Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties
► Carrageenans were selectively sulfated to produce rare diads. ► The new diads synthesized were characterized by 1D and 2D NMR. ► Sulfated derivatives showed higher anticoagulant activities than native carrageenans. ► Sulfation at C2 of anhydro units and C6 of β-d-Galp improved anticoagulant activi...
Gespeichert in:
| Veröffentlicht in: | Carbohydrate polymers 2013-01, Vol.91 (2), p.483-491 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 491 |
|---|---|
| container_issue | 2 |
| container_start_page | 483 |
| container_title | Carbohydrate polymers |
| container_volume | 91 |
| creator | de Araújo, Cristiano A. Noseda, Miguel D. Cipriani, Thales R. Gonçalves, Alan G. Duarte, Maria Eugênia R. Ducatti, Diogo R.B. |
| description | ► Carrageenans were selectively sulfated to produce rare diads. ► The new diads synthesized were characterized by 1D and 2D NMR. ► Sulfated derivatives showed higher anticoagulant activities than native carrageenans. ► Sulfation at C2 of anhydro units and C6 of β-d-Galp improved anticoagulant activity.
Sulfated polysaccharides are recognized for their broad range of biological activities, including anticoagulant properties. The positions occupied by the sulfate groups are often related to the level of the inherent biological activity. Herein the naturally sulfated galactans, kappa-, iota- and theta-carrageenan, were additionally sulfated by regioselective means. The anticoagulant activity of the resulting samples was then studied using the aPTT in vitro assay. The influence of sulfate regiochemistry on the anticoagulant activity was evaluated. From kappa-carrageenan three rare polysaccharides were synthesized, one of them involved a synthetic route with an amphiphilic polysaccharide intermediate containing pivaloyl groups. Iota- and theta-carrageenan were utilized in a selective C6 sulfation at β-d-Galp units to produce different structures comprising trisulfated diads. All the samples were characterized by NMR (1D and 2D). The resulting aPPT measurements suggested that sulfation at C2 of 3,6-anhydro-α-d-Galp and C6 of β-d-Galp increased the anticoagulant activity. |
| doi_str_mv | 10.1016/j.carbpol.2012.08.034 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1139619497</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0144861712008089</els_id><sourcerecordid>1139619497</sourcerecordid><originalsourceid>FETCH-LOGICAL-c532t-5ca51b2f90e6ae1bc9ce44795cc9ee2c022f3a3dce2f61b4af57ca599f21e64e3</originalsourceid><addsrcrecordid>eNqFkUtv1DAUhS0EokPhJwDZILFJ8PUr8QpVFS-pEovSteU411MPmXiwk0r99zjKAEu8uV58596jcwh5DbQBCurDoXE29ac4NowCa2jXUC6ekB10ra6BC_GU7CgIUXcK2gvyIucDLU8BfU4uGAcGmqsd-XmLI7o5PGCVl9HbOcSpir4qy5PdI052ypWdhmq-xypMflxwcrgSG45Vwn2I7h6PIc_psSpyO83BRbtfxvKrTimeMM0B80vyzNsx46vzvCR3nz_9uP5a33z_8u366qZ2krO5ls5K6JnXFJVF6J12KESrpXMakTnKmOeWDw6ZV9AL62VbJFp7BqgE8kvyfttbTv9aMM-meHM4FjsYl2wAuFaghW4LKjfUpZhzQm9OKRxtejRAzZqzOZhzzmbN2dDOlJyL7s35xNIfcfir-hNsAd6dAZudHX2ykwv5H6ekZrqThXu7cd5GY_epMHe35ZIqXUkQbCU-bgSWyB4CJpNdWEsYQirNmSGG_5j9DZ1FqoY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1139619497</pqid></control><display><type>article</type><title>Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals Complete</source><creator>de Araújo, Cristiano A. ; Noseda, Miguel D. ; Cipriani, Thales R. ; Gonçalves, Alan G. ; Duarte, Maria Eugênia R. ; Ducatti, Diogo R.B.</creator><creatorcontrib>de Araújo, Cristiano A. ; Noseda, Miguel D. ; Cipriani, Thales R. ; Gonçalves, Alan G. ; Duarte, Maria Eugênia R. ; Ducatti, Diogo R.B.</creatorcontrib><description>► Carrageenans were selectively sulfated to produce rare diads. ► The new diads synthesized were characterized by 1D and 2D NMR. ► Sulfated derivatives showed higher anticoagulant activities than native carrageenans. ► Sulfation at C2 of anhydro units and C6 of β-d-Galp improved anticoagulant activity.
