Lipopeptides as anti-infectives: A practical perspective

Central European Journal of Biology

Volumn 4, Issue 3, 2009, Pages 258-273

  Pirri, Giovanna ^a   Giuliani, Andrea ^a   Nicoletto, Silvia Fabiole ^a   Pizzuto, Lorena ^a   Rinaldi, Andrea C ^b  

^a Research and Development Unit   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Antibiotics; Antimicrobial peptides; Daptomycin; Echinocandin; Lipid membranes; Lipopeptides; LPS; Polymyxin; Semi synthetic analogues

Indexed keywords

BACTERIA (MICROORGANISMS);

EID: 70350056609     PISSN: 1895104X     EISSN: 16443632     Source Type: Journal    
DOI: 10.2478/s11535-009-0031-3     Document Type: Review

References (106)

1. Nathan C., Goldberg F.M., The profit problem in antibiotic R&D, Nat. Rev. Drug Discov., 2005, 4, 887-891.
2. Payne D.J., Gwynn M.N., Holmes D.J., Pompliano D.L., Drugs for bad bugs: confronting the challenges of antibacterial discovery, Nat. Rev. Drug Discov., 2007, 6, 29-40.
3. Jerala R., Synthetic lipopeptides: a novel class of anti-infectives, Expert Opin. Investig. Drugs, 2007, 16, 1159-1169.
4. Strieker M., Marahiel M.A., The structural diversity of acidic lipopeptide antibiotics, ChemBioChem, 2009, 10, 607-616.
5. Martin N.I., Hu H., Moake M.M., Churey J.J., Whittal R., Worobo R.W., et al., Isolation, structural characterization, and properties of Mattacin (polymyxin M), a cyclic peptide antibiotic produced by Paenibacillus kobensis M, J. Biol. Chem., 2003, 278, 13124-13132.
6. Arnold T.M., Forrest G.N., Messmer K.J., Polymyxin antibiotics for gram-negative infections, Am. J. Health Syst. Pharm., 2007, 64, 819-826.
7. Zavascki A.P., Goldani L.Z., Li J., Nation R.L., Polymyxin B for the treatment of multidrugresistant pathogens: a critical review, J. Antimicrob. Chemother., 2007, 60, 1206-1215.
8. Denning D.W., Echinocandin antifungal drugs, Lancet, 2003, 362, 1142-1151.
9. Tossi A., Host defense peptides: roles and applications, Curr. Prot. Pept. Sci., 2005, 6, 1-3.
10. Giuliani A., Pirri G., Fabiole Nicoletto S., Antimicrobial peptides: an overview of a promising class of therapeutics, Cent. Eur. J. Biol., 2007, 2, 1-33.
11. Hancock R.E.W., Sahl H.-G., Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies, Nat. Biotechnol., 2006, 24, 1551-1557.
12. Radek K., Gallo G., Antimicrobial peptides: natural effectors of the innate immune system, Semin. Immunopathol., 2007, 29, 27-43.
13. Giuliani A., Pirri G., Bozzi A., Di Giulio A., Aschi M., Rinaldi A.C., Antimicrobial peptides: natural templates for synthetic membrane-active compounds, Cell. Mol. Life Sci., 2008, 65, 2450-2460.
14. Scott R.W., DeGrado W.F., Tew G.N., De novo designed synthetic mimics of antimicrobial peptides, Curr. Opin. Biotechnol., 2008, 19, 620-627.
15. Moyle P.M., Toth I., Self-adjuvanting lipopeptide vaccines, Curr. Med. Chem., 2008, 15, 505-516.
16. Ongena M., Jacques P., Bacillus lipopeptides: versatile weapons for plant disease biocontrol, Trends Microbiol., 2007, 16, 115-125.
17. Debono M., Barnhart M., Carrelll C.B., Hoffmann J.A., Occolowitz J.L., Abbott B.J., et al., A21978C, a complex of new acidic peptide antibiotics: isolation, chemistry, and mass spectral structure elucidation, J. Antibiot. (Tokyo), 1987, 40, 761-777.
