On the structure and stability of novel cationic DPPC liposomes doped with gemini surfactants

Domínguez-Arca, Vicente; Sabín, Juan; García‐Río, Luis; Bastos, Margarida; Taboada, Pablo; Barbosa, Sílvia; Prieto, Gerardo

doi:10.1016/j.molliq.2022.120230

Cited by 6 publications

(7 citation statements)

References 69 publications

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“…Due to the presence of phospholipids, liposomes are highly biocompatible and can deliver both hydrophilic and lipophilic drugs to target cells. Recent advancements have significantly overcome the stability problems associated with liposomes through modulation of surface charges, size, lipid composition, and surface functionalization using targeting ligands [ 164 , 165 ]. Surface modification also allows for site-specific delivery of bioactives and prolongs their systemic circulation.…”

Section: Current Nanoparticle-based Delivery Systems For Plant Bioact...mentioning

confidence: 99%

Critical Review in Designing Plant-Based Anticancer Nanoparticles against Hepatocellular Carcinoma

2023

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Hepatocellular carcinoma (HCC), accounting for 85% of liver cancer cases, continues to be the third leading cause of cancer-related deaths worldwide. Although various forms of chemotherapy and immunotherapy have been investigated in clinics, patients continue to suffer from high toxicity and undesirable side effects. Medicinal plants contain novel critical bioactives that can target multimodal oncogenic pathways; however, their clinical translation is often challenged due to poor aqueous solubility, low cellular uptake, and poor bioavailability. Nanoparticle-based drug delivery presents great opportunities in HCC therapy by increasing selectivity and transferring sufficient doses of bioactives to tumor areas with minimal damage to adjacent healthy cells. In fact, many phytochemicals encapsulated in FDA-approved nanocarriers have demonstrated the ability to modulate the tumor microenvironment. In this review, information about the mechanisms of promising plant bioactives against HCC is discussed and compared. Their benefits and risks as future nanotherapeutics are underscored. Nanocarriers that have been employed to encapsulate both pure bioactives and crude extracts for application in various HCC models are examined and compared. Finally, the current limitations in nanocarrier design, challenges related to the HCC microenvironment, and future opportunities are also discussed for the clinical translation of plant-based nanomedicines from bench to bedside.

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Section: Current Nanoparticle-based Delivery Systems For Plant Bioact...mentioning

confidence: 99%

Critical Review in Designing Plant-Based Anticancer Nanoparticles against Hepatocellular Carcinoma

2023

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“…Then, 0.15 mL of TCEP (160 mM, in 0.1 M acetate buffer, pH 4) was added and mixed (vortex) to obtain a solution that was 9.3 mM in (ValPhe) 2 Csa and 12 mM in TCEP. After 16 h, the sample was lyophilized and dissolved in DMSO-d 6 .…”

Section: H Nmr Study Of the Reduction With Tcepmentioning

confidence: 99%

“…A common approach to obtain cationic liposomes, already reported in the 1980s, is to add a cationic lipid analogue such as 1,2-bis(oleoyloxy)-3-(trimethylammonium)propane (DOTAP) to conventional liposomes formed by natural zwitterionic phospholipids . Alternatively, in many cases, different cationic gemini surfactants have been used to prepare liposomes when mixed with phospholipids. , Another approach involved the synthetic modification of phosphatidylethanolamine with an l -lysine derivative . Monocomponent cationic vesicles can be formed with compounds that are not based in phospholipids such as deaqualinum, a bolaamphiphile with two terminal quinolinium units, , diC14-amidine, dioctadecyldimethylammonium bromide, derivatives of vernonia oil, N-[3-(dimethylamino)propyl]-octadecanamide, a polypeptide grafted with a polycation, or gemini surfactants. , Also, quaternary ammonium surfactants − and amino acid-derived surfactants − sometimes evolve into vesicles in the presence of different species.…”

Section: Introductionmentioning

confidence: 99%

“… 5 Alternatively, in many cases, different cationic gemini surfactants have been used to prepare liposomes when mixed with phospholipids. 6 , 7 Another approach involved the synthetic modification of phosphatidylethanolamine with an l -lysine derivative. 8 Monocomponent cationic vesicles can be formed with compounds that are not based in phospholipids such as deaqualinum, a bolaamphiphile with two terminal quinolinium units, 9 , 10 diC14-amidine, 11 dioctadecyldimethylammonium bromide, 12 derivatives of vernonia oil, 13 N-[3-(dimethylamino)propyl]-octadecanamide, 14 a polypeptide grafted with a polycation, 15 or gemini surfactants.…”

