Nano-sized clusters of a teicoplanin ψ-aglycon-fullerene conjugate. Synthesis, antibacterial activity and aggregation studies

European Journal of Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 943-948

  Tollas, Szilvia ^a   Bereczki, Ilona ^a   Sipos, Attila ^a   Rth, Erzsébet ^a   Batta, Gyula ^b   Daróczi, Lajos ^b   Kéki, Sándor ^b   Ostorházi, Eszter ^c   Rozgonyi, Ferenc ^c   Herczegh, Pál ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c SEMMELWEIS UNIVERSITY   (Hungary)

Author keywords

1,3 Dipolar cycloaddition; Fullerene; Multivalent aggregates; Teicoplanin aglycone

Indexed keywords

FULLERENE DERIVATIVE; PSI AGLYCONE FULLERENE; TEICOPLANIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; CYCLOADDITION; DRUG CONJUGATION; DRUG SYNTHESIS; LIGHT SCATTERING;

ANTI-BACTERIAL AGENTS; BACTERIA; CHEMISTRY TECHNIQUES, SYNTHETIC; FULLERENES; TEICOPLANIN;

EID: 84864412443     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.054     Document Type: Article

References (26)

1. A. Malabarba, T.I. Nicas, and R.S. Thompson Structural modifications of glycopeptide antibiotics Med. Res. Rev. 17 1997 69 137 (Pubitemid 27038263)
2. K.C. Nicolaou, C.N.C. Boddy, S. Brase, and N. Winssinger Chemistry, biology, and medicine of the glycopeptide antibiotics Angew. Chem. Int. Ed. 38 1999 2096 2152
3. D. Kahne, C. Leimkuhler, W. Lu, and C. Walsh Glycopeptide and lipoglycopeptide antibiotics Chem. Rev. 105 2005 425 448 (Pubitemid 40356089)
4. R. Nagarajan, A.A. Schabel, J.L. Occolowitz, F.T. Counter, J.L. Ott, and A.M. Felty-Duckworth Synthesis and antibacterial evaluation of N-alkyl vancomycins J. Antibiot. 42 1989 63 72 (Pubitemid 19045380)
5. J.K. Judice, and J.L. Pace Semi-synthetic glycopeptide antibacterials Bioorg. Med. Chem. Lett. 13 2003 4165 4168 (Pubitemid 37410305)
6. R.D. Cooper, N.J. Snyder, M.J. Zweifel, M.A. Staszak, S.C. Wilkie, T.I. Nicas, D.L. Mullen, T.F. Butler, M.J. Rodriguez, B.E. Huff, and R.C.Thompson Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity J. Antibiot. 49 1996 575 581 (Pubitemid 26235668)
7. F. Sztaricskai, Gy Batta, P. Herczegh, A. Balázs, J. Jek, E. Rth, P.T. Szabó, S. Kardos, F. Rozgonyi, and Z. Boda A new series of glycopeptide antibiotics incorporating a squaric acid moiety. Synthesis, structural and antibacterial studies J. Antibiot. 59 2006 564 582 (Pubitemid 44787683)
8. L. Naesens, E. Vanderbinden, E. Rth, J. Jek, G. Andrei, R. Snoeck, C. Pannecogne, E. Illyés, Gy Batta, P. Herczegh, and F. Sztaricskai Anti-influenza virus activity and structure-activity relationship of aglycoristocetin derivatives with cyclobutene-dione carrying hydrophobic chains Antivir. Res. 82 2009 89 94
9. G. Pintér, Gy. Batta, S. Kéki, A. Mándi, I. Komáromi, K. Takács-Novák, F. Sztaricskai, E. Rth, E. Ostorházi, F. Rozgonyi, L. Naesens, and P. Herczegh Diazo transfer-click reaction route to new, lipophilic teicoplanin and ristocetin aglycon derivatives with high antibacterial and anti-influenza virus activity: an aggregation and receptor binding study J. Med. Chem. 52 2009 6053 6061
