Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein
1,4-Naphthoquinone derivatives (NQD) containing lipophilic alkyl chains, i.e. 2-((Z)-heptadec-8-enyl)-3-methyl 1,4-naphthoquinone (QMe), 2-((Z)-heptadec-8-enyl)-3-hydroxy-1,4-naphthoquinone (QOH) and (Z)-octadec-9-enyl 1,4-naphthoquinone-2-carboxylate (QE) were synthesized. The redox behavior of the...
Gespeichert in:
| Veröffentlicht in: | Chemistry and physics of lipids 2009-05, Vol.159 (1), p.45-50 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 50 |
|---|---|
| container_issue | 1 |
| container_start_page | 45 |
| container_title | Chemistry and physics of lipids |
| container_volume | 159 |
| creator | Tauraitė, Daiva Razumas, Valdemaras Butkus, Eugenijus |
| description | 1,4-Naphthoquinone derivatives (NQD) containing lipophilic alkyl chains, i.e. 2-((Z)-heptadec-8-enyl)-3-methyl 1,4-naphthoquinone (QMe), 2-((Z)-heptadec-8-enyl)-3-hydroxy-1,4-naphthoquinone (QOH) and (Z)-octadec-9-enyl 1,4-naphthoquinone-2-carboxylate (QE) were synthesized. The redox behavior of these NQD was studied in ethanol and entrapped in the reversed bicontinuous cubic phase of space group type
Pn3m (Q
224) of aqueous monoolein. In ethanol, cyclic voltammetry curves exhibit two pairs of oxidation–reduction peaks arising from the redox processes controlled by adsorption and molecular diffusion. The NQD molecules are also electrochemically active in the cubic phase, indicating the participation in the 2e
−, 2H
+-redox cycle at pH
<
9. Therefore, it was concluded that the head group of the entrapped NQD reaches the lipid bilayer interface of cubic phase during the process. |
| doi_str_mv | 10.1016/j.chemphyslip.2009.02.002 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67221947</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0009308409000346</els_id><sourcerecordid>67221947</sourcerecordid><originalsourceid>FETCH-LOGICAL-c375t-2e566e0d40bed7faa33ae3c86ed721b977737b3d7c93bc7ba679de44818cceaa3</originalsourceid><addsrcrecordid>eNqNkc2u0zAQhS0E4pYLr4DMhhUJ_knjhB2q-JMqsYG15dhTxZVj-9pORV_mPisurQRLVtZovuMzMwehN5S0lND-_bHVMyxxPmdnY8sIGVvCWkLYE7Shg-ANGzv6FG1I7TScDN0depHzsZZku6XP0R0dOzbwnm3Q497GEGfrrMb0Xdd4Fecyh4fV-uABG0j2pIo9Qf6A89mXGbLNWHmDE5jwC8cUIqRiIWPrcQ5uLTb4PwD4klSMYC6dKsTqYYWwZqzXqbo5W01Mo9M5F-WcrW5xVhlwOOAl-BAcWP8SPTsol-HV7b1HPz9_-rH72uy_f_m2-7hvNBfb0jDY9j0Q05EJjDgoxbkCroe-VoxOoxCCi4kboUc-aTGpXowGum6gg9ZQ8Xv09vpv3adOmYtcbNbgnPKXkWUvGKtHExUcr6BOIecEBxmTXVQ6S0rkJRx5lP-EIy_hSMJkDadqX99M1mkB81d5S6MCuysAddWThSSztuA1GJtAF2mC_Q-b33j_rHI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67221947</pqid></control><display><type>article</type><title>Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals Complete</source><creator>Tauraitė, Daiva ; Razumas, Valdemaras ; Butkus, Eugenijus</creator><creatorcontrib>Tauraitė, Daiva ; Razumas, Valdemaras ; Butkus, Eugenijus</creatorcontrib><description>1,4-Naphthoquinone derivatives (NQD) containing lipophilic alkyl chains, i.e. 2-((Z)-heptadec-8-enyl)-3-methyl 1,4-naphthoquinone (QMe), 2-((Z)-heptadec-8-enyl)-3-hydroxy-1,4-naphthoquinone (QOH) and (Z)-octadec-9-enyl 1,4-naphthoquinone-2-carboxylate (QE) were synthesized. The redox behavior of these NQD was studied in ethanol and entrapped in the reversed bicontinuous cubic phase of space group type
Pn3m (Q
224) of aqueous monoolein. In ethanol, cyclic voltammetry curves exhibit two pairs of oxidation–reduction peaks arising from the redox processes controlled by adsorption and molecular diffusion. The NQD molecules are also electrochemically active in the cubic phase, indicating the participation in the 2e
−, 2H
+-redox cycle at pH
<
