Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation
Certain 17-amino-17-demethoxygeldanamycin derivatives (R = NR′R″, R′, and/or R″ = H and/or alkyl) exhibit femtomolar inhibitory activity toward hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation. Ansamycins, including geldanamycin...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2005-08, Vol.13 (16), p.4960-4971 |
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| container_issue | 16 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Shen, Yuehai Xie, Qian Norberg, Monica Sausville, Edward Woude, George Vande Wenkert, David |
| description | Certain 17-amino-17-demethoxygeldanamycin derivatives (R
=
NR′R″, R′, and/or R″
=
H and/or alkyl) exhibit femtomolar inhibitory activity toward hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation.
Ansamycins, including geldanamycin and the derivative 17-allylamino-17-demethoxygeldanamycin, and radicicol are known for their ability to tightly bind to the ATP-binding site of the amino-terminal domain region of heat shock protein 90. We have found that geldanamycin and some of its derivatives can inhibit hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation at femtomolar levels. Assessment is made of structural requirements for such an activity and evidence is given that distinguishes the target of such an activity from that of heat shock protein 90. |
| doi_str_mv | 10.1016/j.bmc.2005.05.038 |
| format | Article |
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=
NR′R″, R′, and/or R″
=
H and/or alkyl) exhibit femtomolar inhibitory activity toward hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation.
Ansamycins, including geldanamycin and the derivative 17-allylamino-17-demethoxygeldanamycin, and radicicol are known for their ability to tightly bind to the ATP-binding site of the amino-terminal domain region of heat shock protein 90. We have found that geldanamycin and some of its derivatives can inhibit hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation at femtomolar levels. Assessment is made of structural requirements for such an activity and evidence is given that distinguishes the target of such an activity from that of heat shock protein 90.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.05.038</identifier><identifier>PMID: 15978816</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Antineoplastic agents ; Benzoquinones ; Biological and medical sciences ; Cell Line, Tumor ; Geldanamycin ; General aspects ; Hepatocyte Growth Factor - antagonists & inhibitors ; Hepatocyte Growth Factor - metabolism ; Hepatocyte growth factor/scatter factor ; HSP90 Heat-Shock Proteins - antagonists & inhibitors ; HSP90 Heat-Shock Proteins - metabolism ; Humans ; Lactams, Macrocyclic ; Lactones - metabolism ; Lactones - pharmacology ; Macrolides ; Medical sciences ; Met tyrosine kinase receptor ; Pharmacology. Drug treatments ; Protein Kinase Inhibitors - metabolism ; Protein Kinase Inhibitors - pharmacology ; Quinones - metabolism ; Quinones - pharmacology ; Receptors, Cell Surface - antagonists & inhibitors ; Receptors, Cell Surface - metabolism ; Receptors, Urokinase Plasminogen Activator ; Rifabutin - analogs & derivatives ; Rifabutin - metabolism ; Rifabutin - pharmacology ; Structure-Activity Relationship ; Urokinase-plasminogen activation</subject><ispartof>Bioorganic & medicinal chemistry, 2005-08, Vol.13 (16), p.4960-4971</ispartof><rights>2005 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-14688459fd6a2f0c4bdac9804894bb2a40a04fcddd4876109876c92ac98f18123</citedby><cites>FETCH-LOGICAL-c381t-14688459fd6a2f0c4bdac9804894bb2a40a04fcddd4876109876c92ac98f18123</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089605004670$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16950929$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15978816$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shen, Yuehai</creatorcontrib><creatorcontrib>Xie, Qian</creatorcontrib><creatorcontrib>Norberg, Monica</creatorcontrib><creatorcontrib>Sausville, Edward</creatorcontrib><creatorcontrib>Woude, George Vande</creatorcontrib><creatorcontrib>Wenkert, David</creatorcontrib><title>Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Certain 17-amino-17-demethoxygeldanamycin derivatives (R
=
NR′R″, R′, and/or R″
=
H and/or alkyl) exhibit femtomolar inhibitory activity toward hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation.
Ansamycins, including geldanamycin and the derivative 17-allylamino-17-demethoxygeldanamycin, and radicicol are known for their ability to tightly bind to the ATP-binding site of the amino-terminal domain region of heat shock protein 90. We have found that geldanamycin and some of its derivatives can inhibit hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation at femtomolar levels. Assessment is made of structural requirements for such an activity and evidence is given that distinguishes the target of such an activity from that of heat shock protein 90.