Synthesis of Monomethoxypolyethyleneglycol—Cholesteryl Ester and Effect of its Incorporation in Liposomes

Abstract

Abstract. The objective of the present study was to synthesize monomethoxypolyethyleneglycol-5000 cholesteryl ester [PEG-CH] as a cost-effective substitute for polyethyleneglycol-phosphatidylethanolamine and to evaluate the influence of its incorporation in liposomal bilayers for surface modification. PEG-CH was synthesized and characterized by infrared (IR), proton nuclear magnetic resonance spectroscopy ( 1 H NMR), and differential scanning calorimetry (DSC) studies. Influence of incorporation of PEG-CH in liposomes was evaluated on various parameters such as zeta potential, DSC, and encapsulation efficiency of a hydrophilic drug pentoxyfylline. Conventional and PEG-CH containing pentoxyfylline liposomes were formulated and their stability was evaluated at 4°C for 3 months. PEG-CH could be successfully synthesized with good yields and the structure was confirmed by IR, DSC, and 1 H NMR. The incorporation of PEG-CH in liposomes resulted in reduction of the zeta potential and broadening of the DSC endotherm. Furthermore, incorporation of PEG-CH in liposomes decreased the encapsulation efficiency of pentoxifylline in liposomes when compared to conventional liposomes. Conventional and PEG-CH containing pentoxyfylline liposomes did not show any signs of pentoxyfylline degradation when stored at 4°C for 3 months.

Peptide Anchor for Folate-Targeted Liposomal Delivery

“…Liposomes have gained extensive attention as carriers for a wide range of drugs due to properties such as sustained release, altered pharmacokinetics, increased drug stability, ability to overcome drug resistance, and target specific tissues . Folate receptor (FR), one of the most studied molecular targets for directed therapy, is a glycoprotein with high affinity for folate (or folic acid, FA) ( K d ∼ 100 pM). , Two main membrane variants of the FR exist, FRα and FRβ.…”

PEGylated γ-tocotrienol isomer of vitamin E: Synthesis, characterization, in vitro cytotoxicity, and oral bioavailability

“…Results from this study suggest that PEGylation of c-T 3 represents 47 a viable platform for the oral and parenteral delivery of c-T 3 for potential use in the prevention of breast 48 cancer. 49 Ó 2015 Published by Elsevier B.V. 50 51 52 53 1. Introduction 54 Vitamin E from palm oil refers to a family of eight related, lipid 55 soluble, compounds that are divided into two subfamilies known 56 as tocopherols (T) and tocotrienols (T 3 ).…”

Modification of Poly(Glycerol Adipate) with Tocopherol and Cholesterol Modulating Nanoparticle Self-Assemblies and Cellular Responses of Triple-Negative Breast Cancer Cells to SN-38 Delivery

“…Grafting with CHO and TOC increased the T g values of all polymers ( Figure 2 D). Despite the crystalline nature of CHO hemisuccinate and TOC succinate, the resulting polymers exhibited only one T g step and no detectable melting peaks of CHO (T m at 151 °C [ 56 ]) and TOC (T m at 83 °C [ 57 ]) over the investigated temperature range ( Figure S2 ). A higher percentage of CHO grafting increased the T g values of the polymers.…”