Ellipticine derivatives with an affinity to the estrogen receptor. An approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer
In order to obtain breast tumor directed agents, we have prepared mixed compounds using estradiol or (E)-clomiphene as specific vectors of the breast tissue and a DNA intercalator from the ellipticine series as the cytotoxic agent. Among the newly synthesized ellipticine derivatives, only the 2-[3-a...
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| Veröffentlicht in: | Journal of medicinal chemistry 1985-06, Vol.28 (6), p.752-761 |
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| container_end_page | 761 |
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| container_issue | 6 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 28 |
| creator | Delbarre, Alain Oberlin, Robert Roques, Bernard P Borgna, Jean Louis Rochefort, Henri Le Pecq, Jean Bernard Jacquemin-Sablon, Alain |
| description | In order to obtain breast tumor directed agents, we have prepared mixed compounds using estradiol or (E)-clomiphene as specific vectors of the breast tissue and a DNA intercalator from the ellipticine series as the cytotoxic agent. Among the newly synthesized ellipticine derivatives, only the 2-[3-aza-5-(3,17 beta-dihydroxy-1,3,5-estratrien-17 alpha-yl)-4-oxopentamethylene]ellipticinium bromide shows the desired properties, DNA intercalation and affinity for estrogen receptor. Competition experiments with estradiol on the hormone-dependent human MCF-7 breast cancer cell line demonstrate that a transport by the estrogen receptor system is not involved in the antitumor activity of derivative 24. |
| doi_str_mv | 10.1021/jm00383a011 |
| format | Article |
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An approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>In order to obtain breast tumor directed agents, we have prepared mixed compounds using estradiol or (E)-clomiphene as specific vectors of the breast tissue and a DNA intercalator from the ellipticine series as the cytotoxic agent. Among the newly synthesized ellipticine derivatives, only the 2-[3-aza-5-(3,17 beta-dihydroxy-1,3,5-estratrien-17 alpha-yl)-4-oxopentamethylene]ellipticinium bromide shows the desired properties, DNA intercalation and affinity for estrogen receptor. Competition experiments with estradiol on the hormone-dependent human MCF-7 breast cancer cell line demonstrate that a transport by the estrogen receptor system is not involved in the antitumor activity of derivative 24.</description><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Breast Neoplasms - drug therapy</subject><subject>Cattle</subject><subject>Cell Line</subject><subject>Chemistry</subject><subject>DNA - metabolism</subject><subject>Ellipticines - chemical synthesis</subject><subject>Ellipticines - metabolism</subject><subject>Ellipticines - pharmacology</subject><subject>Exact sciences and technology</subject><subject>Female</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Intercalating Agents - chemical synthesis</subject><subject>Intercalating Agents - metabolism</subject><subject>Intercalating Agents - pharmacology</subject><subject>Leukemia L1210 - drug therapy</subject><subject>Neoplasms, Hormone-Dependent - drug therapy</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Receptors, Estrogen - metabolism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1985</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0U2LFDEQBuAgyjqunjwLOYgepNck_ZU-Lsv6gQMqDngM1enKTMaepDdJj-5v8k-adcbBg-ApUPXwkqoi5ClnF5wJ_nq7Y6yUJTDO75EFrwUrKsmq-2TBmBCFaET5kDyKccuy46I8I2cVY13dtQvy83oc7ZSstg7pgMHuIdk9Rvrdpg0FR8EY62y6pcnTtEGKMQW_RkcDapySDxf0MqtpCh705k4NuMfRT9S6hEHDmAPdmg5hXv9JpXFCbY3VFI1Bnah3v7M3Puy8w2LACd2ALtE-IMRENTiN4TF5YGCM-OT4npPVm-vV1bti-fHt-6vLZQFl1aQCuIS26nrN-raHEhvBkVfSDAg1Vk3Jm84Y2ciuN-3Qt3VVad4BDB3mmpTlOXlxiM0j3cx5XrWzUeM4gkM_R9U2vG1FU_8X8kowIVmX4asD1MHHGNCoKdgdhFvFmbo7ofrrhFk_O8bO_Q6Hkz3eLPefH_sQ83pNyMux8cQ6LiWTIrPiwGxM-OPUhvBNNW3Z1mr16Ytiol7Kz1-X6kP2Lw8edFRbPweXd_zPD_4Ca2TCdg</recordid><startdate>198506</startdate><enddate>198506</enddate><creator>Delbarre, Alain</creator><creator>Oberlin, Robert</creator><creator>Roques, Bernard