Investigating bolalipids as solubilizing agents for poorly soluble drugs: Effects of alkyl chain length on solubilization and cytotoxicity

Liu, Feng; Harvey, Richard D.; Modicano, Paola; Hamdi, Farzad; Kyrilis, Fotis L.; Müller, Sindy; Gruhle, Kai; Kastritis, Panagiotis L.; Drescher, Simon; Dailey, Lea Ann

doi:10.1016/j.colsurfb.2022.112369

Cited by 7 publications

(4 citation statements)

References 59 publications

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“…Its solubilization has been superior to sodium dodecyl sulfate (SDS) and the non-ionic surfactant pegylated hydroxystearate (PEG-HS). In our case, increasement in the dissolution can be related to solubilization effect of DQA [40]. 6) [18,41].…”

Section: Drug Release Studiesmentioning

confidence: 52%

Coenzyme Q10 Loaded DQAsomes for Leigh Disease

ERGİN,

SEÇEN,

UNER

et al. 2023

Preprint

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Leigh syndrome (LS), a rare hereditary neurometabolic disorder caused by mitochondrial dysfunction, results from genetic mutations affecting the central nervous system. Endogenous bioactive antioxidant Coenzyme Q10 (CoQ10) deficiency is associated with LS and contributes to various clinical symptoms. Dequalinium chloride (DQA) is a bolalipid with mitochondria-targeting properties. This study aimed to develop CoQ10-loaded DQAsomes to enhance CoQ10 solubility and delivery to mitochondria for potential LS treatment. Human pluripotent cell lines (HPP) and MDCi007-A cells with NDUFV gene anomalies were utilized. DQAsomes were prepared using thin-film technique and characterized for size, zeta potential, encapsulation efficiency, and process efficiency. Drug release, dissolution, and cytotoxicity studies were performed. RT-PCR, ELISA, immunostaining, and Western blot analyses assessed pluripotency and gene expression changes and apoptosis induced by the formulations. DQAsomes exhibited sizes between 165.8-311.2 nm, with anionic zeta potential. Encapsulation efficiency ranged from 34.03–82.48%. Cytotoxicity studies demonstrated improved viability with CoQ10-DQA compared to CoQ10-PBS. CoQ10-DQAsignificantly reduced the expression of pluripotency markers OCT3/4, SOX-2, and NANOG, potentially indicating reduced stemness. CoQ10-loaded DQAsomes present a promising strategy for addressing CoQ10 deficiency in LS. These DQAsomes enhance CoQ10 solubility and bioavailability while potentially modulating cellular pluripotency markers and mitochondrial gene expression.

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Section: Drug Release Studiesmentioning

confidence: 52%

Coenzyme Q10 Loaded DQAsomes for Leigh Disease

ERGİN,

SEÇEN,

UNER

et al. 2023

Preprint

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“…For example, Dailey and co‐workers synthesized a single chain bolalipid with an increasing aliphatic chain length of C 22 , C 24 , and C 26 . [ 226 ] They found that a decrease in the aliphatic chain length is able to reduce the cytotoxicity. Chou and co‐workers used dialkyldimethylammonium bromides (DXDAB) as a component of the prepared lipid vesicle.…”

Section: Lipid‐based Sirna Delivery Systemsmentioning

confidence: 99%

Recent Advances in Engineering Carriers for siRNA Delivery

Yang,

Lin,

Zhang

et al. 2024

Macromolecular Bioscience

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RNA interference (RNAi) technology has been a promising treatment strategy for combating intractable diseases. However, the applications of RNAi in clinical were hampered by extracellular and intracellular barriers. To overcome these barriers, various siRNA delivery systems have been developed in the past two decades. The first approved RNAi therapeutic, Patisiran (ONPATTRO™) using lipids as the carrier, for the treatment of amyloidosis is one of the most important milestones. This has greatly encouraged researchers to work on creating new functional siRNA carriers. In this review, we summarized the recent advances in siRNA carriers consisting of lipids, polymers, and polymer‐modified inorganic particles for cancer therapy. Representative examples are presented to show the structural design of the carriers in order to overcome the delivery hurdles associated with RNAi therapies. Finally, the existing challenges and future perspective for developing RNAi as a clinical modality will be discussed and proposed. We believe that the addressed contributions in this review will promote the development of siRNA delivery systems for future clinical applications.This article is protected by copyright. All rights reserved

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“…This surface tension displayed no significant difference from that of the RBB KN-R-TTAB solution but surpassed that of the RBB KN-R-DTAB solution. The observation implies that surfactants with longer alkyl chains more effectively encapsulate hydrophobic dye-surfactant complexes within the interior of hydrophilic dye-surfactant aggregates due to their higher surface activity [33,34].…”

Section: Effects Of Alkyl Chain Length On Surface Tension Of the Surf...mentioning

confidence: 99%

Role of Alkyl Chain Length in Surfactant-Induced Precipitation of Reactive Brilliant Blue KN-R

Liu,

Chang,

et al. 2024

Molecules

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To develop a cost-effective method for the effective removal of reactive brilliant blue KN-R (RBB KN-R) from wastewater, we investigated the interactions between RBB KN-R and three cationic surfactants with different alkyl chain lengths, namely dodecyltrimethylammonium bromide (DTAB), tetradecyltrimethylammonium bromide (TTAB), and cetyltrimethylammonium bromide (CTAB). Employing a conductivity analysis, surface tension analysis, ultraviolet-visible spectrophotometry, and molecular dynamics simulation, we ascertained that RBB KN-R formed a 1:1 molar ratio dye–surfactant complex with each surfactant through electrostatic attraction. Notably, an augmentation in alkyl chain length correlated with increased binding strength between RBB KN-R and the surfactant. The resulting dye–surfactant complex exhibited heightened surface activity, enabling interactions through hydrophobic forces to generate dye–surfactant aggregates when the molar ratio was below 1:1. Within these mixed aggregates, self-assembly of RBB KN-R molecules occurred, leading to the formation of dye aggregates. Due to the improved hydrophobicity with increased alkyl chain length, TTAB and CTAB could encapsulate dye aggregates within the mixed aggregates, but DTAB could not. The RBB KN-R aggregates tended to distribute on the surface of the RBB KN-R-DTAB mixed aggregates, resulting in low stability. Thus, at a DTAB concentration lower than CMC, insoluble particles readily formed and separated from surfactant aggregates at an RBB KN-R and DTAB molar ratio of 1:4. Analyzing the RBB KN-R precipitate through scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) and measuring the DTAB concentration in the supernate revealed that, at this molar ratio, all RBB KN-R precipitated from the dye–surfactant mixed solution, with only 7.5 ± 0.5% of DTAB present in the precipitate. Furthermore, the removal ratio of RBB KN-R reached nearly 100% within a pH range of 1.0 to 9.0 and standing time of 6 h. The salt type and concentration did not significantly affect the precipitation process. Therefore, this simultaneous achievement of successful RBB KN-R removal and effective separation from DTAB underscores the efficacy of the proposed approach.

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Investigating bolalipids as solubilizing agents for poorly soluble drugs: Effects of alkyl chain length on solubilization and cytotoxicity

Cited by 7 publications

References 59 publications

Coenzyme Q10 Loaded DQAsomes for Leigh Disease

Coenzyme Q10 Loaded DQAsomes for Leigh Disease

Recent Advances in Engineering Carriers for siRNA Delivery

Role of Alkyl Chain Length in Surfactant-Induced Precipitation of Reactive Brilliant Blue KN-R

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