Dermatan sulfate oligosaccharides having reducing end 2, 5-anhydro-d-talose inhibit bovine testicular hyaluronidase activity
Dermatan sulfate oligosaccharides having reducing end 2,5-anhydro-d-talose were prepared by partial N-deacetylation of dermatan sulfate polysaccharide with hydrazine followed by deamination with nitrous acid, and the effect of these oligosaccharides on the activity of bovine testicular hyaluronidase...
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| Veröffentlicht in: | Carbohydrate research 2019-09, Vol.483, p.107754-107754, Article 107754 |
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| creator | Kakizaki, Ikuko Koizumi, Hideyo Kobayashi, Takashi Nakamura, Toshiya Majima, Mitsuo |
| description | Dermatan sulfate oligosaccharides having reducing end 2,5-anhydro-d-talose were prepared by partial N-deacetylation of dermatan sulfate polysaccharide with hydrazine followed by deamination with nitrous acid, and the effect of these oligosaccharides on the activity of bovine testicular hyaluronidase was investigated. Hydrolysis activity and transglycosylation activity of this enzyme were assessed in an independent reaction system by analyzing the products by HPLC. Dermatan sulfate oligosaccharides inhibited hyaluronan hydrolysis by bovine testicular hyaluronidase. Kinetic analysis of the hydrolysis reaction revealed that the inhibition mode by dermatan sulfate oligosaccharides was as competitive as that previously shown by chondroitin sulfate oligosaccharides. Transglycosylation of hyaluronan by bovine testicular hyaluronidase, as a reverse reaction of hydrolysis of hyaluronan, was also inhibited. These inhibitory effects were dependent on the dose and sulfation degree of dermatan sulfate.
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•Oligosaccharides having dermatan sulfate (DS) structure were chemically prepared.•DS oligosaccharides inhibited hyaluronan hydrolysis by testicular hyaluronidase.•The inhibition mode by the DS oligosaccharides on the hydrolysis was competitive.•Transglycosylation by hyaluronidase was also inhibited by the DS oligosaccharides.•Inhibitions were in a dose dependent and DS sulfation degree dependent manner. |
| doi_str_mv | 10.1016/j.carres.2019.107754 |
| format | Article |
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[Display omitted]
•Oligosaccharides having dermatan sulfate (DS) structure were chemically prepared.•DS oligosaccharides inhibited hyaluronan hydrolysis by testicular hyaluronidase.•The inhibition mode by the DS oligosaccharides on the hydrolysis was competitive.•Transglycosylation by hyaluronidase was also inhibited by the DS oligosaccharides.•Inhibitions were in a dose dependent and DS sulfation degree dependent manner.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2019.107754</identifier><identifier>PMID: 31398613</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Animals ; Cattle ; Chromatography, High Pressure Liquid ; Dermatan sulfate ; Dermatan Sulfate - chemistry ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Hyaluronan ; Hyaluronic Acid - chemistry ; Hyaluronidase ; Hyaluronoglucosaminidase - antagonists & inhibitors ; Inhibitor ; Lactones - chemistry ; Male ; Oligosaccharide ; Oligosaccharides - chemical synthesis ; Oligosaccharides - chemistry ; Oligosaccharides - pharmacology ; Testis - enzymology</subject><ispartof>Carbohydrate research, 2019-09, Vol.483, p.107754-107754, Article 107754</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c311t-d5e44486dc5f5ef2f9d2a302b5d6dc903df3c700d01d2d1d25f1f0c011191cde3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0008621518304695$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31398613$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kakizaki, Ikuko</creatorcontrib><creatorcontrib>Koizumi, Hideyo</creatorcontrib><creatorcontrib>Kobayashi, Takashi</creatorcontrib><creatorcontrib>Nakamura, Toshiya</creatorcontrib><creatorcontrib>Majima, Mitsuo</creatorcontrib><title>Dermatan sulfate oligosaccharides having reducing end 2, 5-anhydro-d-talose inhibit bovine testicular hyaluronidase activity</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Dermatan sulfate oligosaccharides having reducing end 2,5-anhydro-d-talose were prepared by partial N-deacetylation of dermatan sulfate polysaccharide with hydrazine followed by deamination with nitrous acid, and the effect of these oligosaccharides on the activity of bovine testicular hyaluronidase was investigated. Hydrolysis activity and transglycosylation activity of this enzyme were assessed in an independent reaction system by analyzing the products by HPLC. Dermatan sulfate oligosaccharides inhibited hyaluronan hydrolysis by bovine testicular hyaluronidase. Kinetic analysis of the hydrolysis reaction revealed that the inhibition mode by dermatan sulfate oligosaccharides was as competitive as that previously shown by chondroitin sulfate oligosaccharides. Transglycosylation of hyaluronan by bovine testicular hyaluronidase, as a reverse reaction of hydrolysis of hyaluronan, was also inhibited. These inhibitory effects were dependent on the dose and sulfation degree of dermatan sulfate.