18. Lakey J.H., Lea E.J., Rudd B.A., Wright H.M., Hopwood D.A., A new channel-forming antibiotic from Streptomyces coelicolor A3(2) which requires calcium for its activity, J. Gen. Microbiol., 1983, 129, 3565-3573.
19. Huber F.M., Pieper R.L., Tietz A.J., The formation of daptomycin by supplying decanoic acid to Streptomyces roseosporus cultures producing the antibiotic complex A21978C, J. Biotechnol., 1988, 7, 283-292.
20. Baltz R.H., McHenney M.A. Hosted T.J., Genetics of lipopeptide antibiotic biosynthesis in Streptomyces fradiae A54145 and Streptomyces roseosporus A21978C, In: Developments in Industrial Microbiology, Baltz R.H., Hegeman G.D., Skatrud P.L., (Eds.), Society for Industrial Microbiology, Fairfax, VA, 1997.
21. Debono M., Abbott B.J., Molloy R.M., Fukuda D.S., Hunt A.H., Daupert V.M., et al., Enzymatic and chemical modifications of lipopeptide antibiotic A21978C: the synthesis and evaluation of daptomycin (LY146032), J. Antibiot. (Tokyo), 1988, 41, 1093-1105.
22. Gu J.-Q., Nguyen K.T., Gandhi C., Rajgarhia V., Baltz R.H., Brian P., et al., Structural characterization of daptomycin analogues A21978C1-3 (D-Asn11) produced by a recombinant Streptomyces roseosporus strain, J. Nat. Prod., 2007, 70, 233-240.
23. Cottagnoud P., Daptomycin: a new treatment for insidious due to gram-positive pathogens, Swiss Med. Wkly, 2008, 138, 93-99.
24. Brody T.M., Larner J., Minneman K.P., Neu H.C., Human Pharmacology: Molecular to Clinical, Mosby, St. Louis, MO, 1994.
25. Miao V., Coëffet-LeGal M.-F., Brian P., Brost R., Penn J., Whiting A., et al., Daptomycin biosynthesis in Streptomyces roseosporus: cloning and analysis of the gene cluster and revision of peptide stereochemistry, Microbiology, 2005, 151, 1507-1523.
26. Boeck L.D., Fukuda D.S., Abbott B.J., Debono M., Deacylation of A21978C, an acidic lipopeptide antibiotic complex, by Actinoplanes utahensis, J. Antibiot., 1988, 41, 1085-1092.
27. Siedlecki J., Hill J., Parr I., Yu X., Morytko M., Zhang Y., et al., Array synthesis of novel lipodepsipeptide, Bioorg. Med. Chem. Lett, 2003, 13, 4245-4249.
28. Grünewald J., Sieber S.A., Mahlert C., Linne U., Marahiel M.A., Synthesis and derivatization of daptomycin: a chemoenzymatic route to acidic lipopeptide antibiotics, J. Am. Chem. Soc., 2004, 126, 17025-17031.
29. Huber F.M., Berry D.M., Pieper R.L., Tietz A.J., The synthesis of A21978C analogs by Streptomyces roseosporus cultivated under carbon limitation and fed fatty acids, Biotech. Lett., 1990, 12, 789-792.
30. Huber F.M., Pieper R.L., Tietz A.J., Dispersal of insoluble fatty acid precursors in stirred bioreactors as a mechanism to control antibiotic factor distribution, In: Ho C.S., Oldshue J.Y., (Eds.), Biotechnology Processes - Scale up and Mixing, American Institute of Chemical Engineers, New York, 1987.
31. Penn J., Li X., Whiting A., Latif M., Gibson T., Silva C.J., et al., Heterologous production of daptomycin in Streptomyces lividans, J. Ind. Microbiol. Biotechnol., 2006, 33, 121-128.
32. Muangsiri W., Kirsch L.E., The kinetics of the alkaline degradation of daptomycin, J. Pharm. Sci., 2001, 90, 1066-1075.
33. Bechinger B., The structure, dynamics and orientation of antimicrobial peptides in membranes by multidimensional solidstate NMR spectroscopy, Biochim. Biophys. Acta, 1999, 1462, 157-183.
