Structure–activity studies on polymyxin derivatives carrying three positive charges only reveal a new class of compounds with strong antibacterial activity

Peptides

Volumn 91, Issue , 2017, Pages 8-12

  Vaara, Martti ^a,b,c   Vaara, Timo ^a   Tyrrell, Jonathan M ^d  

^a Technopolis   (Finland)

^b HELSINKI UNIVERSITY CENTRAL HOSPITAL   (Finland)

^c UNIVERSITY OF HELSINKI   (Finland)

^d Department of Medical Microbiology Infectious Disease   (United Kingdom)

Author keywords

Acinetobacter baumannii; Escherichia coli; Excretion to urine; HK 2; Klebsiella pneumoniae; NAB739, NAB815; Nephrotoxicity; Pseudomonas aeruginosa

Indexed keywords

ANTIBIOTIC AGENT; COLISTIN; NAB 739; NAB 743; NAB 803; NAB 805; NAB 807; NAB 809; NAB 812; NAB 813; NAB 814; NAB 815; NAB 816; NAB 817; NAB 818; NAB 819; NAB 820; NAB 821; NAB 822; NAB 823; NAB 824; POLYMYXIN B; POLYMYXIN DERIVATIVE; RIFAMPICIN; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; NAB 739 PEPTIDE; POLYMYXIN; POLYMYXIN B(1);

ACINETOBACTER BAUMANNII; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENTIATION; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; HK2 CELL LINE; HUMAN; HUMAN CELL; IC50; KIDNEY PROXIMAL TUBULE; KIDNEY TUBULE CELL; KLEBSIELLA PNEUMONIAE; MINIMUM INHIBITORY CONCENTRATION; NEPHROTOXICITY; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANIMAL; BACTERIUM; CELL LINE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; KIDNEY; MACACA FASCICULARIS; RAT; URINE;

ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; CELL LINE; DOSE-RESPONSE RELATIONSHIP, DRUG; KIDNEY; MACACA FASCICULARIS; POLYMYXINS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85015381786     PISSN: 01969781     EISSN: 18735169     Source Type: Journal    
DOI: 10.1016/j.peptides.2017.03.002     Document Type: Article

References (19)

1. [1] Clinical and Laboratory Standards Institute, Methods for Dilution Antimictobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard M07-A10. 2015, CLSI, Wayne, PA, USA.
2. [2] Cochrane, S.A., Vederas, J.C., Lipopeptides from Bacillus and Paenibacillus spp.: a gold mine of antibiotic candidates. Med. Res. Rev. 36 (2016), 4–31.
3. [3] Garonzik, S.M., Li, J., Thamlikitkul, V., Paterson, D.L., Shoham, S., Jacob, J., Silveira, F.P., Forrest, A., Nation, R.L., Population pharmacokinetics of colistin methanesulfonate and formed colistin in critically ill patients from a multicenter study provide dosing suggestions for various categories of patients. Antimicrob. Agents Chemother. 55 (2011), 94–3284.
4. [4] Justo, J.A., Bosso, J.A., Adverse reactions associated with systemic polymyxin therapy. Pharmacotherapy 35 (2015), 28–33.
5. [5] Kadar, B., Kocsis, B., Nagy, K., Szabo, D., The renessaince of polymyxins. Curr. Med. Chem. 20 (2013), 73–3759.
6. [6] Kelesidis, T., Falagas, M.E., The safety of polymyxin antibiotics. Expert Opin. Drug Saf. 14 (2015), 701–1687.
7. [7] Magee, T.V., Brown, M.F., Starr, J.T., Ackley, D.C., Abramite, J.A., Aubrecht, J., et al. Discovery of Dap-3 polymyxin analogues for the treatment of multidrug-resistant Gram-negative nosocomial infections. J. Med. Chem. 56 (2013), 93–5079.
8. [8] Meyers, E., Parker, W.L., Brown, W.E., EM49: a new polypeptide antibiotic active against cell membranes. Ann. N. Y. Acad. Sci. 234 (1974), 493–501.
9. [9] Nummila, K., Kilpeläinen, I., Zähringer, U., Vaara, M., Helander, I., Lipopolysaccharides of polymyxin B-resistant mutants of Escherichia coli are extensively substituted by 2-aminoethyl pyrophosphate and contain aminoarabinose in lipid A. Mol. Microbiol. 16 (1995), 8–271.
10. [10] Pirri, G., Giuliani, A., Nicoletto, S.F., Pizzuto, L., Rinaldi, A.C., Lipopeptides as anti-infectives: a practical perspective. Cent. Eur. J. Biol. 4 (2009), 73–258.
11. [11] Vaara, M., Agents that increase the permeability of the outer membrane. Microbiol. Rev. 56 (1992), 395–411.
12. [12] Vaara, M., Novel derivatives of polymyxins. J. Antimicrob. Chemother. 68 (2013), 1213–1219.
13. [13] Vaara, M., Fox, J., Loidl, G., Siikanen, O., Apajalahti, J., Hansen, F., et al. Novel polymyxin derivatives carrying only three positive charges are effective antibacterial agents. Antimicrob. Agents Chemother. 52 (2008), 36–3229.
14. [14] Vaara, M., Siikanen, O., Apajalahti, J., Fox, J., Frimodt- Møller, N., He, H., et al. A novel polymyxin derivative that lacks the fatty acid tail and carries only three positive charges has strong synergism with agents excluded by the intact outer membrane. Antimicrob. Agents Chemother. 54 (2010), 6–3341.
15. [15] Vaara, M., Vaara, T., Structure–activity studies on novel polymyxin derivatives that carry only three positive charges. Peptides 31 (2010), 21–2318.
16. [16] Vaara, M., Vaara, T., The novel polymyxin derivative NAB739 is remarkably less cytotoxic than polymyxin B and colistin to human kidney proximal tubular cells. Int. J. Antimicrob. Chemother. 41 (2013), 292–293.
17. [17] M. Vaara, T. Vaara, Polymyxin derivative and uses thereof, Patent Application WO2016113470 (2016).
18. [18] Vaara, M., Viljanen, P., Vaara, T., Mäkelä, P.H., An outer membrane-disorganizing peptide PMBN sensitizes E. coli strains to serum bactericidal action. J. Immunol. 132 (1984), 9–2582.
19. [19] Velkov, T., Roberts, K.D., Thompson, P.E., Li, J., Polymyxins a new hope in combating Gram-negative superbugs. Future Med. Chem. 8 (2016), 1017–1025.