Lipopeptides as anti-infectives: a practical perspective

Pirri, Giovanna; Giuliani, Andrea; Nicoletto, Silvia Fabiole; Pizzuto, Lorena; Rinaldi, Andrea C.

doi:10.2478/s11535-009-0031-3

Cited by 92 publications

(108 citation statements)

References 94 publications

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“…It is a naturally occurring compound found in the soil saprotroph Streptomyces roseosporus. 8,9 We have also found a novel anti-MRSA antibiotic, WAP-8294A, that is a complex of 20 closely related components produced by Lysobacter sp. 10 The WAP-8294A2 (1) was isolated as the major component, while A1 (2), A4 (3) and Ax13 (4) were minor components.…”

Section: Introductionmentioning

confidence: 97%

A new anti-MRSA antibiotic complex, WAP-8294A II. Structure characterization of minor components by ESI LCMS and MS/MS

Kato

Hirata

Ohashi³

et al. 2011

J Antibiot

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The anti-MRSA antibiotic, WAP-8294A, was isolated from the fermentation broth of Lysobacter sp. The major component,and 2 mol of L-Ser, D-Orn and D-3-hydroxy-7-Me-octanoic acid. The structure of the WAP-8294A2 was mainly determined as a cyclic depsipeptide by 2D NMR experiments. However, it was difficult to use the NMR experiment to determine the minor components, A1, A4 and Ax13, isolated in small amounts. In the present study, ESI MS/MS was applied to the structure elucidation of these minor components. The structures of these minor components were determined on the basis of the fragmentation pattern of the product ions of WAP-8294A2 in the ESI MS/MS. As a result, it was confirmed that A1 and A4 had the same amino acid sequence as A2, while A1 and A4 had the 3-OH-octanoic acid and 3-OH-8-Me-nonanoic acid, respectively, in the place of the 3-OH-7-Meoctanoic acid in A2. In the structure of Ax13, it was found that Gly of A2 was changed to b-Ala of Ax13.

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Section: Introductionmentioning

confidence: 97%

A new anti-MRSA antibiotic complex, WAP-8294A II. Structure characterization of minor components by ESI LCMS and MS/MS

Kato

Hirata

Ohashi³

et al. 2011

J Antibiot

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“…Although numerous peptide antibiotics have been discovered in almost all known types of organisms, microbial peptides, especially lipopeptide antibiotics and their semisynthetic derivatives, appear to be more useful than other peptide antibiotics. These peptides represent a promising class of antibiotics against MDR pathogens (14,30). Lipopeptide antibiotics generally consist of a fatty acyl side chain and a hydrophilic peptide portion.…”

mentioning

confidence: 99%

Battacin (Octapeptin B5), a New Cyclic Lipopeptide Antibiotic from Paenibacillus tianmuensis Active against Multidrug-Resistant Gram-Negative Bacteria

Qian

Teng

et al. 2012

Antimicrob Agents Chemother

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Hospital-acquired infections caused by drug-resistant bacteria are a significant challenge to patient safety. Numerous clinical isolates resistant to almost all commercially available antibiotics have emerged. Thus, novel antimicrobial agents, specifically those for multidrug-resistant Gram-negative bacteria, are urgently needed. In the current study, we report the isolation, structure elucidation, and preliminary biological characterization of a new cationic lipopeptide antibiotic, battacin or octapeptin B5, produced from a Paenibacillus tianmuensis soil isolate. Battacin kills bacteria in vitro and has potent activity against Gramnegative bacteria, including multidrug-resistant and extremely drug-resistant clinical isolates. Hospital strains of Escherichia coli and Pseudomonas aeruginosa are the pathogens most sensitive to battacin, with MICs of 2 to 4 g/ml. The ability of battacin to disrupt the outer membrane of Gram-negative bacteria is comparable to that of polymyxin B, the last-line therapy for infections caused by antibiotic-resistant Gram-negative bacteria. However, the capacity of battacin to permeate bacterial plasma membranes is less extensive than that of polymyxin B. The bactericidal kinetics of battacin correlate with the depolarization of the cell membrane, suggesting that battacin kills bacteria by disrupting the cytoplasmic membrane. Other studies indicate that battacin is less acutely toxic than polymyxin B and has potent in vivo biological activity against E. coli. Based on the findings of the current study, battacin may be considered a potential therapeutic agent for the treatment of infections caused by antibioticresistant Gram-negative bacteria.

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“…Lipopeptide antibiotics represent an old class of antibiotics, which includes polymyxins but also new entries, such as the recently approved daptomycin. This class of antibiotics was reviewed (Pirri et al, 2009), focusing on their therapeutic applications and placing particular emphasis on the chemical modifications introduced to improve their activity. Another review (Raaijmakers et al, 2010) provides a detailed summary of the versatile functions of lipopeptides in the biology of Pseudomonas and Bacillus species, and highlights their role in competitive interactions with coexisting organisms.…”

Section: Ribosomal-and Nonribosomal-derived Peptides: a Virtually Unlmentioning

confidence: 99%

Marine Peptide Secondary Metabolites

Banaigs

Bonnard

Witczak

et al. 2014

Outstanding Marine Molecules

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A large pro port ion of the marine natural produc ts actu ally u n der clinical inve stigat ion are pept ide sec ondary metabolites with unusual amino acids re sidues. This growing f amily of compounds can be produced via tw o major p athw ays, r ibosomal and nonribosomal. In this c hapt er a re p re sent ed a nd illu strated, with a fe w f amou s examples, ribosomal-and n onribosomal-d erived pe ptides. Atte ntion is focused on fi ve families of biological ly a ctive marine p eptides of d iverse origin, ranging from the old est living ce ll of the world, the cyanobact eria, to more sophisticat ed organisms s uch a s tu nicates or mol lusk s. T he discu ssed pe ptides illu strate d iff erently th e s tructural fe atu re s and diversity f ound in mari ne-derived peptid es; laxaphycins as an example o f true pept ide s; dolast atins, didemnins and kahalalides are discuss ed in connectio n wit h their cl inical trials; a nd azole/azoli ne-c ontaining cyanobactins to exe m plif y the extra ord ina ry c hemi cal dive rs it y wit hin a single organism. Information abou t their biol ogical properties and mec hanisms of a ctio n is disc uss ed when available .

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Lipopeptides as anti-infectives: a practical perspective

Cited by 92 publications

References 94 publications

A new anti-MRSA antibiotic complex, WAP-8294A II. Structure characterization of minor components by ESI LCMS and MS/MS

A new anti-MRSA antibiotic complex, WAP-8294A II. Structure characterization of minor components by ESI LCMS and MS/MS

Battacin (Octapeptin B5), a New Cyclic Lipopeptide Antibiotic from Paenibacillus tianmuensis Active against Multidrug-Resistant Gram-Negative Bacteria

Marine Peptide Secondary Metabolites

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