Lipo-Endomorphin-1 Derivatives with Systemic Activity against Neuropathic Pain without Producing Constipation
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{"title"=>"Lipo-endomorphin-1 derivatives with systemic activity against neuropathic pain without producing constipation", "type"=>"journal", "authors"=>[{"first_name"=>"Pegah", "last_name"=>"Varamini", "scopus_author_id"=>"16744567900"}, {"first_name"=>"Friederike M.", "last_name"=>"Mansfeld", "scopus_author_id"=>"55270562000"}, {"first_name"=>"Joanne T.", "last_name"=>"Blanchfield", "scopus_author_id"=>"6603686633"}, {"first_name"=>"Bruce D.", "last_name"=>"Wyse", "scopus_author_id"=>"7005606706"}, {"first_name"=>"Maree T.", "last_name"=>"Smith", "scopus_author_id"=>"55387899900"}, {"first_name"=>"Istvan", "last_name"=>"Toth", "scopus_author_id"=>"7103307460"}], "year"=>2012, "source"=>"PLoS ONE", "identifiers"=>{"issn"=>"19326203", "pmid"=>"22912681", "scopus"=>"2-s2.0-84865095335", "doi"=>"10.1371/journal.pone.0041909", "pui"=>"365452227", "isbn"=>"1932-6203 (Electronic)\\r1932-6203 (Linking)", "sgr"=>"84865095335"}, "id"=>"a5fd3eed-d965-33bf-87d9-fc9f868e3ca4", "abstract"=>"To enhance the drug-like properties of the endogenous opioid peptide endomorphin-1 (1 = Tyr-Pro-Trp-Phe-NH(2)), the N-terminus of the peptide was modified with 2-aminodecanoic acid, resulting in compound 3. Tyr in compound 1 was replaced with 2,6-dimethyltyrosine yielding compound 2. Derivative 2 was also substituted with 2-aminodecanoic acid producing compound, 4. Lipoamino acid-modified derivatives showed improved metabolic stability and membrane permeability while maintaining high μ-opioid (MOP) receptor binding affinity and acting as a potent agonist. In vivo studies showed dose-dependent antinociceptive activity following intravenous (i.v.) administration of compounds 3 and 4 in a chronic constriction injury (CCI)-rat model of neuropathic pain with ED(50) values of 1.22 (± 0.93) and 0.99 (± 0.89) µmol/kg, respectively. Pre-treatment of animals with naloxone hydrochloride significantly attenuated the anti-neuropathic effects of compound 3, confirming the key role of opioid receptors in mediating antinociception. In contrast to morphine, no significant constipation was produced following i.v. administration of compound 3 at 16 µmol/kg. Furthermore, following chronic administration of equi-potent doses of compound 3 and morphine to rats, there was less antinociceptive tolerance for compound 3 compared with morphine.", "link"=>"http://www.mendeley.com/research/lipoendomorphin1-derivatives-systemic-activity-against-neuropathic-pain-without-producing-constipati", "reader_count"=>8, "reader_count_by_academic_status"=>{"Professor > Associate Professor"=>1, "Researcher"=>2, "Student > Doctoral Student"=>1, "Student > Ph. D. Student"=>2, "Student > Master"=>1, "Professor"=>1}, "reader_count_by_user_role"=>{"Professor > Associate Professor"=>1, "Researcher"=>2, "Student > Doctoral Student"=>1, "Student > Ph. D. Student"=>2, "Student > Master"=>1, "Professor"=>1}, "reader_count_by_subject_area"=>{"Biochemistry, Genetics and Molecular Biology"=>1, "Medicine and Dentistry"=>1, "Neuroscience"=>1, "Pharmacology, Toxicology and Pharmaceutical Science"=>2, "Chemistry"=>3}, "reader_count_by_subdiscipline"=>{"Medicine and Dentistry"=>{"Medicine and Dentistry"=>1}, "Neuroscience"=>{"Neuroscience"=>1}, "Chemistry"=>{"Chemistry"=>3}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>1}, "Pharmacology, Toxicology and Pharmaceutical Science"=>{"Pharmacology, Toxicology and Pharmaceutical Science"=>2}}, "reader_count_by_country"=>{"United States"=>1}, "group_count"=>0}

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/310008"], "description"=>"<div><p>To enhance the drug-like properties of the endogenous opioid peptide endomorphin-1 (<b>1</b> = Tyr-Pro-Trp-Phe-NH<sub>2</sub>), the N-terminus of the peptide was modified with 2-aminodecanoic acid, resulting in compound <b>3</b>. Tyr in compound <b>1</b> was replaced with 2,6-dimethyltyrosine yielding compound <b>2</b>. Derivative <b>2</b> was also substituted with 2-aminodecanoic acid producing compound, <b>4</b>. Lipoamino acid-modified derivatives showed improved metabolic stability and membrane permeability while maintaining high μ-opioid (MOP) receptor