Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells
[Display omitted] In a search of small molecules active against apoptosis-resistant cancer cells, a skeletal rearrangement of alkaloid haemanthamine was utilized to generate a series of compounds possessing the alkaloid montanine ring system. The synthesized compounds were found to inhibit prolifera...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2018-02, Vol.28 (4), p.589-593 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 28 |
| creator | Govindaraju, Karthik Ingels, Aude Hasan, Md Nabiul Sun, Dandan Mathieu, Veronique Masi, Marco Evidente, Antonio Kornienko, Alexander |
| description | [Display omitted]
In a search of small molecules active against apoptosis-resistant cancer cells, a skeletal rearrangement of alkaloid haemanthamine was utilized to generate a series of compounds possessing the alkaloid montanine ring system. The synthesized compounds were found to inhibit proliferation of cancer cells resistant to apoptosis at micromolar concentrations. Selected compounds were also active against patient-derived glioblastoma cells expressing stem-cell markers. This is the first report describing the preparation of synthetic analogues of the montanine-type alkaloids with antiproliferative activity. The compounds prepared in the current investigation appear to be a useful starting point for the development of agents to fight cancers with apoptosis resistance, and thus, associated with poor prognoses. |
| doi_str_mv | 10.1016/j.bmcl.2018.01.041 |
| format | Article |
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In a search of small molecules active against apoptosis-resistant cancer cells, a skeletal rearrangement of alkaloid haemanthamine was utilized to generate a series of compounds possessing the alkaloid montanine ring system. The synthesized compounds were found to inhibit proliferation of cancer cells resistant to apoptosis at micromolar concentrations. Selected compounds were also active against patient-derived glioblastoma cells expressing stem-cell markers. This is the first report describing the preparation of synthetic analogues of the montanine-type alkaloids with antiproliferative activity. The compounds prepared in the current investigation appear to be a useful starting point for the development of agents to fight cancers with apoptosis resistance, and thus, associated with poor prognoses.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2018.01.041</identifier><identifier>PMID: 29409754</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amaryllidaceae Alkaloids - chemical synthesis ; Amaryllidaceae Alkaloids - chemistry ; Amaryllidaceae Alkaloids - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiproliferative activity ; Apoptosis - drug effects ; Apoptosis resistance ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Drug Screening Assays, Antitumor ; Haemanthamine ; Humans ; Isoquinolines - chemical synthesis ; Isoquinolines - chemistry ; Isoquinolines - pharmacology ; Manthine ; Molecular Structure ; Montanine ; Phenanthridines - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-02, Vol.28 (4), p.589-593</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c455t-f43682269fdcd44eabc17f65a57e80b0291cf98ace58a20bbb4441f851daa6173</citedby><cites>FETCH-LOGICAL-c455t-f43682269fdcd44eabc17f65a57e80b0291cf98ace58a20bbb4441f851daa6173</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2018.01.041$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29409754$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Govindaraju, Karthik</creatorcontrib><creatorcontrib>Ingels, Aude</creatorcontrib><creatorcontrib>Hasan, Md Nabiul</creatorcontrib><creatorcontrib>Sun, Dandan</creatorcontrib><creatorcontrib>Mathieu, Veronique</creatorcontrib><creatorcontrib>Masi, Marco</creatorcontrib><creatorcontrib>Evidente, Antonio</creatorcontrib><creatorcontrib>Kornienko, Alexander</creatorcontrib><title>Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
In a search of small molecules active against apoptosis-resistant cancer cells, a skeletal rearrangement of alkaloid haemanthamine was utilized to generate a series of compounds possessing the alkaloid montanine ring system. The synthesized compounds were found to inhibit proliferation of cancer cells resistant to apoptosis at micromolar concentrations. Selected compounds were also active against patient-derived glioblastoma cells expressing stem-cell markers. This is the first report describing the preparation of synthetic analogues of the montanine-type alkaloids with antiproliferative activity. The compounds prepared in the current investigation appear to be a useful starting point for the development of agents to fight cancers with apoptosis resistance, and thus, associated with poor prognoses.