Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents
[Display omitted] •Series of bile acid aryl/heteroaryl amides linked via α-amino acid were synthesized.•Cytotoxic behavior against HT29, MDAMB231, U87MG were tested.•Three conjugates showed good in vitro activity (GI50=1.35, 1.41, 4.52μM) against MDAMB231.•Another three conjugates showed good in vit...
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| Veröffentlicht in: | Steroids 2016-03, Vol.107, p.87-97 |
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| creator | Agarwal, Devesh S. Anantaraju, Hasitha Shilpa Sriram, Dharmarajan Yogeeswari, Perumal Nanjegowda, Shankara H. Mallu, P. Sakhuja, Rajeev |
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•Series of bile acid aryl/heteroaryl amides linked via α-amino acid were synthesized.•Cytotoxic behavior against HT29, MDAMB231, U87MG were tested.•Three conjugates showed good in vitro activity (GI50=1.35, 1.41, 4.52μM) against MDAMB231.•Another three conjugates showed good in vitro activity (GI50=2.49, 2.46, 1.62μM) against U87MG.•Greater than 65% of the synthesized compounds were found to be safer on human normal cell line (HEK293T).
A series of bile acid (Cholic acid and Deoxycholic acid) aryl/heteroaryl amides linked via α-amino acid were synthesized and tested against 3 human cancer cell-lines (HT29, MDAMB231, U87MG) and 1 human normal cell line (HEK293T). Some of the conjugates showed promising results to be new anticancer agents with good in vitro results. More specifically, Cholic acid derivatives 6a (1.35μM), 6c (1.41μM) and 6m (4.52μM) possessing phenyl, benzothiazole and 4-methylphenyl groups showed fairly good activity against the breast cancer cell line with respect to Cisplatin (7.21μM) and comparable with respect to Doxorubicin (1μM), while 6e (2.49μM), 6i (2.46μM) and 6m (1.62μM) showed better activity against glioblastoma cancer cell line with respect to both Cisplatin (2.60μM) and Doxorubicin (3.78μM) drugs used as standards. Greater than 65% of the compounds were found to be safer on human normal cell line. |
| doi_str_mv | 10.1016/j.steroids.2015.12.022 |
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•Series of bile acid aryl/heteroaryl amides linked via α-amino acid were synthesized.•Cytotoxic behavior against HT29, MDAMB231, U87MG were tested.•Three conjugates showed good in vitro activity (GI50=1.35, 1.41, 4.52μM) against MDAMB231.•Another three conjugates showed good in vitro activity (GI50=2.49, 2.46, 1.62μM) against U87MG.•Greater than 65% of the synthesized compounds were found to be safer on human normal cell line (HEK293T).
A series of bile acid (Cholic acid and Deoxycholic acid) aryl/heteroaryl amides linked via α-amino acid were synthesized and tested against 3 human cancer cell-lines (HT29, MDAMB231, U87MG) and 1 human normal cell line (HEK293T). Some of the conjugates showed promising results to be new anticancer agents with good in vitro results. More specifically, Cholic acid derivatives 6a (1.35μM), 6c (1.41μM) and 6m (4.52μM) possessing phenyl, benzothiazole and 4-methylphenyl groups showed fairly good activity against the breast cancer cell line with respect to Cisplatin (7.21μM) and comparable with respect to Doxorubicin (1μM), while 6e (2.49μM), 6i (2.46μM) and 6m (1.62μM) showed better activity against glioblastoma cancer cell line with respect to both Cisplatin (2.60μM) and Doxorubicin (3.78μM) drugs used as standards. Greater than 65% of the compounds were found to be safer on human normal cell line.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2015.12.022</identifier><identifier>PMID: 26748355</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Amides - chemical synthesis ; Amides - chemistry ; Amides - pharmacology ; Amino acid ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Bile Acids and Salts - chemical synthesis ; Bile Acids and Salts - chemistry ; Bile Acids and Salts - pharmacology ; Cancer ; Cell Line, Tumor ; Cholic acid ; Coupling ; Cytotoxicity ; Female ; Heteroaryl amines ; Humans ; Male ; Neoplasms - drug therapy ; Neoplasms - metabolism ; Neoplasms - pathology</subject><ispartof>Steroids, 2016-03, Vol.107, p.87-97</ispartof><rights>2016 Elsevier Inc.