P</creator><creator>Borgna, Jean Louis</creator><creator>Rochefort, Henri</creator><creator>Le Pecq, Jean Bernard</creator><creator>Jacquemin-Sablon, Alain</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>7SQ</scope><scope>7X8</scope></search><sort><creationdate>198506</creationdate><title>Ellipticine derivatives with an affinity to the estrogen receptor. An approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer</title><author>Delbarre, Alain ; Oberlin, Robert ; Roques, Bernard P ; Borgna, Jean Louis ; Rochefort, Henri ; Le Pecq, Jean Bernard ; Jacquemin-Sablon, Alain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a346t-a18a749bc0b7ba3e621e148fdea5e463169ff8689bf7db7544c19aad9e689883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1985</creationdate><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Breast Neoplasms - drug therapy</topic><topic>Cattle</topic><topic>Cell Line</topic><topic>Chemistry</topic><topic>DNA - metabolism</topic><topic>Ellipticines - chemical synthesis</topic><topic>Ellipticines - metabolism</topic><topic>Ellipticines - pharmacology</topic><topic>Exact sciences and technology</topic><topic>Female</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Intercalating Agents - chemical synthesis</topic><topic>Intercalating Agents - metabolism</topic><topic>Intercalating Agents - pharmacology</topic><topic>Leukemia L1210 - drug therapy</topic><topic>Neoplasms, Hormone-Dependent - drug therapy</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Receptors, Estrogen - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Delbarre, Alain</creatorcontrib><creatorcontrib>Oberlin, Robert</creatorcontrib><creatorcontrib>Roques, Bernard P</creatorcontrib><creatorcontrib>Borgna, Jean Louis</creatorcontrib><creatorcontrib>Rochefort, Henri</creatorcontrib><creatorcontrib>Le Pecq, Jean Bernard</creatorcontrib><creatorcontrib>Jacquemin-Sablon, Alain</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Endocrinology Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Delbarre, Alain</au><au>Oberlin, Robert</au><au>Roques, Bernard P</au><au>Borgna, Jean Louis</au><au>Rochefort, Henri</au><au>Le Pecq, Jean Bernard</au><au>Jacquemin-Sablon, Alain</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ellipticine derivatives with an affinity to the estrogen receptor. An approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1985-06</date><risdate>1985</risdate><volume>28</volume><issue>6</issue><spage>752</spage><epage>761</epage><pages>752-761</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>In order to obtain breast tumor directed agents, we have prepared mixed compounds using estradiol or (E)-clomiphene as specific vectors of the breast tissue and a DNA intercalator from the ellipticine series as the cytotoxic agent. Among the newly synthesized ellipticine derivatives, only the 2-[3-aza-5-(3,17 beta-dihydroxy-1,3,5-estratrien-17 alpha-yl)-4-oxopentamethylene]ellipticinium bromide shows the desired properties, DNA intercalation and affinity for estrogen receptor. 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| ispartof | Journal of medicinal chemistry, 1985-06, Vol.28 (6), p.752-761 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkaloids - pharmacology Animals Breast Neoplasms - drug therapy Cattle Cell Line Chemistry DNA - metabolism Ellipticines - chemical synthesis Ellipticines - metabolism Ellipticines - pharmacology Exact sciences and technology Female Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Humans In Vitro Techniques Intercalating Agents - chemical synthesis Intercalating Agents - metabolism Intercalating Agents - pharmacology Leukemia L1210 - drug therapy Neoplasms, Hormone-Dependent - drug therapy Organic chemistry Preparations and properties Receptors, Estrogen - metabolism |
| title | Ellipticine derivatives with an affinity to the estrogen receptor. An approach to develop intercalating drugs with a specific effect on the hormone-dependent breast cancer |
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