Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction
A series of bupropion (1a) analogues (1b−1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H]dopamine ([...
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| Veröffentlicht in: | Journal of medicinal chemistry 2009-11, Vol.52 (21), p.6768-6781 |
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| creator | Carroll, F. Ivy Blough, Bruce E Abraham, Philip Mills, Andrew C Holleman, J. Ashley Wolckenhauer, Scott A Decker, Ann M Landavazo, Antonio McElroy, K. Timothy Navarro, Hernán A Gatch, Michael B Forster, Michael J |
| description | A series of bupropion (1a) analogues (1b−1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H]dopamine ([3H]DA), [3H]serotonin ([3H]5HT), and [3H]norepinephrine ([3H]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [125I]RTI-55 in cloned transporters. Several analogues showed increased [3H]DA uptake inhibition with reduced or little change in [3H]5HT and [3H]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a time course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction. |
| doi_str_mv | 10.1021/jm901189z |
| format | Article |
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Ivy ; Blough, Bruce E ; Abraham, Philip ; Mills, Andrew C ; Holleman, J. Ashley ; Wolckenhauer, Scott A ; Decker, Ann M ; Landavazo, Antonio ; McElroy, K. Timothy ; Navarro, Hernán A ; Gatch, Michael B ; Forster, Michael J</creator><creatorcontrib>Carroll, F. Ivy ; Blough, Bruce E ; Abraham, Philip ; Mills, Andrew C ; Holleman, J. Ashley ; Wolckenhauer, Scott A ; Decker, Ann M ; Landavazo, Antonio ; McElroy, K. Timothy ; Navarro, Hernán A ; Gatch, Michael B ; Forster, Michael J</creatorcontrib><description>A series of bupropion (1a) analogues (1b−1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H]dopamine ([3H]DA), [3H]serotonin ([3H]5HT), and [3H]norepinephrine ([3H]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [125I]RTI-55 in cloned transporters. Several analogues showed increased [3H]DA uptake inhibition with reduced or little change in [3H]5HT and [3H]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a time course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm901189z</identifier><identifier>PMID: 19821577</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Columbus, OH: American Chemical Society</publisher><subject>Adrenergic Uptake Inhibitors - chemical synthesis ; Adrenergic Uptake Inhibitors - chemistry ; Adrenergic Uptake Inhibitors - pharmacology ; Animals ; Biological and medical sciences ; Bupropion - analogs & derivatives ; Bupropion - chemical synthesis ; Bupropion - pharmacology ; Cell Line ; Cocaine - pharmacology ; Cocaine-Related Disorders - drug therapy ; Discrimination Learning - drug effects ; Dopamine Plasma Membrane Transport Proteins - metabolism ; Dopamine Uptake Inhibitors - chemical synthesis ; Dopamine Uptake Inhibitors - chemistry ; Dopamine Uptake Inhibitors - pharmacology ; Drug addictions ; Humans ; Medical sciences ; Mice ; Motor Activity - drug effects ; Neuropharmacology ; Norepinephrine Plasma Membrane Transport Proteins - metabolism ; Pharmacology. Drug treatments ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) ; Psychology. Psychoanalysis. Psychiatry ; Psychopharmacology ; Radioligand Assay ; Rats ; Serotonin Plasma Membrane Transport Proteins - metabolism ; Serotonin Uptake Inhibitors - chemical synthesis ; Serotonin Uptake Inhibitors - chemistry ; Serotonin Uptake Inhibitors - pharmacology ; Structure-Activity Relationship ; Toxicology</subject><ispartof>Journal of medicinal chemistry, 2009-11, Vol.52 (21), p.6768-6781</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a384t-d0f0b85572c1cf445141e101df5732fd233e754d1b1adbf49723f897367999e33</citedby><cites>FETCH-LOGICAL-a384t-d0f0b85572c1cf445141e101df5732fd233e754d1b1adbf49723f897367999e33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm901189z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm901189z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22108243$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19821577$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Carroll, F. Ivy</creatorcontrib><creatorcontrib>Blough, Bruce