Lipopeptid như một chất chống nhiễm khuẩn: một góc nhìn thực tiễn

Giovanna Pirri1, Andrea Giuliani1, Silvia Fabiole Nicoletto1, Lorena Pizzuto1, Andrea C. Rinaldi2
11Research s& Development Unit, Spider Biotech S.r.l, I-10010, Colleretto Giacosa, Italy
22Department of Biomedical Sciences and Technologies, University of Cagliari, 09042, Cagliari, Italy

Tóm tắt

Tóm tắt

Kháng sinh lipopeptide đại diện cho một loại kháng sinh cũ đã được phát hiện cách đây hơn 50 năm, bao gồm cả polymyxin cũ nhưng cũng có những loại mới, chẳng hạn như daptomycin mới được phê duyệt. Chúng thường bao gồm một phần peptide vòng ưa nước gắn kết với một chuỗi axit béo, điều này giúp chúng chèn vào lớp lipid của màng tế bào vi khuẩn. Bài tổng quan này trình bày một cái nhìn tổng thể về loại kháng sinh này, tập trung vào các ứng dụng điều trị và đặc biệt nhấn mạnh các điều chỉnh hóa học được thực hiện để cải thiện hoạt tính của chúng.

Từ khóa

#lipopeptide #kháng sinh #ứng dụng điều trị #sửa đổi hóa học

Tài liệu tham khảo

Jung, 2008, Lipid - specific binding of the calcium - dependent antibiotic daptomycin leads to changes in lipid polymorphism of model membranes http dx org, Chem Phys Lipids, 38, 120, 10.1016/j.chemphyslip.2008.04.004

Giuliani, 2008, Di Giulio Antimicrobial peptides : natural templates for synthetic membrane - active compounds http dx org, Cell Mol Life Sci, 13, 2450, 10.1007/s00018-008-8188-x

Scott, 2007, NMR structural studies of the antibiotic lipopeptide daptomycin in DHPC micelles http dx org, Biochim Biophys Acta, 51, 3116, 10.1016/j.bbamem.2007.08.034

Siedlecki, 2003, Array synthesis of novel lipodepsipeptide http dx org, Bioorg Med Chem Lett, 27, 4245, 10.1016/j.bmcl.2003.07.025

Benz, 1974, ein neuartiges Polypeptid - Antibiotikum aus Aspergillus nidulans var echinulatus : Isolierung und Bausteine http dx org, Helv Chim Acta, 86, 2459, 10.1002/hlca.19740570818

Kurokawa, 1986, Total synthesis of Echinocandins Total synthesis of Echinocandins D via efficient peptide coupling reactions http dx org, Am Chem Soc, 91, 6043, 10.1021/ja00279a065

Ball, 2004, NMR strcture determination and calcium binding effects of lipopeptide antibiotic daptomycin http dx org, Biomol Chem, 49, 1872, 10.1039/b402722a

Debono, 1989, Synthesis of new analogs of Echinocandin B by enzymatic deacylation and chemical reacylation of the Echinocandin B peptide : Synthesis of the antifungal agent Cilofungin, Antibiot, 94, 389

Hausmann, 1956, The Amino Acid Sequence of Polymyxin http dx org, Am Chem Soc, 59, 3663, 10.1021/ja01596a029

Leadbetter, 2004, Hydrophobic vancomycin derivatives with improved ADME properties : discovery of telavancin, Antibiot, 103, 6424

Boeck, 1989, Deacylation of Echinocandin B by Actinoplanes utahensis, Antibiot, 95, 382, 10.7164/antibiotics.42.382

Rotondi, 2005, A well defined amphipathic conformation for the calcium - free cyclic lipopeptide antibiotic daptomycin in aqueous solution http dx org, Biopolymers, 50, 374, 10.1002/bip.20238

Brody, 1994, Human Pharmacology : Molecular to Clinical Mosby St Louis, MO, 24

Jung, 2004, Structural transitions as determinants of the action of the calcium - dependent antibiotic daptomycin http dx org, Chem Biol, 36, 949, 10.1016/j.chembiol.2004.04.020

