Self‐Assembly of the Cyclic Lipopeptide Daptomycin: Spherical Micelle Formation Does Not Depend on the Presence of Calcium Chloride

Kirkham, Steven; Castelletto, Valeria; Hamley, Ian W.; Inoue, Katsuaki; Rambo, Robert P.; Reza, Mehedi; Ruokolainen, Janne

doi:10.1002/cphc.201600308

Cited by 36 publications

(34 citation statements)

References 22 publications

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“…Accumulated evidences suggest that by inserting of its hydrophobic decanoyl chain into bacterial membrane, daptomycin causes membrane permeabilization and potassium ions outflow, leading to rapid bacteria cell death . The formation of spherical micelles by daptomycin has been proposed to facilitate bacterial‐targeted delivery . However, studies also shown that >90% of the total amount of daptomycin in blood is protein‐bounded, which in turn, may affect its antibacterial activity, as demonstrated in protein‐free media .…”

Section: Clinical and Preclinical Examples Of Amphiphilic Drugsmentioning

confidence: 99%

“…[111] The formation of spherical micelles by daptomycin has been proposed to facilitate bacterial-targeted delivery. [112] However, studies also shown that >90% of the total amount of daptomycin in blood is protein-bounded, [113,114] which in turn, may affect its antibacterial activity, as demonstrated in protein-free media. [115] Yet these in vitro protein binding studies failed to predict clinical efficacy of daptomycin, suggesting other important characteristics, such as favorite pharmacokinetics are of vital clinical importance to the success of antibiotic therapy.…”

Section: Amphiphilic Peptidesmentioning

confidence: 99%

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Recent Advances in the Design of Self‐Delivery Amphiphilic Drugs and Vaccines

Liu

2019

Advanced Therapeutics

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Amphiphilic drugs are molecular drugs or drug conjugates possessing both hydrophilic and lipophilic properties. Representative amphiphilic drugs are composed of a pharmaceutical payload, a linker, and an appropriate amphiphilic modification. The physicochemical properties of amphiphilic drugs can be tailored by structure‐based engineering, which ultimately determine the drug molecules’ self‐assemble ability, bioavailability, protein binding, membrane anchoring, organ and intracellular distributions, side effects, and biological efficacy. Unlike the traditional carrier‐assistant drug delivery system, many of the amphiphilic drugs are carrier‐free and can self‐deliver to target sites/cells and access intracellular organelles without an external delivery carrier. This is achieved by molecular designs that control the delivery pathways of amphiphilic drugs at organ/tissue, cellular, and intracellular levels. In this review the recent advances in self‐delivery amphiphilic drugs and vaccines are highlighted, with emphasis on the underlying design principles and emerging applications.

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Section: Clinical and Preclinical Examples Of Amphiphilic Drugsmentioning

confidence: 99%

Section: Amphiphilic Peptidesmentioning

confidence: 99%

Recent Advances in the Design of Self‐Delivery Amphiphilic Drugs and Vaccines

Liu

2019

Advanced Therapeutics

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“…The paper also showed that the PA can also be transported across the blood-brain barrier [52]. One of the most well-known lipopeptides used in treating infections is daptomycin ( Figure 5) [53].…”

Section: Antimicrobial Materialsmentioning

confidence: 91%

“…This combines to cause cell death. The self-assembly of daptomycin was studied outside of the cell and it was shown to aggregate into micelles [53]. This aggregation process may be correlated to its excellent antimicrobial activity.…”

Section: Antimicrobial Materialsmentioning

confidence: 99%

Peptide hormones and lipopeptides: from self‐assembly to therapeutic applications

Hutchinson

Burholt

Hamley

2017

Journal of Peptide Science

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This review describes the properties and activities of lipopeptides and peptide hormones and how the lipidation of peptide hormones could potentially produce therapeutic agents combating some of the most prevalent diseases and conditions. The self‐assembly of these types of molecules is outlined, and how this can impact on bioactivity. Peptide hormones specific to the uptake of food and produced in the gastrointestinal tract are discussed in detail. The advantages of lipidated peptide hormones over natural peptide hormones are summarised, in terms of stability and renal clearance, with potential application as therapeutic agents. © 2017 The Authors Journal of Peptide Science published by European Peptide Society and John Wiley & Sons Ltd.

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“…An example is daptomycin, produced by the Gram positive bacterium, Streptomyces roseoporous, which is used to treat MRSA and self-assembles into micelle structures. 23,24 Synthetic amphiphilic lipopeptides tend to be based on a bio-derived sequence, often containing a linear peptide head group with 1-3 (usually palmitoyl) lipid chains attached. An example is Toll-like receptor agonists.…”

mentioning

confidence: 99%

Self-assembly of bioactive peptides, peptide conjugates, and peptide mimetic materials

2017

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Molecular self-assembly is a multi-disciplinary field of research, with potential chemical and biological applications. One of the main driving forces of self-assembly is molecular amphiphilicity, which can drive formation of complex and stable nanostructures. Self-assembling peptide and peptide conjugates have attracted great attention due to their biocompatibility, biodegradability and biofunctionality. Understanding assembly enables the better design of peptide amphiphiles which may form useful and functional nanostructures. This review covers self-assembly of amphiphilic peptides and peptide mimetic materials, as well as their potential applications. Peptide self-assemblySelf-assembly is defined as the ability of a molecule, without guidance of external factors, to associate through non-covalent interactions to form highly ordered 3-dimensional structures.

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Self‐Assembly of the Cyclic Lipopeptide Daptomycin: Spherical Micelle Formation Does Not Depend on the Presence of Calcium Chloride

Cited by 36 publications

References 22 publications

Recent Advances in the Design of Self‐Delivery Amphiphilic Drugs and Vaccines

Recent Advances in the Design of Self‐Delivery Amphiphilic Drugs and Vaccines

Peptide hormones and lipopeptides: from self‐assembly to therapeutic applications

Self-assembly of bioactive peptides, peptide conjugates, and peptide mimetic materials

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