Synthesis and antibacterial evaluation of some teicoplanin pseudoaglycon derivatives containing alkyl-and arylthiosubstituted maleimides

Journal of Antibiotics

Volumn 68, Issue 9, 2015, Pages 579-585

  Csávás, Magdolna ^a   Miskovics, Adrienn ^a   Szcs, Zsolt ^a   Rth, Erzsébet ^a   Nagy, Zsolt L ^a   Bereczki, Ilona ^a   Herczeg, Mihály ^a   Batta, Gyula ^b   Nemes Nikodém, Éva ^c   Ostorházi, Eszter ^c   Rozgonyi, Ferenc ^c   Borbás, Anikó ^a   Herczegh, Pál ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c SEMMELWEIS UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; MALEIMIDE DERIVATIVE; TEICOPLANIN; TEICOPLANIN DERIVATIVE; TEICOPLATIN PSEUDOAGLYCON DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACILLUS SUBTILIS; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; LIPOPHILICITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; METHICILLIN SUSCEPTIBLE STAPHYLOCOCCUS AUREUS; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS EPIDERMIDIS; SUBSTITUTION REACTION; BACTERIUM; CHEMISTRY; DRUG EFFECTS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACTERIA; DRUG RESISTANCE, BACTERIAL; MALEIMIDES; TEICOPLANIN;

EID: 84942754388     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2015.33     Document Type: Article

References (25)

1. Kahne, D., Leimkuhler, C., Lu, W. & Walsh, C. Glycopeptide and lipoglycopeptide antibiotics. Chem. Rev. 105, 425-448 (2005).
2. von Nussbaum, F., Brands, M., Hinzen, B., Weigand, S. & Habich, D. Antibacterial natural products in medicinal chemistry-exodus or revival? Angew. Chem. Int. Ed. Engl. 45, 5072-5129 (2006).
3. Kristóf, K. et al. Significance of methicillin-Teicoplanin resistant Staphylococcus haemolyticus in bloodstream infections in patients of the Semmelweis University hospitals in Hungary. Eur. J. Clin. Microbiol. Infect. Dis. 30, 691-699 (2011).
4. Xu, H.-W., Shang-Shang Qin, S.-S. & Liu, H.-M. New synthetic antibiotics for the treatment of enterococcus and campylobacter infection. Current Topics Med. Chem. 14, 21-39 (2014).
5. James, R. C., Pierce, J. G., Okano, A., Xie, J. & Boger, D. L. Redesign of glycopeptide antibiotics: Back to the future. ACS Chem. Biol. 7, 797-804 (2012).
6. Ashford, P.-A. & Bew, S. P. Recent advances in the synthesis of new glycopeptide antibiotics. Chem. Soc. Rev. 41, 957-978 (2012).
7. Cooper, R. D. et al. Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity. J. Antibiot. 49, 575-581 (1996).
8. Judice, J. K. & Pace, J. L. Semi-synthetic glycopeptide antibacterials. Bioorg. Med. Chem. Lett. 13, 4165-4168 (2003).
9. Malabarba, A. & Ciabatti, R. Glycopeptide derivatives. Curr. Med. Chem. 8, 1759-1773 (2001).
10. Sztaricskai, F. et al. N-glycosylthioureido aglyco-ristocetins without platelet aggregation activity. J. Antibiot. 60, 529-533 (2007).
11. Pintér, G. et al. Click reaction synthesis of carbohydrate derivatives from ristocetin aglycon with antibacterial and antiviral activity. Bioorg. Med. Chem. Lett. 20, 2713-2717 (2010).
12. Sipos, A. et al. Synthesis of isoindole and benzoisoindole derivatives of teicoplanin pseudoaglycon with remarkable antibacterial and antiviral activities. Bioorg. Med. Chem. Lett. 22, 7092-7096 (2012).
13. Sipos, A. et al. Synthesis of fluorescent ristocetin aglycon derivatives with remarkable antibacterial and antiviral activities. Eur. J. Med. Chem. 56, 361-367 (2012).
14. Naesens, L. et al. Anti-influenza virus activity and structure-Activity relationship of aglycoristocetin derivatives with cyclobutenedione carrying hydrophobic chains. Antiviral Res. 82, 89-94 (2009).
15. Vanderlinden, E. et al. Intracytoplasmic trapping of influenza virus by a lipophilic derivative of aglycoristocetin. J. Virol. 86, 9416-9431 (2012).
16. Pintér, G. et al. A 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, 6053-6061 (2009).
17. Bereczki, I. et al. Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: synthesis and antiviral studies. Bioorg. Med. Chem Lett. 24, 3251-3254 (2014).
18. Smith, M. E. B. et al. Protein modification, bioconjugation, and disulfide bridging using bromomaleimides. J. Am. Chem. Soc. 132, 1960-1965 (2010).
19. Schumacher, F. F. et al. In situ maleimide bridging of disulfides and a new approach to protein PEGylation. Bioconj. Chem. 22, 132-136 (2011).
20. Ryan, C. P. et al. Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis. Chem. Commun. 47, 5452-5454 (2011).
21. Schumacher, F. F. et al. Next generation maleimides enable the controlled assembly of antibody-drug conjugates via native disulfide bond bridging. Org. Biomol. Chem. 12, 7261-7269 (2014).
22. Castañeda, L. et al. A mild synthesis of N-functionalised bromomaleimides, thiomaleimides and bromopyridazinediones. Tetrahedron Lett. 54, 3493-3495 (2003).
23. Marminon, C. et al. Syntheses and antiproliferative activities of rebeccamycin analogues bearing two 7-Azaindole moieties. Bioorg. Med. Chem. 11, 679-687 (2003).
24. Sztaricskai, F. et al. A new series of glycopeptide antibiotics incorporating a squaric acid moiety. J. Antibiot. 59, 564-582 (2006).
25. Martins Alho, M. A., D'Accorso, N. B. & Thiel, I. M. E. Syntheses of some 6-Sheterocyclic derivatives of 1, 2:3, 4-di-O-isopropylidene-α-D-galactopyranose. J. Heterocyclic Chem. 33, 1339-1343 (1996).