Synthesis facilitates an understanding of the structural basis for translation inhibition by the lissoclimides
The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure–activity relationships (S...
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| Veröffentlicht in: | Nature chemistry Jg. 9; H. 11; S. 1140 - 1149 |
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| Format: | Journal Article |
| Sprache: | Englisch |
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01.11.2017
Springer Nature Nature Publishing Group |
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| ISSN: | 1755-4330, 1755-4349, 1755-4349 |
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| Abstract | The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure–activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen–
π
interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors.
Several natural and unnatural lissoclimide cytotoxins have been prepared via semi-synthesis and total synthesis. An X-ray co-crystal structure of chlorolissoclimide with the ribosome and evaluation of cytotoxicity and translation inhibition of new compounds in the series improves our understanding of the molecular basis for cytotoxicity. |
|---|---|
| AbstractList | The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure-activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen-π interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors. The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure-activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen-p interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors. The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure–activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen– π interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors. Several natural and unnatural lissoclimide cytotoxins have been prepared via semi-synthesis and total synthesis. An X-ray co-crystal structure of chlorolissoclimide with the ribosome and evaluation of cytotoxicity and translation inhibition of new compounds in the series improves our understanding of the molecular basis for cytotoxicity. The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure-activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen-π interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors.The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and analogue-oriented synthesis approaches provide a series of lissoclimide natural products and analogues that expand the structure-activity relationships (SARs) in this family. The semisynthesis approach yielded significant quantities of chlorolissoclimide (CL) to permit an evaluation against the National Cancer Institute's 60-cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. Although it shares a binding site with other imide-based natural product translation inhibitors, CL engages in a particularly interesting and novel face-on halogen-π interaction between the ligand's alkyl chloride and a guanine residue. Our analogue-oriented synthesis provides many more lissoclimide compounds, which were tested against aggressive human cancer cell lines and for protein synthesis inhibitory activity. Finally, computational modelling was used to explain the SARs of certain key compounds and set the stage for the structure-guided design of better translation inhibitors. The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semi-synthesis and analogue-oriented synthesis approaches have provided a series of lissoclimide natural products and analogues that expanded the structure-activity relationships in this family. The semi-synthesis approach yielded significant quantities of chlorolissoclimide that permitted evaluation against the NCI’s 60 cell line panel and allowed us to obtain an X-ray co-crystal structure of the synthetic secondary metabolite with the eukaryotic 80S ribosome. While it shares a binding site with other imide-based natural product translation inhibitors, chlorolissoclimide engages in a particularly interesting and novel face-on halogen-π interaction between the ligand’s alkyl chloride and a guanine residue. Our analogue-oriented synthesis provided many more lissoclimide compounds, which were tested against aggressive human cancer cell lines, and for protein synthesis inhibitory activity. Finally, computational modeling was used to explain the SAR of certain key compounds, setting the stage for structure-guided design of better translation inhibitors. Via semi-synthesis and total synthesis, we have made several natural and unnatural lissoclimide cytotoxins. An X-ray co-crystal structure of chlorolissoclimide with the ribosome and evaluation of cytotoxicity and translation inhibition of new compounds in the series improved our understanding of the molecular basis for cytotoxicity. |
| Author | Könst, Zef A. Yusupov, Marat Michalak, Sharon E. Nam, Sangkil Mobley, David L. Yusupova, Gulnara Vanderwal, Christopher D. Cencic, Regina Szklarski, Anne R. Pelletier, Jerry Meyer, Mélanie Pellegrino, Simone Zanette, Camila Horne, David A. Voora, Vamsee K. |
| AuthorAffiliation | c Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697, United States b Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), INSERM U964, CNRS UMR7104, Université de Strasbourg, 67404, Illkirch, France a Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025, United States e Department of Molecular Medicine, Beckman Research Institute, City of Hope Comprehensive Cancer Center, 1500 East Duarte Road, Duarte, California 91010, United States d Department of Biochemistry, McGill University, Montréal, Québec H3G 1Y6, Canada |