</rights><rights>Copyright © 2016 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-c57a72edff71fac820107b956657ea7025840f288624d9a13af272afa98490633</citedby><cites>FETCH-LOGICAL-c438t-c57a72edff71fac820107b956657ea7025840f288624d9a13af272afa98490633</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0039128X15003281$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26748355$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Agarwal, Devesh S.</creatorcontrib><creatorcontrib>Anantaraju, Hasitha Shilpa</creatorcontrib><creatorcontrib>Sriram, Dharmarajan</creatorcontrib><creatorcontrib>Yogeeswari, Perumal</creatorcontrib><creatorcontrib>Nanjegowda, Shankara H.</creatorcontrib><creatorcontrib>Mallu, P.</creatorcontrib><creatorcontrib>Sakhuja, Rajeev</creatorcontrib><title>Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents</title><title>Steroids</title><addtitle>Steroids</addtitle><description>[Display omitted]
•Series of bile acid aryl/heteroaryl amides linked via α-amino acid were synthesized.•Cytotoxic behavior against HT29, MDAMB231, U87MG were tested.•Three conjugates showed good in vitro activity (GI50=1.35, 1.41, 4.52μM) against MDAMB231.•Another three conjugates showed good in vitro activity (GI50=2.49, 2.46, 1.62μM) against U87MG.•Greater than 65% of the synthesized compounds were found to be safer on human normal cell line (HEK293T).
A series of bile acid (Cholic acid and Deoxycholic acid) aryl/heteroaryl amides linked via α-amino acid were synthesized and tested against 3 human cancer cell-lines (HT29, MDAMB231, U87MG) and 1 human normal cell line (HEK293T). Some of the conjugates showed promising results to be new anticancer agents with good in vitro results. More specifically, Cholic acid derivatives 6a (1.35μM), 6c (1.41μM) and 6m (4.52μM) possessing phenyl, benzothiazole and 4-methylphenyl groups showed fairly good activity against the breast cancer cell line with respect to Cisplatin (7.21μM) and comparable with respect to Doxorubicin (1μM), while 6e (2.49μM), 6i (2.46μM) and 6m (1.62μM) showed better activity against glioblastoma cancer cell line with respect to both Cisplatin (2.60μM) and Doxorubicin (3.78μM) drugs used as standards. Greater than 65% of the compounds were found to be safer on human normal cell line.</description><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Amino acid</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Bile Acids and Salts - chemical synthesis</subject><subject>Bile Acids and Salts - chemistry</subject><subject>Bile Acids and Salts - pharmacology</subject><subject>Cancer</subject><subject>Cell Line, Tumor</subject><subject>Cholic acid</subject><subject>Coupling</subject><subject>Cytotoxicity</subject><subject>Female</subject><subject>Heteroaryl amines</subject><subject>Humans</subject><subject>Male</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - metabolism</subject><subject>Neoplasms - pathology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUctuFDEQtBCIbAK_EPnIgZnYnvFjbqAoPKRIHACJm9Vrt7NeZsbBnl0pfATfjDeb5YrUktXdVd3tKkIuOWs54-pq25YFc4q-tIJx2XLRMiGekRU32jTSKP2crBjrhoYL8-OMnJeyZYypbhAvyZlQujedlCvy5-vDvGywxPKWug1kcHVs_A1LTDOF2dN1TGO6iw5GinsYd8dOCrUxIgUXfQM5TbXsrjZ4uOmUUpiix0LHOP9ET_cRDpU5PZIKhRrzEhsHs8NM4Q7npbwiLwKMBV8_vRfk-4ebb9efmtsvHz9fv79tXN-ZpXFSgxboQ9A8gDNVAqbXg1RKagTNhDQ9C8IYJXo_AO8gCC0gwGD6oYrQXZA3x7n3Of3aYVnsFIvDcYQZ065YrtWghOylqFB1hLqcSskY7H2OE-QHy5k9eGG39uSFPXhhubDVi0q8fNqxW0_o_9FO4lfAuyMA60_3EbMtLmJVw8eMbrE-xf_t-AuTTKEv</recordid><startdate>20160301</startdate><enddate>20160301</enddate><creator>Agarwal, Devesh S.</creator><creator>Anantaraju, Hasitha Shilpa</creator><creator>Sriram, Dharmarajan</creator><creator>Yogeeswari, Perumal</creator><creator>Nanjegowda, Shankara H.</creator><creator>Mallu, P.