Preparation of drug-in-cyclodextrin-in-liposomes at a large scale using a membrane contactor: Application to trans -anethole

Gharib, Riham; Greige‐Gerges, Hélène; Jraij, Alia; Auezova, Lizette; Charcosset, Catherine

doi:10.1016/j.carbpol.2016.06.074

Cited by 23 publications

(12 citation statements)

References 45 publications

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“…The vesicles appeared to be oligolamellar and spherical in shape. Similar morphology was found for DCLs loading anethole, [ 12,26 ] estragole, [ 13 ] and eugenol. [ 14 ] Although the sizes of the vesicles imaged by TEM were below those determined by DLS technique, the both techniques showed a size below 300 nm.…”

Section: Resultssupporting

confidence: 70%

Retention of Eucalyptol, a Natural Volatile Insecticide, in Delivery Systems Based on Hydroxypropyl‐β‐Cyclodextrin and Liposomes

Gharib

Jemâa

Charcosset

et al. 2020

Euro J Lipid Sci & Tech

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Eucalyptol (Euc) is a natural monoterpene with insecticide effects. Being highly volatile and sensitive to ambient conditions, its encapsulation would enlarge its application. Euc-loaded conventional liposomes (CL), cyclodextrin/drug inclusion complex, and drug-in-cyclodextrin-in-liposomes (DCL) are prepared to protect Euc from degradation, reduce its evaporation, and provide its controlled release. The liposomal suspension is freeze-dried using hydroxypropyl--cyclodextrin (HP--CD) as cryoprotectant. The liposomes are characterized before and after freeze-drying. The effect of Euc on the fluidity of liposomal membrane is also examined. A release study of Euc from delivery systems, in powder and reconstituted forms, is performed by multiple head extraction at 60°C after 6 months of storage at 4°C. CL and DCL suspensions are homogeneous, show nanometric vesicles size, spherical shape, and negative surface charge before and after freeze-drying. Moreover, HP--CD does not affect the fluidity of liposomes. CL formulations present a weak encapsulation for Euc. The loading capacity of eucalyptol in DCL is 38 times higher than that in CL formulation. In addition, freeze-dried DCL and HP--CD/Euc inclusion complex show a higher retention of eucalyptol than CL delivery system. Both carrier systems HP--CD/Euc and Euc-loaded DCL decrease Euc evaporation and improve its retention. Practical Applications: Eucalyptol is a natural insecticide. It is highly volatile and poorly soluble in water. To enlarge its application, its encapsulation in three delivery systems (conventional liposomes, cyclodextrin/drug inclusion complex, combined system composed of cyclodextrin inclusion complex and liposome) is studied. In this paper it is proved that cyclodextrin/eucalyptol inclusion complex and eucalyptol-in-cyclodextrin-in-liposome are effective delivery systems for encalyptol encapsulation, retention, and release.

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Section: Resultssupporting

confidence: 70%

Retention of Eucalyptol, a Natural Volatile Insecticide, in Delivery Systems Based on Hydroxypropyl‐β‐Cyclodextrin and Liposomes

Gharib

Jemâa

Charcosset

et al. 2020

Euro J Lipid Sci & Tech

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“…Anethole‐loaded S100 liposomes were prepared by the ethanol injection method using soybean phospholipids (Lipoid S100) and cholesterol as described previously (Gharib et al ). Phospholipids (12·5 mmol l −1 ) were dissolved in ethanol (10 ml) with cholesterol and anethole at a Lipoid S100 : cholesterol:anethole molar ratio of 1 : 1 : 1·35.…”