| AuthorAffiliation_xml | – name: e Department of Molecular Medicine, Beckman Research Institute, City of Hope Comprehensive Cancer Center, 1500 East Duarte Road, Duarte, California 91010, United States – name: c Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697, United States – name: b Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), INSERM U964, CNRS UMR7104, Université de Strasbourg, 67404, Illkirch, France – name: a Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025, United States – name: d Department of Biochemistry, McGill University, Montréal, Québec H3G 1Y6, Canada |
| Author_xml | – sequence: 1 givenname: Zef A. surname: Könst fullname: Könst, Zef A. organization: Department of Chemistry, University of California – sequence: 2 givenname: Anne R. surname: Szklarski fullname: Szklarski, Anne R. organization: Department of Chemistry, University of California – sequence: 3 givenname: Simone surname: Pellegrino fullname: Pellegrino, Simone organization: Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), INSERM U964, CNRS UMR7104, Université de Strasbourg – sequence: 4 givenname: Sharon E. surname: Michalak fullname: Michalak, Sharon E. organization: Department of Chemistry, University of California – sequence: 5 givenname: Mélanie surname: Meyer fullname: Meyer, Mélanie organization: Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), INSERM U964, CNRS UMR7104, Université de Strasbourg – sequence: 6 givenname: Camila orcidid: 0000-0003-1411-0086 surname: Zanette fullname: Zanette, Camila organization: Department of Pharmaceutical Sciences, University of California – sequence: 7 givenname: Regina surname: Cencic fullname: Cencic, Regina organization: Department of Biochemistry, McGill University – sequence: 8 givenname: Sangkil surname: Nam fullname: Nam, Sangkil organization: Department of Molecular Medicine, Beckman Research Institute, City of Hope Comprehensive Cancer Center – sequence: 9 givenname: Vamsee K. surname: Voora fullname: Voora, Vamsee K. organization: Department of Chemistry, University of California – sequence: 10 givenname: David A. surname: Horne fullname: Horne, David A. organization: Department of Molecular Medicine, Beckman Research Institute, City of Hope Comprehensive Cancer Center – sequence: 11 givenname: Jerry surname: Pelletier fullname: Pelletier, Jerry organization: Department of Biochemistry, McGill University – sequence: 12 givenname: David L. surname: Mobley fullname: Mobley, David L. organization: Department of Pharmaceutical Sciences, University of California – sequence: 13 givenname: Gulnara surname: Yusupova fullname: Yusupova, Gulnara organization: Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), INSERM U964, CNRS UMR7104, Université de Strasbourg – sequence: 14 givenname: Marat surname: Yusupov fullname: Yusupov, Marat email: marat@igbmc.fr organization: Institut de Génétique et de Biologie Moléculaire et Cellulaire (IGBMC), INSERM U964, CNRS UMR7104, Université de Strasbourg – sequence: 15 givenname: Christopher D. surname: Vanderwal fullname: Vanderwal, Christopher D. email: cdv@uci.edu organization: Department of Chemistry, University of California |
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| Copyright | Springer Nature Limited 2017 Copyright Nature Publishing Group Nov 2017 Distributed under a Creative Commons Attribution 4.0 International License |
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| Keywords | CORE DICHLOROLISSOCLIMIDE PROTEIN LACTIMIDOMYCIN CYTOTOXIC DITERPENE ALKALOIDS RIBOSOME |
| Language | English |
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| Snippet | The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semisynthesis and... The lissoclimides are unusual succinimide-containing labdane diterpenoids that were reported to be potent cytotoxins. Our short semi-synthesis and... |
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| SubjectTerms | 631/535/1266 639/638/309/2420 639/638/549/977 Analogs Analytical Chemistry Animals Antineoplastic Agents, Phytogenic - chemical synthesis Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology Binding sites Biochemistry Biological Products - chemical synthesis Biological Products - chemistry Biological Products - pharmacology Biotechnology Cancer Cell Line, Tumor Cell Proliferation - drug effects Chemistry Chemistry, Multidisciplinary Chemistry/Food Science Computer applications Crystal structure Crystallography, X-Ray Cytotoxins Diterpenes Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Drug Screening Assays, Antitumor Eukaryotic Initiation Factors - antagonists & inhibitors Eukaryotic Initiation Factors - metabolism Guanine Humans Inhibitors Inorganic Chemistry Life Sciences Metabolites Mice Models, Molecular Molecular Conformation Natural products Organic Chemistry Peptides, Cyclic Physical Chemistry Physical Sciences Protein biosynthesis Protein Biosynthesis - drug effects Protein synthesis Science & Technology Semisynthesis Structure-activity relationships Succinimide Succinimides - chemical synthesis Succinimides - chemistry Succinimides - pharmacology Translation Tumor cell lines |
| Title | Synthesis facilitates an understanding of the structural basis for translation inhibition by the lissoclimides |
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