New symmetrically esterified m-bromobenzyl non-aminobisphosphonates inhibited breast cancer growth and metastases
Although there was growing evidence in the potential use of Bisphosphonates (BPs) in cancer therapy, their strong osseous affinities that contrast their poor soft tissue uptake limited their use. Here, we developed a new strategy to overcome BPs hydrophilicity by masking the phosphonic acid through...
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| Veröffentlicht in: | PloS one 2009-03, Vol.4 (3), p.e4685 |
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| creator | Abdelkarim, Mohamed Guenin, Erwann Sainte-Catherine, Odile Vintonenko, Nadejda Peyri, Nicole Perret, Gerard Yves Crepin, Michel Khatib, Abdel-Majid Lecouvey, Marc Di Benedetto, Mélanie |
| description | Although there was growing evidence in the potential use of Bisphosphonates (BPs) in cancer therapy, their strong osseous affinities that contrast their poor soft tissue uptake limited their use. Here, we developed a new strategy to overcome BPs hydrophilicity by masking the phosphonic acid through organic protecting groups and introducing hydrophobic functions in the side chain.
We synthesized non-nitrogen BPs (non N-BPs) containing bromobenzyl group (BP7033Br) in their side chain that were symmetrically esterified with hydrophobic 4-methoxphenyl (BP7033BrALK) and assessed their effects on breast cancer estrogen-responsive cells (T47D, MCF-7) as well as on non responsive ones (SKBR3, MDA-MB-231 and its highly metastatic derived D3H2LN subclone). BP7033Br ALK was more efficient in inhibiting tumor cell proliferation, migration and survival when compared to BP7033Br. Although both compounds inhibited tumor growth without side effects, only BP7033Br ALK abrogated tumor angiogenesis and D3H2LN cells-induced metastases formation.
Taken together these data suggest the potential therapeutic use of this new class of esterified Bisphosphonates (BPs) in the treatment of tumor progression and metastasis without toxic adverse effects. |
| doi_str_mv | 10.1371/journal.pone.0004685 |
| format | Article |
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We synthesized non-nitrogen BPs (non N-BPs) containing bromobenzyl group (BP7033Br) in their side chain that were symmetrically esterified with hydrophobic 4-methoxphenyl (BP7033BrALK) and assessed their effects on breast cancer estrogen-responsive cells (T47D, MCF-7) as well as on non responsive ones (SKBR3, MDA-MB-231 and its highly metastatic derived D3H2LN subclone). BP7033Br ALK was more efficient in inhibiting tumor cell proliferation, migration and survival when compared to BP7033Br. Although both compounds inhibited tumor growth without side effects, only BP7033Br ALK abrogated tumor angiogenesis and D3H2LN cells-induced metastases formation.
Taken together these data suggest the potential therapeutic use of this new class of esterified Bisphosphonates (BPs) in the treatment of tumor progression and metastasis without toxic adverse effects.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0004685</identifier><identifier>PMID: 19262688</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>Acids ; Angiogenesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Apoptosis ; Bisphosphonates ; Breast cancer ; Breast Neoplasms - drug therapy ; Breast Neoplasms - pathology ; Cancer ; Cancer metastasis ; Cancer treatment ; Cell Biology/Cell Adhesion ; Cell Biology/Cell Growth and Division ; Cell growth ; Cell Line, Tumor ; Cell Movement - drug effects ; Cell proliferation ; Cell Proliferation - drug effects ; Cell survival ; Cell Survival - drug effects ; Chains ; Cytotoxicity ; Development and progression ; Diphosphonates - chemistry ; Diphosphonates - pharmacology ; Esterification ; Estrogens ; Evaluation ; Female ; Gene expression ; Growth ; Health aspects ; Humans ; Hydrophobic and Hydrophilic Interactions ; Hydrophobicity ; Ligands ; Masking ; Mesothelioma ; Metastases ; Metastasis ; Neoplasm Metastasis - drug therapy ; Neoplasm Metastasis - prevention & control ; Nitrogen ; Oncology/Breast Cancer ; Pharmacology/Drug Development ; Phosphonates ; Protecting groups ; Side effects ; Signal transduction ; Structure-Activity Relationship ; Tumors</subject><ispartof>PloS one, 2009-03, Vol.4 (3), p.e4685</ispartof><rights>COPYRIGHT 2009 Public Library of Science</rights><rights>2009 Abdelkarim et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><rights>Abdelkarim et al. 2009</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c762t-c94366683eaf0e424f580c01135e5767006340a98298a8aa2c275b76aa2703003</citedby><cites>FETCH-LOGICAL-c762t-c94366683eaf0e424f580c01135e5767006340a98298a8aa2c275b76aa2703003</cites><orcidid>0000-0002-7125-9074</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2650402/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2650402/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,724,777,781,861,882,2096,2915,23847,27905,27906,53772,53774,79349,79350</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19262688$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00416602$$DView