E</creatorcontrib><creatorcontrib>Abraham, Philip</creatorcontrib><creatorcontrib>Mills, Andrew C</creatorcontrib><creatorcontrib>Holleman, J. Ashley</creatorcontrib><creatorcontrib>Wolckenhauer, Scott A</creatorcontrib><creatorcontrib>Decker, Ann M</creatorcontrib><creatorcontrib>Landavazo, Antonio</creatorcontrib><creatorcontrib>McElroy, K. Timothy</creatorcontrib><creatorcontrib>Navarro, Hernán A</creatorcontrib><creatorcontrib>Gatch, Michael B</creatorcontrib><creatorcontrib>Forster, Michael J</creatorcontrib><title>Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of bupropion (1a) analogues (1b−1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H]dopamine ([3H]DA), [3H]serotonin ([3H]5HT), and [3H]norepinephrine ([3H]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [125I]RTI-55 in cloned transporters. Several analogues showed increased [3H]DA uptake inhibition with reduced or little change in [3H]5HT and [3H]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a time course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.</description><subject>Adrenergic Uptake Inhibitors - chemical synthesis</subject><subject>Adrenergic Uptake Inhibitors - chemistry</subject><subject>Adrenergic Uptake Inhibitors - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Bupropion - analogs & derivatives</subject><subject>Bupropion - chemical synthesis</subject><subject>Bupropion - pharmacology</subject><subject>Cell Line</subject><subject>Cocaine - pharmacology</subject><subject>Cocaine-Related Disorders - drug therapy</subject><subject>Discrimination Learning - drug effects</subject><subject>Dopamine Plasma Membrane Transport Proteins - metabolism</subject><subject>Dopamine Uptake Inhibitors - chemical synthesis</subject><subject>Dopamine Uptake Inhibitors - chemistry</subject><subject>Dopamine Uptake Inhibitors - pharmacology</subject><subject>Drug addictions</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Motor Activity - drug effects</subject><subject>Neuropharmacology</subject><subject>Norepinephrine Plasma Membrane Transport Proteins - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer</subject><subject>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)</subject><subject>Psychology. Psychoanalysis. Psychiatry</subject><subject>Psychopharmacology</subject><subject>Radioligand Assay</subject><subject>Rats</subject><subject>Serotonin Plasma Membrane Transport Proteins - metabolism</subject><subject>Serotonin Uptake Inhibitors - chemical synthesis</subject><subject>Serotonin Uptake Inhibitors - chemistry</subject><subject>Serotonin Uptake Inhibitors - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Toxicology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1LwzAYB_AgipvTg19AcvHgoZonSdf2uI35AgMH6rmkeXEZXVOSVpif3oyN7eIpPOT3_B_4I3QL5BEIhaf1piAAefF7hoaQUpLwnPBzNCSE0oSOKRugqxDWhBAGlF2iARQ5hTTLhsh9bJtupYMNWDQKT62r3beVosbzH1H3orOuwc7gad961-6GSSMi6XVcCHjpOt10NvLlSviNkC6GedHa-G2cxzMnhW00nihl5S7rGl0YUQd9c3hH6Ot5_jl7TRbvL2-zySIRLOddooghVZ6mGZUgDecpcNBAQJk0Y9QoypjOUq6gAqEqw4uMMpMXGRtnRVFoxkboYZ8rvQvBa1O23m6E35ZAyl1p5bG0aO_2tu2rjVYneWgpgvsDECFWY7xopA1HRymQnHJ2ckKGcu16H6sK_xz8A7nRgUM</recordid><startdate>20091112</startdate><enddate>20091112</enddate><creator>Carroll, F. 