Synthesis and Preliminary Investigations of the siRNA Delivery Potential of Novel, Single-Chain Rigid Cationic Carotenoid Lipids

Pungente, Michael D.; Jubeli, Emile; Øpstad, Christer L.; Al‐Kawaz, Mais; Barakat, Nour; Ibrahim, Tarek; Khalique, Nada Abdul; Raju, Liji; Jones, Rachel; Leopold, Philip L.; Sliwka, Hans‐Richard; Partali, Vassilia

doi:10.3390/molecules17033484

Cited by 14 publications

(20 citation statements)

References 30 publications

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“…375 In 2012, Pungente et al developed five carotenoids-derived single-tailed rigid cationic lipids, which were expected to be capable of selfassembling and delivering siRNA efficiently. 376 As shown in Then, these lipids were obtained via esterification followed by amination or quaternization. Results indicated that these singletailed rigid cationic lipids were able to deliver siRNA to eukaryotic cells in vitro.…”

Section: Cationic Lipidsmentioning

confidence: 99%

Lipids and Lipid Derivatives for RNA Delivery

et al. 2021

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RNA-based therapeutics have shown great promise in treating a broad spectrum of diseases through various mechanisms including knockdown of pathological genes, expression of therapeutic proteins, and programmed gene editing. Due to the inherent instability and negative-charges of RNA molecules, RNA-based therapeutics can make the most use of delivery systems to overcome biological barriers and to release the RNA payload into the cytosol. Among different types of delivery systems, lipid-based RNA delivery systems, particularly lipid nanoparticles (LNPs), have been extensively studied due to their unique properties, such as simple chemical synthesis of lipid components, scalable manufacturing processes of LNPs, and wide packaging capability. LNPs represent the most widely used delivery systems for RNA-based therapeutics, as evidenced by the clinical approvals of three LNP-RNA formulations, patisiran, BNT162b2, and mRNA-1273. This review covers recent advances of lipids, lipid derivatives, and lipid-derived macromolecules used in RNA delivery over the past several decades. We focus mainly on their chemical structures, synthetic routes, characterization, formulation methods, and structure–activity relationships. We also briefly describe the current status of representative preclinical studies and clinical trials and highlight future opportunities and challenges.

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Section: Cationic Lipidsmentioning

confidence: 99%

Lipids and Lipid Derivatives for RNA Delivery

et al. 2021

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“…Very recently Sliwka et al . synthetized some new cationic carotenoid lipids, where a quaternary ammonium moiety is responsible for the amphipatic character of the molecules [12,13].…”

Section: Hydrophilic Salts Of Carotenoid Estersmentioning

confidence: 99%

Hydrophilic Carotenoids: Recent Progress

et al. 2012

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Carotenoids are substantially hydrophobic antioxidants. Hydrophobicity is this context is rather a disadvantage, because their utilization in medicine as antioxidants or in food chemistry as colorants would require some water dispersibility for their effective uptake or use in many other ways. In the past 15 years several attempts were made to synthetize partially hydrophilic carotenoids. This review compiles the recently synthetized hydrophilic carotenoid derivatives.

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“…The cholesterol-based cationic lipid has been used as the major hydrophobic domain of liposomes for gene delivery due to being less toxic than other cationic lipids [ 16 ]. Many cholesterol-based cationic lipids have been synthesized, among which 3β-[ N -( N ', N '-dimethylaminoethyl)-carbamoyl] cholesterol (DC-Chol, Figure 1 ) showed efficient transfection in gene delivery and was used as the commercially available liposome reagent [ 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Cholesterol-Based Cationic Lipids as Transfecting Agents of DNA for Efficient Gene Delivery

Huan

Wan

et al. 2015

IJMS

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The design, synthesis and biological evaluation of the cationic lipid gene delivery vectors based on cholesterol and natural amino acids lysine or histidine are described. Cationic liposomes composed of the newly synthesized cationic lipids 1a or 1b and neutral lipid DOPE (1,2-dioleoyl-l-α-glycero-3-phosphatidyl-ethanolamine) exhibited good transfection efficiency. pEGFP-N1 plasmid DNA was transferred into 293T cells by cationic liposomes formed from cationic lipids 1a and 1b, and the transfection activity of the cationic lipids was superior (1a) or parallel (1b) to that of the commercially available 3β-[N-(N',N'-dimethylaminoethyl)-carbamoyl] cholesterol (DC-Chol) derived from the same cholesterol backbone with different head groups. Combined with the results of agarose gel electrophoresis, transfection experiments with various molar ratios of the cationic lipids and DOPE and N/P (+/−) molar charge ratios, a more effective formulation was formed, which could lead to relatively high transfection efficiency. Cationic lipid 1a represents a potential agent for the liposome used in gene delivery due to low cytotoxicity and impressive gene transfection activity.

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Synthesis and Preliminary Investigations of the siRNA Delivery Potential of Novel, Single-Chain Rigid Cationic Carotenoid Lipids

Cited by 14 publications

References 30 publications

Lipids and Lipid Derivatives for RNA Delivery

Lipids and Lipid Derivatives for RNA Delivery

Hydrophilic Carotenoids: Recent Progress

Novel Cholesterol-Based Cationic Lipids as Transfecting Agents of DNA for Efficient Gene Delivery

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