record in HAL$$Hfree_for_read</backlink></links><search><contributor>Jin, Dong-Yan</contributor><creatorcontrib>Abdelkarim, Mohamed</creatorcontrib><creatorcontrib>Guenin, Erwann</creatorcontrib><creatorcontrib>Sainte-Catherine, Odile</creatorcontrib><creatorcontrib>Vintonenko, Nadejda</creatorcontrib><creatorcontrib>Peyri, Nicole</creatorcontrib><creatorcontrib>Perret, Gerard Yves</creatorcontrib><creatorcontrib>Crepin, Michel</creatorcontrib><creatorcontrib>Khatib, Abdel-Majid</creatorcontrib><creatorcontrib>Lecouvey, Marc</creatorcontrib><creatorcontrib>Di Benedetto, Mélanie</creatorcontrib><title>New symmetrically esterified m-bromobenzyl non-aminobisphosphonates inhibited breast cancer growth and metastases</title><title>PloS one</title><addtitle>PLoS One</addtitle><description>Although there was growing evidence in the potential use of Bisphosphonates (BPs) in cancer therapy, their strong osseous affinities that contrast their poor soft tissue uptake limited their use. Here, we developed a new strategy to overcome BPs hydrophilicity by masking the phosphonic acid through organic protecting groups and introducing hydrophobic functions in the side chain.
We synthesized non-nitrogen BPs (non N-BPs) containing bromobenzyl group (BP7033Br) in their side chain that were symmetrically esterified with hydrophobic 4-methoxphenyl (BP7033BrALK) and assessed their effects on breast cancer estrogen-responsive cells (T47D, MCF-7) as well as on non responsive ones (SKBR3, MDA-MB-231 and its highly metastatic derived D3H2LN subclone). BP7033Br ALK was more efficient in inhibiting tumor cell proliferation, migration and survival when compared to BP7033Br. Although both compounds inhibited tumor growth without side effects, only BP7033Br ALK abrogated tumor angiogenesis and D3H2LN cells-induced metastases formation.
Taken together these data suggest the potential therapeutic use of this new class of esterified Bisphosphonates (BPs) in the treatment of tumor progression and metastasis without toxic adverse effects.</description><subject>Acids</subject><subject>Angiogenesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis</subject><subject>Bisphosphonates</subject><subject>Breast cancer</subject><subject>Breast Neoplasms - drug therapy</subject><subject>Breast Neoplasms - pathology</subject><subject>Cancer</subject><subject>Cancer metastasis</subject><subject>Cancer treatment</subject><subject>Cell Biology/Cell Adhesion</subject><subject>Cell Biology/Cell Growth and Division</subject><subject>Cell growth</subject><subject>Cell Line, Tumor</subject><subject>Cell Movement - drug effects</subject><subject>Cell proliferation</subject><subject>Cell Proliferation - drug effects</subject><subject>Cell 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symmetrically esterified m-bromobenzyl non-aminobisphosphonates inhibited breast cancer growth and metastases</title><author>Abdelkarim, Mohamed ; Guenin, Erwann ; Sainte-Catherine, Odile ; Vintonenko, Nadejda ; Peyri, Nicole ; Perret, Gerard Yves ; Crepin, Michel ; Khatib, Abdel-Majid ; Lecouvey, Marc ; Di Benedetto, Mélanie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c762t-c94366683eaf0e424f580c01135e5767006340a98298a8aa2c275b76aa2703003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Acids</topic><topic>Angiogenesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis</topic><topic>Bisphosphonates</topic><topic>Breast cancer</topic><topic>Breast Neoplasms - drug therapy</topic><topic>Breast Neoplasms - pathology</topic><topic>Cancer</topic><topic>Cancer metastasis</topic><topic>Cancer 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Yves</au><au>Crepin, Michel</au><au>Khatib, Abdel-Majid</au><au>Lecouvey, Marc</au><au>Di Benedetto, Mélanie</au><au>Jin, Dong-Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New symmetrically esterified m-bromobenzyl non-aminobisphosphonates inhibited breast cancer growth and metastases</atitle><jtitle>PloS one</jtitle><addtitle>PLoS One</addtitle><date>2009-03-05</date><risdate>2009</risdate><volume>4</volume><issue>3</issue><spage>e4685</spage><pages>e4685-</pages><issn>1932-6203</issn><eissn>1932-6203</eissn><abstract>Although there was growing evidence in the potential use of Bisphosphonates (BPs) in cancer therapy, their strong osseous affinities that contrast their poor soft tissue uptake limited their use. Here, we developed a new strategy to overcome BPs hydrophilicity by masking the phosphonic acid through organic protecting groups and introducing hydrophobic functions in the side chain.
