New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents
RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts t...
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| Veröffentlicht in: | European journal of medicinal chemistry 2013-11, Vol.69, p.670-677 |
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| container_title | European journal of medicinal chemistry |
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| creator | Song, Doona Yang, Jee Sun Oh, Changmok Cui, Shuolin Kim, Bo-Kyung Won, Misun Lee, Jang-ik Kim, Hwan Mook Han, Gyoonhee |
| description | RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents.
[Display omitted] New aliphatic sulfonamido-quaternary ammonium salts were synthesized and evaluated for their activities. These results suggest that they are remarkably potent agents for anticancer chemotherapy through leading apoptosis.
•The novel 24 aliphatic sulfonamido-quaternary ammonium salts were synthesized.•18 compounds showed potent antitumor activities on gastric cancer cell lines.•Most of compounds induced up-regulation of the RhoB expression.•Compound 5b (propane-1,3-diamine derivative) induced the highest anticancer activity. |
| doi_str_mv | 10.1016/j.ejmech.2013.09.022 |
| format | Article |
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[Display omitted] New aliphatic sulfonamido-quaternary ammonium salts were synthesized and evaluated for their activities. These results suggest that they are remarkably potent agents for anticancer chemotherapy through leading apoptosis.
•The novel 24 aliphatic sulfonamido-quaternary ammonium salts were synthesized.•18 compounds showed potent antitumor activities on gastric cancer cell lines.•Most of compounds induced up-regulation of the RhoB expression.•Compound 5b (propane-1,3-diamine derivative) induced the highest anticancer activity.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2013.09.022</identifier><identifier>PMID: 24095759</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Aliphatic sulfonamido-quaternary ammonium salts ; Anticancer chemotherapeutic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; HeLa Cells ; Humans ; Molecular Structure ; NSC126188 ; Open-ring moiety of quaternary ammonium salts ; Perifosine ; Quaternary Ammonium Compounds - chemical synthesis ; Quaternary Ammonium Compounds - chemistry ; Quaternary Ammonium Compounds - pharmacology ; RhoB ; rhoB GTP-Binding Protein - antagonists & inhibitors ; rhoB GTP-Binding Protein - biosynthesis ; rhoB GTP-Binding Protein - metabolism ; Salts - chemical synthesis ; Salts - chemistry ; Salts - pharmacology ; Structure-Activity Relationship ; Sulfonamides - chemistry</subject><ispartof>European journal of medicinal chemistry, 2013-11, Vol.69, p.670-677</ispartof><rights>2013 Elsevier Masson SAS</rights><rights>Copyright © 2013 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-a843016e9e976629da70b6d0513ced24b72cab874bab6f1cb77e7da89445c6913</citedby><cites>FETCH-LOGICAL-c362t-a843016e9e976629da70b6d0513ced24b72cab874bab6f1cb77e7da89445c6913</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523413005953$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24095759$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Song, Doona</creatorcontrib><creatorcontrib>Yang, Jee Sun</creatorcontrib><creatorcontrib>Oh, Changmok</creatorcontrib><creatorcontrib>Cui, Shuolin</creatorcontrib><creatorcontrib>Kim, Bo-Kyung</creatorcontrib><creatorcontrib>Won, Misun</creatorcontrib><creatorcontrib>Lee, Jang-ik</creatorcontrib><creatorcontrib>Kim, Hwan Mook</creatorcontrib><creatorcontrib>Han, Gyoonhee</creatorcontrib><title>New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents.
[Display omitted] New aliphatic sulfonamido-quaternary ammonium salts were synthesized and evaluated for their activities. These results suggest that they are remarkably potent agents for anticancer chemotherapy through leading apoptosis.
•The novel 24 aliphatic sulfonamido-quaternary ammonium salts were synthesized.•18 compounds showed potent antitumor activities on gastric cancer cell lines.•Most of compounds induced up-regulation of the RhoB expression.•Compound 5b (propane-1,3-diamine derivative) induced the highest anticancer activity.</description><subject>Aliphatic sulfonamido-quaternary ammonium salts</subject><subject>Anticancer chemotherapeutic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>NSC126188</subject><subject>Open-ring moiety of quaternary ammonium salts</subject><subject>Perifosine</subject><subject>Quaternary Ammonium Compounds - chemical synthesis</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Quaternary Ammonium Compounds - pharmacology</subject><subject>RhoB</subject><subject>rhoB GTP-Binding Protein - antagonists & inhibitors</subject><subject>rhoB GTP-Binding Protein - biosynthesis</subject><subject>rhoB GTP-Binding Protein - metabolism</subject><subject>Salts - chemical synthesis</subject><subject>Salts - chemistry</subject><subject>Salts - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Sulfonamides - chemistry</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1LwzAUhoMobk7_gUgvvWlN0jRZbgQRv0D0Rq_DaXrmMpp2S1rFf2_m1EshkHB48h7eh5BTRgtGmbxYFbjyaJcFp6wsqC4o53tkypSc5yWvxD6ZpkmZV7wUE3IU44pSWklKD8mEC6orVekpsU_4kcXPblji4GwGrVsvYfuKY7voO_Cu6fPNCAOGDsJnBt73nRt9FqEdYgbpdAmHzmLI7BJ9n5ICrHH8jnvDbojH5GABbcSTn3tGXm9vXq7v88fnu4frq8fclpIPOcxFmYqhRq2k5LoBRWvZ0IqVFhsuasUt1HMlaqjlgtlaKVQNzLUQlZWalTNyvstdh34zYhyMd9Fi20KH_RgNE0JzxUUlEip2qA19jAEXZh2cTwUNo2ar16zMTq_Z6jVUm63MGTn72TDWHpu_T78-E3C5AzD1fHcYTLQOk5zGBbSDaXr3_4YvHPqPqg</recordid><startdate>20131101</startdate><enddate>20131101</enddate><creator>Song, Doona</creator><creator>Yang, Jee