LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase
Eleven derivatives of 1,1′-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electr...
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| Veröffentlicht in: | European journal of medicinal chemistry 2001-03, Vol.36 (3), p.215-225 |
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| container_title | European journal of medicinal chemistry |
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| creator | Campos, Joaquı́n del Carmen Núñez, Marı́a Rodrı́guez, Vicente Entrena, Antonio Hernández-Alcoceba, Rubén Fernández, Félix Lacal, Juan Carlos Gallo, Miguel A Espinosa, Antonio |
| description | Eleven derivatives of 1,1′-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electron-releasing, neutral or electron-withdrawing groups. A one-parameter regression equation has been derived which satisfactorily describes the ex vivo inhibitory potency of ChoK of the title compounds. The electronic effect plays a critical function in the ex vivo inhibition of ChoK although the role of electrostatic interactions could be altered due to a solvation process of both ChoK and ligands. |
| doi_str_mv | 10.1016/S0223-5234(01)01219-3 |
| format | Article |
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The C-4 substituents include electron-releasing, neutral or electron-withdrawing groups. A one-parameter regression equation has been derived which satisfactorily describes the ex vivo inhibitory potency of ChoK of the title compounds. The electronic effect plays a critical function in the ex vivo inhibition of ChoK although the role of electrostatic interactions could be altered due to a solvation process of both ChoK and ligands.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/S0223-5234(01)01219-3</identifier><identifier>PMID: 11337100</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Antineoplastic agents ; antiproliferative agents ; Biological and medical sciences ; Chemotherapy ; choline kinase ; Choline Kinase - antagonists & inhibitors ; Drug Design ; electrostatic effects ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Magnetic Resonance Spectroscopy ; Medical sciences ; Models, Chemical ; Models, Molecular ; Pharmacology. Drug treatments ; Pyridinium Compounds - chemical synthesis ; Pyridinium Compounds - chemistry ; Pyridinium Compounds - pharmacology ; quantitative structure–activity relationship ; Spectrometry, Mass, Fast Atom Bombardment ; Structure-Activity Relationship</subject><ispartof>European journal of medicinal chemistry, 2001-03, Vol.36 (3), p.215-225</ispartof><rights>2001 Éditions scientifiques et médicales Elsevier SAS</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-76ecca23292a4246f6f770741641b6a3c9be1536e6b03593d59dda8e57f14b23</citedby><cites>FETCH-LOGICAL-c389t-76ecca23292a4246f6f770741641b6a3c9be1536e6b03593d59dda8e57f14b23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523401012193$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=959301$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11337100$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Campos, Joaquı́n</creatorcontrib><creatorcontrib>del Carmen Núñez, Marı́a</creatorcontrib><creatorcontrib>Rodrı́guez, Vicente</creatorcontrib><creatorcontrib>Entrena, Antonio</creatorcontrib><creatorcontrib>Hernández-Alcoceba, Rubén</creatorcontrib><creatorcontrib>Fernández, Félix</creatorcontrib><creatorcontrib>Lacal, Juan Carlos</creatorcontrib><creatorcontrib>Gallo, Miguel A</creatorcontrib><creatorcontrib>Espinosa, Antonio</creatorcontrib><title>LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Eleven derivatives of 1,1′-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electron-releasing, neutral or electron-withdrawing groups. A one-parameter regression equation has been derived which satisfactorily describes the ex vivo inhibitory potency of ChoK of the title compounds. The electronic effect plays a critical function in the ex vivo inhibition of ChoK although the role of electrostatic interactions could be altered due to a solvation process of both ChoK and ligands.