10. G. Werner, T.M. Coque, A.M. Hammerum, R. Hope, W. Hryniewicz, A. Johnson, I. Klare, K.G. Kristinsson, R. Leclercq, C.H. Lester, M. Lillie, C. Novais, B. Olsson-Liljequist, L.V. Peixe, E. Sadowy, G.S. Simonsen, J. Top, J. Vuopio-Varkila, R.J. Willems, W. Witte, and N. Woodford Emergence and spread of vancomycin resistance among enterococci in Europe Euro. Surveill. 13 47 2008 562 572
11. S. Evers, R. Quintilioni, and P. Courvalin Genetics of glycopeptide resistance in enterococci Microb. Drug Resist. 2 1996 219 223 (Pubitemid 26249929)
12. C.T. Walsh, S.L. Fisher, I.S. Park, M. Prahalad, and Z. Wu Bacterial resistance to vancomycin: five genes and one missing hydrogen bond tell the story Chem. Biol. 3 1996 21 28 (Pubitemid 126682705)
13. U.N. Sundram, J.H. Griffin, and T.I. Nicas Novel vancomycin dimers with activity against vancomycin-resistant enterococci J. Am. Chem. Soc. 118 1996 13107 13108 (Pubitemid 27055331)
14. K.C. Nicolaou, R. Hughes, S.Y. Cho, H. Winssinger, H. Labischinshi, and R. Endermann Synthesis and biological evaluation of vancomycin-resistant bacteria: target-accelerated combinatorical synthesis Chem-Eur J. 7 2001 3824 3843 (Pubitemid 32845429)
15. J. Rao, J. Lahiri, R.M. Weis, and G.M.Whitesides Design, synthesis and characterisation of a high-affinity trivalent system derived from vancomycin on l-Lys-d-Ala-d-Ala J. Am. Chem. Soc. 122 2000 2698 2710 (Pubitemid 30191027)
16. H. Arimoto, K. Nishimura, T. Kinumi, I. Hayakawa, and D. Uemura Multi-valent polymer on vancomycin: enhanced antibacterial activity against VRE Chem. Commun. 1999 1361 1362 (Pubitemid 29373722)
17. E.-Y. Zhang, and C.-R. Wang Fullerene self-assembly and supramolecular nanostructures Curr. Opin. Colloid Interface Sci. 14 2009 148 156
18. A. Hirsch, and M. Brettreich Fullerenes - Chemistry and Reactions 2005 Wiley-VCH
19. R. Partha, and J.L.Conyers Biomedical applications of functionalized fullerene-based nanomaterials Int. J. Nanomed. 4 2009 261 275
20. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew. Chem. Int. Ed. 40 2001 2004 2021
21. C.W. Tornoe, C. Christensen, and M. Meldal Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper (I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67 2002 3057 3064 (Pubitemid 34457265)
22. M. Prato, and M. Maggini Fulleropyrrolidines: a family of full-fledged fullerene derivatives Acc. Chem. Res. 31 1998 519 526 (Pubitemid 128473644)
23. C.G. Parker, R.A. Domaoal, K.S. Anderson, and D.A. Spiegel An antibody-recruiting small molecule that targets HIV gp120 J. Am. Chem. Soc. 45 2009 16392 16394
24. P.S. Shirude, V.A. Kumar, and K.N. Ganesh BisPNA targeting to DNA: effect of neutral loop on DNA duplex strand invasion by aepPNA-N7GlaepPNA-C substituted peptide nucleic acids Eur. J. Org. Chem. 24 2005 5207 5215
25. S. Samal, and K.E. Geckeler Unexpected solute aggregation in water on dilution Chem. Comm. 2001 2224 2225 (Pubitemid 33052114)
26. F. Hallwass, M. Engelsberg, and A.M. Simas Lack of evidence of dilution history-dependence upon solute aggregation in water. A nuclear magnetic resonance determination of self-diffusion coefficients Chem. Comm. 2002 2530 2531 (Pubitemid 36158609)