Sulfated polysaccharides are recognized for their broad range of biological activities, including anticoagulant properties. The positions occupied by the sulfate groups are often related to the level of the inherent biological activity. Herein the naturally sulfated galactans, kappa-, iota- and theta-carrageenan, were additionally sulfated by regioselective means. The anticoagulant activity of the resulting samples was then studied using the aPTT in vitro assay. The influence of sulfate regiochemistry on the anticoagulant activity was evaluated. From kappa-carrageenan three rare polysaccharides were synthesized, one of them involved a synthetic route with an amphiphilic polysaccharide intermediate containing pivaloyl groups. Iota- and theta-carrageenan were utilized in a selective C6 sulfation at β-d-Galp units to produce different structures comprising trisulfated diads. All the samples were characterized by NMR (1D and 2D). The resulting aPPT measurements suggested that sulfation at C2 of 3,6-anhydro-α-d-Galp and C6 of β-d-Galp increased the anticoagulant activity.</description><identifier>ISSN: 0144-8617</identifier><identifier>EISSN: 1879-1344</identifier><identifier>DOI: 10.1016/j.carbpol.2012.08.034</identifier><identifier>PMID: 23121936</identifier><identifier>CODEN: CAPOD8</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Anticoagulant activity ; Anticoagulants - chemistry ; Anticoagulants - pharmacology ; Applied sciences ; Biological and medical sciences ; Blood. Blood coagulation. Reticuloendothelial system ; Carrageenan - chemistry ; Carrageenan - isolation & purification ; Carrageenans ; Exact sciences and technology ; Galactans - chemistry ; Humans ; in vitro studies ; kappa carrageenan ; Medical sciences ; Modified polysaccharides ; Natural polymers ; nuclear magnetic resonance spectroscopy ; Nuclear Magnetic Resonance, Biomolecular ; Partial Thromboplastin Time ; Pharmacology. Drug treatments ; Physicochemistry of polymers ; Regiochemistry ; Starch and polysaccharides ; Structure-Activity Relationship ; Sulfates ; Sulfation</subject><ispartof>Carbohydrate polymers, 2013-01, Vol.91 (2), p.483-491</ispartof><rights>2012 Elsevier Ltd</rights><rights>2014 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c532t-5ca51b2f90e6ae1bc9ce44795cc9ee2c022f3a3dce2f61b4af57ca599f21e64e3</citedby><cites>FETCH-LOGICAL-c532t-5ca51b2f90e6ae1bc9ce44795cc9ee2c022f3a3dce2f61b4af57ca599f21e64e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0144861712008089$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26592985$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23121936$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>de Araújo, Cristiano A.</creatorcontrib><creatorcontrib>Noseda, Miguel D.</creatorcontrib><creatorcontrib>Cipriani, Thales R.</creatorcontrib><creatorcontrib>Gonçalves, Alan G.</creatorcontrib><creatorcontrib>Duarte, Maria Eugênia R.</creatorcontrib><creatorcontrib>Ducatti, Diogo R.B.</creatorcontrib><title>Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties</title><title>Carbohydrate polymers</title><addtitle>Carbohydr Polym</addtitle><description>► Carrageenans were selectively sulfated to produce rare diads. ► The new diads synthesized were characterized by 1D and 2D NMR. ► Sulfated derivatives showed higher anticoagulant activities than native carrageenans. ► Sulfation at C2 of anhydro units and C6 of β-d-Galp improved anticoagulant activity.
