{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T15:04:50Z","timestamp":1761059090007,"version":"build-2065373602"},"reference-count":35,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2010,6,23]],"date-time":"2010-06-23T00:00:00Z","timestamp":1277251200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2010,7,26]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:italic>Cyanobacterial hepatotoxins (microcystins and nodularins) cause numerous animal poisonings worldwide each year and are threats to human health. However, we found that extracts from several cyanobacteria isolates failed to induce hepatotoxicity even if they contained high concentrations of the liver toxin microcystin. The antitoxic activity abolishes all morphological hallmarks of microcystin\u2010induced apoptosis, and therefore invalidates cell\u2010based assays of the microcystin content of bloom\u2010forming cyanobacteria. The antitoxin was purified from a cyanobacterial isolate (<\/jats:italic>Nostoc <jats:italic>sp. XSPORK 13A) from the Baltic Sea, and the activity was shown to reside in a novel cyclic peptide of the nostocyclopeptide family (nostocyclopeptide M1, Ncp\u2010M1) that consists of seven amino acids (Tyr<jats:sup>1<\/jats:sup>\u2010Tyr<jats:sup>2<\/jats:sup>\u2010<jats:sc>D<\/jats:sc>\u2010HSe<jats:sup>3<\/jats:sup>\u2010<jats:sc>L<\/jats:sc>\u2010Pro<jats:sup>4<\/jats:sup>\u2010<jats:sc>L<\/jats:sc>\u2010Val<jats:sup>5<\/jats:sup>\u2010(2<\/jats:italic>S<jats:italic>,4<\/jats:italic>S<jats:italic>)\u20104\u2010MPr<jats:sup>6<\/jats:sup>\u2010Tyr<jats:sup>7<\/jats:sup>;<\/jats:italic> M<jats:italic><jats:sub>W<\/jats:sub>=881) with an imino linkage between Tyr1 and Tyr7. Ncp\u2010M1 did not compete with labelled microcystin for binding to protein phosphatase 2A; this explains why the antitoxin did not interfere with phosphatase\u2010based microcystin assays. Currently used agents that interfere with microcystin action, such as inhibitors of ROS formation, microcystin uptake and Cam\u2010kinase activity, are themselves inherently toxic. Since Ncp\u2010M1 is potent and nontoxic it promises to become a useful mechanistic tool as soon as its exact cellular target is elucidated.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cbic.201000179","type":"journal-article","created":{"date-parts":[[2010,6,23]],"date-time":"2010-06-23T13:03:27Z","timestamp":1277298207000},"page":"1594-1599","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":45,"title":["A Novel Cyanobacterial Nostocyclopeptide is a Potent Antitoxin against Microcystins"],"prefix":"10.1002","volume":"11","author":[{"given":"Jouni","family":"Jokela","sequence":"first","affiliation":[]},{"given":"Lars","family":"Herfindal","sequence":"additional","affiliation":[]},{"given":"Matti","family":"Wahlsten","sequence":"additional","affiliation":[]},{"given":"Perttu","family":"Permi","sequence":"additional","affiliation":[]},{"given":"Frode","family":"Selheim","sequence":"additional","affiliation":[]},{"given":"Vitor","family":"Vascon\u00e7elos","sequence":"additional","affiliation":[]},{"given":"Stein Ove","family":"D\u00f8skeland","sequence":"additional","affiliation":[]},{"given":"Kaarina","family":"Sivonen","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2010,7,19]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2004.06.003"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt1266"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2007.01.012"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6976.2006.00022.x"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-012373944-5.00005-5"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/np010597b"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200800415"},{"key":"e_1_2_6_8_2","first-page":"577","volume":"40","author":"Honkanen R. E.","year":"1991","journal-title":"Mol. Pharmacol."},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.cdd.4400590"},{"key":"e_1_2_6_10_2","first-page":"215","volume":"23","author":"Rao P. V. L.","year":"2002","journal-title":"J. Environ. Biol."},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac035118n"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/0041-0101(94)90354-9"},{"key":"e_1_2_6_13_2","first-page":"451","volume":"73","author":"Chu F. S.","year":"1990","journal-title":"J. Assoc. Off. Anal. Chem."},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0041-0101(99)00163-4"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-5793(90)80245-E"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0041-0101(98)00083-X"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1177\/030098588902600309"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.taap.2004.06.002"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxicon.2005.04.005"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/psc.325"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-004-0118-0"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/np000316k"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0667458"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200800314"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2958.2009.06816.x"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.2174\/138955706776073475"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-4827(91)90523-W"},{"key":"e_1_2_6_28_2","unstructured":"J. Kotai Instructions for Preparation of Modified Nutrient Solution Z8 for Algae Norwegian Institute for Water Research Oslo Norway 1972."},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2672.2005.02687.x"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)01192-1"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/0041-0101(86)90083-8"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/0076-6879(88)59039-0"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcp.1041630203"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0091-679X(08)61797-5"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.cdd.4401798"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.201000179","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.201000179","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:00:37Z","timestamp":1760288437000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.201000179"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,7,19]]},"references-count":35,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2010,7,26]]}},"alternative-id":["10.1002\/cbic.201000179"],"URL":"https:\/\/doi.org\/10.1002\/cbic.201000179","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"type":"print","value":"1439-4227"},{"type":"electronic","value":"1439-7633"}],"subject":[],"published":{"date-parts":[[2010,7,19]]},"assertion":[{"value":"2010-03-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2010-07-19","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}