binding affinity and acting as a potent agonist. <em>In vivo</em> studies showed dose-dependent antinociceptive activity following intravenous (i.v.) administration of compounds <b>3</b> and <b>4</b> in a chronic constriction injury (CCI)-rat model of neuropathic pain with ED<sub>50</sub> values of 1.22 (±0.93) and 0.99 (±0.89) µmol/kg, respectively. Pre-treatment of animals with naloxone hydrochloride significantly attenuated the anti-neuropathic effects of compound <b>3</b>, confirming the key role of opioid receptors in mediating antinociception. In contrast to morphine, no significant constipation was produced following i.v. administration of compound <b>3</b> at 16 µmol/kg. Furthermore, following chronic administration of equi-potent doses of compound <b>3</b> and morphine to rats, there was less antinociceptive tolerance for compound <b>3</b> compared with morphine.</p> </div>", "links"=>[], "tags"=>["lipo-endomorphin-1", "derivatives", "systemic", "neuropathic", "producing", "constipation"], "article_id"=>121152, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909", "stats"=>{"downloads"=>1, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Lipo_Endomorphin_1_Derivatives_with_Systemic_Activity_against_Neuropathic_Pain_without_Producing_Constipation/121152", "title"=>"Lipo-Endomorphin-1 Derivatives with Systemic Activity against Neuropathic Pain without Producing Constipation", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 00:19:12"}
  • {"files"=>["https://ndownloader.figshare.com/files/589077"], "description"=>"<p>Binding affinity of compound A) <b>1</b>, <b>2</b>, and <b>4</b>; B) <b>1,</b> and <b>3</b> determined by competitive displacement of [<sup>3</sup>H]DAMGO from whole SH-SY5Y cells. Data presented are mean (± SEM) from three separate experiments, each performed in triplicate.</p>", "links"=>[], "tags"=>["radioligand", "binding", "endomorphin-1", "analogs", "mop"], "article_id"=>259552, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g002", "stats"=>{"downloads"=>1, "page_views"=>18, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Competitive_radioligand_binding_of_endomorphin_1_and_its_analogs_to_MOP_receptors_/259552", "title"=>"Competitive radioligand binding of endomorphin-1 and its analogs to MOP receptors.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 02:39:12"}
  • {"files"=>["https://ndownloader.figshare.com/files/589799"], "description"=>"<p>A) Lack of inhibitory effect of <b>3</b> in doses up to 16 µmol/kg on castor-oil induced diarrhea in rats in contrast to the significant inhibitory effects of morphine at 2 µmol kg/kg. B) Lack of effect of analog <b>3</b> (16 µmol/kg) and vehicle in contrast to the inhibitory effect of morphine (2 µmol/kg) on the gastrointestinal transit of a charcoal meal in rats. Data are the mean (± SEM). ***<i>p</i><0.001, <i>vs.</i> vehicle (<i>n</i> = 8).</p>", "links"=>[], "tags"=>["morphine", "bolus"], "article_id"=>260282, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g009", "stats"=>{"downloads"=>0, "page_views"=>3, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Constipation_inducing_activity_of_compound_3_relative_to_morphine_following_single_i_v_bolus_dose_administration_/260282", "title"=>"Constipation-inducing activity of compound 3 relative to morphine following single i.v. bolus dose administration.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 00:04:42"}
  • {"files"=>["https://ndownloader.figshare.com/files/589448"], "description"=>"<p>Analogs <b>3</b> and <b>4</b> produced dose-dependent analgesia after single i.v. bolus administration to CCI-rats. The data are mean (± SEM).</p>", "links"=>[], "tags"=>["dose-response", "curves", "compounds"], "article_id"=>259925, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g005", "stats"=>{"downloads"=>1, "page_views"=>3, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Antinociceptive_dose_response_curves_for_compounds_3_and_4_/259925", "title"=>"Antinociceptive dose-response curves for compounds 3 and 4.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 02:45:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/589520"], "description"=>"<p>The highest doses of compounds <b>1</b> and <b>2</b> did not produce pain relief at 16 µmol/kg after single bolus i.v. administration to CCI-rats. Each value represents mean (± SEM) (<i>n</i> = 6–8).</p>", "links"=>[], "tags"=>["antinociception", "produced", "compounds"], "article_id"=>260006, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g006", "stats"=>{"downloads"=>0, "page_views"=>1, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Insignificant_antinociception_produced_by_compounds_1_and_2_/260006", "title"=>"Insignificant antinociception produced by compounds 1 and 2.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 00:00:06"}
