Design and Synthesis of Redox Stable Analogues of Sunflower Trypsin Inhibitors (SFTI-1) on Solid Support, Potent Inhibitors of Matriptase
Matriptase is a member of the emerging class of type II transmembrane serine proteases. It was found that the sunflower trypsin inhibitor (SFTI-1), isolated from sunflower seeds, inhibits matriptase with a subnanomolar K i of 0.92 nM. On the basis of this result, we designed and synthesized its prot...
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| Veröffentlicht in: | Organic letters 2007-01, Vol.9 (1), p.9-12 |
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| container_title | Organic letters |
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| creator | Jiang, Sheng Li, Peng Lee, Sheau-Ling Lin, Cheng Yong Long, Ya-Qiu Johnson, Michael D Dickson, Robert B Roller, Peter P |
| description | Matriptase is a member of the emerging class of type II transmembrane serine proteases. It was found that the sunflower trypsin inhibitor (SFTI-1), isolated from sunflower seeds, inhibits matriptase with a subnanomolar K i of 0.92 nM. On the basis of this result, we designed and synthesized its proteolytically stable analogues, SFTI-2 and SFTI-3. SFTI-3 exhibited very good binding affinity to matriptase, and it was metabolically stable. |
| doi_str_mv | 10.1021/ol0621497 |
| format | Article |
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It was found that the sunflower trypsin inhibitor (SFTI-1), isolated from sunflower seeds, inhibits matriptase with a subnanomolar K i of 0.92 nM. On the basis of this result, we designed and synthesized its proteolytically stable analogues, SFTI-2 and SFTI-3. 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Lett</addtitle><description>Matriptase is a member of the emerging class of type II transmembrane serine proteases. It was found that the sunflower trypsin inhibitor (SFTI-1), isolated from sunflower seeds, inhibits matriptase with a subnanomolar K i of 0.92 nM. On the basis of this result, we designed and synthesized its proteolytically stable analogues, SFTI-2 and SFTI-3. SFTI-3 exhibited very good binding affinity to matriptase, and it was metabolically stable.</description><subject>Cyclization</subject><subject>Drug Design</subject><subject>Helianthus - chemistry</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Peptides - chemical synthesis</subject><subject>Peptides - chemistry</subject><subject>Peptides - pharmacology</subject><subject>Serine Endopeptidases - metabolism</subject><subject>Serine Proteinase Inhibitors - chemical synthesis</subject><subject>Serine Proteinase Inhibitors - chemistry</subject><subject>Serine Proteinase Inhibitors - pharmacology</subject><subject>Trypsin Inhibitors - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkN1KwzAYhoMobk4PvAHJieLAatL0L4eiTgcTxc7jkjbJ1tElNUnRXYJ3bXRjeuDR9_fwwPcCcIzRJUYhvtINSkIc0XQH9HEckiBFcbi77RPUAwfWLhDCfkP3QQ-nmIYoDfvg81bYeqYgUxzmK-XmfrRQS_giuP6AuWNlI-C1Yo2edeLnkndKNvpdGDg1q9bWCo7VvC5rp42F5_loOg7wEGoFc93U3tq1rTbuAj5rJ5T7C3vZI3Ombh2z4hDsSdZYcbSpA_A6upvePASTp_vxzfUkYAQTF0SUV5X_I4s5L0lIuaCyrCKSyTJFpBQZjwSlNMvKOMkk41RSkkoWc4GlpzIyAGdrb2v0m3_JFcvaVqJpmBK6s0WSkTRJI-rB4RqsjLbWCFm0pl4ysyowKr5zL7a5e_ZkI-3KpeC_5CZoD5yuAVbZYqE74xO1_4i-AMDjin0</recordid><startdate>20070104</startdate><enddate>20070104</enddate><creator>Jiang, Sheng</creator><creator>Li, Peng</creator><creator>Lee, Sheau-Ling</creator><creator>Lin, Cheng Yong</creator><creator>Long, Ya-Qiu</creator><creator>Johnson, Michael D</creator><creator>Dickson, Robert B</creator><creator>Roller, Peter P</creator><general>American Chemical Society</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>20070104</creationdate><title>Design and Synthesis of Redox Stable Analogues of Sunflower Trypsin Inhibitors (SFTI-1) on Solid Support, Potent Inhibitors of Matriptase</title><author>Jiang, Sheng ; Li, Peng ; Lee, Sheau-Ling ; Lin, Cheng Yong ; Long, Ya-Qiu ; Johnson, Michael D ; Dickson, Robert B ; Roller, Peter P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-49dcc11585ddb329de9fbc438fb703be8d4e99988b568fad9f937fa5de1f43883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Cyclization</topic><topic>Drug Design</topic><topic>Helianthus - chemistry</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Peptides - chemical synthesis</topic><topic>Peptides - chemistry</topic><topic>Peptides - pharmacology</topic><topic>Serine Endopeptidases - metabolism</topic><topic>Serine Proteinase Inhibitors - chemical synthesis</topic><topic>Serine Proteinase Inhibitors - chemistry</topic><topic>Serine Proteinase Inhibitors - pharmacology</topic><topic>Trypsin Inhibitors - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Sheng</creatorcontrib><creatorcontrib>Li, Peng</creatorcontrib><creatorcontrib>Lee, Sheau-Ling</creatorcontrib><creatorcontrib>Lin, Cheng Yong</creatorcontrib><creatorcontrib>Long, Ya-Qiu</creatorcontrib><creatorcontrib>Johnson, Michael D</creatorcontrib><creatorcontrib>Dickson, Robert B</creatorcontrib><creatorcontrib>Roller, Peter P</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Sheng</au><au>Li, Peng</au><au>Lee, Sheau-Ling</au><au>Lin, Cheng Yong</au><au>Long, Ya-Qiu</au><au>Johnson, Michael D</au><au>Dickson, Robert B</au><au>Roller, Peter P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and Synthesis of Redox Stable Analogues of Sunflower Trypsin Inhibitors (SFTI-1) on Solid Support, Potent Inhibitors of Matriptase</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2007-01, Vol.9 (1), p.9-12 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | Cyclization Drug Design Helianthus - chemistry Molecular Structure Oxidation-Reduction Peptides - chemical synthesis Peptides - chemistry Peptides - pharmacology Serine Endopeptidases - metabolism Serine Proteinase Inhibitors - chemical synthesis Serine Proteinase Inhibitors - chemistry Serine Proteinase Inhibitors - pharmacology Trypsin Inhibitors - chemistry |
| title | Design and Synthesis of Redox Stable Analogues of Sunflower Trypsin Inhibitors (SFTI-1) on Solid Support, Potent Inhibitors of Matriptase |
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