Temperature-responsive self-assembled nanostructures from lysine-based surfactants with high chain length asymmetry: from tubules and helical ribbons to micelles and vesicles

Oliveira, Isabel S.; Lo, Mikail; Araújo, Maria João; Marques, Eduardo F.

doi:10.1039/c9sm00399a

Cited by 24 publications

(22 citation statements)

References 66 publications

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“…Compositions based on amphiphilic lysine derivatives were documented as drug delivery vehicles containing encapsulated 5-fluorouracil [ 42 ] for cancer treatment as well as the component for design of coating against protein adsorption on nanoparticles [ 43 ]. In [ 44 ] promising stimuli-responsive double-tailed lysine-based surfactants were obtained.…”

Section: Self-assembly Of Amphiphilic Compoundsmentioning

confidence: 99%

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

Kashapov

Gaynanova

Gabdrakhmanov

et al. 2020

IJMS

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This review focuses on synthetic and natural amphiphilic systems prepared from straight-chain and macrocyclic compounds capable of self-assembly with the formation of nanoscale aggregates of different morphology and their application as drug carriers. Since numerous biological species (lipid membrane, bacterial cell wall, mucous membrane, corneal epithelium, biopolymers, e.g., proteins, nucleic acids) bear negatively charged fragments, much attention is paid to cationic carriers providing high affinity for encapsulated drugs to targeted cells. First part of the review is devoted to self-assembling and functional properties of surfactant systems, with special attention focusing on cationic amphiphiles, including those bearing natural or cleavable fragments. Further, lipid formulations, especially liposomes, are discussed in terms of their fabrication and application for intracellular drug delivery. This section highlights several features of these carriers, including noncovalent modification of lipid formulations by cationic surfactants, pH-responsive properties, endosomal escape, etc. Third part of the review deals with nanocarriers based on macrocyclic compounds, with such important characteristics as mucoadhesive properties emphasized. In this section, different combinations of cyclodextrin platform conjugated with polymers is considered as drug delivery systems with synergetic effect that improves solubility, targeting and biocompatibility of formulations.

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Section: Self-assembly Of Amphiphilic Compoundsmentioning

confidence: 99%

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

Kashapov

Gaynanova

Gabdrakhmanov

et al. 2020

IJMS

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“…The polar headgroup of LAAs, which contains both donor and acceptor hydrogen bonding groups that are capable of intra-and intermolecular interactions, adds further complexity to their self-assembly behavior. LAAs can form a wide variety of self-assembled nanostrucures, from tubules and helical ribbons to micelles and vesicles [16][17][18]. On the other hand, the constrained cyclic pyrrolidine This review focuses on several aspects that are related to the enzyme-based production of lipoaminoacids, their biological applications as gene delivery vectors, and future trends.…”

Section: Structure and Characterizationmentioning

confidence: 99%

“…The polar headgroup of LAAs, which contains both donor and acceptor hydrogen bonding groups that are capable of intra-and intermolecular interactions, adds further complexity to their self-assembly behavior. LAAs can form a wide variety of self-assembled nanostrucures, from tubules and helical ribbons to micelles and vesicles [16][17][18]. On the other hand, the constrained cyclic pyrrolidine structure Catalysts 2019, 9, 977 3 of 18 of proline (a β-sheet breaker) hinders intermolecular hydrogen bonding [19] and the bulkier headgroup of proline-based cationic LAAs usually leads to less efficient DNA binding [20].…”