Sulfated polysaccharides are recognized for their broad range of biological activities, including anticoagulant properties. The positions occupied by the sulfate groups are often related to the level of the inherent biological activity. Herein the naturally sulfated galactans, kappa-, iota- and theta-carrageenan, were additionally sulfated by regioselective means. The anticoagulant activity of the resulting samples was then studied using the aPTT in vitro assay. The influence of sulfate regiochemistry on the anticoagulant activity was evaluated. From kappa-carrageenan three rare polysaccharides were synthesized, one of them involved a synthetic route with an amphiphilic polysaccharide intermediate containing pivaloyl groups. Iota- and theta-carrageenan were utilized in a selective C6 sulfation at β-d-Galp units to produce different structures comprising trisulfated diads. All the samples were characterized by NMR (1D and 2D). The resulting aPPT measurements suggested that sulfation at C2 of 3,6-anhydro-α-d-Galp and C6 of β-d-Galp increased the anticoagulant activity.</description><subject>Anticoagulant activity</subject><subject>Anticoagulants - chemistry</subject><subject>Anticoagulants - pharmacology</subject><subject>Applied sciences</subject><subject>Biological and medical sciences</subject><subject>Blood. Blood coagulation. Reticuloendothelial system</subject><subject>Carrageenan - chemistry</subject><subject>Carrageenan - isolation & purification</subject><subject>Carrageenans</subject><subject>Exact sciences and technology</subject><subject>Galactans - chemistry</subject><subject>Humans</subject><subject>in vitro studies</subject><subject>kappa carrageenan</subject><subject>Medical sciences</subject><subject>Modified polysaccharides</subject><subject>Natural polymers</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Partial Thromboplastin Time</subject><subject>Pharmacology. Drug treatments</subject><subject>Physicochemistry of polymers</subject><subject>Regiochemistry</subject><subject>Starch and polysaccharides</subject><subject>Structure-Activity Relationship</subject><subject>Sulfates</subject><subject>Sulfation</subject><issn>0144-8617</issn><issn>1879-1344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtv1DAUhS0EokPhJwDZILFJ8PUr8QpVFS-pEovSteU411MPmXiwk0r99zjKAEu8uV58596jcwh5DbQBCurDoXE29ac4NowCa2jXUC6ekB10ra6BC_GU7CgIUXcK2gvyIucDLU8BfU4uGAcGmqsd-XmLI7o5PGCVl9HbOcSpir4qy5PdI052ypWdhmq-xypMflxwcrgSG45Vwn2I7h6PIc_psSpyO83BRbtfxvKrTimeMM0B80vyzNsx46vzvCR3nz_9uP5a33z_8u366qZ2krO5ls5K6JnXFJVF6J12KESrpXMakTnKmOeWDw6ZV9AL62VbJFp7BqgE8kvyfttbTv9aMM-meHM4FjsYl2wAuFaghW4LKjfUpZhzQm9OKRxtejRAzZqzOZhzzmbN2dDOlJyL7s35xNIfcfir-hNsAd6dAZudHX2ykwv5H6ekZrqThXu7cd5GY_epMHe35ZIqXUkQbCU-bgSWyB4CJpNdWEsYQirNmSGG_5j9DZ1FqoY</recordid><startdate>20130116</startdate><enddate>20130116</enddate><creator>de Araújo, Cristiano A.</creator><creator>Noseda, Miguel D.</creator><creator>Cipriani, Thales R.</creator><creator>Gonçalves, Alan G.</creator><creator>Duarte, Maria Eugênia R.</creator><creator>Ducatti, Diogo R.B.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>6I.</scope><scope>AAFTH</scope><scope>FBQ</scope><scope>IQODW</scope><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>20130116</creationdate><title>Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties</title><author>de Araújo, Cristiano A. ; Noseda, Miguel D. ; Cipriani, Thales R. ; Gonçalves, Alan G. ; Duarte, Maria Eugênia R. ; Ducatti, Diogo R.B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c532t-5ca51b2f90e6ae1bc9ce44795cc9ee2c022f3a3dce2f61b4af57ca599f21e64e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Anticoagulant activity</topic><topic>Anticoagulants - chemistry</topic><topic>Anticoagulants - pharmacology</topic><topic>Applied sciences</topic><topic>Biological and medical sciences</topic><topic>Blood. Blood coagulation. Reticuloendothelial system</topic><topic>Carrageenan - chemistry</topic><topic>Carrageenan - isolation & purification</topic><topic>Carrageenans</topic><topic>Exact sciences and technology</topic><topic>Galactans - chemistry</topic><topic>Humans</topic><topic>in vitro studies</topic><topic>kappa carrageenan</topic><topic>Medical sciences</topic><topic>Modified polysaccharides</topic><topic>Natural polymers</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Partial Thromboplastin Time</topic><topic>Pharmacology. Drug treatments</topic><topic>Physicochemistry of polymers</topic><topic>Regiochemistry</topic><topic>Starch and polysaccharides</topic><topic>Structure-Activity Relationship</topic><topic>Sulfates</topic><topic>Sulfation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>de Araújo, Cristiano A.