34. Bechinger B., Lohner K., Detergent-like actions of linear amphipathic cationic antimicrobial peptides, Biochim. Biophys. Acta, 2006, 1758, 1529-1539.
35. Ho S.W., Jung D., Calhoun J.R., Lear J.D., Okon M., Scott W.R.P., et al., Effect of divalent cations on the structure of the antibiotic daptomycin, Euro. Biophysics J., 2008, 37, 421-433.
36. Jung D., Rozek A., Okon M., Hancock R.E.W., Structural transitions as determinants of the action of the calcium-dependent antibiotic daptomycin, Chem. Biol., 2004, 11, 949-957.
37. Straus S.K., Hancock R.E., Mode of action of the new antibiotic for Gram-positive pathogens daptomycin: comparison with cationic antimicrobial peptide and lipopeptides, Biochim. Biophy. Acta, 2006, 1758, 1215-1223.
38. Jung D., Powers J.P., Straus S.K., Hancock R.E.W., Lipid-specific binding of the calcium-dependent antibiotic daptomycin leads to changes in lipid polymorphism of model membranes, Chem. Phys. Lipids, 2008, 154, 120-128.
39. Thorne G.M., Alder J., Daptomycin: a novel lipopeptide antibiotic, Clin. Microb. Newsletter, 2002, 25, 33-40.
40. Silverman J.A., Perlmutter N.G., Shapiro H.M., Correlation of daptomycin bactericidal activity and membrane depolarization in Staphylococcus aureus, Antimicrob. Agents Chemother., 2003, 47, 2538-2544.
41. Muthaiyan A., Silverman J.A., Jayaswal R.K., Wilkinson B.J., Transcriptional profiling reveals that daptomycin induces the Staphylococcus aureus cell wall stress stimulon and genes responsive to membrane depolarization, Antimicrob. Agents Chemother., 2008, 52, 980-990.
42. English B.K., Maryniw E.M., Talati A.J., Meals E.A., Diminished macrophage inflammatory response to staphylococcus aureus isolates exposed to daptomycin versus vancomycin or oxacillin, Antimicrob. Agents Chemother., 2006, 50, 2225-2227.
43. Kanafani Z.A., Corey G.R., Daptomycin: a rapidly bactericidal lipopeptide for the treatment of Grampositive infections, Expert Rev. Anti Infect. Ther., 2007, 5, 177-184.
44. Nguyen K.T., Ritz D., Gu J.-Q., Alexander D., Chu M., Miao V., et al., Combinatorial biosynthesis of novel antibiotics related to daptomycin, Proc. Natl. Acad. Sci. USA, 2006, 103, 17462-17467.
45. Kopp F., Grunewald J., Mahlert C., Marahiel M.A., Chemoenzymetic design of acidic lipopeptide hybrids: new insights into the structure-activity relationship of daptomycin and A54145, Biochemistry, 2006, 45, 10474-10481.
46. Eliopoulos G.M., Willey S., Reiszner E., Spitzer P.G., Caputo G., Moellering R., In vitro and in vivo activity of LY 146032, a new cyclic lipopeptide antibiotic, Antimicrob. Agents Chemother., 1986, 30, 532-535.
47. Andrew J.H., Wale M.C., Wale L.J., Greenwood D., The effect of cultural conditions on the activity of LY146032 against staphylococci and streptococci, J. Antimicrob. Chemother., 1987, 20, 213-221.
48. Chow A.W., Cheng N., In vitro activities of daptomycin (LY146032) and paldimycin (U-70, 138F) against anaerobic Gram-positive bacteria, Antimicrob. Agents Chemother., 1988, 32, 788-790.
49. Ball L.J., Goult C.M., Donarsi J.A., Micklefield J., Ramesh V., NMR strcture determination and calcium binding effects of lipopeptide antibiotic daptomycin", Org. Biomol. Chem., 2004, 2, 1872-1878.
50. Rotondi K.S., Gierasch L.M., A well defined amphipathic conformation for the calcium- free cyclic lipopeptide antibiotic, daptomycin, in aqueous solution, Biopolymers, 2005, 80, 374-385.
