A new series of glycopeptide antibiotics incorporating a squaric acid moiety: Synthesis, structural and antibacterial studies

Journal of Antibiotics

Volumn 59, Issue 9, 2006, Pages 564-582

  Sztaricskai, Ferenc ^a   Batta, Gyula ^a   Herczegh, Pal ^a   Balázs, Attila ^a   Jeko, József ^a   Roth, Erzsébet ^a   Szabó, Pál T ^b   Kardos, Szilvia ^c   Rozgonyi, Ferenc ^c   Boda, Zoltán ^d  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c SEMMELWEIS UNIVERSITY   (Hungary)

^d UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Antibacterial; Glycopeptide antibiotics; Squaric acid amides; Synthesis

Indexed keywords

4 PHENYLBENZYLAMINE; AGLYCO EREMOMYCIN; AGLYCO RISTOCETIN; AGLYCO VANCOMYCIN; AGLYCONE; BENZYLAMINE DERIVATIVE; EREMOMYCIN; HYDROFLUORIC ACID; POLYPEPTIDE ANTIBIOTIC AGENT; RISTOCETIN; RISTOCETIN A; SQUARIC ACID DERIVATIVE; TEICOPLANIN DERIVATIVE; TRIGLYCINE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONFERENCE PAPER; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; GLYCOSIDATION; HYDROLYSIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NITROGEN NUCLEAR MAGNETIC RESONANCE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; VANCOMYCIN RESISTANT ENTEROCOCCUS;

ANTI-BACTERIAL AGENTS; ENTEROCOCCUS FAECALIS; GLYCOPEPTIDES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; RISTOCETIN; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; VANCOMYCIN;

EID: 33751206191     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2006.77     Document Type: Conference Paper

References (31)