Section: Structure and Characterizationmentioning

confidence: 99%

Lipoaminoacids Enzyme-Based Production and Application as Gene Delivery Vectors

et al. 2019

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Biosurfactant compounds have been studied in many applications, including biomedical, food, cosmetic, agriculture, and bioremediation areas, mainly due to their low toxicity, high biodegradability, and multifunctionality. Among biosurfactants, the lipoplexes of lipoaminoacids play a key role in medical and pharmaceutical fields. Lipoaminoacids (LAAs) are amino acid-based surfactants that are obtained from the condensation reaction of natural origin amino acids with fatty acids or fatty acid derivatives. LAA can be produced by biocatalysis as an alternative to chemical synthesis and thus become very attractive from both the biomedical and the environmental perspectives. Gemini LAAs, which are made of two hydrophobic chains and two amino acid head groups per molecule and linked by a spacer at the level of the amino acid residues, are promising candidates as both drug and gene delivery and protein disassembly agents. Gemini LAA usually show lower critical micelle concentration, interact more efficiently with proteins, and are better solubilising agents for hydrophobic drugs when compared to their monomeric counterparts due to their dimeric structure. A clinically relevant human gene therapy vector must overcome or avoid detect and silence foreign or misplaced DNA whilst delivering sustained levels of therapeutic gene product. Many non-viral DNA vectors trigger these defence mechanisms, being subsequently destroyed or rendered silent. The development of safe and persistently expressing DNA vectors is a crucial prerequisite for a successful clinical application, and it one of the main strategic tasks of non-viral gene therapy research.

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“…The 12Lys12 surfactant forms hydrogels composed by μm‐sized crystalline tubules, with a tubule–micelle transition taking place at a characteristic temperature, T m . More recently, we explored the effect of asymmetry in the hydrophobic tail length on the self‐assembly properties of this type of surfactants [30b] . Three series of isomers designated by 8Lys n and m Lys8, with m , n= 12, 14 and 16, and 12Lys16 and 16Lys12, were studied at pH 12.0 (to achieve solubility in water).…”

Section: Introductionmentioning

confidence: 99%

“…Three series of isomers designated by 8Lys n and m Lys8, with m , n= 12, 14 and 16, and 12Lys16 and 16Lys12, were studied at pH 12.0 (to achieve solubility in water). The ability of the amphiphiles to form tubular aggregates and induce gelation at low concentration and for T < T m was demonstrated, [30b] creating the opportunity for exploring the tubules as potential carriers of biomolecules of interest.…”

Section: Introductionmentioning

confidence: 99%

Stimuli‐Sensitive Self‐Assembled Tubules Based on Lysine‐Derived Surfactants for Delivery of Antimicrobial Proteins

Oliveira

Machado

Araújo

et al. 2020

Chemistry A European J

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Drug delivery vectors based on amphiphiles have important features such as versatile physicochemical properties and stimuli‐responsiveness. Amino acid‐based surfactants are especially promising amphiphiles due to their enhanced biocompatibility compared to conventional surfactants. They can self‐organize into micelles, vesicles and complex hierarchical structures, such as fibers, twisted and coiled ribbons, and tubules. In this work, we investigated the self‐assembly and drug loading properties of a family of novel anionic double‐tailed lysine‐derived surfactants, with variable degree of tail length mismatch, designated as mLys10 and 10Lysn, where m and n are the number of carbon atoms in the tails. These surfactants form tubular aggregates with assorted morphologies in water that undergo gelation due to dense entanglement, as evidenced by light and electron microscopy. Lysozyme (LZM), an enzyme with antimicrobial properties, was selected as model protein for loading. After the characterization of the interfacial properties and phase behavior of the amphiphiles, the LZM‐loading ability of the tubules was investigated, under varying experimental conditions, to assess the efficiency of the aggregates as pH‐ and temperature‐sensitive nanocarriers. Further, the toxicological profile of the surfactants per se and surfactant/LZM hydrogels was obtained, using human skin fibroblasts (BJ‐5ta cell line). Overall, the results show that the tubule‐based hydrogels exhibit very interesting properties for the transport and controlled release of molecules of therapeutic interest.

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Temperature-responsive self-assembled nanostructures from lysine-based surfactants with high chain length asymmetry: from tubules and helical ribbons to micelles and vesicles

Abstract: Stimuli-sensitive self-assembled nanostructures are relevant for efficient drug delivery and nanomaterial templating.

Cited by 24 publications

References 66 publications

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

Lipoaminoacids Enzyme-Based Production and Application as Gene Delivery Vectors

Stimuli‐Sensitive Self‐Assembled Tubules Based on Lysine‐Derived Surfactants for Delivery of Antimicrobial Proteins

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