Sun</creator><creator>Oh, Changmok</creator><creator>Cui, Shuolin</creator><creator>Kim, Bo-Kyung</creator><creator>Won, Misun</creator><creator>Lee, Jang-ik</creator><creator>Kim, Hwan Mook</creator><creator>Han, Gyoonhee</creator><general>Elsevier Masson SAS</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></search><sort><creationdate>20131101</creationdate><title>New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents</title><author>Song, Doona ; Yang, Jee Sun ; Oh, Changmok ; Cui, Shuolin ; Kim, Bo-Kyung ; Won, Misun ; Lee, Jang-ik ; Kim, Hwan Mook ; Han, Gyoonhee</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-a843016e9e976629da70b6d0513ced24b72cab874bab6f1cb77e7da89445c6913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aliphatic sulfonamido-quaternary ammonium salts</topic><topic>Anticancer chemotherapeutic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>NSC126188</topic><topic>Open-ring moiety of quaternary ammonium salts</topic><topic>Perifosine</topic><topic>Quaternary Ammonium Compounds - chemical synthesis</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Quaternary Ammonium Compounds - pharmacology</topic><topic>RhoB</topic><topic>rhoB GTP-Binding Protein - antagonists & inhibitors</topic><topic>rhoB GTP-Binding Protein - biosynthesis</topic><topic>rhoB GTP-Binding Protein - metabolism</topic><topic>Salts - chemical synthesis</topic><topic>Salts - chemistry</topic><topic>Salts - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Sulfonamides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Doona</creatorcontrib><creatorcontrib>Yang, Jee Sun</creatorcontrib><creatorcontrib>Oh, Changmok</creatorcontrib><creatorcontrib>Cui, Shuolin</creatorcontrib><creatorcontrib>Kim, Bo-Kyung</creatorcontrib><creatorcontrib>Won, Misun</creatorcontrib><creatorcontrib>Lee, Jang-ik</creatorcontrib><creatorcontrib>Kim, Hwan Mook</creatorcontrib><creatorcontrib>Han, Gyoonhee</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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Song, Doona</au><au>Yang, Jee Sun</au><au>Oh, Changmok</au><au>Cui, Shuolin</au><au>Kim, Bo-Kyung</au><au>Won, Misun</au><au>Lee, Jang-ik</au><au>Kim, Hwan Mook</au><au>Han, Gyoonhee</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2013-11-01</date><risdate>2013</risdate><volume>69</volume><spage>670</spage><epage>677</epage><pages>670-677</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>RhoB is expressed during tumor cell proliferation, survival, invasion, and metastasis. In malignant progression, the expression levels of RhoB are commonly attenuated. RhoB is known to be linked to the regulation of the PI3K/Akt survival pathways. Based on aliphatic amido-quaternary ammonium salts that induce apoptosis via up-regulation of RhoB, we synthesized novel aliphatic sulfonamido-quaternary ammonium salts. These new synthetic compounds were evaluated for their biological activities using an in vitro RhoB promoter assay in HeLa cells, and in a growth inhibition assay using human cancer cell lines including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. Compound 5b (ethyl-dimethyl-{3-[methyl-(tetradecane-1-sulfonyl)-amino]-propyl}-ammonium; iodide) was the most promising anticancer agent in the series, based upon the potency of growth inhibition and RhoB promotion. These new aliphatic sulfonamido-quaternary ammonium salts could be a valuable series for development of new anticancer chemotherapeutic agents.
[Display omitted] New aliphatic sulfonamido-quaternary ammonium salts were synthesized and evaluated for their activities. These results suggest that they are remarkably potent agents for anticancer chemotherapy through leading apoptosis.
•The novel 24 aliphatic sulfonamido-quaternary ammonium salts were synthesized.•18 compounds showed potent antitumor activities on gastric cancer cell lines.•Most of compounds induced up-regulation of the RhoB expression.•Compound 5b (propane-1,3-diamine derivative) induced the highest anticancer activity.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>24095759</pmid><doi>10.1016/j.ejmech.2013.09.022</doi><tpages>8</tpages></addata></record> |
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| subjects | Aliphatic sulfonamido-quaternary ammonium salts Anticancer chemotherapeutic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Cell Line, Tumor Cell Proliferation - drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor HeLa Cells Humans Molecular Structure NSC126188 Open-ring moiety of quaternary ammonium salts Perifosine Quaternary Ammonium Compounds - chemical synthesis Quaternary Ammonium Compounds - chemistry Quaternary Ammonium Compounds - pharmacology RhoB rhoB GTP-Binding Protein - antagonists & inhibitors rhoB GTP-Binding Protein - biosynthesis rhoB GTP-Binding Protein - metabolism Salts - chemical synthesis Salts - chemistry Salts - pharmacology Structure-Activity Relationship Sulfonamides - chemistry |
| title | New synthetic aliphatic sulfonamido-quaternary ammonium salts as anticancer chemotherapeutic agents |
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