Novel Ferrocenic Steroidal Drug Derivatives and Their Bioactivities
Seven novel ferrocenic derivatives, compounds 1−7, were synthesized from steroidal drugs by Aldol condensation reaction. The derivatives were purified by chromatography, and their structures were determined on the basis of HR-ESI-MS and two-dimensional NMR spectroscopy. The purity of all derivatives...
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| Veröffentlicht in: | Journal of medicinal chemistry 2010-05, Vol.53 (10), p.3937-3943 |
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| creator | Manosroi, Jiradej Rueanto, Kanjana Boonpisuttinant, Korawinwich Manosroi, Worapaka Biot, Christophe Akazawa, Hiroyuki Akihisa, Toshihiro Issarangporn, Witchapong Manosroi, Aranya |
| description | Seven novel ferrocenic derivatives, compounds 1−7, were synthesized from steroidal drugs by Aldol condensation reaction. The derivatives were purified by chromatography, and their structures were determined on the basis of HR-ESI-MS and two-dimensional NMR spectroscopy. The purity of all derivatives was more than 95%. Compounds 1−5 demonstrated anti-proliferative activity on HeLa cell line by SRB assay more than their parent compounds. All seven derivatives showed anti-oxidative activities evaluated by DPPH scavenging and metal ion chelating, while their parent compounds gave no activity. Compound 1 indicated the most potent anti-proliferative activity similar to doxorubicin, with the GI50 at 0.223 ± 0.014 μg/mL. Compounds 6 and 7 demonstrated similar potent in vivo anti-inflammatory to their parent compounds (prednisolone and hydrocortisone) at 80.99 ± 13.5 and 68.24 ± 10.4% edema inhibition, respectively. This study has suggested that the novel compound 1 was the most potential derivative that can be further developed for cancer treatment. |
| doi_str_mv | 10.1021/jm901866m |
| format | Article |
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The derivatives were purified by chromatography, and their structures were determined on the basis of HR-ESI-MS and two-dimensional NMR spectroscopy. The purity of all derivatives was more than 95%. Compounds 1−5 demonstrated anti-proliferative activity on HeLa cell line by SRB assay more than their parent compounds. All seven derivatives showed anti-oxidative activities evaluated by DPPH scavenging and metal ion chelating, while their parent compounds gave no activity. Compound 1 indicated the most potent anti-proliferative activity similar to doxorubicin, with the GI50 at 0.223 ± 0.014 μg/mL. Compounds 6 and 7 demonstrated similar potent in vivo anti-inflammatory to their parent compounds (prednisolone and hydrocortisone) at 80.99 ± 13.5 and 68.24 ± 10.4% edema inhibition, respectively. This study has suggested that the novel compound 1 was the most potential derivative that can be further developed for cancer treatment.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm901866m</identifier><identifier>PMID: 20408531</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Antioxidants - chemical synthesis ; Antioxidants - pharmacology ; Biochemistry ; Biochemistry, Molecular Biology ; Biphenyl Compounds - chemistry ; Drug Screening Assays, Antitumor ; Edema - drug therapy ; Ferrous Compounds - chemical synthesis ; Ferrous Compounds - pharmacology ; Free Radical Scavengers - chemical synthesis ; Free Radical Scavengers - pharmacology ; HeLa Cells ; Humans ; Iron Chelating Agents - chemical synthesis ; Iron Chelating Agents - pharmacology ; Life Sciences ; Magnetic Resonance Spectroscopy ; Male ; Metallocenes ; Picrates - chemistry ; Rats ; Rats, Sprague-Dawley ; Spectrometry, Mass, Electrospray Ionization ; Steroids - chemical synthesis ; Steroids - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2010-05, Vol.53 (10), p.3937-3943</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-20a58d8a1ff629139c51190e7bfe0a9ee98de253993056985b0ee182e00eeaa33</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm901866m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm901866m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20408531$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00641566$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Manosroi, Jiradej</creatorcontrib><creatorcontrib>Rueanto, Kanjana</creatorcontrib><creatorcontrib>Boonpisuttinant, Korawinwich</creatorcontrib><creatorcontrib>Manosroi, Worapaka</creatorcontrib><creatorcontrib>Biot, Christophe</creatorcontrib><creatorcontrib>Akazawa, Hiroyuki</creatorcontrib><creatorcontrib>Akihisa, Toshihiro</creatorcontrib><creatorcontrib>Issarangporn, Witchapong</creatorcontrib><creatorcontrib>Manosroi, Aranya</creatorcontrib><title>Novel Ferrocenic Steroidal Drug Derivatives and Their Bioactivities</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Seven novel ferrocenic derivatives, compounds 1−7, were synthesized from steroidal drugs by Aldol condensation reaction. The derivatives were purified by chromatography, and their structures were determined on the basis of HR-ESI-MS and two-dimensional NMR spectroscopy. The purity of all derivatives was more than 95%. Compounds 1−5 demonstrated anti-proliferative activity on HeLa cell line by SRB assay more than their parent compounds. All seven derivatives showed anti-oxidative activities evaluated by DPPH scavenging and metal ion chelating, while their parent compounds gave no activity. Compound 1 indicated the most potent anti-proliferative activity similar to doxorubicin, with the GI50 at 0.223 ± 0.014 μg/mL. Compounds 6 and 7 demonstrated similar potent in vivo anti-inflammatory to their parent compounds (prednisolone and hydrocortisone) at 80.99 ± 13.5 and 68.24 ± 10.4% edema inhibition, respectively. This study has suggested that the novel compound 1 was the most potential derivative that can be further developed for cancer treatment.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - pharmacology</subject><subject>Biochemistry</subject><subject>Biochemistry, Molecular Biology</subject><subject>Biphenyl Compounds - chemistry</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Edema - drug therapy</subject><subject>Ferrous Compounds - chemical synthesis</subject><subject>Ferrous Compounds - pharmacology</subject><subject>Free Radical Scavengers - chemical synthesis</subject><subject>Free Radical Scavengers - pharmacology</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Iron Chelating Agents - chemical synthesis</subject><subject>Iron Chelating Agents - pharmacology</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Metallocenes</subject><subject>Picrates - chemistry</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Steroids - chemical synthesis</subject><subject>Steroids - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkL1OwzAURi0EouVn4AVQFoQYAvfaSWqPpaWAVMEAzJab3FBXSV3sJBJvT1ChLEyf9OnoDIexM4RrBI43q1oByiyr99gQUw5xIiHZZ0MAzmOecTFgRyGsAEAgF4dswCEBmQocssmT66iKZuS9y2lt8-ilIe9sYapo6tv3aEredqaxHYXIrIvodUnWR7fWmbw_bWMpnLCD0lSBTn_2mL3N7l4nD_H8-f5xMp7HRiSyiTmYVBbSYFlmXKFQeYqogEaLksAoIiUL4qlQSkCaKZkugAglJ-jXGCGO2dXWuzSV3nhbG_-pnbH6YTzX3x9AlmCaZR327OWW3Xj30VJodG1DTlVl1uTaoEdCiBGilH_W3LsQPJU7NYL-zqt3eXv2_MfaLmoqduRvzx642AImD3rlWr_ug_wj-gLKEX9B</recordid><startdate>20100527</startdate><enddate>20100527</enddate><creator>Manosroi, Jiradej</creator><creator>Rueanto, Kanjana</creator><creator>Boonpisuttinant, Korawinwich</creator><creator>Manosroi, Worapaka</creator><creator>Biot, Christophe</creator><creator>Akazawa, Hiroyuki</creator><creator>Akihisa, Toshihiro</creator><creator>Issarangporn, Witchapong</creator><creator>Manosroi, Aranya</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><scope>7X8</scope><scope>1XC</scope></search><sort><creationdate>20100527</creationdate><title>Novel Ferrocenic Steroidal Drug Derivatives and Their Bioactivities</title><author>Manosroi, Jiradej ; Rueanto, Kanjana ; Boonpisuttinant, Korawinwich ; Manosroi, Worapaka ; Biot, Christophe ; Akazawa, Hiroyuki ; Akihisa, Toshihiro ; Issarangporn, Witchapong ; Manosroi, Aranya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-20a58d8a1ff629139c51190e7bfe0a9ee98de253993056985b0ee182e00eeaa33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - pharmacology</topic><topic>Biochemistry</topic><topic>Biochemistry, Molecular