Section: Introductionmentioning

confidence: 99%

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Reduction-Responsive Cationic Vesicles from Bolaamphiphiles with Ionizable Amino Acid or Dipeptide Polar Heads

Bernal-Martínez,

Angulo-Pachón,

Galindo

et al. 2023

Langmuir

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This paper presents a study of the aggregation of cationic bolaamphiphilic molecules into vesicles. These molecules are based on a cystamine core with protonated terminal dipeptide groups. The study found that vesicles can be formed at pH 4 for all of the dipeptide-terminated bolaamphiphiles containing different combinations of L-valine, L-phenylalanine, and L-tryptophan. The concentration for aggregation onset was determined by using pyrene as a fluorescent probe or light dispersion for compounds with tryptophan. Dynamic light scattering (DLS) studies and transmission electron microscopy (TEM) reveal that the vesicles have diameters ranging from 140 to 500 nm and show the capability of loading hydrophobic cargos, such as Nile red, and their liberation in reductive environments. Furthermore, the bolaamphiphiles are only fully protonated and prone to vesicle formation at acidic pH, making them a promising alternative for gastrointestinal delivery.

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“…A number of factors can influence the key physicochemical parameters of modified liposomes: (1) surfactant head group structure [23,35,36]; (2) surfactant alkyl tail length [36,37]; (3) surfactant degree of oligomerization (monomeric, gemini, or trimeric) [38][39][40]; and (4) the lipid/surfactant ratio [41,42]. There are examples of liposome modification with alkyltriphenylphosphonium surfactants [37,[43][44][45], amino acid-based surfactants [46,47], imidazolium surfactants [43,[48][49][50], pyrrolidinium surfactants [51][52][53], metallosurfactants [54], and GS [21,[55][56][57][58].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Properties, and Biomedical Application of Dicationic Gemini Surfactants with Dodecane Spacer and Carbamate Fragments

Vasileva,

Gaynanova,

Valeeva

et al. 2023

IJMS

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A synthesis procedure and aggregation properties of a new homologous series of dicationic gemini surfactants with a dodecane spacer and two carbamate fragments (N,N′-dialkyl-N,N′-bis(2-(ethylcarbamoyloxy)ethyl)-N,N′-dimethyldodecan-1,6-diammonium dibromide, n-12-n(Et), where n = 10, 12, 14) were comprehensively described. The critical micelle concentrations of gemini surfactants were obtained using tensiometry, conductometry, spectrophotometry, and fluorimetry. The thermodynamic parameters of adsorption and micellization, i.e., maximum surface excess (Гmax), the surface area per surfactant molecule (Amin), degree of counterion binding (β), and Gibbs free energy of micellization (∆Gmic), were calculated. Functional activity of the surfactants, including the solubilizing capacity toward Orange OT and indomethacin, incorporation into the lipid bilayer, minimum inhibitory concentration, and minimum bactericidal and fungicidal concentrations, was determined. Synthesized gemini surfactants were further used for the modification of liposomes dual-loaded with α-tocopherol and donepezil hydrochloride for intranasal treatment of Alzheimer’s disease. The obtained liposomes have high stability (more than 5 months), a significant positive charge (approximately + 40 mV), and a high degree of encapsulation efficiency toward rhodamine B, α-tocopherol, and donepezil hydrochloride. Korsmeyer-Peppas, Higuchi, and first-order kinetic models were used to process the in vitro release curves of donepezil hydrochloride. Intranasal administration of liposomes loaded with α-tocopherol and donepezil hydrochloride for 21 days prevented memory impairment and decreased the number of Aβ plaques by 37.6%, 40.5%, and 72.6% in the entorhinal cortex, DG, and CA1 areas of the hippocampus of the brain of transgenic mice with Alzheimer’s disease model (APP/PS1) compared with untreated animals.

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On the structure and stability of novel cationic DPPC liposomes doped with gemini surfactants

Cited by 6 publications

References 69 publications

Critical Review in Designing Plant-Based Anticancer Nanoparticles against Hepatocellular Carcinoma

Critical Review in Designing Plant-Based Anticancer Nanoparticles against Hepatocellular Carcinoma

Reduction-Responsive Cationic Vesicles from Bolaamphiphiles with Ionizable Amino Acid or Dipeptide Polar Heads

Synthesis, Properties, and Biomedical Application of Dicationic Gemini Surfactants with Dodecane Spacer and Carbamate Fragments

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