Section: Methodsmentioning

confidence: 99%

Antibacterial activity of free or encapsulated selected phenylpropanoids against Escherichia coli and Staphylococcus epidermidis

et al. 2020

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Aims Antibacterial activities of phenylpropenes (PPs) (eugenol, isoeugenol, estragole and trans‐anethole) and hydroxycinnamic acids (HCAs) (p‐coumaric, caffeic and ferulic acids) were assessed against Escherichia coli and Staphylococcus epidermidis. Effect of cyclodextrin and liposome encapsulation on the PPs activity was also evaluated. Methods and Results All PPs inhibited the bacterial growth in the hundred micromolar range, while HCAs did not, as determined by broth macrodilution. Anethole and estragole showed a higher efficiency than eugenol and isoeugenol, and E. coli was more susceptible than S. epidermidis. Hydroxypropyl‐β‐cyclodextrin/PP complexes and anethole‐loaded Lipoid S100‐liposomes were prepared by freeze‐drying and ethanol injection respectively. Both formulations were substantially less active than free PPs. For instance, E. coli growth inhibition was about 14% for all HP‐β‐CD/PP complexes evaluated at MIC50 values of free PPs (P < 0·05), and about 12% for liposomal anethole evaluated at minimal bactericidal concentration value of free anethole (P < 0·05). Conclusions Hydrophobicity appears to be crucial for PPs antibacterial activity. Encapsulation in cyclodextrin and liposome seems to retain the PPs preventing their interaction with bacteria. Significance and Impact of the Study This study highlights the structural features of simple phenylpropanoids related to their antibacterial activity. The limitations of conventional encapsulation systems on the activity of PPs should be considered in future applications.

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“…DCL nanoconstruct, which was firstly proposed by McCormack and Gregoriadis (1994) [ 11 ], was already used for the delivery of a number of lipophilic bioactive molecules, including anti-inflammatory, anesthetic, immunosuppressive, and anti-cancer drugs [ 12 , 13 ]. Based on that, we suppose that the encapsulation of β-CD-complexed mTHPC into liposomes increases the drug loading capacity, entrapment efficiency, avoids burst release of the drug, and prolongs its systemic circulation.…”

Section: Introductionmentioning

confidence: 99%

Temoporfin-in-Cyclodextrin-in-Liposome—A New Approach for Anticancer Drug Delivery: The Optimization of Composition

et al. 2018

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The main goal of this study was to use hybrid delivery system for effective transportation of temoporfin (meta-tetrakis(3-hydroxyphenyl)chlorin, mTHPC) to target tissue. We suggested to couple two independent delivery systems (liposomes and inclusion complexes) to achieve drug-in-cyclodextrin-in-liposome (DCL) nanoconstructs. We further optimized the composition of DCLs, aiming to alter in a more favorable way a distribution of temoporfin in tumor tissue. We have prepared DCLs with different compositions varying the concentration of mTHPC and the type of β-cyclodextrin (β-CD) derivatives (Hydroxypropyl-, Methyl- and Trimethyl-β-CD). DCLs were prepared by thin-hydration technique and mTHPC/β-CD complexes were added at hydration step. The size was about 135 nm with the surface charge of (−38 mV). We have demonstrated that DCLs are stable and almost all mTHPC is bound to β-CDs in the inner aqueous liposome core. Among all tested DCLs, trimethyl-β-CD-based DCL demonstrated a homogenous accumulation of mTHPC across tumor spheroid volume, thus supposing optimal mTHPC distribution.

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Preparation of drug-in-cyclodextrin-in-liposomes at a large scale using a membrane contactor: Application to trans -anethole

Cited by 23 publications

References 45 publications

Retention of Eucalyptol, a Natural Volatile Insecticide, in Delivery Systems Based on Hydroxypropyl‐β‐Cyclodextrin and Liposomes

Retention of Eucalyptol, a Natural Volatile Insecticide, in Delivery Systems Based on Hydroxypropyl‐β‐Cyclodextrin and Liposomes

Antibacterial activity of free or encapsulated selected phenylpropanoids against Escherichia coli and Staphylococcus epidermidis

Temoporfin-in-Cyclodextrin-in-Liposome—A New Approach for Anticancer Drug Delivery: The Optimization of Composition

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