</creator><creator>Sakhuja, Rajeev</creator><general>Elsevier Inc</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>20160301</creationdate><title>Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents</title><author>Agarwal, Devesh S. ; Anantaraju, Hasitha Shilpa ; Sriram, Dharmarajan ; Yogeeswari, Perumal ; Nanjegowda, Shankara H. ; Mallu, P. ; Sakhuja, Rajeev</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-c57a72edff71fac820107b956657ea7025840f288624d9a13af272afa98490633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Amides - chemical synthesis</topic><topic>Amides - chemistry</topic><topic>Amides - pharmacology</topic><topic>Amino acid</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Bile Acids and Salts - chemical synthesis</topic><topic>Bile Acids and Salts - chemistry</topic><topic>Bile Acids and Salts - pharmacology</topic><topic>Cancer</topic><topic>Cell Line, Tumor</topic><topic>Cholic acid</topic><topic>Coupling</topic><topic>Cytotoxicity</topic><topic>Female</topic><topic>Heteroaryl amines</topic><topic>Humans</topic><topic>Male</topic><topic>Neoplasms - drug therapy</topic><topic>Neoplasms - metabolism</topic><topic>Neoplasms - pathology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Agarwal, Devesh S.</creatorcontrib><creatorcontrib>Anantaraju, Hasitha Shilpa</creatorcontrib><creatorcontrib>Sriram, Dharmarajan</creatorcontrib><creatorcontrib>Yogeeswari, Perumal</creatorcontrib><creatorcontrib>Nanjegowda, Shankara H.</creatorcontrib><creatorcontrib>Mallu, P.</creatorcontrib><creatorcontrib>Sakhuja, Rajeev</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>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Agarwal, Devesh S.</au><au>Anantaraju, Hasitha Shilpa</au><au>Sriram, Dharmarajan</au><au>Yogeeswari, Perumal</au><au>Nanjegowda, Shankara H.</au><au>Mallu, P.</au><au>Sakhuja, Rajeev</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2016-03-01</date><risdate>2016</risdate><volume>107</volume><spage>87</spage><epage>97</epage><pages>87-97</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><abstract>[Display omitted]
•Series of bile acid aryl/heteroaryl amides linked via α-amino acid were synthesized.•Cytotoxic behavior against HT29, MDAMB231, U87MG were tested.•Three conjugates showed good in vitro activity (GI50=1.35, 1.41, 4.52μM) against MDAMB231.•Another three conjugates showed good in vitro activity (GI50=2.49, 2.46, 1.62μM) against U87MG.•Greater than 65% of the synthesized compounds were found to be safer on human normal cell line (HEK293T).
A series of bile acid (Cholic acid and Deoxycholic acid) aryl/heteroaryl amides linked via α-amino acid were synthesized and tested against 3 human cancer cell-lines (HT29, MDAMB231, U87MG) and 1 human normal cell line (HEK293T). Some of the conjugates showed promising results to be new anticancer agents with good in vitro results. More specifically, Cholic acid derivatives 6a (1.35μM), 6c (1.41μM) and 6m (4.52μM) possessing phenyl, benzothiazole and 4-methylphenyl groups showed fairly good activity against the breast cancer cell line with respect to Cisplatin (7.21μM) and comparable with respect to Doxorubicin (1μM), while 6e (2.49μM), 6i (2.46μM) and 6m (1.62μM) showed better activity against glioblastoma cancer cell line with respect to both Cisplatin (2.60μM) and Doxorubicin (3.78μM) drugs used as standards. Greater than 65% of the compounds were found to be safer on human normal cell line.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>26748355</pmid><doi>10.1016/j.steroids.2015.12.022</doi><tpages>11</tpages></addata></record> |
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| subjects | Amides - chemical synthesis Amides - chemistry Amides - pharmacology Amino acid Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Bile Acids and Salts - chemical synthesis Bile Acids and Salts - chemistry Bile Acids and Salts - pharmacology Cancer Cell Line, Tumor Cholic acid Coupling Cytotoxicity Female Heteroaryl amines Humans Male Neoplasms - drug therapy Neoplasms - metabolism Neoplasms - pathology |
| title | Synthesis, characterization and biological evaluation of bile acid-aromatic/heteroaromatic amides linked via amino acids as anti-cancer agents |
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