</creatorcontrib><creatorcontrib>Noseda, Miguel D.</creatorcontrib><creatorcontrib>Cipriani, Thales R.</creatorcontrib><creatorcontrib>Gonçalves, Alan G.</creatorcontrib><creatorcontrib>Duarte, Maria Eugênia R.</creatorcontrib><creatorcontrib>Ducatti, Diogo R.B.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>AGRIS</collection><collection>Pascal-Francis</collection><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>Carbohydrate polymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>de Araújo, Cristiano A.</au><au>Noseda, Miguel D.</au><au>Cipriani, Thales R.</au><au>Gonçalves, Alan G.</au><au>Duarte, Maria Eugênia R.</au><au>Ducatti, Diogo R.B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties</atitle><jtitle>Carbohydrate polymers</jtitle><addtitle>Carbohydr Polym</addtitle><date>2013-01-16</date><risdate>2013</risdate><volume>91</volume><issue>2</issue><spage>483</spage><epage>491</epage><pages>483-491</pages><issn>0144-8617</issn><eissn>1879-1344</eissn><coden>CAPOD8</coden><abstract>► Carrageenans were selectively sulfated to produce rare diads. ► The new diads synthesized were characterized by 1D and 2D NMR. ► Sulfated derivatives showed higher anticoagulant activities than native carrageenans. ► Sulfation at C2 of anhydro units and C6 of β-d-Galp improved anticoagulant activity.
Sulfated polysaccharides are recognized for their broad range of biological activities, including anticoagulant properties. The positions occupied by the sulfate groups are often related to the level of the inherent biological activity. Herein the naturally sulfated galactans, kappa-, iota- and theta-carrageenan, were additionally sulfated by regioselective means. The anticoagulant activity of the resulting samples was then studied using the aPTT in vitro assay. The influence of sulfate regiochemistry on the anticoagulant activity was evaluated. From kappa-carrageenan three rare polysaccharides were synthesized, one of them involved a synthetic route with an amphiphilic polysaccharide intermediate containing pivaloyl groups. Iota- and theta-carrageenan were utilized in a selective C6 sulfation at β-d-Galp units to produce different structures comprising trisulfated diads. All the samples were characterized by NMR (1D and 2D). The resulting aPPT measurements suggested that sulfation at C2 of 3,6-anhydro-α-d-Galp and C6 of β-d-Galp increased the anticoagulant activity.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><pmid>23121936</pmid><doi>10.1016/j.carbpol.2012.08.034</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0144-8617 |
| ispartof | Carbohydrate polymers, 2013-01, Vol.91 (2), p.483-491 |
| issn | 0144-8617 1879-1344 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1139619497 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Anticoagulant activity Anticoagulants - chemistry Anticoagulants - pharmacology Applied sciences Biological and medical sciences Blood. Blood coagulation. Reticuloendothelial system Carrageenan - chemistry Carrageenan - isolation & purification Carrageenans Exact sciences and technology Galactans - chemistry Humans in vitro studies kappa carrageenan Medical sciences Modified polysaccharides Natural polymers nuclear magnetic resonance spectroscopy Nuclear Magnetic Resonance, Biomolecular Partial Thromboplastin Time Pharmacology. Drug treatments Physicochemistry of polymers Regiochemistry Starch and polysaccharides Structure-Activity Relationship Sulfates Sulfation |
| title | Selective sulfation of carrageenans and the influence of sulfate regiochemistry on anticoagulant properties |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T20%3A47%3A34IST&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=Selective%20sulfation%20of%20carrageenans%20and%20the%20influence%20of%20sulfate%20regiochemistry%20on%20anticoagulant%20properties&rft.jtitle=Carbohydrate%20polymers&rft.au=de%20Ara%C3%BAjo,%20Cristiano%20A.&rft.date=2013-01-16&rft.volume=91&rft.issue=2&rft.spage=483&rft.epage=491&rft.pages=483-491&rft.issn=0144-8617&rft.eissn=1879-1344&rft.coden=CAPOD8&rft_id=info:doi/10.1016/j.carbpol.2012.08.034&rft_dat=%3Cproquest_cross%3E1139619497%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=1139619497&rft_id=info:pmid/23121936&rft_els_id=S0144861712008089&rfr_iscdi=true |