Fluorescent Inhibitors for IspF, an Enzyme in the Non-Mevalonate Pathway for Isoprenoid Biosynthesis and a Potential Target for Antimalarial Therapy
Designed inhibitors (like 1) of IspF, a key enzyme in the non‐mevalonate pathway for terpene biosynthesis and a potential antimalarial target, were synthesized and evaluated. Since fluorescent probes were introduced in these ligands, their affinity towards IspF from E. coli could be determined by fl...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2006-02, Vol.45 (7), p.1069-1074 |
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| container_end_page | 1074 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Crane, Christine M. Kaiser, Johannes Ramsden, Nicola L. Lauw, Susan Rohdich, Felix Eisenreich, Wolfgang Hunter, William N. Bacher, Adelbert Diederich, François |
| description | Designed inhibitors (like 1) of IspF, a key enzyme in the non‐mevalonate pathway for terpene biosynthesis and a potential antimalarial target, were synthesized and evaluated. Since fluorescent probes were introduced in these ligands, their affinity towards IspF from E. coli could be determined by fluorescence titrations. The binding modes of two ligands in ternary complexes with IspF and a ZnII ion were clarified by X‐ray analysis. |
| doi_str_mv | 10.1002/anie.200503003 |
| format | Article |
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Since fluorescent probes were introduced in these ligands, their affinity towards IspF from E. coli could be determined by fluorescence titrations. The binding modes of two ligands in ternary complexes with IspF and a ZnII ion were clarified by X‐ray analysis.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200503003</identifier><identifier>PMID: 16392111</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Antimalarials - chemical synthesis ; Antimalarials - pharmacology ; Binding Sites ; Crystallography, X-Ray ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; Escherichia coli - drug effects ; Escherichia coli Proteins - antagonists & inhibitors ; Escherichia coli Proteins - chemistry ; fluorescence ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - pharmacology ; inhibitors ; IspF ; Ligands ; Magnetic Resonance Spectroscopy ; Models, Molecular ; non-mevalonate pathway ; Phosphorus-Oxygen Lyases - antagonists & inhibitors ; Phosphorus-Oxygen Lyases - chemistry ; protein crystal structure analysis ; Terpenes - metabolism</subject><ispartof>Angewandte Chemie International Edition, 2006-02, Vol.45 (7), p.1069-1074</ispartof><rights>Copyright © 2006 WILEY‐VCH Verlag GmbH & Co. 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The binding modes of two ligands in ternary complexes with IspF and a ZnII ion were clarified by X‐ray analysis.</description><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - pharmacology</subject><subject>Binding Sites</subject><subject>Crystallography, X-Ray</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli Proteins - antagonists & inhibitors</subject><subject>Escherichia coli Proteins - chemistry</subject><subject>fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - pharmacology</subject><subject>inhibitors</subject><subject>IspF</subject><subject>Ligands</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>non-mevalonate pathway</subject><subject>Phosphorus-Oxygen Lyases - antagonists & inhibitors</subject><subject>Phosphorus-Oxygen Lyases - chemistry</subject><subject>protein crystal structure analysis</subject><subject>Terpenes - metabolism</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkT9v2zAQxYmiRfOva8eCU6fKIUWJlEbHsFMDiZPBgEeClE41W5lUSbqp-jnygcvERtot0x0Ov_cOdw-hj5RMKCH5pbIGJjkhJWGEsDfolJY5zZgQ7G3qC8YyUZX0BJ2F8D3xVUX4e3RCOatzSukpelz0e-chNGAjXtqt0SY6H3DnPF6GYfEFK4vn9s-4A2wsjlvAK2ezW_ilemdVBHyv4vZBjUeFGzxYZ1p8ZVwYbeKDCcmjxQrfu5i2GNXjtfLfID5LpmmyU73yz_MteDWMF-hdp_oAH471HK0X8_Xsa3Zzd72cTW-ypqA5y3StCw0lI3lREq5bVYmiFIqKglDGG64bXqXSQts2IqegOVRdwUXH6q5hmp2jzwfbwbufewhR7kx6RN8rC24fJBecsVKUr4K0rjkp8jyBkwPYeBeCh04OPl3nR0mJfMpLPuUlX_JKgk9H573eQfsPPwaUgPoAPJgexlfs5HS1nP9vnh20JkT4_aJV_kc6jYlSblbXks42tdhcMSnYX-gossQ</recordid><startdate>20060206</startdate><enddate>20060206</enddate><creator>Crane, Christine M.</creator><creator>Kaiser, Johannes</creator><creator>Ramsden, Nicola L.</creator><creator>Lauw, Susan</creator><creator>Rohdich, Felix</creator><creator>Eisenreich, Wolfgang</creator><creator>Hunter, William N.</creator><creator>Bacher, Adelbert</creator><creator>Diederich, François</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>M7N</scope><scope>7X8</scope></search><sort><creationdate>20060206</creationdate><title>Fluorescent Inhibitors for IspF, an Enzyme in the Non-Mevalonate Pathway for Isoprenoid Biosynthesis and a Potential Target for Antimalarial Therapy</title><author>Crane, Christine M. ; 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| subjects | Antimalarials - chemical synthesis Antimalarials - pharmacology Binding Sites Crystallography, X-Ray Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Escherichia coli - drug effects Escherichia coli Proteins - antagonists & inhibitors Escherichia coli Proteins - chemistry fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - pharmacology inhibitors IspF Ligands Magnetic Resonance Spectroscopy Models, Molecular non-mevalonate pathway Phosphorus-Oxygen Lyases - antagonists & inhibitors Phosphorus-Oxygen Lyases - chemistry protein crystal structure analysis Terpenes - metabolism |
| title | Fluorescent Inhibitors for IspF, an Enzyme in the Non-Mevalonate Pathway for Isoprenoid Biosynthesis and a Potential Target for Antimalarial Therapy |
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