51. Scott W.R.P., Baek S.-B., Jung D., Hancock R.E.W., Straus S.K., NMR structural studies of the antibiotic lipopeptide daptomycin in DHPC micelles, Biochim. Biophys. Acta, 2007, 1768, 3116-3126.
52. van Bambeke F., Mingeot-Leclercq M.P., Struelens M.J., Tulkens P.M. The bacterial envelope as a target for novel anti-MRSA antibiotics, Trends Pharmacol. Sci., 2008, 29, 124-134.
53. Doekel S., Coëffet-Le Gal M.-F., Gu J.-Q., Chu M., Baltz R.H., Brian P., Non-ribosomal peptide synthetase module fusions to produce derivatives of daptomycin in Streptomyces roseosporus, Microbiology, 2008, 154, 2872-2880.
54. Kato A., Nakaya S., Kokubo N., Aiba Y., Ohashi Y., Hirata H., A new anti-MRSA antibiotic complex, WAP-8294A. I. Taxonomy, isolation and biological activities, J. Antibiot., 1998, 51, 929-935.
55. 2, A novel anti-MRSA antibiotic reduced by Lysobacter sp., J. Am. Chem. Soc., 1997, 119, 6680-6681.
56. th, 253, (Chem. Abstr., 1999, 131, 115328).
57. Harada K.-I., Suzuki M., Kato A., Fuji K., Oka H., Ito Y., Separation of WAP-8294A components, a novel anti-methicillin-resistant Staphylococcus aureus antibiotic using high-speed counter-current chromatography, J. Chromat. A, 2001, 932, 75-81.
58. Jones T.S.G., Chemical evidence for the multiplicity of the antibiotics produced by Bacillus polymyxa, Annals of the New York Academy of Sciences, 1949, 51, 909-916.
59. 1, J. Am. Chem. Soc., 1956, 78, 3663-3667.
60. Biserte G.A, Dautrevaux M., Structure of polymyxin B, Bull. Soc. Chim. Biol.,1957, 795-812.
61. Vogler K., Studer R.O., Lanz P., Lergier W., Böhni E., Total synthesis of two cyclodecapeptides exerting polymyxin-like activity, Experientia, 1961, 17, 223-224.
62. Orwa J.A., Govaerts C., Busson R., Roets E., van Schepdael A., Hoogmartens J., Isolation and structural characterization of polymyxin B components, J. Chromat. A, 2001, 912, 369-373.
63. Li J., Nation R.L., Milne R.W., Turnidge J.D., Coulthard K., Evaluation of colistin as an agent against multi-resistant Gram-negative bacteria, Int. J. Antimicrob. Agents, 2005, 25, 11-25.
64. Li J., Milne R.W., Nation R.L., Turnidge J.D., Coulthard K., Valentine J., Simple method for assaying colistin methanesulfonate in plasma and urine using high-performance liquid chromatography, Antimicrob. Agents Chemother., 2002, 46, 3304-3307.
65. Duwe A.K., Rupar C.A., Horsman G.B., Vas S.I., In vitro cytotoxicity and antibiotic activity of polymyxin B nonapeptide, Antimicrob. Agents Chemother., 1996, 30, 340-341.
66. Storm D.R., Rosenthal K.S., Swanson P.E., Polymyxin and related peptide antibiotics, Annu. Rev. Biochem., 1977, 46, 723-763.
67. Danner R.L., Joiner K.A., Rubin M., Paterson W.H., Johnson N., Ayers K.M., et al., Purification, toxicity, and antiendotoxin activity of polymyxin B nonapeptide, Antimicrob. Agents Chemother. 1989, 33, 1428-1434.
68. Vaara M., Agents that increase the permeability of the outer membrane, Microbiol. Rev., 1992, 56, 395-411.
69. Vaara M., Vaara T., Sensitization of Gram-negative bacteria to antibiotics and complement by a nontoxic oligopeptide, Nature, 1983, 303, 526-528.
70. Vaara M., Vaara T., Polycations sensitize enteric bacteria to antibiotics, Antimicrob. Agents Chemother., 1983, 24, 107-113.