[Display omitted]
•Oligosaccharides having dermatan sulfate (DS) structure were chemically prepared.•DS oligosaccharides inhibited hyaluronan hydrolysis by testicular hyaluronidase.•The inhibition mode by the DS oligosaccharides on the hydrolysis was competitive.•Transglycosylation by hyaluronidase was also inhibited by the DS oligosaccharides.•Inhibitions were in a dose dependent and DS sulfation degree dependent manner.</description><subject>Animals</subject><subject>Cattle</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Dermatan sulfate</subject><subject>Dermatan Sulfate - chemistry</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Hyaluronan</subject><subject>Hyaluronic Acid - chemistry</subject><subject>Hyaluronidase</subject><subject>Hyaluronoglucosaminidase - antagonists & inhibitors</subject><subject>Inhibitor</subject><subject>Lactones - chemistry</subject><subject>Male</subject><subject>Oligosaccharide</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Oligosaccharides - chemistry</subject><subject>Oligosaccharides - pharmacology</subject><subject>Testis - enzymology</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2LFDEQhoMo7rj6D0Ry9GCPqaQ_L4KsuyoseFnBW8ikKtsZejprkh4Y2B9vhl49eghJiuetSh7G3oLYgoD2435rTYyUtlLAUEpd19TP2Ab6TlW1bH89ZxshRF-1EpoL9iqlfbmKtmtfsgsFauhbUBv2-IXiwWQz87RMzmTiYfL3IRlrRxM9UuKjOfr5nkfCxZ4PNCOXH3hTmXk8YQwVVtlMIRH38-h3PvNdKAnimVL2dplM5OPJTEsMs0dTOGOzP_p8es1eODMlevO0X7KfN9d3V9-q2x9fv199vq2sAsgVNlTXdd-ibVxDTroBpVFC7hostUEodMp2QqAAlFhW48AJKwBgAIukLtn7te9DDL-X8ip98MnSNJmZwpK0lB30jWjFUNB6RW0MKUVy-iH6g4knDUKfveu9Xr3rs3e9ei-xd08Tlt2B8F_or-gCfFoBKv88eoo6WU-zJfSRbNYY_P8n_AEbVJiG</recordid><startdate>20190901</startdate><enddate>20190901</enddate><creator>Kakizaki, Ikuko</creator><creator>Koizumi, Hideyo</creator><creator>Kobayashi, Takashi</creator><creator>Nakamura, Toshiya</creator><creator>Majima, Mitsuo</creator><general>Elsevier 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>20190901</creationdate><title>Dermatan sulfate oligosaccharides having reducing end 2, 5-anhydro-d-talose inhibit bovine testicular hyaluronidase activity</title><author>Kakizaki, Ikuko ; Koizumi, Hideyo ; Kobayashi, Takashi ; Nakamura, Toshiya ; Majima, Mitsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c311t-d5e44486dc5f5ef2f9d2a302b5d6dc903df3c700d01d2d1d25f1f0c011191cde3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Animals</topic><topic>Cattle</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Dermatan sulfate</topic><topic>Dermatan Sulfate - chemistry</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Hyaluronan</topic><topic>Hyaluronic Acid - chemistry</topic><topic>Hyaluronidase</topic><topic>Hyaluronoglucosaminidase - antagonists & inhibitors</topic><topic>Inhibitor</topic><topic>Lactones - chemistry</topic><topic>Male</topic><topic>Oligosaccharide</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Oligosaccharides - pharmacology</topic><topic>Testis - enzymology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kakizaki, Ikuko</creatorcontrib><creatorcontrib>Koizumi, Hideyo</creatorcontrib><creatorcontrib>Kobayashi, Takashi</creatorcontrib><creatorcontrib>Nakamura, Toshiya</creatorcontrib><creatorcontrib>Majima, Mitsuo</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>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kakizaki, Ikuko</au><au>Koizumi, Hideyo</au><au>Kobayashi, Takashi</au><au>Nakamura, Toshiya</au><au>Majima, Mitsuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dermatan sulfate oligosaccharides having reducing end 2, 5-anhydro-d-talose inhibit bovine testicular hyaluronidase activity</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2019-09-01</date><risdate>2019</risdate><volume>483</volume><spage>107754</spage><epage>107754</epage><pages>107754-107754</pages><artnum>107754</artnum><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>Dermatan sulfate oligosaccharides having reducing end 2,5-anhydro-d-talose were prepared by partial N-deacetylation of dermatan sulfate polysaccharide with hydrazine followed by deamination with nitrous acid, and the effect of these oligosaccharides on the activity of bovine testicular hyaluronidase was investigated. Hydrolysis activity and transglycosylation activity of this enzyme were assessed in an independent reaction system by analyzing the products by HPLC. Dermatan sulfate oligosaccharides inhibited hyaluronan hydrolysis by bovine testicular hyaluronidase. Kinetic analysis of the hydrolysis reaction revealed that the inhibition mode by dermatan sulfate oligosaccharides was as competitive as that previously shown by chondroitin sulfate oligosaccharides. Transglycosylation of hyaluronan by bovine testicular hyaluronidase, as a reverse reaction of hydrolysis of hyaluronan, was also inhibited. These inhibitory effects were dependent on the dose and sulfation degree of dermatan sulfate.
[Display omitted]
•Oligosaccharides having dermatan sulfate (DS) structure were chemically prepared.•DS oligosaccharides inhibited hyaluronan hydrolysis by testicular hyaluronidase.•The inhibition mode by the DS oligosaccharides on the hydrolysis was competitive.•Transglycosylation by hyaluronidase was also inhibited by the DS oligosaccharides.•Inhibitions were in a dose dependent and DS sulfation degree dependent manner.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>31398613</pmid><doi>10.1016/j.carres.2019.107754</doi><tpages>1</tpages></addata></record> |
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| subjects | Animals Cattle Chromatography, High Pressure Liquid Dermatan sulfate Dermatan Sulfate - chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Hyaluronan Hyaluronic Acid - chemistry Hyaluronidase Hyaluronoglucosaminidase - antagonists & inhibitors Inhibitor Lactones - chemistry Male Oligosaccharide Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Oligosaccharides - pharmacology Testis - enzymology |
| title | Dermatan sulfate oligosaccharides having reducing end 2, 5-anhydro-d-talose inhibit bovine testicular hyaluronidase activity |
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