  • {"files"=>["https://ndownloader.figshare.com/files/589187"], "description"=>"<p>Dose-response curves for the inhibitory effects of compounds A) <b>1</b>, <b>2</b>, and <b>4</b>; B) <b>1</b>, and <b>3</b> on forskolin-stimulated cAMP formation in SH-SY5Y cells. Data presented are mean (± SEM) from three separate experiments, each performed in triplicate.</p>", "links"=>[], "tags"=>["forskolin-induced"], "article_id"=>259671, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g003", "stats"=>{"downloads"=>0, "page_views"=>1, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Inhibition_of_forskolin_induced_cAMP_formation_/259671", "title"=>"Inhibition of forskolin-induced cAMP formation.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 02:41:11"}
  • {"files"=>["https://ndownloader.figshare.com/files/589928"], "description"=>"[a]<p>The apparent permeability, <i>P</i><sub>app</sub> (cm/s), across Caco-2 cell monolayers. Analysis were done using LC/MS and each point is expressed as mean ± SEM.</p>[b]<p>The <i>K</i><sub>iμ</sub> values of <b>1</b>, <b>2</b>, <b>3</b> and <b>4</b> for the MOP receptor were obtained using competitive radioligand binding assay. Competitive displacement of the MOP selective radioligand, [<sup>3</sup>H]DAMGO, was determined from whole SH-SY5Y cells in the presence of DPDPE (1 µM). Binding affinity values (<i>K</i><sub>iμ</sub>) were determined using seven concentrations of each compound in the range 10 pM to 1 µM performed in three independent experiments, each in triplicate. Data expressed as mean ± SEM. Competitive binding curves are shown in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0041909#pone-0041909-g002\" target=\"_blank\">Fig. 2</a>.</p>[c]<p>The IC<sub>50</sub> values (nM) were estimated from dose-response curves shown in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0041909#pone-0041909-g003\" target=\"_blank\">Fig. 3</a>. Inhibition of forskolin-stimulated cAMP formation was measured to determine the agonist activity of the compounds. Experiments were performed three independent times, each in triplicate.</p>[d]<p>These values are obtained from the same experiment. ND, not determined. Each value represents mean ± SEM. *<i>p</i><0.05, compared to compound <b>1</b> in the same experiment.</p>", "links"=>[], "tags"=>["chemistry", "neuroscience", "pharmacology", "anesthesiology and pain management", "Gastroenterology and hepatology", "neurological disorders"], "article_id"=>260399, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.t001", "stats"=>{"downloads"=>0, "page_views"=>3, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Summary_of_in_vitro_results_/260399", "title"=>"Summary of <i>in vitro</i> results.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2012-08-17 00:06:39"}
  • {"files"=>["https://ndownloader.figshare.com/files/589320"], "description"=>"<p>Paw withdrawal threshold (PWT) versus time curves for single bolus i.v. doses of compounds A) <b>3;</b> B) <b>4</b>, and vehicle in CCI-rats; C) The extent and duration of antinociception (areas under the ΔPWT versus time curves, ΔPWT AUC values) produced by single i.v. bolus doses of compounds <b>3</b> and <b>4</b> at 0.8 and 0.5 µmol/kg, respectively, was significantly greater than that produced by vehicle. This effect was comparable with the effect of morphine at 2 µmol/kg. Each value represents mean (± SEM). **<i>p</i><0.01, ***<i>p</i><0.001 compounds <b>3</b> and <b>4 </b><i>vs</i>. vehicle treated CCI-rats (<i>n</i> = 6–8).</p>", "links"=>[], "tags"=>["dosing", "compounds", "ipsilateral", "hindpaw"], "article_id"=>259804, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g004", "stats"=>{"downloads"=>1, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Intravenous_dosing_of_compounds_3_and_4_in_the_ipsilateral_hindpaw_of_CCI_rats_/259804", "title"=>"Intravenous dosing of compounds 3 and 4 in the ipsilateral hindpaw of CCI-rats.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 02:43:24"}