9. Therefore, it was concluded that the head group of the entrapped NQD reaches the lipid bilayer interface of cubic phase during the process.</description><identifier>ISSN: 0009-3084</identifier><identifier>EISSN: 1873-2941</identifier><identifier>DOI: 10.1016/j.chemphyslip.2009.02.002</identifier><identifier>PMID: 19428362</identifier><language>eng</language><publisher>Ireland: Elsevier Ireland Ltd</publisher><subject>1,4-Naphthoquinone derivatives ; Cubic phase ; Cyclic voltammetry ; Electrochemical activity ; Electrochemistry ; Glycerides - chemistry ; Liquid Crystals - chemistry ; Naphthoquinones - chemical synthesis ; Naphthoquinones - chemistry ; Oxidation-Reduction ; Water - chemistry ; X-Ray Diffraction</subject><ispartof>Chemistry and physics of lipids, 2009-05, Vol.159 (1), p.45-50</ispartof><rights>2009 Elsevier Ireland Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c375t-2e566e0d40bed7faa33ae3c86ed721b977737b3d7c93bc7ba679de44818cceaa3</citedby><cites>FETCH-LOGICAL-c375t-2e566e0d40bed7faa33ae3c86ed721b977737b3d7c93bc7ba679de44818cceaa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0009308409000346$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19428362$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tauraitė, Daiva</creatorcontrib><creatorcontrib>Razumas, Valdemaras</creatorcontrib><creatorcontrib>Butkus, Eugenijus</creatorcontrib><title>Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein</title><title>Chemistry and physics of lipids</title><addtitle>Chem Phys Lipids</addtitle><description>1,4-Naphthoquinone derivatives (NQD) containing lipophilic alkyl chains, i.e. 2-((Z)-heptadec-8-enyl)-3-methyl 1,4-naphthoquinone (QMe), 2-((Z)-heptadec-8-enyl)-3-hydroxy-1,4-naphthoquinone (QOH) and (Z)-octadec-9-enyl 1,4-naphthoquinone-2-carboxylate (QE) were synthesized. The redox behavior of these NQD was studied in ethanol and entrapped in the reversed bicontinuous cubic phase of space group type
Pn3m (Q
224) of aqueous monoolein. In ethanol, cyclic voltammetry curves exhibit two pairs of oxidation–reduction peaks arising from the redox processes controlled by adsorption and molecular diffusion. The NQD molecules are also electrochemically active in the cubic phase, indicating the participation in the 2e
−, 2H
+-redox cycle at pH
<
9. Therefore, it was concluded that the head group of the entrapped NQD reaches the lipid bilayer interface of cubic phase during the process.</description><subject>1,4-Naphthoquinone derivatives</subject><subject>Cubic phase</subject><subject>Cyclic voltammetry</subject><subject>Electrochemical activity</subject><subject>Electrochemistry</subject><subject>Glycerides - chemistry</subject><subject>Liquid Crystals - chemistry</subject><subject>Naphthoquinones - chemical synthesis</subject><subject>Naphthoquinones - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Water - chemistry</subject><subject>X-Ray Diffraction</subject><issn>0009-3084</issn><issn>1873-2941</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkc2u0zAQhS0E4pYLr4DMhhUJ_knjhB2q-JMqsYG15dhTxZVj-9pORV_mPisurQRLVtZovuMzMwehN5S0lND-_bHVMyxxPmdnY8sIGVvCWkLYE7Shg-ANGzv6FG1I7TScDN0depHzsZZku6XP0R0dOzbwnm3Q497GEGfrrMb0Xdd4Fecyh4fV-uABG0j2pIo9Qf6A89mXGbLNWHmDE5jwC8cUIqRiIWPrcQ5uLTb4PwD4klSMYC6dKsTqYYWwZqzXqbo5W01Mo9M5F-WcrW5xVhlwOOAl-BAcWP8SPTsol-HV7b1HPz9_-rH72uy_f_m2-7hvNBfb0jDY9j0Q05EJjDgoxbkCroe-VoxOoxCCi4kboUc-aTGpXowGum6gg9ZQ8Xv09vpv3adOmYtcbNbgnPKXkWUvGKtHExUcr6BOIecEBxmTXVQ6S0rkJRx5lP-EIy_hSMJkDadqX99M1mkB81d5S6MCuysAddWThSSztuA1GJtAF2mC_Q-b33j_rHI</recordid><startdate>20090501</startdate><enddate>20090501</enddate><creator>Tauraitė, Daiva</creator><creator>Razumas, Valdemaras</creator><creator>Butkus, Eugenijus</creator><general>Elsevier Ireland Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090501</creationdate><title>Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein</title><author>Tauraitė, Daiva ; Razumas, Valdemaras ; Butkus, Eugenijus</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c375t-2e566e0d40bed7faa33ae3c86ed721b977737b3d7c93bc7ba679de44818cceaa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>1,4-Naphthoquinone derivatives</topic><topic>Cubic phase</topic><topic>Cyclic voltammetry</topic><topic>Electrochemical activity</topic><topic>Electrochemistry</topic><topic>Glycerides - chemistry</topic><topic>Liquid Crystals - chemistry</topic><topic>Naphthoquinones - chemical synthesis</topic><topic>Naphthoquinones - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Water - chemistry</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tauraitė, Daiva</creatorcontrib><creatorcontrib>Razumas, Valdemaras</creatorcontrib><creatorcontrib>Butkus, Eugenijus</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry and physics of lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tauraitė, Daiva</au><au>Razumas, Valdemaras</au><au>Butkus, Eugenijus</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein</atitle><jtitle>Chemistry and physics of lipids</jtitle><addtitle>Chem Phys Lipids</addtitle><date>2009-05-01</date><risdate>2009</risdate><volume>159</volume><issue>1</issue><spage>45</spage><epage>50</epage><pages>45-50</pages><issn>0009-3084</issn><eissn>1873-2941</eissn><abstract>1,4-Naphthoquinone derivatives (NQD) containing lipophilic alkyl chains, i.e. 2-((Z)-heptadec-8-enyl)-3-methyl 1,4-naphthoquinone (QMe), 2-((Z)-heptadec-8-enyl)-3-hydroxy-1,4-naphthoquinone (QOH) and (Z)-octadec-9-enyl 1,4-naphthoquinone-2-carboxylate (QE) were synthesized. The redox behavior of these NQD was studied in ethanol and entrapped in the reversed bicontinuous cubic phase of space group type
Pn3m (Q
224) of aqueous monoolein. In ethanol, cyclic voltammetry curves exhibit two pairs of oxidation–reduction peaks arising from the redox processes controlled by adsorption and molecular diffusion. The NQD molecules are also electrochemically active in the cubic phase, indicating the participation in the 2e
−, 2H
+-redox cycle at pH
<
9. Therefore, it was concluded that the head group of the entrapped NQD reaches the lipid bilayer interface of cubic phase during the process.</abstract><cop>Ireland</cop><pub>Elsevier Ireland Ltd</pub><pmid>19428362</pmid><doi>10.1016/j.chemphyslip.2009.02.002</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-3084 |
| ispartof | Chemistry and physics of lipids, 2009-05, Vol.159 (1), p.45-50 |
| issn | 0009-3084 1873-2941 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67221947 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 1,4-Naphthoquinone derivatives Cubic phase Cyclic voltammetry Electrochemical activity Electrochemistry Glycerides - chemistry Liquid Crystals - chemistry Naphthoquinones - chemical synthesis Naphthoquinones - chemistry Oxidation-Reduction Water - chemistry X-Ray Diffraction |
| title | Lipophilic 1,4-naphthoquinone derivatives: synthesis and redox properties in solution and entrapped in the aqueous cubic liquid-crystalline phase of monoolein |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-21T17%3A18%3A36IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Lipophilic%201,4-naphthoquinone%20derivatives:%20synthesis%20and%20redox%20properties%20in%20solution%20and%20entrapped%20in%20the%20aqueous%20cubic%20liquid-crystalline%20phase%20of%20monoolein&rft.jtitle=Chemistry%20and%20physics%20of%20lipids&rft.au=Taurait%C4%97,%20Daiva&rft.date=2009-05-01&rft.volume=159&rft.issue=1&rft.spage=45&rft.epage=50&rft.pages=45-50&rft.issn=0009-3084&rft.eissn=1873-2941&rft_id=info:doi/10.1016/j.chemphyslip.2009.02.002&rft_dat=%3Cproquest_cross%3E67221947%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=67221947&rft_id=info:pmid/19428362&rft_els_id=S0009308409000346&rfr_iscdi=true |