</description><subject>Antineoplastic agents</subject><subject>antiproliferative agents</subject><subject>Biological and medical sciences</subject><subject>Chemotherapy</subject><subject>choline kinase</subject><subject>Choline Kinase - antagonists & inhibitors</subject><subject>Drug Design</subject><subject>electrostatic effects</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Models, Chemical</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyridinium Compounds - chemical synthesis</subject><subject>Pyridinium Compounds - chemistry</subject><subject>Pyridinium Compounds - pharmacology</subject><subject>quantitative structure–activity relationship</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Structure-Activity Relationship</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFq3DAQhkVpaDZpH6HFUAjtwemMZMvrUwihaQsbcmh6FrI07iqxpY1kl-zb184uSW4BgdDo-2eGj7GPCKcIKL_9Bs5FXnJRfAH8CsixzsUbtsBKLnPBy-ItWzwhh-wopVsAKCXAO3aIKESFAAt2u_pzdZ2Rp_h3m4U264OlLjOh34TR2zSXGpc22-is827sX3zp6fjMeUsPWRtiNqxpeq1d4wYX_Jw069A5T9md8zrRe3bQ6i7Rh_19zG4uv99c_MxX1z9-XZyvciOW9ZBXkozRXPCa64IXspVtVUFVoCywkVqYuiEshSTZgChrYcvaWr2ksmqxaLg4Zie7tpsY7kdKg-pdMtR12lMYk6pgCZMenMByB5oYUorUqk10vY5bhaBmx-rRsZoFKkD16FiJKfdpP2BserLPqb3UCfi8B3Qyumuj9salJ66eloZ5_NmOosnFP0dRJePIG7IukhmUDe6VRf4DGDeX_Q</recordid><startdate>20010301</startdate><enddate>20010301</enddate><creator>Campos, Joaquı́n</creator><creator>del Carmen Núñez, Marı́a</creator><creator>Rodrı́guez, Vicente</creator><creator>Entrena, Antonio</creator><creator>Hernández-Alcoceba, Rubén</creator><creator>Fernández, Félix</creator><creator>Lacal, Juan Carlos</creator><creator>Gallo, Miguel A</creator><creator>Espinosa, Antonio</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><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>7X8</scope></search><sort><creationdate>20010301</creationdate><title>LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase</title><author>Campos, Joaquı́n ; del Carmen Núñez, Marı́a ; Rodrı́guez, Vicente ; Entrena, Antonio ; Hernández-Alcoceba, Rubén ; Fernández, Félix ; Lacal, Juan Carlos ; Gallo, Miguel A ; Espinosa, Antonio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-76ecca23292a4246f6f770741641b6a3c9be1536e6b03593d59dda8e57f14b23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Antineoplastic agents</topic><topic>antiproliferative agents</topic><topic>Biological and medical sciences</topic><topic>Chemotherapy</topic><topic>choline kinase</topic><topic>Choline Kinase - antagonists & inhibitors</topic><topic>Drug Design</topic><topic>electrostatic effects</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Models, Chemical</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyridinium Compounds - chemical synthesis</topic><topic>Pyridinium Compounds - chemistry</topic><topic>Pyridinium Compounds - pharmacology</topic><topic>quantitative structure–activity relationship</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Campos, Joaquı́n</creatorcontrib><creatorcontrib>del Carmen Núñez, Marı́a</creatorcontrib><creatorcontrib>Rodrı́guez, Vicente</creatorcontrib><creatorcontrib>Entrena, Antonio</creatorcontrib><creatorcontrib>Hernández-Alcoceba, Rubén</creatorcontrib><creatorcontrib>Fernández, Félix</creatorcontrib><creatorcontrib>Lacal, Juan Carlos</creatorcontrib><creatorcontrib>Gallo, Miguel A</creatorcontrib><creatorcontrib>Espinosa, Antonio</creatorcontrib><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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Campos, Joaquı́n</au><au>del Carmen Núñez, Marı́a</au><au>Rodrı́guez, Vicente</au><au>Entrena, Antonio</au><au>Hernández-Alcoceba, Rubén</au><au>Fernández, Félix</au><au>Lacal, Juan Carlos</au><au>Gallo, Miguel A</au><au>Espinosa, Antonio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2001-03-01</date><risdate>2001</risdate><volume>36</volume><issue>3</issue><spage>215</spage><epage>225</epage><pages>215-225</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Eleven derivatives of 1,1′-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electron-releasing, neutral or electron-withdrawing groups. A one-parameter regression equation has been derived which satisfactorily describes the ex vivo inhibitory potency of ChoK of the title compounds. The electronic effect plays a critical function in the ex vivo inhibition of ChoK although the role of electrostatic interactions could be altered due to a solvation process of both ChoK and ligands.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>11337100</pmid><doi>10.1016/S0223-5234(01)01219-3</doi><tpages>11</tpages></addata></record> |
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| ispartof | European journal of medicinal chemistry, 2001-03, Vol.36 (3), p.215-225 |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Antineoplastic agents antiproliferative agents Biological and medical sciences Chemotherapy choline kinase Choline Kinase - antagonists & inhibitors Drug Design electrostatic effects Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Magnetic Resonance Spectroscopy Medical sciences Models, Chemical Models, Molecular Pharmacology. Drug treatments Pyridinium Compounds - chemical synthesis Pyridinium Compounds - chemistry Pyridinium Compounds - pharmacology quantitative structure–activity relationship Spectrometry, Mass, Fast Atom Bombardment Structure-Activity Relationship |
| title | LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase |
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