</description><subject>Antineoplastic agents</subject><subject>Benzoquinones</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Geldanamycin</subject><subject>General aspects</subject><subject>Hepatocyte Growth Factor - antagonists & inhibitors</subject><subject>Hepatocyte Growth Factor - metabolism</subject><subject>Hepatocyte growth factor/scatter factor</subject><subject>HSP90 Heat-Shock Proteins - antagonists & inhibitors</subject><subject>HSP90 Heat-Shock Proteins - metabolism</subject><subject>Humans</subject><subject>Lactams, Macrocyclic</subject><subject>Lactones - metabolism</subject><subject>Lactones - pharmacology</subject><subject>Macrolides</subject><subject>Medical sciences</subject><subject>Met tyrosine kinase receptor</subject><subject>Pharmacology. Drug treatments</subject><subject>Protein Kinase Inhibitors - metabolism</subject><subject>Protein Kinase Inhibitors - pharmacology</subject><subject>Quinones - metabolism</subject><subject>Quinones - pharmacology</subject><subject>Receptors, Cell Surface - antagonists & inhibitors</subject><subject>Receptors, Cell Surface - metabolism</subject><subject>Receptors, Urokinase Plasminogen Activator</subject><subject>Rifabutin - analogs & derivatives</subject><subject>Rifabutin - metabolism</subject><subject>Rifabutin - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Urokinase-plasminogen activation</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1vGyEQQFHUKnE-fkAvEZfmtg7sYgzKKbJip1KqHtqeEQuzLe4ubABb8qH_vWxsKbdKo5kDb2aYh9AnSuaUUH6_nbeDmdeELOZTNOIMzSjjrGoaST-gGZFcVERIfoEuU9oSQmom6Tm6oAu5FILyGfq7gd5qr4eDcR5biG6vs9sDdv63a112wePQ4efN-v77uhrAOp3B4q-QcT7EkJwH_Md5nQBHMDDmECsLI3gLPuNdDMfHaux1GpwPv8BjbfLbluCv0cdO9wluTvUK_Vw__Vg9Vy_fNl9Wjy-VaQTNVblJCLaQneW67ohhrdVGCsKEZG1ba0Y0YZ2x1jKx5JTIko2sJ6ajgtbNFbo7zh1jeN1BympwyUDfaw9hlxQXhNZSLgtIj6Apt6UInRqjG3Q8KErU5FxtVXGuJudqikaUntvT8F1bBL13nCQX4PMJ0MnovovaG5feOS4XRNaycA9HDoqKvYOoknHgTZFe3GZlg_vPN_4BVfOhJw</recordid><startdate>20050815</startdate><enddate>20050815</enddate><creator>Shen, Yuehai</creator><creator>Xie, Qian</creator><creator>Norberg, Monica</creator><creator>Sausville, Edward</creator><creator>Woude, George Vande</creator><creator>Wenkert, David</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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>20050815</creationdate><title>Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation</title><author>Shen, Yuehai ; Xie, Qian ; Norberg, Monica ; Sausville, Edward ; Woude, George Vande ; Wenkert, David</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-14688459fd6a2f0c4bdac9804894bb2a40a04fcddd4876109876c92ac98f18123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Antineoplastic agents</topic><topic>Benzoquinones</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Geldanamycin</topic><topic>General aspects</topic><topic>Hepatocyte Growth Factor - antagonists & inhibitors</topic><topic>Hepatocyte Growth Factor - metabolism</topic><topic>Hepatocyte growth factor/scatter factor</topic><topic>HSP90 Heat-Shock Proteins - antagonists & inhibitors</topic><topic>HSP90 Heat-Shock Proteins - metabolism</topic><topic>Humans</topic><topic>Lactams, Macrocyclic</topic><topic>Lactones - metabolism</topic><topic>Lactones - pharmacology</topic><topic>Macrolides</topic><topic>Medical sciences</topic><topic>Met tyrosine kinase receptor</topic><topic>Pharmacology. Drug treatments</topic><topic>Protein Kinase Inhibitors - metabolism</topic><topic>Protein Kinase Inhibitors - pharmacology</topic><topic>Quinones - metabolism</topic><topic>Quinones - pharmacology</topic><topic>Receptors, Cell Surface - antagonists & inhibitors</topic><topic>Receptors, Cell Surface - metabolism</topic><topic>Receptors, Urokinase Plasminogen Activator</topic><topic>Rifabutin - analogs & derivatives</topic><topic>Rifabutin - metabolism</topic><topic>Rifabutin - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Urokinase-plasminogen activation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shen, Yuehai</creatorcontrib><creatorcontrib>Xie, Qian</creatorcontrib><creatorcontrib>Norberg, Monica</creatorcontrib><creatorcontrib>Sausville, Edward</creatorcontrib><creatorcontrib>Woude, George Vande</creatorcontrib><creatorcontrib>Wenkert, David</creatorcontrib><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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shen, Yuehai</au><au>Xie, Qian</au><au>Norberg, Monica</au><au>Sausville, Edward</au><au>Woude, George Vande</au><au>Wenkert, David</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2005-08-15</date><risdate>2005</risdate><volume>13</volume><issue>16</issue><spage>4960</spage><epage>4971</epage><pages>4960-4971</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Certain 17-amino-17-demethoxygeldanamycin derivatives (R
=
NR′R″, R′, and/or R″
=
H and/or alkyl) exhibit femtomolar inhibitory activity toward hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation.
Ansamycins, including geldanamycin and the derivative 17-allylamino-17-demethoxygeldanamycin, and radicicol are known for their ability to tightly bind to the ATP-binding site of the amino-terminal domain region of heat shock protein 90. We have found that geldanamycin and some of its derivatives can inhibit hepatocyte growth factor/scatter factor-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation at femtomolar levels. Assessment is made of structural requirements for such an activity and evidence is given that distinguishes the target of such an activity from that of heat shock protein 90.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15978816</pmid><doi>10.1016/j.bmc.2005.05.038</doi><tpages>12</tpages></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Antineoplastic agents Benzoquinones Biological and medical sciences Cell Line, Tumor Geldanamycin General aspects Hepatocyte Growth Factor - antagonists & inhibitors Hepatocyte Growth Factor - metabolism Hepatocyte growth factor/scatter factor HSP90 Heat-Shock Proteins - antagonists & inhibitors HSP90 Heat-Shock Proteins - metabolism Humans Lactams, Macrocyclic Lactones - metabolism Lactones - pharmacology Macrolides Medical sciences Met tyrosine kinase receptor Pharmacology. Drug treatments Protein Kinase Inhibitors - metabolism Protein Kinase Inhibitors - pharmacology Quinones - metabolism Quinones - pharmacology Receptors, Cell Surface - antagonists & inhibitors Receptors, Cell Surface - metabolism Receptors, Urokinase Plasminogen Activator Rifabutin - analogs & derivatives Rifabutin - metabolism Rifabutin - pharmacology Structure-Activity Relationship Urokinase-plasminogen activation |
| title | Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation |
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