Beyond Poly(ethylene glycol): Linear Polyglycerol as a Multifunctional Polyether for Biomedical and Pharmaceutical Applications

Abstract

Polyglycerols (sometimes also called "polyglycidols") represent a class of highly biocompatible and multihydroxy-functional polymers that may be considered as a multifunctional analogue of poly(ethylene glycol) (PEG). Various architectures based on a polyglycerol scaffold are feasible depending on the monomer employed. While polymerization of glycidol leads to hyperbranched polyglycerols, the precisely defined linear analogue is obtained by using suitably protected glycidol as a monomer, followed by removal of the protective group in a postpolymerization step. This review summarizes the properties and synthetic approaches toward linear polyglycerols (linPG), which are at present mainly based on the application of ethoxyethyl glycidyl ether (EEGE) as an acetal-protected glycidol derivative. Particular emphasis is placed on the manifold functionalization strategies including, e.g., the synthesis of end-functional linPGs or multiheterofunctional modifications at the polyether backbone. Potential applications like bioconjugation and utilization as a component in degradable biomaterials or for diagnostics, in which polyglycerol acts as a promising PEG substitute are discussed. In the last section, the important role of linear polyglycerol as a macroinitiator or as a highly hydrophilic segment in block co- or terpolymers is highlighted.

Polyglycerol Surfmers and Surfactants for Direct and Inverse Miniemulsion

“…Cesium hydroxide monohydrate (CsOH⋅H 2 O, Sigma-Aldrich, ≥99.5%), benzene (Sigma-Aldrich, anhydrous, 99.8%), methanol (Sigma-Aldrich, anhydrous 99.8%), hydrochloric acid (HCl, Sigma-Aldrich, ACS reagent, 37%), 2,3-epoxypropanol (Sigma-Aldrich, 96%), ethyl vinyl ether (Sigma-Aldrich, 98.0%), magnesium sulfate (MgSO 4 , Fluka, anhydrous, reagent grade, ≥99.5%), p-toluenesulfonic acid (p-TsOH, Sigma-Aldrich, ACS reagent, ≥98.5%), HES solution (200k, 0.5 degree of substitution, Fresenius Kabi), toluene-2,4-diisocyanate (TDI, Sigma-Aldrich, 95%), sodium chloride (NaCl, Fisher Scientific, ≥99%), Lutensol AT50 (a fatty alcohol ethoxylate C 16 / 18 -(EO) 50 , BASF), sodium dodecyl sulfate (SDS, Fluka, ACS reagent, ≥99%), N-acetyl-l-cysteine (Sigma-Aldrich, analytical grade, ≥99% (TLC)), 2,2′-Azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VA-044, Stockhausen GmbH und Co. KG), 2-hydroxyethyl methacrylate (HEMA, Sigma-Aldrich, ≥99%), acrylamide (AAm, Sigma-Aldrich, 98%), hexadecane (Sigma-Aldrich, ReagentPlus, 99%), tetrahydrofuran (THF, Fisher Scientific, analytical grade), cyclohexane (Fisher Scientific, analytical grade), toluene (Fisher Scientific, analytical grade), chloroform-d (CDCl 3 -d, Acros Organics, 99.8 at% D), dimethyl sulfoxide-d 6 (DMSO-d 6 , Carl Roth, 99.8 at% D), and tetrahydrofurane-d 8 (Deutero GmbH, ≥99.5 at% D) were used as received. Ethoxyethylprotected glycidyl ether was synthesized according to the published procedure by Fitton et al [16] AGE (Sigma-Aldrich, 99%), tBuGE (SigmaAldrich, >99%), and the synthesized EEGE were stored over CaH 2 and distilled in vacuo over molecular sieve before use to remove traces of water.…”

“…[7] One promising material is poly(glycerol) (PG) derivative, which is accessible by highly controlled anionic polymerization with multiple functionality and architecture. [7,8] Also some commercial PG-based surfactants, such as poly glycerolpolyricinoleate, are known. [9] Up to now, PG-based Pluronics are www.advancedsciencenews.com www.mbs-journal.…”

Studi Mekanisme Reaksi Oligomerisasi Gliserol Menggunakan Metode Ab Initio

“…Penggunaan poligliserol sebagaimana telah diketahui adalah sebagai bahan kosmetik, pengemulsi, pelumas, medis, plastik (Taghizadeh et al, 2013), dan kemasan yang dapat terdegradasi. Poligliserol juga telah dapat menggantikan fungsi dari polietilen glikol karena sifatnya yang biokompatibel dan multifungsi (Thomas et al, 2014).…”

Homoserine Lactone as a Structural Key Element for the Synthesis of Multifunctional Polymers

“…Polyglycidol is soluble in aqueous media, shows no toxicity towards cells and is licensed by the Food and Drug Administration (FDA) [13,14]. It is a highly functionalized polymer with a hydroxyl group in every repeating unit, allowing for various further modifications [15,16]. Hans et al presented the application of polyglycidol, as a multifunctional macroinitiator, for the ring-opening polymerization of ε-caprolactone [17,18].…”