Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway
The spread of cancer cells to distant organs, in a process called metastasis, is the main factor that contributes to most death in cancer patients. Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the fo...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2017-03, Vol.65 (11), p.2299-2306 |
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| creator | Jantaree, Phatcharida Lirdprapamongkol, Kriengsak Kaewsri, Wilailak Thongsornkleeb, Charnsak Choowongkomon, Kiattawee Atjanasuppat, Korakot Ruchirawat, Somsak Svasti, Jisnuson |
| description | The spread of cancer cells to distant organs, in a process called metastasis, is the main factor that contributes to most death in cancer patients. Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the food additive divanillin, the homodimer of vanillin, and their structurally related compounds, apocynin and diapocynin, in hepatocellular carcinoma cells. The Transwell invasion assay showed that the dimeric forms exhibited a potency higher than those of vanillin and apocynin in inhibiting invasion, with IC50 values of 23.3 ± 7.4 to 41.3 ± 4.2 μM for the dimers, which are 26–34-fold lower than IC50 values of vanillin and apocynin (p < 0.05). Both monomeric and dimeric forms target regulation of the invasion process by inhibiting phosphorylation of FAK and Akt. Molecular docking studies suggested that the dimers should bind more tightly than vanillin and apocynin to the Y397 pocket of the FAK FERM domain. Thus, the food additive divanillin has antimetastatic potential greater than that of the flavoring agent vanillin. |
| doi_str_mv | 10.1021/acs.jafc.6b05697 |
| format | Article |
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Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the food additive divanillin, the homodimer of vanillin, and their structurally related compounds, apocynin and diapocynin, in hepatocellular carcinoma cells. The Transwell invasion assay showed that the dimeric forms exhibited a potency higher than those of vanillin and apocynin in inhibiting invasion, with IC50 values of 23.3 ± 7.4 to 41.3 ± 4.2 μM for the dimers, which are 26–34-fold lower than IC50 values of vanillin and apocynin (p < 0.05). Both monomeric and dimeric forms target regulation of the invasion process by inhibiting phosphorylation of FAK and Akt. Molecular docking studies suggested that the dimers should bind more tightly than vanillin and apocynin to the Y397 pocket of the FAK FERM domain. Thus, the food additive divanillin has antimetastatic potential greater than that of the flavoring agent vanillin.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.6b05697</identifier><identifier>PMID: 28248106</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Acetophenones - chemistry ; Acetophenones - pharmacology ; Benzaldehydes - chemistry ; Benzaldehydes - pharmacology ; Cell Line, Tumor ; Cell Movement - drug effects ; Dimerization ; Focal Adhesion Protein-Tyrosine Kinases - metabolism ; Humans ; Molecular Docking Simulation ; Neoplasm Metastasis - physiopathology ; Neoplasm Metastasis - prevention & control ; Neoplasms - drug therapy ; Neoplasms - metabolism ; Neoplasms - pathology ; Neoplasms - physiopathology ; Phosphatidylinositol 3-Kinases - metabolism ; Proto-Oncogene Proteins c-akt - metabolism ; Signal Transduction - drug effects</subject><ispartof>Journal of agricultural and food chemistry, 2017-03, Vol.65 (11), p.2299-2306</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a317t-e42fa4aea1f671b7e2c42eee02becd9fe245ef0222e35f8c15b1a282166cba533</citedby><cites>FETCH-LOGICAL-a317t-e42fa4aea1f671b7e2c42eee02becd9fe245ef0222e35f8c15b1a282166cba533</cites><orcidid>0000-0002-2217-4517 ; 