Characterization of drug encapsulation and retention in archaea-inspired tetraether liposomes

Leriche, Geoffray; Cifelli, Jessica L.; Sibucao, Kevin Carlo Abril; Patterson, Joseph P.; Koyanagi, Takaoki; Gianneschi, Nathan C.; Yang, Jerry

doi:10.1039/c6ob02832b

Cited by 34 publications

(26 citation statements)

References 40 publications

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“…In addition, a tetraether liposomal formulation also demonstrated high retention for three different encapsulated drugs commonly used in chemotherapy. 12 In particular, we showed that liposomes comprised of a pure tetraether lipid exhibited a decrease in the rate of leakage of the neutral drug Cytarabine compared to liposomes formed from a commercial diacyl lipid.…”

Section: Membrane Permeability Tetraether Lipids Nucleoside Drug Lipomentioning

confidence: 89%

Evaluation of tetraether lipid-based liposomal carriers for encapsulation and retention of nucleoside-based drugs

Paolucci

Leriche

Koyanagi

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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Although liposomal nanoparticles are one of the most versatile class of drug delivery systems, stable liposomal formulation of small neutral drug molecules still constitutes a challenge due to the low drug retention of current lipid membrane technologies. In this study, we evaluate the encapsulation and retention of seven nucleoside analog-based drugs in liposomes made of archaea-inspired tetraether lipids, which are known to enhance packing and membrane robustness compared to conventional bilayer-forming lipids. Liposomes comprised of the pure tetraether lipid generally showed improved retention of drugs (up to 4-fold) compared with liposomes made from a commercially available diacyl lipid. Interestingly, we did not find a significant correlation between the liposomal leakage rates of the molecules with typical parameters used to assess lipophilicity of drugs (such logD or topological polar surface area), suggesting that specific structural elements of the drug molecules can have a dominant effect on leakage from liposomes over general lipophilic character.

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Section: Membrane Permeability Tetraether Lipids Nucleoside Drug Lipomentioning

confidence: 89%

Evaluation of tetraether lipid-based liposomal carriers for encapsulation and retention of nucleoside-based drugs

Paolucci

Leriche

Koyanagi

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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“…However, drug delivery may not effectively target the desired site or may have effects on healthy tissues causing adverse effects [3][4][5]. Thus, various formulations for chemotherapeutic drugs have been developed [6,7].…”

Section: Introductionmentioning

confidence: 99%

Liposomal Cytarabine as Cancer Therapy: From Chemistry to Medicine

et al. 2019

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Cancer is the second leading cause of death worldwide. The main modality to fight against cancer is surgery, radiotherapy, and chemotherapy, and more recently targeted therapy, gene therapy and immunotherapy, which play important roles in treating cancer patients. In the last decades, chemotherapy has been well developed. Nonetheless, administration of the drug is not always successful, as limited drug dosage can reach the tumor cells.. In this context, the possibility to use an encapsulated anti-cancer drug may potentially solve the problem. Liposomal cytarabine is a formulation with pronounced effectiveness in lymphomatous meningitis and reduced cardiotoxicity if compared to liposomal anthracyclines. Thus, the future liposomal cytarabine use could be extended to other diseases given its reduction in cytotoxic side effects compared to the free formulation. This review summarizes the chemistry and biology of liposomal cytarabine, with exploration of its clinical implications.

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“…Since these bolalipids are able to span the membrane of classical phospholipid bilayers, they can be used to stabilize liposomes for drug delivery purposes. The applicability of this approach was already tested for a large variety of natural and artificial bolalipids [12,16–22]. …”

Section: Introductionmentioning

confidence: 99%

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

Drescher¹,

Garamus

Garvey³

et al. 2017

Beilstein J. Org. Chem.

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In the present work, we describe the synthesis of a single-chain, phenylene-modified bolalipid with two phosphocholine headgroups, PC-C18pPhC18-PC, using a Sonogashira cross-coupling reaction as a key step. The aggregation behaviour was studied as a function of temperature using transmission electron microscopy (TEM), differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, and small angle neutron scattering (SANS). We show that our new bolalipid self-assembles into nanofibres, which transform into flexible nanofibres at 27 °C and further to small elongated micelles at 45 °C. Furthermore, the miscibility of the bolalipid with bilayer-forming phosphatidylcholines (DMPC, DPPC, and DSPC) was investigated by means of DSC, TEM, FTIR, and small angle X-ray scattering (SAXS). We could show that the PC-C18pPhC18-PC is partially miscible with saturated phosphatidylcholines; however, closed lipid vesicles with an increased thermal stability were not found. Instead, bilayer fragments and disk-like aggregates are formed.

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Characterization of drug encapsulation and retention in archaea-inspired tetraether liposomes

Cited by 34 publications

References 40 publications

Evaluation of tetraether lipid-based liposomal carriers for encapsulation and retention of nucleoside-based drugs

Evaluation of tetraether lipid-based liposomal carriers for encapsulation and retention of nucleoside-based drugs

Liposomal Cytarabine as Cancer Therapy: From Chemistry to Medicine

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

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