{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T05:36:28Z","timestamp":1760852188733},"reference-count":27,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2005,7,29]],"date-time":"2005-07-29T00:00:00Z","timestamp":1122595200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["The Journal of Peptide Research"],"published-print":{"date-parts":[[2005,9]]},"abstract":"<jats:p><jats:bold>Abstract:\u2002<\/jats:bold> A series of position 4\u2010substituted endomorphin\u20102 (Tyr\u2010Pro\u2010Phe\u2010Phe\u2010NH<jats:sub>2<\/jats:sub>) analogs containing 3\u2010(1\u2010naphthyl)\u2010alanine (1\u2010Nal) or 3\u2010(2\u2010naphthyl)\u2010alanine (2\u2010Nal) in <jats:sc>l<\/jats:sc>\u2010 or <jats:sc>d<\/jats:sc>\u2010configuration, was synthesized. The opioid activity profiles of these peptides were determined in the <jats:italic>\u03bc<\/jats:italic>\u2010opioid receptor representative binding assay and in the Guinea\u2010Pig Ileum assay\/Mouse Vas Deferens assay (GPI\/MVD) bioassays in vitro, as well as in the mouse hot\u2010plate test of analgesia in vivo. In the binding assay the affinity of all new analogs for the <jats:italic>\u03bc<\/jats:italic>\u2010opioid receptor was reduced compared with endomorphin\u20102. The two most potent analogs were [<jats:sc>d<\/jats:sc>\u20101\u2010Nal<jats:sup>4<\/jats:sup>]\u2010 and [<jats:sc>d<\/jats:sc>\u20102\u2010Nal<jats:sup>4<\/jats:sup>]endomorphin\u20102, with IC<jats:sub>50<\/jats:sub> values 14\u2003\u00b1\u20031.25 and 19\u2003\u00b1\u20032.1\u2003n<jats:sc>m<\/jats:sc>, respectively, compared with 1.9\u2003\u00b1\u20030.21\u2003n<jats:sc>m<\/jats:sc> for endomorphin\u20102. In the GPI assay these analogs were found to be weak antagonists and they were inactive in the MVD assay. The in vitro GPI assay results were in agreement with those obtained in the in vivo hot\u2010plate test. Antinociception induced by endomorphin\u20102 was reversed by concomitant intracerebroventricula (i.c.v.) administration of [<jats:sc>d<\/jats:sc>\u20101\u2010Nal<jats:sup>4<\/jats:sup>]\u2010 and [<jats:sc>d<\/jats:sc>\u20102\u2010Nal<jats:sup>4<\/jats:sup>]\u2010endomorphin\u20102, indicating that these analogs were <jats:italic>\u03bc<\/jats:italic>\u2010opioid antagonists. Their antagonist activity was compared with that of naloxone. At a dose 5\u2003<jats:italic>\u03bc<\/jats:italic>g per animal naloxone almost completely inhibited antinociceptive action of endomorphin\u20102, while [<jats:sc>d<\/jats:sc>\u20101\u2010Nal<jats:sup>4<\/jats:sup>]endomorphin\u20102 in about 46%.<\/jats:p>","DOI":"10.1111\/j.1399-3011.2005.00282.x","type":"journal-article","created":{"date-parts":[[2005,7,29]],"date-time":"2005-07-29T16:39:38Z","timestamp":1122655178000},"page":"125-131","source":"Crossref","is-referenced-by-count":11,"title":["Novel endomorphin\u20102 analogs with <i>\u03bc<\/i>\u2010opioid receptor antagonist activity"],"prefix":"10.1111","volume":"66","author":[{"given":"R.","family":"Kruszynski","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J.","family":"Fichna","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J.\u2010C.","family":"Do\u2010Rego","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"N.N.","family":"Chung","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"P.W.","family":"Schiller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"P.","family":"Kosson","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J.","family":"Costentin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A.","family":"Janecka","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2008,12,5]]},"reference":[{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/386499a0"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0196-9781(97)00259-3"},{"key":"e_1_2_7_4_2","first-page":"1007","article-title":"Pharmacological characterization of endomorphin\u20101 and endomorphin\u20102 in mouse brain","volume":"286","author":"Goldberg I.E.","year":"1998","journal-title":"J. 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