γ-Lactone-functionalized antitumoral acetogenins are the most potent inhibitors of Mitochondrial Complex I
To study the relevance of the terminal α,β-unsaturated γ-methyl-γ-lactone moiety of the antitumoral acetogenins of Annonaceae for potent mitochondrial complex I inhibition, we have prepared a series of semisynthetic acetogenins with modifications only in this part of the molecule, from the natural r...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2001-03, Vol.11 (5), p.681-684 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Tormo, José R Estornell, Ernesto Gallardo, Teresa González, M.Carmen Cavé, Adrien Granell, Susana Cortes, Diego Zafra-Polo, M.Carmen |
| description | To study the relevance of the terminal α,β-unsaturated γ-methyl-γ-lactone moiety of the antitumoral acetogenins of Annonaceae for potent mitochondrial complex I inhibition, we have prepared a series of semisynthetic acetogenins with modifications only in this part of the molecule, from the natural rolliniastatin-1 (
1) and cherimolin-1 (
2). Some of the hydroxylated derivatives (
1b, 1d and
1e) in addition to two infrequent natural β-hydroxy γ-methyl γ-lactone acetogenins, laherradurin (
3) and itrabin (
4), are more potent complex I inhibitors than any other known compounds.
Graphic |
| doi_str_mv | 10.1016/S0960-894X(01)00036-1 |
| format | Article |
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1) and cherimolin-1 (
2). Some of the hydroxylated derivatives (
1b, 1d and
1e) in addition to two infrequent natural β-hydroxy γ-methyl γ-lactone acetogenins, laherradurin (
3) and itrabin (
4), are more potent complex I inhibitors than any other known compounds.
Graphic</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(01)00036-1</identifier><identifier>PMID: 11266168</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cattle ; Electron Transport Complex I ; Furans - chemical synthesis ; Furans - chemistry ; Furans - pharmacology ; General aspects ; Lactones - chemical synthesis ; Lactones - chemistry ; Lactones - pharmacology ; Magnoliopsida - chemistry ; Medical sciences ; Mitochondria, Heart - drug effects ; Mitochondria, Heart - enzymology ; Molecular Structure ; Multienzyme Complexes - antagonists & inhibitors ; Multienzyme Complexes - metabolism ; NADH, NADPH Oxidoreductases - antagonists & inhibitors ; NADH, NADPH Oxidoreductases - metabolism ; Pharmacology. Drug treatments ; Submitochondrial Particles - drug effects ; Submitochondrial Particles - enzymology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2001-03, Vol.11 (5), p.681-684</ispartof><rights>2001 Elsevier Science Ltd</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-4ebe5161b0f19a5723175abc19b920db5083eabcd7f03036c12c60d628922f103</citedby><cites>FETCH-LOGICAL-c389t-4ebe5161b0f19a5723175abc19b920db5083eabcd7f03036c12c60d628922f103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X01000361$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=903540$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11266168$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tormo, José R</creatorcontrib><creatorcontrib>Estornell, Ernesto</creatorcontrib><creatorcontrib>Gallardo, Teresa</creatorcontrib><creatorcontrib>González, M.Carmen</creatorcontrib><creatorcontrib>Cavé, Adrien</creatorcontrib><creatorcontrib>Granell, Susana</creatorcontrib><creatorcontrib>Cortes, Diego</creatorcontrib><creatorcontrib>Zafra-Polo, M.Carmen</creatorcontrib><title>γ-Lactone-functionalized antitumoral acetogenins are the most potent inhibitors of Mitochondrial Complex I</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>To study the relevance of the terminal α,β-unsaturated γ-methyl-γ-lactone moiety of the antitumoral acetogenins of Annonaceae for potent mitochondrial complex I inhibition, we have prepared a series of semisynthetic acetogenins with modifications only in this part of the molecule, from the natural rolliniastatin-1 (
1) and cherimolin-1 (
2). Some of the hydroxylated derivatives (
1b, 1d and
1e) in addition to two infrequent natural β-hydroxy γ-methyl γ-lactone acetogenins, laherradurin (
3) and itrabin (
4), are more potent complex I inhibitors than any other known compounds.
