Chemo-Enzymatic Synthesis of Oligoglycerol Derivatives

Singh, Abhishek Kumar; Nguyen, Rémi; Galy, Nicolas; Haag, Rainer; Sharma, Sunil K.; Len, Christophe

doi:10.3390/molecules21081038

Cited by 12 publications

(14 citation statements)

References 35 publications

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“…The oligomers of glycerol such as di-, tri-and tetraglycerol have been well studied for various applications such as emulsier, thickeners, and antifogging agents, etc. 26,27 Our group has earlier synthesized functionalized glycerol oligomers using a chemoenzymatic pathway. 27 As an extension of our ongoing research program to design and develop glycerol oligomers based nanocarriers, we decided to use diglycerol for the synthesis of amphiphilic nano-transporters as glycerol is renewable, nontoxic, and biodegradable.…”

Section: Introductionmentioning

confidence: 99%

“…26,27 Our group has earlier synthesized functionalized glycerol oligomers using a chemoenzymatic pathway. 27 As an extension of our ongoing research program to design and develop glycerol oligomers based nanocarriers, we decided to use diglycerol for the synthesis of amphiphilic nano-transporters as glycerol is renewable, nontoxic, and biodegradable. 28 Furthermore, as the hydrophilic-lipophilic balance (HLB) have a vital role in the aggregation and transport capacity of amphiphiles, 29,30 our interest is to ne tune the physicochemical characterization of amphiphilic systems by varying hydrophilic and hydrophobic components.…”

Section: Introductionmentioning

confidence: 99%

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Oligo-glycerol based non-ionic amphiphilic nanocarriers for lipase mediated controlled drug release

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Oligo-glycerol based non-ionic amphiphilic nanocarriers for lipase mediated controlled drug release

et al. 2020

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“…Glycerol oligomers may be found in many polymerization or polycondensation reactions as a superior building block . We have reported earlier the synthesis of various glycerol oligomer building blocks by following the chemoenzymatic pathway, and a few of these moieties have been further utilized towards the synthesis of amphiphilic nanocarriers …”

Section: Introductionmentioning

confidence: 99%

Fabrication of oligo‐glycerol based hydrolase responsive amphiphilic nanocarriers

Mittal

Singh

Kumar

et al. 2020

Polymers for Advanced Techs

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Herein, we report on the synthesis of a new class of novel non-ionic amphiphiles using triglycerol as a core, which is further functionalized with hydrophilic units poly(ethylene glycol) monomethyl ether (M n : 350 and 550) and a pair of hydrophobic alkyl chains (C 18 or C 15 ) via chemo-enzymatic approach. Fluorescence measurements and dynamic light scattering studies showed that all of the synthesized amphiphilic systems spontaneously self-assemble in aqueous solution, which is further confirmed by the transmission electron microscopy. Encapsulation of hydrophobic moieties like Nile red and nimodipine was studied using ultraviolet-visible (UV-vis) and fluorescence spectrometer techniques. A cytotoxicity study of the amphiphiles using A549, HeLa, and MCF7 cell, which showed that all of the synthesized nanocarriers are well tolerated at the concentrations studied. The release profile of encapsulated Nile red in synthesized amphiphilic system was studied in the presence of the immobilized enzyme (Novozym 435).amphiphile, cytotoxicity, encapsulation, self-assembly 1 | INTRODUCTION Molecular self-assembly, the spontaneous process of forming ordered aggregates without external intervention is gaining attention by researchers from different disciplines because of its widespread applications. The phenomenon is derived mostly by various noncovalent interactions such as hydrophobic, ionic, π-π stacking, and electrostatic interaction adopting the minimal Gibbs free energy and thermodynamic stability. 1-4 The natural self-assembly phenomenon, for example, polypeptide chains folding into proteins or conformational changes of nucleic acids into their different functional forms etc, have inspired the scientific community to mimic the process using newly designed molecules. 5,6 Self-assembly of amphiphilic macromolecules provide a unique and newer opportunity for designing novel material for advanced applications in biomedicine and bionanotechnology. 7-11 Among the diverse and various promising applications of amphiphilic macromolecules, the area of drug delivery is challenging because of the limited aqueous-solubility and short circulation half-life of most clinically used drugs. [12][13][14] Carrier-mediated drug delivery not only can maximize the bioavailability but also allow targeting the active site in the body while minimizing the side effects.Amphiphiles can self-assemble into a variety of nano and microscale structures in the aqueous medium, where the majorly known 3-D structures include vesicles, micelles, and molecular gels. [15][16][17] Micelles vary in diameter in the range of 5 to 100 nm and may consist of spheres, discs, and wormlike assemblies, 18 whereas vesicles are found in hollow, spherical, and lamellar type morphologies within the diameter range of 20 nm to micrometer. 19 Since micelles formed by small molecules have simple synthesis, high loading capacity, and low toxicity, they may be able to target many cancer tissues and ensure the accumulation within the small vasculatures of tumors. 20,21 However, o...

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“…One of the many directions of industrial chemical transformation of glycerin is its oligomerization, leading to the formation of polyglycerols (PGL)—a mixture of oligomeric polyols (Behr et al, ; Sutter et al, ) that are used in various ways as independent substances (Singh et al, ), and as synthetic blocks in processes of polycondensation, for example, in the preparation of polyglycerol polyricinoleate (PGPR). PGPR is widely used in the food industry as a safe emulsifier (E‐476) in water‐in‐oil emulsions, in particular in the production of chocolate.…”

Section: Introductionmentioning

confidence: 99%

Production and Emulsifying Effect of Esters on The Basis of Polyglycerol and Еpoxidized Derivatives of Sunflower and Soybean Oil

Shikhaliev

Stolpovskaya

Krysin

et al. 2018

J Americ Oil Chem Soc

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Oligo and polyesters of polyglycerol and polyricinoleic acid are widely used as emulsifiers in various industries. New promising emulsifiers for oil-water systems were obtained based on the condensation of glycerol and its oligomers with epoxidized derivatives of vegetable oils. The type of the resulting emulsion was studied. The influence of the composition of the emulsion and the hydrophilic-lipophilic balance (HLB) of the emulsifier on the type of the resulting emulsions was investigated. It was shown that the synthesized emulsifiers significantly increase the viscosity of the emulsion. Complex structural and functional spectral analysis of synthesized substances showed that the main reactions leading to the formation of the desired products were the opening of epoxide cycles, the transesterification of esters, and the condensation of fatty-acid derivatives. This new combination of renewable raw materials is of undoubted interest for deeper chemical processing of vegetable oils. KeywordsEpoxidized vegetable oils Á Emulsifiers Á Polyglycerol Á Polyricinoleate Á Renewable raw materials J Am Oil Chem Soc (2018) 95: 1561-1574.

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Chemo-Enzymatic Synthesis of Oligoglycerol Derivatives

Cited by 12 publications

References 35 publications

Oligo-glycerol based non-ionic amphiphilic nanocarriers for lipase mediated controlled drug release

Oligo-glycerol based non-ionic amphiphilic nanocarriers for lipase mediated controlled drug release

Fabrication of oligo‐glycerol based hydrolase responsive amphiphilic nanocarriers

Production and Emulsifying Effect of Esters on The Basis of Polyglycerol and Еpoxidized Derivatives of Sunflower and Soybean Oil

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