ziracin). 38th ICAAC. San Diego, USA (1998). Abstract C–106.
  • TSITSI JML, CALVER AD, LUKE B et al.: A double-blind, randomized, multicenter study of ziracin versus ceftriaxone in patients with S. pneumoniae. 38th ICAAC. San Diego, USA (1998). Abstract L–109.
  • BRIELAND JK, LOEBENBERG D, MENZEL F, CACCIA PA, HARE R: Efficacy of ziracine (SCH 27899), a new everninomicin antibiotic, against a replicative legionella pneumopphila lung infection in mice. 38th ICAAC. San Diego, USA (1998). Abstract B–44.
  • AARESTRUP FM: Association between decreased susceptibility to a new antibiotic for treatment of human diseases, everninomicin (SCH 27899), and resistance to an antibiotic used for growth promotion in animals, avilamycin. Microb. Drug Resist. (1998) 4:137–141.
  • LIN AH, MURRAY RW, MAROTTI KR: Linezolid binds to the 50S ribosomal subunit and competes with the binding of eperezolid, chloramphenicol and lincomycin. 37th ICAAC. Toronto, Canada (1997). Abstract C–101.
  • DEMYAN WF, SWANEY SM, SHINABARGER DL: The oxazolidinone linezolid inhibits translation initiation in bacteria. 37th ICAAC. Toronto, Canada (1997). Abstract C–102.
  • STALKER DJ, WAJSZCZUK CP, BATTS DH: Linezolidsafety, tolerance, and pharmacokinetics following oral dosing twice daily for 14.5 days. 37th ICAAC Toronto, Canada (1997). Abstract A–115.
  • BRICKNER SJ, HUTCHINSON DK, BARBACHYN MR et al:Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug resistant Gram positive bacterial infections. J. Med. Chem. (1996) 39:673–679.
  • ZHU J: SNAr based macrocyclization via birayl etherformation: application in natural product synthesis. Synlett (1997) 133–144.
  • •New cycloetherification reaction useful for the synthesis of vancomycin type glycopeptides.
  • EVANS DA, WOOD MR, TROTTER BW, RICHARDSON TI, BARROW JC, KATZ JL: Total synthesis of vancomycin and eremomycin aglycons. Angew. Chem. Int. Ed. Engl. (1998) 37:2700–2704.
  • •Total synthesis of vancomycin aglycon.
  • NICOLAOU KC, TAKAYANAGI M, JAIN NF et al.: Total synthesis of vancomycin aglycon-part 3: final stages. Angew. Chem. Int. Ed. Engl. (1998) 37:2717–2719.
  • •Total synthesis of vancomycin aglycon.
  • BOGEL D, MIYAZAKI S, KIM SH, WU JH, LOISELEUR O, CASTLE SL: Diastereoselective total synthesis of the vancomycin aglycon with ordered atropisomer equili- brations. J. Am. Chem. Soc. (1999) 121:3226–3227.
  • •Total synthesis of vancomycin aglycon.
  • GERHARD U, MACKAY JP, MAPLESTONE RA, WILLIAMS DH: The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics. J. Am. Chem. Soc. (1993) 115:232–237.
  • GRDADOLNIK SG, PRISTOVSEK P, MIERKE DF: Vancomycin: conformational consequences of the sugar substituent. J. Med. Chem. (1998) 41:2090–2099.
  • NICOLAOU KC, MITCHELL HJ, JAIN NF, WINSSINGER N,HUGHES R, BANDO T: Total synthesis of vancomycin. Angew. Chem. Int. Ed. Engl. (1999) 38:240–244.
  • THOMPSON C, GE M, KAHNE D: Synthesis of vancomycin from the aglycon. J. Am. Chem. Soc. (1999) 121:1237–1244.
  • LAZZARINI A, BORGHI A, ZERILLI LF, FERRARI P, COLOMBO L, LANCINI GC: Novel teicoplanins by directed biosynthesis. J. Antibiot (1997) 50:180–183.
  • WU Z, WALSH CT: Phosphinate analogs of D,D-dipeptides: slow-binding inhibition and proteolysis protection of VanX, a D-,D-dipeptidase required for vancomycin resistance in Enterococcus faecium. Proc. Natl. Acad. Sci. USA (1995) 92:11603–11607.
  • ELLSWORTH BA, TOM NJ, BARTLETT PA: Synthesis and evaluation of inhibitors of bacterial u-alanine:o-alanine ligases. Chem. Biol. (1996) 3:37–44.
  • WU Z, WALSH CT: Dithiol compounds: potent, time-dependent inhibitors of VanX, a zinc-dependent D,D-dipeptidase required for vancomycin resistance in Enterococcus faecium. J. Am. Chem. Soc. (1996) 118:1785–1786.

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