We synthesized non-nitrogen BPs (non N-BPs) containing bromobenzyl group (BP7033Br) in their side chain that were symmetrically esterified with hydrophobic 4-methoxphenyl (BP7033BrALK) and assessed their effects on breast cancer estrogen-responsive cells (T47D, MCF-7) as well as on non responsive ones (SKBR3, MDA-MB-231 and its highly metastatic derived D3H2LN subclone). BP7033Br ALK was more efficient in inhibiting tumor cell proliferation, migration and survival when compared to BP7033Br. Although both compounds inhibited tumor growth without side effects, only BP7033Br ALK abrogated tumor angiogenesis and D3H2LN cells-induced metastases formation.
Taken together these data suggest the potential therapeutic use of this new class of esterified Bisphosphonates (BPs) in the treatment of tumor progression and metastasis without toxic adverse effects.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>19262688</pmid><doi>10.1371/journal.pone.0004685</doi><tpages>e4685</tpages><orcidid>https://orcid.org/0000-0002-7125-9074</orcidid><oa>free_for_read</oa></addata></record> |
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| recordid | cdi_plos_journals_1290367173 |
| source | MEDLINE; DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Public Library of Science (PLoS); PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Acids Angiogenesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis Bisphosphonates Breast cancer Breast Neoplasms - drug therapy Breast Neoplasms - pathology Cancer Cancer metastasis Cancer treatment Cell Biology/Cell Adhesion Cell Biology/Cell Growth and Division Cell growth Cell Line, Tumor Cell Movement - drug effects Cell proliferation Cell Proliferation - drug effects Cell survival Cell Survival - drug effects Chains Cytotoxicity Development and progression Diphosphonates - chemistry Diphosphonates - pharmacology Esterification Estrogens Evaluation Female Gene expression Growth Health aspects Humans Hydrophobic and Hydrophilic Interactions Hydrophobicity Ligands Masking Mesothelioma Metastases Metastasis Neoplasm Metastasis - drug therapy Neoplasm Metastasis - prevention & control Nitrogen Oncology/Breast Cancer Pharmacology/Drug Development Phosphonates Protecting groups Side effects Signal transduction Structure-Activity Relationship Tumors |
| title | New symmetrically esterified m-bromobenzyl non-aminobisphosphonates inhibited breast cancer growth and metastases |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T05%3A18%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_plos_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=New%20symmetrically%20esterified%20m-bromobenzyl%20non-aminobisphosphonates%20inhibited%20breast%20cancer%20growth%20and%20metastases&rft.jtitle=PloS%20one&rft.au=Abdelkarim,%20Mohamed&rft.date=2009-03-05&rft.volume=4&rft.issue=3&rft.spage=e4685&rft.pages=e4685-&rft.issn=1932-6203&rft.eissn=1932-6203&rft_id=info:doi/10.1371/journal.pone.0004685&rft_dat=%3Cgale_plos_%3EA473382160%3C/gale_plos_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1290367173&rft_id=info:pmid/19262688&rft_galeid=A473382160&rft_doaj_id=oai_doaj_org_article_3b593742a6f2449fa9ac9584e68396f4&rfr_iscdi=true |