Mimicking Helical Antibacterial Peptides with Nonpeptidic Folding Oligomers

Violette, Aude; Fournel, Sylvie; Lamour, Karen; Chaloin, Olivier; Frisch, Benoı̂t; Briand, Jean‐Paul; Monteil, H.; Guichard, Gilles

doi:10.1016/j.chembiol.2006.03.009

Cited by 123 publications

(131 citation statements)

References 38 publications

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“…56 In the area of modifications of natural products by combinatorial methods to produce entirely different compounds that may bear little if any resemblance to the original, but are legitimately assignable to the "NM" category, citations are given in previous reviews. 3,[57][58][59][60][61][62][63][64] In addition, one should consult the recent reports from Waldmann's group 65,66 and those by Ganesan, 67 Shang and Tan, 68 Constantino, 69 and Violette et al 70 on the use of privileged structures as skeletons around which to build libraries. Another paper of interest in this regard is the editorial by Macarron from GSK, 9 as this may be the first time where data from industry on the results of HTS screens of combichem libraries versus potential targets were reported with a discussion of lead discovery rates.…”

Section: Resultsmentioning

confidence: 99%

Natural Products as Sources of New Drugs over the Last 25 Years

2007

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This review is an updated and expanded version of two prior reviews that were published in this journal in 1997 and 2003. In the case of all approved agents the time frame has been extended to include the 25 1 / 2 years from 01/1981 to 06/2006 for all diseases worldwide and from 1950 (earliest so far identified) to 06/2006 for all approved antitumor drugs worldwide. We have continued to utilize our secondary subdivision of a "natural product mimic" or "NM" to join the original primary divisions. From the data presented, the utility of natural products as sources of novel structures, but not necessarily the final drug entity, is still alive and well. Thus, in the area of cancer, over the time frame from around the 1940s to date, of the 155 small molecules, 73% are other than "S" (synthetic), with 47% actually being either natural products or directly derived therefrom. In other areas, the influence of natural product structures is quite marked, with, as expected from prior information, the antiinfective area being dependent on natural products and their structures. Although combinatorial chemistry techniques have succeeded as methods of optimizing structures and have, in fact, been used in the optimization of many recently approved agents, we are able to identify only one de noVo combinatorial compound approved as a drug in this 25 plus year time frame. We wish to draw the attention of readers to the rapidly evolving recognition that a significant number of natural product drugs/leads are actually produced by microbes and/or microbial interactions with the "host from whence it was isolated", and therefore we consider that this area of natural product research should be expanded significantly.It is over nine years since the publication of our first, 1 and three years since the second, 2 analysis of the sources of new and approved drugs for the treatment of human diseases, both of which indicated that natural products continued to play a highly significant role in the drug discovery and development process.That this influence of Nature in one guise or another has continued is shown by inspection of the information given below, where with the advantage of now over 25 years of data, we have been able to refine the system, eliminating a few duplicative entries that crept into the original data sets. In particular, as behooves authors from the National Cancer Institute (NCI), in the specific case of cancer treatments, we have gone back to consult the records of the FDA and added to these, comments from investigators who have informed us over the past two years of compounds that may have been approved in other countries and that were not captured in our earlier searches. These cancer data will be presented as a stand-alone section as well as including the last 25 years of data in the overall discussion.As we mentioned in our 2003 review, 2

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Section: Resultsmentioning

confidence: 99%

Natural Products as Sources of New Drugs over the Last 25 Years

2007

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“…Based on their work, several different helical peptides using β-peptides or α/β-peptides have been developed [71]. In addition to the work of Patch and Barron [72], who designed amphiphilic, helical peptoids of antibacterial N-substituted glycine oligomers [72], Violette et al [73] investigated antimicrobial foldamers with a urea backbone. It was reported that electrical charge, facial amphiphilicity, and a hydrophobic/hydrophilic balance are typically important factors in designing nontoxic antimicrobial compounds.…”