1. Sztaricskai F, Bognár R. The chemistry of the vancomycin group of antibiotics in recent developments in the chemistry of natural carbon compounds. Vol. 10: 91-209, Szántay Cs, ed., Akadémiai Kiadó, Budapest (1984)
2. Nicolaou KC, Boddy CN, Bräse S, Winssinger N. Biology and medicine of the glycopeptide antibiotics. Angew Chem Int Ed 38: 2096-2152 (1999)
3. Sztaricskai F, Pelyvás FI. Chemistry of carbohydrate components in glycopeptide antibiotics. Drugs and Pharm.Sci., Nagarajan R, ed., Marcel Dekker Inc. New York, 63: 105-193 (1994)
4. Williams DH, Bardsley B. The vancomycin group of antibiotics and the fight against resistant bacteria. Angew Chem Int Ed 38: 1172-1193 (1999)
5. Wanner J, Tang O, Mclomas CC, Crowley BM, Jiang W, Moss J, Boger DL. A new improved method for deglycosidation of glycopeptide antibiotics exemplified with vancomycin, ristocetin and ramoplanin. Bioorg Med Chem Lett 13: 1169-1173 (2003)
6. Ellestad GA, Leese RA, Morton GO, Barbatschi F, Gorew E, McGahren WJ. Avoparcin and epiavoparcin. J Am Chem Soc 103: 5522-5524 (1981)
7. Herrin TR, Thomas AM, Perun IJ, Mao JC, Fesik SN. Preparation of biologically active ristocetin derivatives replacements of the 1′-amino group. J Med Chem 28: 1371-1375 (1985)
8. Tietze LF, Arlt M, Beller M, Glüsenkamp KH, Jäde E, Rajewsky MF. Squaric acid diethyl ester: a new coupling reagent for the formation of drug biopolymer conjugates. Synthesis of squaric acid ester amides and diamides. Chem Ber 124: 1215-1221 (1991)
9. Tevyashova A, Sztaricskai F, Batta Gy, Herczegh P, Jeney A. Formation of squaric acid amides of anthracycline antibiotics. Synthesis and cytotoxic properties. Bioorg Med Chem Lett 14: 4783-4789 (2004)
10. Sztaricskai F, Sum A, Roth E, Pelyvás FI, Sándor Sz, Batta Gy, Herczegh P, Reményi J, Miklán Zs, Hudecz F. A new class of semisynthetic anthracycline glycoside antibiotics incorporating a squaric acid moiety. J Antibiot 58: 704-714 (2005)
11. Cooper RDG, Snyder NJ, Zweifel MJ, Staszak MA, Wilkie SC, Nicas TI, Mullen DL, Butler ThF, Rodriguez MJ, Huff BE, Thomspson RC. Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity. J Antibiot 49: 575-581 (1996)
12. Kahne D, Leimkuhler C, Lu W, Walsch Ch. Glycopeptide and lipoglycopeptide antibiotics. Chem Rev 105: 425-448 (2005)
13. Mu YQ, Nodwell M, Pace JL, Shaw J-J, Judice JK. Vancomycin disulfide derivatives as antibacterial agents. Bioorg Med Chem Lett 14: 735-738 (2004)
14. Kobrin MB, Katrukha HS, Fedorova GB. Preparation and properties of derivatives at the amino group of ristocetin aglycone. J Antibiot 42: 1441-1442 (1989)
15. Pavlov AYu, Olsuf'eva EN, Miroshnikova OM, Reznikova MI, Lazhko EI, Malabarba A, Ciabatti R, Preobrazhenskaya MN. Synthesis and antibacterial activity of nonnatural. aglycones of glycopeptide antibiotics of the vancomycin group. Russian J Bioorg Chem 23: 383-393 (1997)
16. Printsevskaya A, Solovieva SE, Olsufjeva EN, Mirchink EP, Isakova EB, DeClerq E, Balzarini J, Preobrazhenskaya MN. Structure-activity relationship studies of a series of antiviral and antibacterial aglycon derivatives of the glycopeptide antibiotics vancomycin, eremomycin, and dechloroeremomycin. J Med Chem 48: 3885-3890 (2005)
17. Hawkes GE, Molinari H, Singh S, Lian LY. A N-15 NMR study of intermolecular interactions between vancomycin and AC-D-Ala-D-Ala. J Magnetic Resonance 74: 188-192 (1987)
18. Molinari H, Pastore A, Lian LY, Hawkes GE, Sales K. Structure of vancomycin and a vancomycin/D-Ala-D-Ala complex in solution. Biochemistry 29: 2271-2277 (1990)
19. 15NMR. Chem Comm 501-502 (2001)
20. Malabarba A, Ferrari P, Gallo GG, Kettenring J, Cavalleri B. Teicoplanin, antibiotics from Actinoplanes teichomyceticus Nov. sp. J Antibiot 39: 1430-1442 (1986)
21. Bongini A, Feeney J, Williamson MP, Williams DH. Assignment of the carbon-13 spectrum of vancomycin and its derivatives. J Chem Soc Perkin Trans 2 201-206 (1981)
22. Williamson MP, Williams DH. A carbon-13 nuclear magnetic esonance study of ristocetin A and B and their derivatives. J Chem Soc Perkin Trans 1 1483-1491 (1981)
23. 13C assignment, motial behaviour, dimerization and complexation with Ac-D-Ala-D-Ala. J Antibiot 44: 1208-1221 (1991)
24. Loll PJ, Axelsen PH. The structural biology of molecular recognition by vancomycin. Annual Review of Biophysics and Biomolecular Structure 29: 265-289 (2000)
25. ACD Software; Toronto, ON, Canada, M5H 3V9; www.acdlabs.com
26. Boger DL. Vancomycin, teicoplanin and ramoplanin: synthetic and mechanistic studies. Med Research Reviews 21: 356-381 (2001)
27. Knausz M, Ghidán Á, Grossato A, Rozgonyi F. Rapid detection of methicillin resistance in teicoplanin-resistant coagulase-negative Staphylococci by a penicillin-binding protein 2′ latex agglutination method. J Microbiol Methods 60: 413-416 (2005)
28. Ghidán Á, Jeney Cs, Maródi LCs, Csiszár K, Rozgonyi F. PCR detection of the vanA gene in a vancomycin-resistant Enterococcus faecalis clinical isolate from Hungary. J Antimicrob Chemother 46: 325-327 (2000)
29. National Committee for Clinical Laboratory Standards Performance Standards for Antimicrobial Susceptibility Testing. 12th Informational supplement M100-S12. NCCLS, Wayne, PA. USA (2002)
30. Ford ChW. In: Oxazolidinones: a new class of antibiotics. Ed., Moellering R Jr., 8th International Congress on Infections Diseases Industry-Sponsored Symposium, (Pharmacia and Upjohn), Boston, May 17 (1998)
31. Goddard TD, Kneller DG. SPARKY 3, University of California, San Francisco