71. Vaara M., Vaara T., Polycations as outer membrane-disorganizing agents, Antimicrob. Agents Chemother., 1983, 24, 114-122.
72. Ito-Kagawa M., Koyama Y., Studies on the selectivity of action of colistin, colistin nonapeptide and colistin heptapeptide on the cell envelope of Escherichia coli, J. Antibiot., 1984, 37, 926-928.
73. Lam C., Hildebrandt J., Schutze E., Wenzel A.F., Membrane-disorganizing property of polymyxin B nonapeptide, J. Antimicrob. Chemother., 1986, 18, 9-15.
74. McCashion R.N., Lynch W.H., Effects of polymyxin B nonapeptide on Aeromonas salmonicida,Antimicrob. Agents Chemother., 1987, 31, 1414-1419.
75. Kubesch P., Whesling M., Tummler B., Membrane permeability of Pseudomonas aeruginosa to 4-quinolones, Zentralbl. Bakteriol. Mikrobiol. Hyg. ABT. 1, 1987, 265, 197-202.
76. Moestrup S.K., Cui S., Vorum H., Bregengård C., Bjorn S.E., Norris K., et al., Evidence that epithelial glycoprotein 330/megalin mediates uptake of polybasic drugs, J. Clin. Investig., 1995, 96, 1404-1413.
77. 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., 2008, 52, 3229-3236.
78. Tsubery H., Ofek I., Cohen S., Fridkin M., The functional association of polymyxin B with bacterial lipopolysaccharide is stereospecific: studies on polymyxin B nonapeptide, Biochemistry, 2000, 39, 11838-11844.
79. Heineman B., Kaplan M.A., Muir R.D., Hooper I.R., Amphomycin, a new antibiotic, Antibiot. Chemother., 1953, 3, 1239-1242.
80. Bodanszky M., Chaturvedi N.C., Scozzie J.A., The structure of fatty acids from the antibiotic amphomycin, J. Antibiot., 1969, 22, 399-408.
81. Bodanszky M., Siegler G.F., Bodanszky A., Structure of the peptide antibiotic Amphomycin, J. Am. Chem. Soc., 1973, 95, 2352-2357.
82. th National ACS (American Chemical Society Meeting) Meeting & Exposition, San Diego, CA, 13-17 March 2005.
83. Sgarbi P.W.M., Boyd V.A., Cameron D.R., Chen Y., Jia Q., Nodwell M., et al., Synthesis and structureactivity relationship (SAR) studies on the lipophilic tail of the lipopeptide antibiotic Amphomycin, presented at the 229th National ACS (American Chemical Society Meeting) Meeting & Exposition, San Diego, CA, 13-17 March 2005.
84. th Canadian Chemistry Conference (CSC) and Exhibition, Saskatoon, CDN, 28 May-1 June 2005.
85. th Annual Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC) and the concurrent 46th Annual Infectious Diseases Society of America (IDSA) meeting, Washington, DC, 25-28 October 2008.
86. Benz F., Knusel F., Nuesch J., Treichler H., Voser W., Nyfeler R., et al., Echinocandin B, ein neuartiges Polypeptid-Antibiotikum aus Aspergillus nidulans var. echinulatus: Isolierung und Bausteine, Helv. Chim. Acta, 1974, 57, 2459-2477.
87. Keller-Juslen C., Kuhn M., Loosli H.-R., Petcher T.J., Weber H.P., von Wartburg A., Struktur des Cyclopeptid-Antibiotikums SL 7810 (= Echinocandin B), Tetrahedron Lett., 1976, 4147-4150, (in German).
88. Koyama G., The crystal and molecular structure of 3-hydroxy-4-methyl-proline, Helv. Chim. Acta, 1974, 57, 2477-2483.
89. von Traber R., Keller-Juslen C., Loosli H.-R., Kuhn M., von Wartburg A., Cyclopeptid-Antibiotika aus Aspergillus-Arten. Struktur der Echinocandine C und D, Helv. Chim. Acta, 1979, 62, 1252-1267, (in German).
90. Kurokawa N., Ohfune Y., Total synthesis of echinocandins. 1. Stereocontrolled syntheses of the constituent amino acids, J. Am. Chem. Soc., 1986, 108, 6041-6043.