Kato, 1997, Tennen Yuki Kagobutsu Toronkai Koen Yoshishu th, Chem Abstr, 56, 253

Debono, 1987, a complex of new acidic peptide antibiotics : isolation chemistry and mass spectral structure elucidation, Antibiot, 17, 21978

Denning, 2003, Echinocandin antifungal drugs http dx org, Lancet, 8, 1142, 10.1016/S0140-6736(03)14472-8

Judice, 2003, Semi - synthetic glycopeptide antibacterials http dx org, Bioorg Med Chem Lett, 106, 4165, 10.1016/j.bmcl.2003.08.067

Scott, 2008, De novo designed synthetic mimics of antimicrobial peptides http dx org, Curr Opin Biotechnol, 14, 620, 10.1016/j.copbio.2008.10.013

Van Bambeke, 2008, The bacterial envelope as a target for novel anti - MRSA antibiotics, Trends Pharmacol Sci, 52, 124, 10.1016/j.tips.2007.12.004

Taft, 1990, Cilofungin Inhibition of - β - glucan synthesis : the lipophilic side chain is essential for inhibition of enzyme activity, Antibiot, 93, 1

Rinaldi, 2008, Healing beauty ? More biotechnology cosmetic products that claim drug - like properties reach the market http dx org, EMBO Reports, 99, 1073, 10.1038/embor.2008.200

Jerala, 2007, Synthetic lipopeptides : a novel class of anti - infectives Expert http dx org, Investig Drugs, 3, 1159, 10.1517/13543784.16.8.1159

Doekel, 2008, Coëffet - Le Gal Non - ribosomal peptide synthetase module fusions to produce derivatives of daptomycin in Streptomyces roseosporus http dx org, Microbiology, 53, 2872, 10.1099/mic.0.2008/020685-0

Lakey, 1983, A new channel - forming antibiotic from Streptomyces coelicolor which requires calcium for its activity, Gen Microbiol, 18, 3565, 10.1099/00221287-129-12-3565

Moyle, 2008, Self - adjuvanting lipopeptide vaccines http dx org, Curr Med Chem, 15, 505, 10.2174/092986708783503249

Diekema, 2005, Activity of available and investigational antifungal agents against Rhodotorula species http dx org, Clin Microbiol, 97, 476, 10.1128/JCM.43.1.476-478.2005

Payne, 2007, Drugs for bad bugs : confronting the challenges of antibacterial discovery http dx org, Nat Rev Drug Discov, 2, 29, 10.1038/nrd2201

Kubesch, 1987, Membrane permeability of Pseudomonas aeruginosa to - quinolones, Zentralbl Bakteriol Mikrobiol, 75, 4

Penn, 2006, Heterologous production of daptomycin in Streptomyces lividans http dx org, Ind Microbiol Biotechnol, 31, 121, 10.1007/s10295-005-0033-8

Nguyen, 2006, Combinatorial biosynthesis of novel antibiotics related to daptomycin http dx org, Proc Natl Acad Sci USA, 44, 17462, 10.1073/pnas.0608589103

Moestrup, 1995, Evidence that epithelial glycoprotein / megalin mediates uptake of polybasic drugs http dx org, Clin Investig, 76, 1404, 10.1172/JCI118176

Tossi, 2005, Host defense peptides : roles and applications http dx org, Curr Prot Pept Sci, 9, 1, 10.2174/1389203053027539

Keller, 1976, von Wartburg Struktur des Cyclopeptid - Antibiotikums ( in, Tetrahedron Lett, 87, 7810

Nathan, 2005, The profit problem in antibiotic http dx org, Rev Drug Discov, 1, 887, 10.1038/nrd1878

Keller, 1979, von Traber von Wartburg Cyclopeptid - Antibiotika aus Aspergillus - Arten Struktur der Echinocandine C und D ( in German ) http dx org, Helv Chim Acta, 89, 1252, 10.1002/hlca.19790620436

