Synthesis and evaluation of biological activities of vibsanin A analogs
[Display omitted] Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy....
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2017-10, Vol.27 (19), p.4536-4539 |
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| container_end_page | 4539 |
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| container_issue | 19 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 27 |
| creator | Matsuki, Wataru Miyazaki, So Yoshida, Keisuke Ogura, Akihiro Sasazawa, Yukiko Takao, Ken-ichi Simizu, Siro |
| description | [Display omitted]
Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs. |
| doi_str_mv | 10.1016/j.bmcl.2017.08.059 |
| format | Article |
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Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2017.08.059</identifier><identifier>PMID: 28888819</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Acute myeloid leukemia ; Cell Differentiation - drug effects ; Cell Line, Tumor ; Differentiation ; Diterpenes - chemical synthesis ; Diterpenes - chemistry ; Diterpenes - pharmacology ; Dose-Response Relationship, Drug ; Humans ; Molecular Structure ; Myeloid Cells - drug effects ; Myeloid Cells - pathology ; Protein kinase C ; Protein Kinase C - metabolism ; Structure-Activity Relationship ; Vibsanin A</subject><ispartof>Bioorganic & medicinal chemistry letters, 2017-10, Vol.27 (19), p.4536-4539</ispartof><rights>2017 Elsevier Ltd</rights><rights>Copyright © 2017 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c422t-3c121a447e149625d39b960b6243c2bc2ad3c111c03cbd5fa69e4c6b5631c1983</citedby><cites>FETCH-LOGICAL-c422t-3c121a447e149625d39b960b6243c2bc2ad3c111c03cbd5fa69e4c6b5631c1983</cites><orcidid>0000-0002-4793-5706</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X1730865X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28888819$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matsuki, Wataru</creatorcontrib><creatorcontrib>Miyazaki, So</creatorcontrib><creatorcontrib>Yoshida, Keisuke</creatorcontrib><creatorcontrib>Ogura, Akihiro</creatorcontrib><creatorcontrib>Sasazawa, Yukiko</creatorcontrib><creatorcontrib>Takao, Ken-ichi</creatorcontrib><creatorcontrib>Simizu, Siro</creatorcontrib><title>Synthesis and evaluation of biological activities of vibsanin A analogs</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.</description><subject>Acute myeloid leukemia</subject><subject>Cell Differentiation - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Differentiation</subject><subject>Diterpenes - chemical synthesis</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Myeloid Cells - drug effects</subject><subject>Myeloid Cells - pathology</subject><subject>Protein kinase C</subject><subject>Protein Kinase C - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Vibsanin A</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEFLwzAYhoMobk7_gAfp0UtrkqZpA17G0CkMPKjgLSTpV81om9m0hf17UzY9mst3yPO-fN-D0DXBCcGE320T3Zg6oZjkCS4SnIkTNCeMszhlODtFcyw4jgvBPmbowvstxoRhxs7RjBbTI2KO1q_7tv8Cb32k2jKCUdWD6q1rI1dF2rrafVqj6kiZ3o62t-Cnj9Fqr1rbRsuQUoHxl-isUrWHq-NcoPfHh7fVU7x5WT-vlpvYMEr7ODWEEsVYDoQJTrMyFTosqTllqaHaUFUGhBCDU6PLrFJcADNcZzwlhogiXaDbQ--uc98D-F421huoa9WCG7wkIs3zjHPBAkoPqOmc9x1UctfZRnV7SbCcBMqtnATKSaDEhQwCQ-jm2D_oBsq_yK-xANwfAAhXjhY66Y2F1kBpOzC9LJ39r_8HNOGBSQ</recordid><startdate>20171001</startdate><enddate>20171001</enddate><creator>Matsuki, Wataru</creator><creator>Miyazaki, So</creator><creator>Yoshida, Keisuke</creator><creator>Ogura, Akihiro</creator><creator>Sasazawa, Yukiko</creator><creator>Takao, Ken-ichi</creator><creator>Simizu, Siro</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><orcidid>https://orcid.org/0000-0002-4793-5706</orcidid></search><sort><creationdate>20171001</creationdate><title>Synthesis and evaluation of biological activities of vibsanin A analogs</title><author>Matsuki, Wataru ; Miyazaki, So ; Yoshida, Keisuke ; Ogura, Akihiro ; Sasazawa, Yukiko ; Takao, Ken-ichi ; Simizu, Siro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c422t-3c121a447e149625d39b960b6243c2bc2ad3c111c03cbd5fa69e4c6b5631c1983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acute myeloid leukemia</topic><topic>Cell Differentiation - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Differentiation</topic><topic>Diterpenes - chemical synthesis</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Myeloid Cells - drug effects</topic><topic>Myeloid Cells - pathology</topic><topic>Protein kinase C</topic><topic>Protein Kinase C - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Vibsanin A</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsuki, Wataru</creatorcontrib><creatorcontrib>Miyazaki, So</creatorcontrib><creatorcontrib>Yoshida, Keisuke</creatorcontrib><creatorcontrib>Ogura, Akihiro</creatorcontrib><creatorcontrib>Sasazawa, Yukiko</creatorcontrib><creatorcontrib>Takao, Ken-ichi</creatorcontrib><creatorcontrib>Simizu, Siro</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><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsuki, Wataru</au><au>Miyazaki, So</au><au>Yoshida, Keisuke</au><au>Ogura, Akihiro</au><au>Sasazawa, Yukiko</au><au>Takao, Ken-ichi</au><au>Simizu, Siro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of biological activities of vibsanin A analogs</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2017-10-01</date><risdate>2017</risdate><volume>27</volume><issue>19</issue><spage>4536</spage><epage>4539</epage><pages>4536-4539</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
Vibsanin A is an 11-membered vibsane diterpenoid and is reported to induce myeloid cell differentiation via activation of protein kinase C (PKC) without tumor-promoting activity. Therefore, vibsanin A is thought to be an attractive compound for acute myeloid leukemia (AML) therapy. In this study, we synthesized vibsanin A analogs and compared the activity of these compounds for PKC activation and myeloid cell differentiation. We found that the hydroxymethyl group in vibsanin A is an important substituent to induce differentiation of AML cells. Collectively, our results showed the biochemical features of vibsanin A and provided new insights into the development of new antileukemic drugs.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>28888819</pmid><doi>10.1016/j.bmcl.2017.08.059</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4793-5706</orcidid></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2017-10, Vol.27 (19), p.4536-4539 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Acute myeloid leukemia Cell Differentiation - drug effects Cell Line, Tumor Differentiation Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Dose-Response Relationship, Drug Humans Molecular Structure Myeloid Cells - drug effects Myeloid Cells - pathology Protein kinase C Protein Kinase C - metabolism Structure-Activity Relationship Vibsanin A |
| title | Synthesis and evaluation of biological activities of vibsanin A analogs |
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