Section: Bioactive Oligopeptidesmentioning

confidence: 99%

Development of biomaterial surfaces with and without microbial nanosegments

Alarfaj¹,

Lee²,

Munusamy

et al. 2015

Journal of Polymer Engineering

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Abstract Infections by microorganisms are a major problem in public health throughout the world. Artificial materials, including biomedical goods, inherently lack defense against microbial development. Therefore, microbial cells can adhere on any type of artificial surface, particularly in a moist environment, and start to multiply to form a huge population. In this review, we will discuss a strategy for designing antimicrobial polymers and antimicrobial surfaces. Generally, there are five types of antimicrobial polymers: (a) polymeric biocides, (b) biocidal polymers, (c) biocide-releasing polymers, (d) bioactive oligopeptides, and (e) antimicrobial surfaces. Antimicrobial surfaces preventing the growth of microorganisms are a promising method to inhibit the spread of microbial infections. The antimicrobial surfaces can reject the attachment of microbes and/or kill microbes in the vicinity and can be designed to kill microbes on contact. It is recommended that the material surface not release biocidal substances, therefore preventing exhaustion of biocide release to kill microbes. Furthermore, the antimicrobial surfaces are desired to be nontoxic to human cells. The development of contact-active antimicrobial surfaces by grafting antimicrobial nanosegments onto the material surface will be an important topic in the future.

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“…1,2 Bactericidal peptidomimetics comprised of unnatural amino acids were thereby developed to circumvent the drawbacks of AMPs, which are protease-resistant and of improved bioavailability. 5 In recent years, several peptidomimetic analogues of AMPs, such as β-peptides, 6−9 arylamides, 10,11 and peptoids, 3,12,13 have received significant research interest.…”

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confidence: 99%

“…5 In recent years, several peptidomimetic analogues of AMPs, such as β-peptides, 6−9 arylamides, 10,11 and peptoids, 3,12,13 have received significant research interest.…”

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confidence: 99%

Lipidated Peptidomimetics with Improved Antimicrobial Activity

Amin

Padhee

et al. 2012

ACS Med. Chem. Lett.

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We report a series of lipidated α-AApeptides that mimic the structure and function of natural antimicrobial lipopeptides. Several short lipidated α-AApeptides show broadspectrum activity against a range of clinically related Grampositive and Gram-negative bacteria as well as fungus. Their antimicrobial activity and selectivity are comparable or even superior to the clinical candidate pexiganan as well as previously reported linear α-AApeptides. The further development of lipidated α-AApeptides will lead to a new class of antibiotics to combat drug resistance. KEYWORDS: antimicrobial peptides, peptidomimetics, drug resistance, lipidation, α-AApeptides A ntimicrobial peptides (AMPs) are found in most living organisms as an integral component of their innate defense against invading pathogens.1,2 Unlike conventional antibiotics that target specific substrates involved in bacterial metabolism, AMPs are believed to kill bacteria via a nonspecific interaction with their membranes, which has less chance of inducing the development of resistance by bacteria.1,2 Short cationic amphiphilic AMPs tend to interact with the negatively charged phospholipids on the bacterial membrane, which accounts for their selectivity for bacteria against eukaryotic cells whose membranes are more zwitterionic.3,4 Because of their selectivity for bacteria, low propensity for development of drug resistance, and broad-spectrum antimicrobial potency, AMPs are considered an emerging class of antimicrobial agents. 1−3 Nevertheless, the therapeutic application of AMPs is impeded by their intrinsic instability in the context of proteolytic degradation.1,2 Bactericidal peptidomimetics comprised of unnatural amino acids were thereby developed to circumvent the drawbacks of AMPs, which are protease-resistant and of improved bioavailability. 5 In recent years, several peptidomimetic analogues of AMPs, such as β-peptides, 6−9 arylamides, 10,11 and peptoids, 3,12,13 have received significant research interest.Lipidated peptides such as polymyxin B 14 and daptomycin 15 are lipo-antibiotics, which possess fatty acid tails that are integral to their bactericidal activities. It has been shown that attachment of saturated linear fatty acids to peptide termini greatly enhanced AMPs' antimicrobial activities toward both Gram-positive and Gram-negative strains. 16−19 More recently, short peptoid mimetics alkylated with lipids of 10 or 13 carbons were demonstrated to bear improved selectivity, without losing any antimicrobial activities. 13 It was suspected that lipid alkylation improves the hydrophobicity of charged peptides 18 and facilitates the interaction with cytoplasmic membranes.18 It is thereby envisioned that the development of lipidated peptidomimetics may overcome some of the drawbacks associated with current lipopeptide antibiotics. Herein, we report the development of lipidated α-AApeptides as potential antimicrobial agents. We have recently developed a novel class of peptidomimetics based on the α-chiral PNA (peptide nucleic acid) back...

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Mimicking Helical Antibacterial Peptides with Nonpeptidic Folding Oligomers

Cited by 123 publications

References 38 publications

Natural Products as Sources of New Drugs over the Last 25 Years

Natural Products as Sources of New Drugs over the Last 25 Years

Development of biomaterial surfaces with and without microbial nanosegments

Lipidated Peptidomimetics with Improved Antimicrobial Activity

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