Bechinger, 2006, Detergent - like actions of linear amphipathic cationic antimicrobial peptides http dx org, Biochim Biophys Acta, 34, 1529, 10.1016/j.bbamem.2006.07.001

Kato, 1998, A new anti - MRSA antibiotic complex Taxonomy isolation and biological activities, Antibiot, 54, 8294

Yeaman, 1998, Platelet microbicidal proteins and neutrophil defensin disrupt the Staphylococcus aureus cytoplasmic membrane by distinct mechanisms of action http dx org, Clin Investig, 105, 178, 10.1172/JCI562

Koyama, 1974, The crystal and molecular structure of - hydroxy - - methyl - proline http dx org, Helv Chim Acta, 88, 2477, 10.1002/hlca.19740570819

Kopp, 2006, Chemoenzymetic design of acidic lipopeptide hybrids : new insights into the structure - activity relationship of daptomycin and A http dx org, Biochemistry, 45, 10474, 10.1021/bi0609422

Bechinger, 1999, The structure dynamics and orientation of antimicrobial peptides in membranes by multidimensional solidstate NMR spectroscopy http dx org, Biochim Biophys Acta, 33, 157, 10.1016/S0005-2736(99)00205-9

Huber, 1990, The synthesis of analogs by Streptomyces roseosporus cultivated under carbon limitation and fed fatty acids http dx org, Biotech Lett, 29, 21978, 10.1007/BF01022596

Radek, 2007, Antimicrobial peptides : natural effectors of the innate immune system http dx org, Semin Immunopathol, 12, 27, 10.1007/s00281-007-0064-5

Cottagnoud, 2008, Daptomycin : a new treatment for insidious due to gram - positive pathogens, Swiss Med Wkly, 23, 93

Baltz, 1997, Hosted Genetics of lipopeptide antibiotic biosynthesis in Streptomyces fradiae A and Streptomyces roseosporus In : Developments in Industrial Microbiology ) Society for Industrial Microbiology Fairfax, VA, 20, 21978

Debono, 1988, Enzymatic and chemical modifications of lipopeptide antibiotic the synthesis and evaluation of daptomycin, Antibiot, 21, 21978

Arnold, 2007, Polymyxin antibiotics for gram - negative infections http dx org, Health Syst Pharm, 6, 819, 10.2146/ajhp060473

Miao, 2005, Coëffet - LeGal Daptomycin biosynthesis in Streptomyces roseosporus : cloning and analysis of the gene cluster and revision of peptide stereochemistry http dx org, Microbiology, 25, 1507, 10.1099/mic.0.27757-0

Vogler, 1961, Total synthesis of two cyclodecapeptides exerting polymyxin - like activity http dx org, Experientia, 61, 223, 10.1007/BF02160629

Nagarajan, 1993, Structure - activity relationships of vancomycin - type glycopeptide antibiotics, Antibiot, 101, 1181, 10.7164/antibiotics.46.1181

Li, 2005, Evaluation of colistin as an agent against multi - resistant Gram - negative bacteria http dx org, Int J Antimicrob Agents, 63, 11, 10.1016/j.ijantimicag.2004.10.001

Nagarajan, 1989, Synthesis and antibacterial evaluation of N - alkyl vancomycins, Antibiot, 100, 63, 10.7164/antibiotics.42.63

Grünewald, 2004, Synthesis and derivatization of daptomycin : a chemoenzymatic route to acidic lipopeptide antibiotics http dx org, Am Chem Soc, 28, 17025, 10.1021/ja045455t

Tsubery, 2000, The functional association of polymyxin B with bacterial lipopolysaccharide is stereospecific : studies on polymyxin B nonapeptide http dx org, Biochemistry, 78, 11838, 10.1021/bi000386q

Gu, 2007, Structural characterization of daptomycin analogues produced by a recombinant Streptomyces roseosporus strain http dx org, Nat Prod, 22, 21978

Balbovec, 1992, 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 http dx org, Med Chem, 92, 194, 10.1021/jm00079a027

Nasto, 2007, Biotech at the beauty counter http dx org, Nat Biotechnol, 98, 617, 10.1038/nbt0607-617