Graphic</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cattle</subject><subject>Electron Transport Complex I</subject><subject>Furans - chemical synthesis</subject><subject>Furans - chemistry</subject><subject>Furans - pharmacology</subject><subject>General aspects</subject><subject>Lactones - chemical synthesis</subject><subject>Lactones - chemistry</subject><subject>Lactones - pharmacology</subject><subject>Magnoliopsida - chemistry</subject><subject>Medical sciences</subject><subject>Mitochondria, Heart - drug effects</subject><subject>Mitochondria, Heart - enzymology</subject><subject>Molecular Structure</subject><subject>Multienzyme Complexes - antagonists & inhibitors</subject><subject>Multienzyme Complexes - metabolism</subject><subject>NADH, NADPH Oxidoreductases - antagonists & inhibitors</subject><subject>NADH, NADPH Oxidoreductases - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Submitochondrial Particles - drug effects</subject><subject>Submitochondrial Particles - enzymology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1u1DAURi1ERaeFRwBZQkJlkXJv4jjxCqERP5UGsQAkdpbj3DCGxB5sB5W-Fu_BM5HpjMqS1fWVzmd_Pow9RrhEQPniIygJRavElwvA5wBQyQLvsRUKKYpKQH2fre6QU3aW0jcAFCDEA3aKWEqJsl2x739-Fxtjc_BUDLO32QVvRndDPTc-uzxPIZqRG0s5fCXvfOImEs9b4lNIme9CJp-581vXuRxi4mHg75eT3QbfR7dk12HajXTNrx6yk8GMiR4d5zn7_Ob1p_W7YvPh7dX61aawVatyIaijGiV2MKAydVNW2NSms6g6VULf1dBWtOx9M0C1fNtiaSX0smxVWQ4I1Tl7drh3F8OPmVLWk0uWxtF4CnPSjVSqrESzgPUBtDGkFGnQu-gmE39pBL23rG8t671CDahvLWtcck-OD8zdRP2_1FHrAjw9AiZZMw7ReOvSHaegqsW-58sDRYuMn46iTtaRt9S7SDbrPrj_FPkLW8CbQQ</recordid><startdate>20010312</startdate><enddate>20010312</enddate><creator>Tormo, José R</creator><creator>Estornell, Ernesto</creator><creator>Gallardo, Teresa</creator><creator>González, M.Carmen</creator><creator>Cavé, Adrien</creator><creator>Granell, Susana</creator><creator>Cortes, Diego</creator><creator>Zafra-Polo, M.Carmen</creator><general>Elsevier Ltd</general><general>Elsevier</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>20010312</creationdate><title>γ-Lactone-functionalized antitumoral acetogenins are the most potent inhibitors of Mitochondrial Complex I</title><author>Tormo, José R ; Estornell, Ernesto ; Gallardo, Teresa ; González, M.Carmen ; Cavé, Adrien ; Granell, Susana ; Cortes, Diego ; Zafra-Polo, M.Carmen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-4ebe5161b0f19a5723175abc19b920db5083eabcd7f03036c12c60d628922f103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cattle</topic><topic>Electron Transport Complex I</topic><topic>Furans - chemical synthesis</topic><topic>Furans - chemistry</topic><topic>Furans - pharmacology</topic><topic>General aspects</topic><topic>Lactones - chemical synthesis</topic><topic>Lactones - chemistry</topic><topic>Lactones - pharmacology</topic><topic>Magnoliopsida - chemistry</topic><topic>Medical sciences</topic><topic>Mitochondria, Heart - drug effects</topic><topic>Mitochondria, Heart - enzymology</topic><topic>Molecular Structure</topic><topic>Multienzyme Complexes - antagonists & inhibitors</topic><topic>Multienzyme Complexes - metabolism</topic><topic>NADH, NADPH Oxidoreductases - antagonists & inhibitors</topic><topic>NADH, NADPH Oxidoreductases - metabolism</topic><topic>Pharmacology. 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1) and cherimolin-1 (
2). Some of the hydroxylated derivatives (
1b, 1d and
1e) in addition to two infrequent natural β-hydroxy γ-methyl γ-lactone acetogenins, laherradurin (
3) and itrabin (
4), are more potent complex I inhibitors than any other known compounds.
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| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cattle Electron Transport Complex I Furans - chemical synthesis Furans - chemistry Furans - pharmacology General aspects Lactones - chemical synthesis Lactones - chemistry Lactones - pharmacology Magnoliopsida - chemistry Medical sciences Mitochondria, Heart - drug effects Mitochondria, Heart - enzymology Molecular Structure Multienzyme Complexes - antagonists & inhibitors Multienzyme Complexes - metabolism NADH, NADPH Oxidoreductases - antagonists & inhibitors NADH, NADPH Oxidoreductases - metabolism Pharmacology. Drug treatments Submitochondrial Particles - drug effects Submitochondrial Particles - enzymology |
| title | γ-Lactone-functionalized antitumoral acetogenins are the most potent inhibitors of Mitochondrial Complex I |
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