Synthesis and evaluation of 3- and 7-substituted geranylgeranyl pyrophosphate analogs
Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in post-translational modification of small GTP binding proteins. Attention is now turning to the development of GGTase I inhibitors. Here, we present the synthesis and biological evaluatio...
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| Published in | Bioorganic & medicinal chemistry Vol. 18; no. 6; pp. 1889 - 1892 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Oxford
Elsevier Ltd
15.03.2008
Elsevier |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0960-894X 0968-0896 1464-3405 1464-3405 1464-3391 |
| DOI | 10.1016/j.bmcl.2008.02.014 |
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| Abstract | Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in post-translational modification of small GTP binding proteins. Attention is now turning to the development of GGTase I inhibitors. Here, we present the synthesis and biological evaluation of four GGPP analogs versus mammalian GGTase I and the discovery that 7-allyl GGPP is a surprisingly efficient GGTase I substrate. |
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| AbstractList | Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in posttranslational modification of small GTP binding proteins. Attention is now turning to the development of GGTase I inhibitors. Here, we present the synthesis and biological evaluation of four GGPP analogs versus mammalian GGTase I and the discovery that 7-allyl GGPP is a surprisingly efficient GGTase I substrate. Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in post-translational modification of small GTP binding proteins. Attention is now turning to the development of GGTase I inhibitors. Here, we present the synthesis and biological evaluation of four GGPP analogs versus mammalian GGTase I and the discovery that 7-allyl GGPP is a surprisingly efficient GGTase I substrate. Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in post-translational modification of small GTP binding proteins. Attention is now turning to the development of GGTase I inhibitors. Here, we present the synthesis and biological evaluation of four GGPP analogs versus mammalian GGTase I and the discovery that 7-allyl GGPP is a surprisingly efficient GGTase I substrate.Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in post-translational modification of small GTP binding proteins. Attention is now turning to the development of GGTase I inhibitors. Here, we present the synthesis and biological evaluation of four GGPP analogs versus mammalian GGTase I and the discovery that 7-allyl GGPP is a surprisingly efficient GGTase I substrate. |
| Author | Maynor, Michelle Rickert, Emily L. Gibbs, Richard A. Scott, Sarah A. |
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| CitedBy_id | crossref_primary_10_1016_j_tet_2012_05_107 crossref_primary_10_1016_j_tet_2013_08_056 crossref_primary_10_1124_jpet_109_160192 crossref_primary_10_1016_j_bmcl_2016_06_034 crossref_primary_10_1016_j_tetlet_2014_01_063 crossref_primary_10_1016_j_pharmthera_2014_02_007 crossref_primary_10_1007_s12035_020_01870_0 |
| Cites_doi | 10.1172/JCI30868 10.1021/cb700062b 10.1016/S0960-894X(00)00337-1 10.1016/j.semcancer.2004.04.004 10.1074/jbc.272.22.14459 10.1016/S0960-894X(01)00292-X 10.1038/nrc969 10.1039/b517572k 10.2174/0929867013372111 10.1124/jpet.102.036061 10.1172/JCI32108 10.1021/jm9900873 10.1021/bi050725l 10.1002/cmdc.200500010 10.1021/jm9902786 10.1016/j.tips.2006.11.005 10.1016/j.jmb.2004.08.056 10.1016/j.bbrc.2006.12.094 10.1194/jlr.R600002-JLR200 10.1074/jbc.M600168200 10.1006/abio.1995.1108 10.1021/ol026176i 10.1016/j.bmcl.2007.01.097 10.1021/ja070274n 10.1021/ja00046a070 10.1021/bi0509503 10.1194/jlr.R500012-JLR200 |
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| Keywords | Post-translational modification Palladium-catalyzed coupling Geranylgeranylation Isoprenoids Catalytic reaction Enzyme Palladium Complexes Transferases Isoprenoid Biological activity Posttranslational modification Substrate Organic diphosphate Platinoid Complexes Inhibitor Chemical synthesis |
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| Snippet | Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in post-translational modification of small GTP... Protein prenyl transferases have been a focus of anti-cancer drug discovery in recent years due to their roles in posttranslational modification of small GTP... |
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| SubjectTerms | Alkyl and Aryl Transferases - antagonists & inhibitors Animals Biological and medical sciences Farnesyltranstransferase - antagonists & inhibitors Geranylgeranylation Humans Isoprenoids Magnetic Resonance Spectroscopy Medical sciences Mice Miscellaneous Molecular Structure Palladium-catalyzed coupling Pharmacology. Drug treatments Polyisoprenyl Phosphates - chemical synthesis Polyisoprenyl Phosphates - pharmacology Post-translational modification Protein Prenylation Protein Processing, Post-Translational |
| Title | Synthesis and evaluation of 3- and 7-substituted geranylgeranyl pyrophosphate analogs |
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