Martin, 2003, Isolation structural characterization and properties of Mattacin ( polymyxin a cyclic peptide antibiotic produced by Paenibacillus kobensis http dx org, Biol Chem, 5, 13124, 10.1074/jbc.M212364200

Boeck, 1988, Deacylation of an acidic lipopeptide antibiotic complex by Actinoplanes utahensis, Antibiot, 26, 21978

Muangsiri, 2001, The kinetics of the alkaline degradation of daptomycin http dx org, Pharm Sci, 32, 1066, 10.1002/jps.1060

Giuliani, 2007, Fabiole Nicoletto Antimicrobial peptides : an overview of a promising class of therapeutics http dx org, Cent Eur J Biol, 10, 1, 10.2478/s11535-007-0010-5

Hancock, 2006, Antimicrobial and host - defense peptides as new anti - infective therapeutic strategies http dx org, Nat Biotechnol, 11, 1551, 10.1038/nbt1267

Kanafani, 2007, Daptomycin : a rapidly bactericidal lipopeptide for the treatment of Grampositive infections Expert Anti Infect http dx org, Rev Ther, 43, 177, 10.1586/14787210.5.2.177

Bodanszky, 1973, Structure of the peptide antibiotic Amphomycin http dx org, Am Chem Soc, 81, 2352, 10.1021/ja00788a040

Biserte, 1957, Structure of polymyxin B, Bull Soc Chim Biol, 60, 795

Kurokawa, 1986, Total synthesis of echinocandins Stereocontrolled syntheses of the constituent amino acids http dx org, Am Chem Soc, 90, 6041, 10.1021/ja00279a064

Ongena, 2007, Bacillus lipopeptides : versatile weapons for plant disease biocontrol http dx org, Trends Microbiol, 16, 115, 10.1016/j.tim.2007.12.009

Bodanszky, 1969, The structure of fatty acids from the antibiotic amphomycin, Antibiot, 80, 399, 10.7164/antibiotics.22.399

Heineman, 1953, Amphomycin a new antibiotic, Antibiot Chemother, 79, 1239

Strieker, 2009, The structural diversity of acidic lipopeptide antibiotics http dx org, ChemBioChem, 4, 607, 10.1002/cbic.200800546

Huber, 1988, The formation of daptomycin by supplying decanoic acid to Streptomyces roseosporus cultures producing the antibiotic complex http dx org, Biotechnol, 19, 21978, 10.1016/0168-1656(88)90040-5

Ito, 1984, Studies on the selectivity of action of colistin colistin nonapeptide and colistin heptapeptide on the cell envelope of Escherichia coli, Antibiot, 72, 926

Straus, 2006, Mode of action of the new antibiotic for Gram - positive pathogens daptomycin : comparison with cationic antimicrobial peptide and lipopeptides http dx org, Biochim Biophy Acta, 37, 1215, 10.1016/j.bbamem.2006.02.009

Vaara, 1983, Sensitization of Gram - negative bacteria to antibiotics and complement by a nontoxic oligopeptide http dx org, Nature, 69, 303, 10.1038/303526a0

Thorne, 2002, Daptomycin : a novel lipopeptide antibiotic http dx org, Clin Microb Newsletter, 39, 33, 10.1016/S0196-4399(02)80007-1

Storm, 1977, Polymyxin and related peptide antibiotics http dx org, Annu Rev Biochem, 66, 723, 10.1146/annurev.bi.46.070177.003451

Vaara, 1992, Agents that increase the permeability of the outer membrane, Microbiol Rev, 68, 395, 10.1128/MMBR.56.3.395-411.1992

Nakaya, 1997, A novel anti - MRSA antibiotic reduced by Lysobacter sp http dx org, Am Chem Soc, 55, 6680

Debono, 1988, Synthesis and evaluation of LY a member of a series of semi - synthetic analogues of the antifungal lipopeptide Echinocandin http dx org, Acad Sci, 96, 544, 10.1111/j.1749-6632.1988.tb40398.x