  • {"files"=>["https://ndownloader.figshare.com/files/589676"], "description"=>"<p>Single i.v. bolus doses of compounds <b>3</b> and <b>4</b> produced insignificant anti-allodynic responses in the contralateral hindpaws of CCI-rats in contrast to morphine at equi-effective doses. Each value is the mean (± SEM). ***<i>p</i><0.001, <i>vs.</i> vehicle treated CCI-rats, <i>p</i>>0.05 for compounds <b>3</b> and <b>4 </b><i>vs.</i> vehicle (<i>n</i> = 6–8).</p>", "links"=>[], "tags"=>["duration", "antinociception", "contralateral", "hindpaw"], "article_id"=>260151, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g007", "stats"=>{"downloads"=>0, "page_views"=>3, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Extent_and_duration_of_antinociception_in_the_contralateral_hindpaw_of_CCI_rats_/260151", "title"=>"Extent and duration of antinociception in the contralateral hindpaw of CCI-rats.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 00:02:31"}
  • {"files"=>["https://ndownloader.figshare.com/files/589854"], "description"=>"<p>Five consecutive i.v. bolus doses of compound <b>3</b> (1.6 µmol/kg) or morphine (2 µmol/kg) were administered twice-daily to CCI-rats. The mean (± SEM) ΔPWT AUC values were significantly lower for the 5<sup>th</sup> dose c.f. the 1<sup>st</sup> dose, demonstrating that antinociceptive tolerance had developed; however, the extent of tolerance developed to the analgesic effects of compound <b>3</b> was lower than that of morphine. There was no evidence of antinociceptive tolerance in the negative control group rats for treated with compound <b>3</b> for the 1<sup>st</sup> dose followed by vehicle for doses 2–4 and then compound <b>3</b> for the 5<sup>th</sup> dose. Data are the mean (± SEM). **<i>p</i><0.01, ***<i>p</i><0.001, <i>vs.</i> 1<sup>st</sup> dose of the compounds (<i>n</i> = 8).</p>", "links"=>[], "tags"=>["analgesic"], "article_id"=>260344, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g010", "stats"=>{"downloads"=>0, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Development_of_tolerance_to_the_analgesic_effect_of_compound_3_and_morphine_/260344", "title"=>"Development of tolerance to the analgesic effect of compound 3 and morphine.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 00:05:44"}
  • {"files"=>["https://ndownloader.figshare.com/files/589736"], "description"=>"<p>The anti-allodynic effects of single i.v. bolus doses of compound <b>3</b> were abolished by naloxone (10 mg/kg s.c.) in the ipsilateral hindpaws of opioid-naive CCI-rats (1.6 µmol/kg, <i>n</i> = 6) in a manner similar to morphine (2 µmol/kg) Each value is the mean (± SEM). **<i>p</i><0.01, <i>vs.</i> vehicle pre-treated rats (<i>n</i> = 6).</p>", "links"=>[], "tags"=>["opioid", "receptor"], "article_id"=>260225, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g008", "stats"=>{"downloads"=>0, "page_views"=>42, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Pre_treatment_with_the_opioid_receptor_antagonist_/260225", "title"=>"Pre-treatment with the opioid receptor antagonist.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 00:03:45"}
  • {"files"=>["https://ndownloader.figshare.com/files/589002"], "description"=>"<p>Structure of endomorphin-1 (1) and its derivatives (2–4).</p>", "links"=>[], "tags"=>["endomorphin-1", "derivatives"], "article_id"=>259487, "categories"=>["Genetics", "Neuroscience", "Chemistry", "Pharmacology"], "users"=>["Pegah Varamini", "Friederike M. Mansfeld", "Joanne T. Blanchfield", "Bruce D. Wyse", "Maree T. Smith", "Istvan Toth"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0041909.g001", "stats"=>{"downloads"=>0, "page_views"=>6, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Structure_of_endomorphin_1_1_and_its_derivatives_2_8211_4_/259487", "title"=>"Structure of endomorphin-1 (1) and its derivatives (2–4).", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-08-17 02:38:07"}

PMC Usage Stats | Further Information

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Relative Metric

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