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Timothy ; Navarro, Hernán A ; Gatch, Michael B ; Forster, Michael J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a384t-d0f0b85572c1cf445141e101df5732fd233e754d1b1adbf49723f897367999e33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Adrenergic Uptake Inhibitors - chemical synthesis</topic><topic>Adrenergic Uptake Inhibitors - chemistry</topic><topic>Adrenergic Uptake Inhibitors - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Bupropion - analogs & derivatives</topic><topic>Bupropion - chemical synthesis</topic><topic>Bupropion - pharmacology</topic><topic>Cell Line</topic><topic>Cocaine - pharmacology</topic><topic>Cocaine-Related Disorders - drug therapy</topic><topic>Discrimination Learning - drug effects</topic><topic>Dopamine Plasma Membrane Transport Proteins - metabolism</topic><topic>Dopamine Uptake Inhibitors - chemical synthesis</topic><topic>Dopamine Uptake Inhibitors - chemistry</topic><topic>Dopamine Uptake Inhibitors - pharmacology</topic><topic>Drug addictions</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Motor Activity - drug effects</topic><topic>Neuropharmacology</topic><topic>Norepinephrine Plasma Membrane Transport Proteins - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer</topic><topic>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)</topic><topic>Psychology. Psychoanalysis. Psychiatry</topic><topic>Psychopharmacology</topic><topic>Radioligand Assay</topic><topic>Rats</topic><topic>Serotonin Plasma Membrane Transport Proteins - metabolism</topic><topic>Serotonin Uptake Inhibitors - chemical synthesis</topic><topic>Serotonin Uptake Inhibitors - chemistry</topic><topic>Serotonin Uptake Inhibitors - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Carroll, F. Ivy</creatorcontrib><creatorcontrib>Blough, Bruce E</creatorcontrib><creatorcontrib>Abraham, Philip</creatorcontrib><creatorcontrib>Mills, Andrew C</creatorcontrib><creatorcontrib>Holleman, J. 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Ashley</au><au>Wolckenhauer, Scott A</au><au>Decker, Ann M</au><au>Landavazo, Antonio</au><au>McElroy, K. Timothy</au><au>Navarro, Hernán A</au><au>Gatch, Michael B</au><au>Forster, Michael J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2009-11-12</date><risdate>2009</risdate><volume>52</volume><issue>21</issue><spage>6768</spage><epage>6781</epage><pages>6768-6781</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of bupropion (1a) analogues (1b−1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a 1a analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [3H]dopamine ([3H]DA), [3H]serotonin ([3H]5HT), and [3H]norepinephrine ([3H]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [125I]RTI-55 in cloned transporters. Several analogues showed increased [3H]DA uptake inhibition with reduced or little change in [3H]5HT and [3H]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a time course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.</abstract><cop>Columbus, OH</cop><pub>American Chemical Society</pub><pmid>19821577</pmid><doi>10.1021/jm901189z</doi><tpages>14</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2009-11, Vol.52 (21), p.6768-6781 |
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| subjects | Adrenergic Uptake Inhibitors - chemical synthesis Adrenergic Uptake Inhibitors - chemistry Adrenergic Uptake Inhibitors - pharmacology Animals Biological and medical sciences Bupropion - analogs & derivatives Bupropion - chemical synthesis Bupropion - pharmacology Cell Line Cocaine - pharmacology Cocaine-Related Disorders - drug therapy Discrimination Learning - drug effects Dopamine Plasma Membrane Transport Proteins - metabolism Dopamine Uptake Inhibitors - chemical synthesis Dopamine Uptake Inhibitors - chemistry Dopamine Uptake Inhibitors - pharmacology Drug addictions Humans Medical sciences Mice Motor Activity - drug effects Neuropharmacology Norepinephrine Plasma Membrane Transport Proteins - metabolism Pharmacology. Drug treatments Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) Psychology. Psychoanalysis. Psychiatry Psychopharmacology Radioligand Assay Rats Serotonin Plasma Membrane Transport Proteins - metabolism Serotonin Uptake Inhibitors - chemical synthesis Serotonin Uptake Inhibitors - chemistry Serotonin Uptake Inhibitors - pharmacology Structure-Activity Relationship Toxicology |
| title | Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction |
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