Index Link

  • RootNode

Item

{"_buckets": {"deposit": "29aaeebf-df32-48e9-b452-7b209e662d4d"}, "_deposit": {"id": "2311", "owners": [], "pid": {"revision_id": 0, "type": "recid", "value": "2311"}, "status": "published"}, "_oai": {"id": "oai:meral.edu.mm:recid/2311", "sets": ["user-uy"]}, "communities": ["ccm", "ccp", "kyauksetu", "ltc", "maas", "miit", "mlmu", "mmu", "mtlu", "mtu", "mub", "mude", "mufl", "pathein", "scu", "suoe", "tcu", "tgu", "tuh", "tum", "ucsm", "ucsmtla", "ucsmub", "ucspathein", "ucstaungoo", "ucsy", "udmm", "udmy", "uit", "um", "um1", "um2", "umkn", "umm", "uphy", "urj", "uvs", "uy", "yau", "ydbu", "ytu", "yude", "yueco", "yufl", "yuoe"], "control_number": "2311", "item_1583103067471": {"attribute_name": "Title", "attribute_value_mlt": [{"subitem_1551255647225": "Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones", "subitem_1551255648112": "en"}]}, "item_1583103085720": {"attribute_name": "Description", "attribute_value_mlt": [{"interim": "Melatonin had previously been shown to reduce up to four 2,2-\r azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid) cation radicals (ABTS•+)\r via a scavenger cascade ending with N1\r -acetyl-N2\r -formyl-5-\r methoxykynuramine (AFMK). However, when melatonin is added to the\r reaction system in much lower quantities than ABTS•+, the number of\r radicals scavenged per melatonin molecule is considerably higher and can\r attain a value of ten. Under conditions allowing for such a stoichiometry,\r novel products have been detected which derive from AFMK (1). These were\r separated by repeated chromatography and the major compounds were\r characterized by spectroscopic methods, such as mass spectrometry (HPLCMS,\r EI-MS and ESI-HRMS), 1\r H nuclear magnetic resonance (NMR) and 13C NMR, heteronuclear multiple bond connectivity (HMBC) correlations.\r The identified substances are formed by re-cyclization and represent 3-\r indolinones carrying the side chain at C2; the N-formyl group can be\r maintained, but deformylated analogs seem to be also generated, according\r to MS. The primary product from AFMK (1) is N-(1-formyl-5-methoxy-3-\r oxo-2,3-dihydro-1H-indol-2-ylidenemethyl)-acetamide (2), which is obtained\r after purification as E- and Z-isomers (2a, 2b); a secondary product has been\r identified as N-(1-formyl-2-hydroxy-5-methoxy-3-oxo-2,3-dihydro-1H-indol-\r 2-ylmethyl)-acetamide (3). When H2O2 is added to the ABTS•+ reaction\r mixture in quantities not already leading to substantial reduction of this\r radical, compound 3 is isolated as the major product, whereas 2a and 2b are\r virtually absent. The substances formed differ from all previously known\r oxidation products which derive from melatonin and are, among these, the\r first 3-indolinones. Moreover, the aliphatic side chain at C2 is reminiscent of\r other substances which have been synthesized in the search for melatonin\r receptor ligands."}]}, "item_1583103108160": {"attribute_name": "Keywords", "attribute_value_mlt": [{"interim": "ABTS"}]}, "item_1583103131163": {"attribute_name": "Journal articles", "attribute_value_mlt": [{}]}, "item_1583103147082": {"attribute_name": "Conference papaers", "attribute_value_mlt": [{}]}, "item_1583103211336": {"attribute_name": "Books/reports/chapters", "attribute_value_mlt": [{}]}, "item_1583103233624": {"attribute_name": "Thesis/dissertations", "attribute_value_mlt": [{"subitem_supervisor(s)": []}]}, "item_1583105942107": {"attribute_name": "Authors", "attribute_value_mlt": [{"subitem_authors": [{"subitem_authors_fullname": "Rosen, Joachim"}, {"subitem_authors_fullname": "Ni Ni Than"}, {"subitem_authors_fullname": "Koch, Dorothea"}, {"subitem_authors_fullname": "Poeggeler, Burkhard"}, {"subitem_authors_fullname": "Laatsch, Hartmut"}, {"subitem_authors_fullname": "Hardeland, Rüdiger"}]}]}, "item_1583108359239": {"attribute_name": "Upload type", "attribute_value_mlt": [{"interim": "Publication"}]}, "item_1583108428133": {"attribute_name": "Publication type", "attribute_value_mlt": [{"interim": "Journal article"}]}, "item_1583159729339": {"attribute_name": "Publication date", "attribute_value": "2006"}, "item_1583159847033": {"attribute_name": "Identifier", "attribute_value": "http://uyr.uy.edu.mm/handle/123456789/113"}, "item_title": "Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones", "item_type_id": "21", "owner": "1", "path": ["1582967633684"], "permalink_uri": "http://hdl.handle.net/20.500.12678/0000002311", "pubdate": {"attribute_name": "Deposited date", "attribute_value": "2020-03-05"}, "publish_date": "2020-03-05", "publish_status": "0", "recid": "2311", "relation": {}, "relation_version_is_last": true, "title": ["Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones"], "weko_shared_id": -1}

Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones

http://hdl.handle.net/20.500.12678/0000002311
21e822ef-4849-466d-9161-3b3295195811
29aaeebf-df32-48e9-b452-7b209e662d4d
Publication type
Journal article
Upload type
Publication
Title
Title Interactions of melatonin and its metabolites with the ABTS cation radical: extension of the radical scavenger cascade and formation of a novel class of oxidation products, C2-substituted 3-indolinones
Language en
Publication date 2006
Authors
Rosen, Joachim
Ni Ni Than
Koch, Dorothea
Poeggeler, Burkhard
Laatsch, Hartmut
Hardeland, Rüdiger
Description
Melatonin had previously been shown to reduce up to four 2,2-
azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid) cation radicals (ABTS•+)
via a scavenger cascade ending with N1
-acetyl-N2
-formyl-5-
methoxykynuramine (AFMK). However, when melatonin is added to the
reaction system in much lower quantities than ABTS•+, the number of
radicals scavenged per melatonin molecule is considerably higher and can
attain a value of ten. Under conditions allowing for such a stoichiometry,
novel products have been detected which derive from AFMK (1). These were
separated by repeated chromatography and the major compounds were
characterized by spectroscopic methods, such as mass spectrometry (HPLCMS,
EI-MS and ESI-HRMS), 1
H nuclear magnetic resonance (NMR) and 13C NMR, heteronuclear multiple bond connectivity (HMBC) correlations.
The identified substances are formed by re-cyclization and represent 3-
indolinones carrying the side chain at C2; the N-formyl group can be
maintained, but deformylated analogs seem to be also generated, according
to MS. The primary product from AFMK (1) is N-(1-formyl-5-methoxy-3-
oxo-2,3-dihydro-1H-indol-2-ylidenemethyl)-acetamide (2), which is obtained
after purification as E- and Z-isomers (2a, 2b); a secondary product has been
identified as N-(1-formyl-2-hydroxy-5-methoxy-3-oxo-2,3-dihydro-1H-indol-
2-ylmethyl)-acetamide (3). When H2O2 is added to the ABTS•+ reaction
mixture in quantities not already leading to substantial reduction of this
radical, compound 3 is isolated as the major product, whereas 2a and 2b are
virtually absent. The substances formed differ from all previously known
oxidation products which derive from melatonin and are, among these, the
first 3-indolinones. Moreover, the aliphatic side chain at C2 is reminiscent of
other substances which have been synthesized in the search for melatonin
receptor ligands.
Keywords
ABTS
Identifier http://uyr.uy.edu.mm/handle/123456789/113
Journal articles
Conference papaers
Books/reports/chapters
Thesis/dissertations
0
0
views
downloads
Views Downloads

Export

OAI-PMH
  • OAI-PMH DublinCore
Other Formats