Biology</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Edema - drug therapy</topic><topic>Ferrous Compounds - chemical synthesis</topic><topic>Ferrous Compounds - pharmacology</topic><topic>Free Radical Scavengers - chemical synthesis</topic><topic>Free Radical Scavengers - pharmacology</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Iron Chelating Agents - chemical synthesis</topic><topic>Iron Chelating Agents - pharmacology</topic><topic>Life Sciences</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Metallocenes</topic><topic>Picrates - chemistry</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Steroids - chemical synthesis</topic><topic>Steroids - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Manosroi, Jiradej</creatorcontrib><creatorcontrib>Rueanto, Kanjana</creatorcontrib><creatorcontrib>Boonpisuttinant, Korawinwich</creatorcontrib><creatorcontrib>Manosroi, Worapaka</creatorcontrib><creatorcontrib>Biot, Christophe</creatorcontrib><creatorcontrib>Akazawa, Hiroyuki</creatorcontrib><creatorcontrib>Akihisa, Toshihiro</creatorcontrib><creatorcontrib>Issarangporn, Witchapong</creatorcontrib><creatorcontrib>Manosroi, Aranya</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>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Manosroi, Jiradej</au><au>Rueanto, Kanjana</au><au>Boonpisuttinant, Korawinwich</au><au>Manosroi, Worapaka</au><au>Biot, Christophe</au><au>Akazawa, Hiroyuki</au><au>Akihisa, Toshihiro</au><au>Issarangporn, Witchapong</au><au>Manosroi, Aranya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Ferrocenic Steroidal Drug Derivatives and Their Bioactivities</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2010-05-27</date><risdate>2010</risdate><volume>53</volume><issue>10</issue><spage>3937</spage><epage>3943</epage><pages>3937-3943</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>Seven novel ferrocenic derivatives, compounds 1−7, were synthesized from steroidal drugs by Aldol condensation reaction. The derivatives were purified by chromatography, and their structures were determined on the basis of HR-ESI-MS and two-dimensional NMR spectroscopy. The purity of all derivatives was more than 95%. Compounds 1−5 demonstrated anti-proliferative activity on HeLa cell line by SRB assay more than their parent compounds. All seven derivatives showed anti-oxidative activities evaluated by DPPH scavenging and metal ion chelating, while their parent compounds gave no activity. Compound 1 indicated the most potent anti-proliferative activity similar to doxorubicin, with the GI50 at 0.223 ± 0.014 μg/mL. Compounds 6 and 7 demonstrated similar potent in vivo anti-inflammatory to their parent compounds (prednisolone and hydrocortisone) at 80.99 ± 13.5 and 68.24 ± 10.4% edema inhibition, respectively. This study has suggested that the novel compound 1 was the most potential derivative that can be further developed for cancer treatment.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20408531</pmid><doi>10.1021/jm901866m</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2010-05, Vol.53 (10), p.3937-3943 |
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| subjects | Animals Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Antioxidants - chemical synthesis Antioxidants - pharmacology Biochemistry Biochemistry, Molecular Biology Biphenyl Compounds - chemistry Drug Screening Assays, Antitumor Edema - drug therapy Ferrous Compounds - chemical synthesis Ferrous Compounds - pharmacology Free Radical Scavengers - chemical synthesis Free Radical Scavengers - pharmacology HeLa Cells Humans Iron Chelating Agents - chemical synthesis Iron Chelating Agents - pharmacology Life Sciences Magnetic Resonance Spectroscopy Male Metallocenes Picrates - chemistry Rats Rats, Sprague-Dawley Spectrometry, Mass, Electrospray Ionization Steroids - chemical synthesis Steroids - pharmacology Structure-Activity Relationship |
| title | Novel Ferrocenic Steroidal Drug Derivatives and Their Bioactivities |
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