Liposomes containing cholesterol and mitochondria-penetrating peptide (MPP) for targeted delivery of antimycin A to A549 cells

Mallick, Sudipta; Thủy, Lê Thị Thanh; Lee, Seulgi; Park, Jong-II; Choi, Joon Sig

doi:10.1016/j.colsurfb.2017.10.052

Cited by 38 publications

(28 citation statements)

References 22 publications

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“…Cholesterol-based drug carriers have been designed as delivery systems such as nanoparticles, micelles and liposomal formulations. The presence of cholesterol in a liposomal formulation has been reported to improve the stability of the formulation by preventing the phase transition of phospholipids [ 15 ].…”

Section: Cholesterol and Its Function As A Drug Carriermentioning

confidence: 99%

“…The Chol-FRFK/D liposomes had a higher cellular uptake and mitochondrial targeting compared to the two controls, DQAsomes and DOTAP/DOPE (D/D) liposomes. Treating A549 cells with Chol-FRFK/D liposomes showed an IC 50 of 10 µM compared to an IC 50 of 50 µM for free AMA [ 15 ]. Drug encapsulation in the Chol-FRFK/D liposomes was 100% since AMA could be accommodated both in the lipid bilayer membrane and the inside of the core.…”

Section: Application Of Cholesterol-based Carriers In Anticancer Dmentioning

confidence: 99%

“…The Chol-FRFK/D-AMA formulation was very cytotoxic that it caused mitochondria-mediated apoptosis in A549 cells. The Chol-FRFK/D liposomes are a promising anticancer delivery system for anticancer therapy [ 15 ].…”

Section: Application Of Cholesterol-based Carriers In Anticancer Dmentioning

confidence: 99%

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The Efficacy of Cholesterol-Based Carriers in Drug Delivery

Ruwizhi

Aderibigbe

2020

Molecules

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Several researchers have reported the use of cholesterol-based carriers in drug delivery. The presence of cholesterol in cell membranes and its wide distribution in the body has led to it being used in preparing carriers for the delivery of a variety of therapeutic agents such as anticancer, antimalarials and antivirals. These cholesterol-based carriers were designed as micelles, nanoparticles, copolymers, liposomes, etc. and their routes of administration include oral, intravenous and transdermal. The biocompatibility, good bioavailability and biological activity of cholesterol-based carriers make them potent prodrugs. Several in vitro and in vivo studies revealed cholesterol-based carriers potentials in delivering bioactive agents. In this manuscript, a critical review of the efficacy of cholesterol-based carriers is reported.

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Section: Cholesterol and Its Function As A Drug Carriermentioning

confidence: 99%

Section: Application Of Cholesterol-based Carriers In Anticancer Dmentioning

confidence: 99%

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The Efficacy of Cholesterol-Based Carriers in Drug Delivery

Ruwizhi

Aderibigbe

2020

Molecules

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“…A new liposomal formulation for drug delivery purposes was recently developed, based on the N -terminal cholesterol conjugation with a mitochondria-penetrating peptide (MPP) sequence, consisting of four amino acids [phenylalanine-arginine-phenylalanine-lysine (FRFK)]. More specifically, the synthesis of cholesterol-phenylalanine-arginine-phenylalanine-lysine ( Chol-FRFK ) 64 was achieved by coupling cholesteryl chloroformate 7 with amino acid-bound resins ( 62 ), followed by resin cleavage using TFA and the removal of protecting groups (Scheme 15) [22]. The authors developed the liposomes using dioleoyl- sn -glycero-3-phosphoethanolamine (DOPE) and Chol-FRFK 64 for delivery of the hydrophobic drug antimycin A specifically targeted toward mitochondria and lung cancer A549 cells.…”

Section: Drug Delivery Applicationsmentioning

confidence: 99%

Cholesterol-Based Compounds: Recent Advances in Synthesis and Applications

2018

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This review reports on the latest developments (since 2014) in the chemistry of cholesterol and its applications in different research fields. These applications range from drug delivery or bioimaging applications to cholesterol-based liquid crystals and gelators. A brief overview of the most recent synthetic procedures to obtain new cholesterol derivatives is also provided, as well as the latest anticancer, antimicrobial, and antioxidant new cholesterol-based derivatives. This review discusses not only the synthetic details of the preparation of new cholesterol derivatives or conjugates, but also gives a short summary concerning the specific application of such compounds.

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“…In detail, MPPs rely on alternating an equal number of cationic and hydrophobic amino acids for ensuring efficient cellular uptake and mitochondrial entry. On the one hand, the cationic amino acids aid interaction and charge-driven uptake through the negatively charged plasma membrane, facilitating access to the cytosol and driving the sequences toward the mitochondria; on the other hand, the hydrophobic residues ensure the preservation of a high degree of lipophilicity that allows partitioning of the peptides through the mitochondrial lipid bilayer and reduces the risk of membrane entrapment (8,9).…”

mentioning

confidence: 99%

Analysis of hydrophobic and hydrophilic moments of short penetrating peptides for enhancing mitochondrial localization: prediction and validation

et al. 2019

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Pharmaceutical interest in targeting mitochondria is increasing because of their contribution in incurable diseases. However, the inner mitochondrial layer represents a major hurdle to overcome for most drugs. Penetrating peptides are a promising strategy for drug delivery, but the absence of standard principles and reliable prediction tools limits the design and discovery of sequences with improved organelle specificity. In our hypothesis, peptide local flexibility represents a valuable source to predict peptide performance. Here, a pool of short nonnatural peptides was designed with the same amino acid content but different positioning. Molecular dynamics and membrane‐transfer simulations were used to generate the low‐energy conformers in extra, intracellular, and membrane‐inserted environments. The contributions of the hydrophobic and hydrophilic side chain–exposed surfaces revealed that the amino acid's relative position significantly affected the simulated peptide's dynamics. Based on the structural versatility, we predicted the peptides' behavior and the sequence with the most efficient membrane penetration and mitochondrial localization. The prediction and the improved performance of our peptides were experimentally confirmed and compared with a reported mitochondrial‐targeting sequence. We demonstrated that an accurate understanding of the structural versatility is a valid aid for future works in designing sequences with improved mitochondrial targeting.—Pirisinu, M., Blasco, P., Tian, X., Sen, Y., Bode, A. M., Liu, K., Dong, Z. Analysis of hydrophobic and hydrophilic moments of short penetrating peptides for enhancing mitochondrial localization: prediction and validation. FASEB J. 33, 7970–7984 (2019). http://www.fasebj.org

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Liposomes containing cholesterol and mitochondria-penetrating peptide (MPP) for targeted delivery of antimycin A to A549 cells

Cited by 38 publications

References 22 publications

The Efficacy of Cholesterol-Based Carriers in Drug Delivery

The Efficacy of Cholesterol-Based Carriers in Drug Delivery

Cholesterol-Based Compounds: Recent Advances in Synthesis and Applications

Analysis of hydrophobic and hydrophilic moments of short penetrating peptides for enhancing mitochondrial localization: prediction and validation

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