</description><subject>Amaryllidaceae Alkaloids - chemical synthesis</subject><subject>Amaryllidaceae Alkaloids - chemistry</subject><subject>Amaryllidaceae Alkaloids - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiproliferative activity</subject><subject>Apoptosis - drug effects</subject><subject>Apoptosis resistance</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Haemanthamine</subject><subject>Humans</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - chemistry</subject><subject>Isoquinolines - pharmacology</subject><subject>Manthine</subject><subject>Molecular Structure</subject><subject>Montanine</subject><subject>Phenanthridines - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUuLFDEUhYMoTjv6B1xIlm6qTKpvPQIiyOALBlyo4C7cSt3qTluVlEm6pf-9KXocdOMiCSTfOUnOYey5FKUUsnl1KPvZTGUlZFcKWQqQD9hGQgPFFkT9kG2EakTRKfh-xZ7EeBBCggB4zK4qBUK1NWzY4cvZpT0lazg6nPzuSJH7kec9PnuX0FlHRTovxHH6kQE7RP7Lpj1Hk-zJpjPHHVoXE8fFL8lHG4tAec7SxA06Q4Ebmqb4lD0acYr07G69Zt_ev_t687G4_fzh083b28JAXadihG3TVVWjxsEMAIS9ke3Y1Fi31IleVEqaUXVoqO6wEn3fA4Acu1oOiI1st9fszcV3OfYzDYZcCjjpJdgZw1l7tPrfE2f3eudPuu62sq1Wg5d3BsH_zHkkPdu4fgEd-WPUUimVB8CKVhfUBB9joPH-Gin0WpI-6LUkvZakhdS5pCx68fcD7yV_WsnA6wtAOaaTpaCjsZSTHGwgk_Tg7f_8fwPKT6dr</recordid><startdate>20180215</startdate><enddate>20180215</enddate><creator>Govindaraju, Karthik</creator><creator>Ingels, Aude</creator><creator>Hasan, Md Nabiul</creator><creator>Sun, Dandan</creator><creator>Mathieu, Veronique</creator><creator>Masi, Marco</creator><creator>Evidente, Antonio</creator><creator>Kornienko, Alexander</creator><general>Elsevier Ltd</general><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><scope>5PM</scope></search><sort><creationdate>20180215</creationdate><title>Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells</title><author>Govindaraju, Karthik ; Ingels, Aude ; Hasan, Md Nabiul ; Sun, Dandan ; Mathieu, Veronique ; Masi, Marco ; Evidente, Antonio ; Kornienko, Alexander</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c455t-f43682269fdcd44eabc17f65a57e80b0291cf98ace58a20bbb4441f851daa6173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Amaryllidaceae Alkaloids - chemical synthesis</topic><topic>Amaryllidaceae Alkaloids - chemistry</topic><topic>Amaryllidaceae Alkaloids - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiproliferative activity</topic><topic>Apoptosis - drug effects</topic><topic>Apoptosis resistance</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Haemanthamine</topic><topic>Humans</topic><topic>Isoquinolines - chemical synthesis</topic><topic>Isoquinolines - chemistry</topic><topic>Isoquinolines - pharmacology</topic><topic>Manthine</topic><topic>Molecular Structure</topic><topic>Montanine</topic><topic>Phenanthridines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Govindaraju, Karthik</creatorcontrib><creatorcontrib>Ingels, Aude</creatorcontrib><creatorcontrib>Hasan, Md Nabiul</creatorcontrib><creatorcontrib>Sun, Dandan</creatorcontrib><creatorcontrib>Mathieu, Veronique</creatorcontrib><creatorcontrib>Masi, Marco</creatorcontrib><creatorcontrib>Evidente, Antonio</creatorcontrib><creatorcontrib>Kornienko, Alexander</creatorcontrib><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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Govindaraju, Karthik</au><au>Ingels, Aude</au><au>Hasan, Md Nabiul</au><au>Sun, Dandan</au><au>Mathieu, Veronique</au><au>Masi, Marco</au><au>Evidente, Antonio</au><au>Kornienko, Alexander</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-02-15</date><risdate>2018</risdate><volume>28</volume><issue>4</issue><spage>589</spage><epage>593</epage><pages>589-593</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
In a search of small molecules active against apoptosis-resistant cancer cells, a skeletal rearrangement of alkaloid haemanthamine was utilized to generate a series of compounds possessing the alkaloid montanine ring system. The synthesized compounds were found to inhibit proliferation of cancer cells resistant to apoptosis at micromolar concentrations. Selected compounds were also active against patient-derived glioblastoma cells expressing stem-cell markers. This is the first report describing the preparation of synthetic analogues of the montanine-type alkaloids with antiproliferative activity. The compounds prepared in the current investigation appear to be a useful starting point for the development of agents to fight cancers with apoptosis resistance, and thus, associated with poor prognoses.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29409754</pmid><doi>10.1016/j.bmcl.2018.01.041</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Amaryllidaceae Alkaloids - chemical synthesis Amaryllidaceae Alkaloids - chemistry Amaryllidaceae Alkaloids - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiproliferative activity Apoptosis - drug effects Apoptosis resistance Cell Line, Tumor Cell Proliferation - drug effects Drug Screening Assays, Antitumor Haemanthamine Humans Isoquinolines - chemical synthesis Isoquinolines - chemistry Isoquinolines - pharmacology Manthine Molecular Structure Montanine Phenanthridines - chemistry |
| title | Synthetic analogues of the montanine-type alkaloids with activity against apoptosis-resistant cancer cells |
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