Physicochemical and Structural Properties of Glycerin Gel Prepared using Glycyrrhizic Acid Diethyl Ester

Glycyrrhizic acid diethyl ester (GZ-DE) was developed as a prodrug of glycyrrhizic acid (GZ), a hepatitis therapeutic drug. We fortuitously found that GZ-DE gels with glycerin selectively while searching for a safe solvent with which to dissolve GZ-DE. Based on this gelation, the aim of this study w...

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Veröffentlicht in:Journal of Oleo Science 2014, Vol.63(12), pp.1309-1322
Hauptverfasser: Koga, Kenjiro, Kimura, Toshiyuki, Sakai, Kenichi, Kushida, Hiroshi, Yoshikawa, Nobuji
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container_end_page 1322
container_issue 12
container_start_page 1309
container_title Journal of Oleo Science
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creator Koga, Kenjiro
Kimura, Toshiyuki
Sakai, Kenichi
Kushida, Hiroshi
Yoshikawa, Nobuji
description Glycyrrhizic acid diethyl ester (GZ-DE) was developed as a prodrug of glycyrrhizic acid (GZ), a hepatitis therapeutic drug. We fortuitously found that GZ-DE gels with glycerin selectively while searching for a safe solvent with which to dissolve GZ-DE. Based on this gelation, the aim of this study was to investigate the preparation of the gel and study the rheology, physicochemical and structural properties of the glycerin gel by differential scanning calorimeter (DSC), capillary electrophoresis (CEP), nuclear magnetic resonance (NMR), and small angle X-ray scattering (SAXS). The glycerin gel was prepared by the addition of at least 2.0% w/w GZ-DE. This gel did not flow at room temperature. After mixing glycerin and GZ-DE, a gel was formed after 2 days at 25°C or 3 h at 60°C. Glycerin gel containing 2.4% w/w GZ-DE provided the following results: 1) The glycerin gel exhibited creep at a constant stress of less than 10 Pa, but it is a fragile gel, showing Newtonian flow at 10 Pa stress. 2) Dynamic viscoelastic measurements showed that the elastic modulus (G’) exceeds the viscous modulus (G’’), indicating that glycerin gel has solid-like properties. 3) DSC showed a significant difference between the glass transition temperature of glycerin and glycerin gel. 4) CEP did not reveal a new compound in the glycerin gel. 5) NMR confirmed that glycerin gel is a physical gel. 6) SAXS measurements revealed that the glycerin gel has an oval-shaped basic frame (119 nm long and 65 nm wide).
doi_str_mv 10.5650/jos.ess14086
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We fortuitously found that GZ-DE gels with glycerin selectively while searching for a safe solvent with which to dissolve GZ-DE. Based on this gelation, the aim of this study was to investigate the preparation of the gel and study the rheology, physicochemical and structural properties of the glycerin gel by differential scanning calorimeter (DSC), capillary electrophoresis (CEP), nuclear magnetic resonance (NMR), and small angle X-ray scattering (SAXS). The glycerin gel was prepared by the addition of at least 2.0% w/w GZ-DE. This gel did not flow at room temperature. After mixing glycerin and GZ-DE, a gel was formed after 2 days at 25°C or 3 h at 60°C. Glycerin gel containing 2.4% w/w GZ-DE provided the following results: 1) The glycerin gel exhibited creep at a constant stress of less than 10 Pa, but it is a fragile gel, showing Newtonian flow at 10 Pa stress. 2) Dynamic viscoelastic measurements showed that the elastic modulus (G’) exceeds the viscous modulus (G’’), indicating that glycerin gel has solid-like properties. 3) DSC showed a significant difference between the glass transition temperature of glycerin and glycerin gel. 4) CEP did not reveal a new compound in the glycerin gel. 5) NMR confirmed that glycerin gel is a physical gel. 6) SAXS measurements revealed that the glycerin gel has an oval-shaped basic frame (119 nm long and 65 nm wide).</description><identifier>ISSN: 1345-8957</identifier><identifier>EISSN: 1347-3352</identifier><identifier>DOI: 10.5650/jos.ess14086</identifier><identifier>PMID: 25452268</identifier><language>eng</language><publisher>Japan: Japan Oil Chemists' Society</publisher><subject>Calorimetry, Differential Scanning ; Chemical Phenomena ; Constants ; Drugs ; Electrophoresis ; Electrophoresis, Capillary ; Esters ; gelation ; Gels - chemistry ; glycerin ; Glycerol - chemical synthesis ; Glycerol - chemistry ; glycyrrhizic acid ; Glycyrrhizic Acid - analogs &amp; derivatives ; Glycyrrhizic Acid - chemistry ; Magnetic Resonance Spectroscopy ; NMR ; Nuclear magnetic resonance ; Prodrugs - chemistry ; rheology ; SAXS ; Scattering, Small Angle ; Searching ; Stresses ; Temperature ; Time Factors</subject><ispartof>Journal of Oleo Science, 2014, Vol.63(12), pp.1309-1322</ispartof><rights>2014 by Japan Oil Chemists' Society</rights><rights>Copyright Japan Science and Technology Agency 2014</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c631t-f0417bb74695b0b6197c0935ca85c42a4641f8d2ca188883584f6929c0c17c1b3</citedby><cites>FETCH-LOGICAL-c631t-f0417bb74695b0b6197c0935ca85c42a4641f8d2ca188883584f6929c0c17c1b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25452268$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Koga, Kenjiro</creatorcontrib><creatorcontrib>Kimura, Toshiyuki</creatorcontrib><creatorcontrib>Sakai, Kenichi</creatorcontrib><creatorcontrib>Kushida, Hiroshi</creatorcontrib><creatorcontrib>Yoshikawa, Nobuji</creatorcontrib><creatorcontrib>Faculty of Science and Technology</creatorcontrib><creatorcontrib>Faculty of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Tokyo University of Science</creatorcontrib><creatorcontrib>Cokey Systems Co.Ltd</creatorcontrib><creatorcontrib>Hokuriku University</creatorcontrib><creatorcontrib>Research and Development Division</creatorcontrib><title>Physicochemical and Structural Properties of Glycerin Gel Prepared using Glycyrrhizic Acid Diethyl Ester</title><title>Journal of Oleo Science</title><addtitle>J Oleo Sci</addtitle><description>Glycyrrhizic acid diethyl ester (GZ-DE) was developed as a prodrug of glycyrrhizic acid (GZ), a hepatitis therapeutic drug. 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source MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry
subjects Calorimetry, Differential Scanning
Chemical Phenomena
Constants
Drugs
Electrophoresis
Electrophoresis, Capillary
Esters
gelation
Gels - chemistry
glycerin
Glycerol - chemical synthesis
Glycerol - chemistry
glycyrrhizic acid
Glycyrrhizic Acid - analogs & derivatives
Glycyrrhizic Acid - chemistry
Magnetic Resonance Spectroscopy
NMR
Nuclear magnetic resonance
Prodrugs - chemistry
rheology
SAXS
Scattering, Small Angle
Searching
Stresses
Temperature
Time Factors
title Physicochemical and Structural Properties of Glycerin Gel Prepared using Glycyrrhizic Acid Diethyl Ester
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