91. Kurokawa N., Ohfune Y., Total synthesis of Echinocandins. 2. Total synthesis of Echinocandins D via efficient peptide coupling reactions, J. Am. Chem. Soc., 1986, 108, 6043-6045.
92. Balbovec J.M., Black R.M., Hammond M.L., Heck J.V., Zambias R.A., Abruzzo G., et al., Synthesis, Stability and biological evaluation of water soluble prodrugs of a new Echinocandin Lipopeptide. Discovery of a potential clinical agent for the treatment of systemic Candidiasis and Pneumocystis Carinii Pneumonia (PCP), J. Med. Chem, 1992, 35, 194-198.
93. Taft C.S., Selitrennikoff C.P., Cilofungin Inhibition of (1,3)-β-glucan synthesis: the lipophilic side chain is essential for inhibition of enzyme activity, J. Antibiot., 1990, 43, 433-437.
94. Debono M., Abbott B.J., Fukuda D.S., Barnhart M., Willard K.E., Molloy R.M., et al., Synthesis of new analogs of Echinocandin B by enzymatic deacylation and chemical reacylation of the Echinocandin B peptide: Synthesis of the antifungal agent Cilofungin (LY121019), J. Antibiot., 1989, 42, 389-397.
95. Boeck L.D., Fukuda D.S., Abbott B.J., Debono M., Deacylation of Echinocandin B by Actinoplanes utahensis, J. Antibiot., 1989, 42, 382-388.
96. Debono M., Abbott B.J., Turner J.R., Howard L.C., Gordee R.S., Hunt A.H., et al., Synthesis and evaluation of LY121019, a member of a series of semi-synthetic analogues of the antifungal lipopeptide Echinocandin B, Ann. N.Y. Acad. Sci., 1988, 544, 152-167.
97. Diekema D.J., Petroelje B., Messer S.A., Hollis R.J., Pfaller M.A., Activity of available and investigational antifungal agents against Rhodotorula species, J. Clin. Microbiol., 2005, 43, 476-478.
98. Nasto B., Biotech at the beauty counter, Nat. Biotechnol., 2007, 25, 617-619.
99. Rinaldi A., Healing beauty? More biotechnology cosmetic products that claim drug-like properties reach the market, EMBO Reports, 2008, 9, 1073-1077.
100. Nagarajan R., Schabel A.A., Occolowitz J.L., Counter F.T., Ott J.L., Felty-Duckworth A.M., Synthesis and antibacterial evaluation of N-alkyl vancomycins., J. Antibiot. (Tokyo), 1989, 42, 63-72.
101. Nagarajan R., Structure-activity relationships of vancomycin-type glycopeptide antibiotics, J. Antibiot. (Tokyo), 1993, 46, 1181-1195.
102. Higgins D.L., Chang R., Debabov D.V., Leung J., Wu T., Krause K.M., et al., Telavancin, a multifunctional lipoglycopeptide, disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother., 2005, 49, 1127-1134.
103. Leadbetter M.R., Adams S.M., Bazzini B., Fatheree P.R., Karr D.E., Krause K.M., et al., Hydrophobic vancomycin derivatives with improved ADME properties: discovery of telavancin (TD-6424), J. Antibiot. (Tokyo), 2004, 57, 326-336.
104. Xiong Y.Q., Yeaman M.R., Bayer A.S., In vitro antibacterial activities of platelet microbicidal protein and neutrophil defensin against Staphylococcus aureus are influenced by antibiotics differing in mechanism of action, Antimicrob. Agents Chemother., 1999, 43, 1111-1117.
105. Yeaman M.R., Bayer A.S., Koo S.P., Foss W., Sullam P.M., Platelet microbicidal proteins and neutrophil defensin disrupt the Staphylococcus aureus cytoplasmic membrane by distinct mechanisms of action, J. Clin. Investig., 1998, 101, 178-187.
106. Judice J.K., Pace J.L., Semi-synthetic glycopeptide antibacterials, Bioorg. Med. Chem. Lett., 2003, 13, 4165-4168.