0000-0001-5858-5433</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jafc.6b05697$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jafc.6b05697$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28248106$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jantaree, Phatcharida</creatorcontrib><creatorcontrib>Lirdprapamongkol, Kriengsak</creatorcontrib><creatorcontrib>Kaewsri, Wilailak</creatorcontrib><creatorcontrib>Thongsornkleeb, Charnsak</creatorcontrib><creatorcontrib>Choowongkomon, Kiattawee</creatorcontrib><creatorcontrib>Atjanasuppat, Korakot</creatorcontrib><creatorcontrib>Ruchirawat, Somsak</creatorcontrib><creatorcontrib>Svasti, Jisnuson</creatorcontrib><title>Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The spread of cancer cells to distant organs, in a process called metastasis, is the main factor that contributes to most death in cancer patients. Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the food additive divanillin, the homodimer of vanillin, and their structurally related compounds, apocynin and diapocynin, in hepatocellular carcinoma cells. The Transwell invasion assay showed that the dimeric forms exhibited a potency higher than those of vanillin and apocynin in inhibiting invasion, with IC50 values of 23.3 ± 7.4 to 41.3 ± 4.2 μM for the dimers, which are 26–34-fold lower than IC50 values of vanillin and apocynin (p < 0.05). Both monomeric and dimeric forms target regulation of the invasion process by inhibiting phosphorylation of FAK and Akt. Molecular docking studies suggested that the dimers should bind more tightly than vanillin and apocynin to the Y397 pocket of the FAK FERM domain. Thus, the food additive divanillin has antimetastatic potential greater than that of the flavoring agent vanillin.</description><subject>Acetophenones - chemistry</subject><subject>Acetophenones - pharmacology</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzaldehydes - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Movement - drug effects</subject><subject>Dimerization</subject><subject>Focal Adhesion Protein-Tyrosine Kinases - metabolism</subject><subject>Humans</subject><subject>Molecular Docking Simulation</subject><subject>Neoplasm Metastasis - physiopathology</subject><subject>Neoplasm Metastasis - prevention & control</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - metabolism</subject><subject>Neoplasms - pathology</subject><subject>Neoplasms - physiopathology</subject><subject>Phosphatidylinositol 3-Kinases - metabolism</subject><subject>Proto-Oncogene Proteins c-akt - metabolism</subject><subject>Signal Transduction - drug effects</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kE1PwkAQhjdGI4jePZn9ARZ2t922HAmKEDCS-HFtpsssLLZb0l1i-A_-aMuH3jxNJvM-bzIPIbecdTkTvAfKddegVTfOmYz7yRlpcylYIDlPz0mbNZkglTFvkSvn1oyxVCbskrREKqKUs7hNvsdVWS1MibWjlaYfYE1RGEvBLuhgU6mdbZYHVDWCQ-pXSJ_Rg_PgjaLzyqP1Boo9Ot6WYOkQrMKaDrEoHM13dGJXJjfe2OUBHg2mvfkknPYGn56-mqWFYn-ag199we6aXGgoHN6cZoe8jx7fhuNg9vI0GQ5mAYQ88QFGQkMECFzHCc8TFCoSiMhEjmrR1ygiiZoJITCUOlVc5hyal3kcqxxkGHYIO_aqunKuRp1talNCvcs4y_Zis0ZsthebncQ2yN0R2WzzEhd_wK_JJnB_DBzQals3r7n_-34APE6GGA</recordid><startdate>20170322</startdate><enddate>20170322</enddate><creator>Jantaree, Phatcharida</creator><creator>Lirdprapamongkol, Kriengsak</creator><creator>Kaewsri, Wilailak</creator><creator>Thongsornkleeb, Charnsak</creator><creator>Choowongkomon, Kiattawee</creator><creator>Atjanasuppat, Korakot</creator><creator>Ruchirawat, Somsak</creator><creator>Svasti, Jisnuson</creator><general>American Chemical Society</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><orcidid>https://orcid.org/0000-0002-2217-4517</orcidid><orcidid>https://orcid.org/0000-0001-5858-5433</orcidid></search><sort><creationdate>20170322</creationdate><title>Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway</title><author>Jantaree, Phatcharida ; Lirdprapamongkol, Kriengsak ; Kaewsri, Wilailak ; Thongsornkleeb, Charnsak ; Choowongkomon, Kiattawee ; Atjanasuppat, Korakot ; Ruchirawat, Somsak ; Svasti, Jisnuson</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a317t-e42fa4aea1f671b7e2c42eee02becd9fe245ef0222e35f8c15b1a282166cba533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acetophenones - chemistry</topic><topic>Acetophenones - pharmacology</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzaldehydes - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Movement - drug effects</topic><topic>Dimerization</topic><topic>Focal Adhesion Protein-Tyrosine Kinases - metabolism</topic><topic>Humans</topic><topic>Molecular Docking Simulation</topic><topic>Neoplasm Metastasis - physiopathology</topic><topic>Neoplasm Metastasis - prevention & control</topic><topic>Neoplasms - drug therapy</topic><topic>Neoplasms - metabolism</topic><topic>Neoplasms - pathology</topic><topic>Neoplasms - physiopathology</topic><topic>Phosphatidylinositol 3-Kinases - metabolism</topic><topic>Proto-Oncogene Proteins c-akt - metabolism</topic><topic>Signal Transduction - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jantaree, Phatcharida</creatorcontrib><creatorcontrib>Lirdprapamongkol, Kriengsak</creatorcontrib><creatorcontrib>Kaewsri, Wilailak</creatorcontrib><creatorcontrib>Thongsornkleeb, Charnsak</creatorcontrib><creatorcontrib>Choowongkomon, Kiattawee</creatorcontrib><creatorcontrib>Atjanasuppat, Korakot</creatorcontrib><creatorcontrib>Ruchirawat, Somsak</creatorcontrib><creatorcontrib>Svasti, Jisnuson</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jantaree, Phatcharida</au><au>Lirdprapamongkol, Kriengsak</au><au>Kaewsri, Wilailak</au><au>Thongsornkleeb, Charnsak</au><au>Choowongkomon, Kiattawee</au><au>Atjanasuppat, Korakot</au><au>Ruchirawat, Somsak</au><au>Svasti, Jisnuson</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2017-03-22</date><risdate>2017</risdate><volume>65</volume><issue>11</issue><spage>2299</spage><epage>2306</epage><pages>2299-2306</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>The spread of cancer cells to distant organs, in a process called metastasis, is the main factor that contributes to most death in cancer patients. Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the food additive divanillin, the homodimer of vanillin, and their structurally related compounds, apocynin and diapocynin, in hepatocellular carcinoma cells. The Transwell invasion assay showed that the dimeric forms exhibited a potency higher than those of vanillin and apocynin in inhibiting invasion, with IC50 values of 23.3 ± 7.4 to 41.3 ± 4.2 μM for the dimers, which are 26–34-fold lower than IC50 values of vanillin and apocynin (p < 0.05). Both monomeric and dimeric forms target regulation of the invasion process by inhibiting phosphorylation of FAK and Akt. Molecular docking studies suggested that the dimers should bind more tightly than vanillin and apocynin to the Y397 pocket of the FAK FERM domain. Thus, the food additive divanillin has antimetastatic potential greater than that of the flavoring agent vanillin.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28248106</pmid><doi>10.1021/acs.jafc.6b05697</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-2217-4517</orcidid><orcidid>https://orcid.org/0000-0001-5858-5433</orcidid></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2017-03, Vol.65 (11), p.2299-2306 |
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| language | eng |
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| subjects | Acetophenones - chemistry Acetophenones - pharmacology Benzaldehydes - chemistry Benzaldehydes - pharmacology Cell Line, Tumor Cell Movement - drug effects Dimerization Focal Adhesion Protein-Tyrosine Kinases - metabolism Humans Molecular Docking Simulation Neoplasm Metastasis - physiopathology Neoplasm Metastasis - prevention & control Neoplasms - drug therapy Neoplasms - metabolism Neoplasms - pathology Neoplasms - physiopathology Phosphatidylinositol 3-Kinases - metabolism Proto-Oncogene Proteins c-akt - metabolism Signal Transduction - drug effects |
| title | Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway |
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