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Item
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Several new oxidation products were obtained, which\r were separated by repeated chromatography and characterized by spectroscopic methods such as\r mass spectrometry (ESI-MS and ESI-HRMS), 1\r H-NMR and 13C-NMR, HMBC, HSQC, H,H COSY\r correlations and IR spectroscopy. The main products were oligomers of 1 (3 dimers, 1 trimer and 2\r tetramers). In all cases, the amino group N2 was involved in the reactions. Two of the dimers turned\r out to be cis (2a) and trans (2b) isomers containing an azo bond. In the other dimer (3a), the\r nitrogen atom N2 was attached to atom C5 of the second aromatic amine, with loss of the methoxy\r group. In the trimer (5), one N2 formed a bridge to C5 of unit B, as in the respective dimer, while this\r one of C had bridged to C6 of B. One of the tetramers (6) was composed of a trimer 5 attached to N2\r of a fourth 1 molecule via an azo bond as in 2a/b. In the other tetramer (7), an additional C–C bond\r between rings B and C in 6 is assumed. Although oligomers of AMK may only attain low in vivo\r concentrations, the types of reactions observed shed light on the physiologically possible\r metabolism of AMK once reacted with a free radical. The displacement of a methoxy group, rarely\r seen in the oxidation of methoxylated biomolecules, underlines the reactivity of AMK (1).\r Preliminary data show that, in the presence of ABTS cation radicals, AMK (1) can interact with side\r chains of aromatic amino acids, a finding which may be crucial for understanding to date\r unidentified protein modification by a melatonin metabolite detected earlier in experiments with\r radioactively labeled melatonin."}]}, "item_1583103108160": {"attribute_name": "Keywords", "attribute_value_mlt": [{"interim": "ABTS cation radical"}]}, "item_1583103120197": {"attribute_name": "Files", "attribute_type": "file", "attribute_value_mlt": [{"accessrole": "open_access", "date": [{"dateType": "Available", "dateValue": "2020-05-05"}], "displaytype": "preview", "download_preview_message": "", "file_order": 0, "filename": "Reactions of the melatonin metabolite N1.pdf", "filesize": [{"value": "270 Kb"}], "format": "application/pdf", "future_date_message": "", "is_thumbnail": false, "licensetype": "license_free", "mimetype": "application/pdf", "size": 270000.0, "url": {"url": "https://meral.edu.mm/record/2177/files/Reactions of the melatonin metabolite N1.pdf"}, "version_id": "32250e96-ee2f-41fc-bb9e-4ebfc903d6c5"}]}, "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": "Ni Ni Than"}, {"subitem_authors_fullname": "Heer, Christina"}, {"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": "2005"}, "item_1583159847033": {"attribute_name": "Identifier", "attribute_value": "http://uyr.uy.edu.mm/handle/123456789/108"}, "item_title": "Reactions of the melatonin metabolite N1-acetyl-5- methoxykynuramine (AMK) with the ABTS cation radical: identification of new oxidation products", "item_type_id": "21", "owner": "1", "path": ["1582967633684"], "permalink_uri": "http://hdl.handle.net/20.500.12678/0000002177", "pubdate": {"attribute_name": "Deposited date", "attribute_value": "2020-03-05"}, "publish_date": "2020-03-05", "publish_status": "0", "recid": "2177", "relation": {}, "relation_version_is_last": true, "title": ["Reactions of the melatonin metabolite N1-acetyl-5- methoxykynuramine (AMK) with the ABTS cation radical: identification of new oxidation products"], "weko_shared_id": -1}
Reactions of the melatonin metabolite N1-acetyl-5- methoxykynuramine (AMK) with the ABTS cation radical: identification of new oxidation products
http://hdl.handle.net/20.500.12678/0000002177
http://hdl.handle.net/20.500.12678/0000002177ffa0b49d-b749-44bd-85f4-ce5b4d5c7604
e90f77c2-9a4c-4229-a09e-e1778f85a248
Name / File | License | Actions |
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Publication type | ||||||
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Journal article | ||||||
Upload type | ||||||
Publication | ||||||
Title | ||||||
Title | Reactions of the melatonin metabolite N1-acetyl-5- methoxykynuramine (AMK) with the ABTS cation radical: identification of new oxidation products | |||||
Language | en | |||||
Publication date | 2005 | |||||
Authors | ||||||
Ni Ni Than | ||||||
Heer, Christina | ||||||
Laatsch, Hartmut | ||||||
Hardeland, Rüdiger | ||||||
Description | ||||||
The melatonin metabolite N1 -acetyl-5-methoxykynuramine (AMK; 1), which was previously shown to be a potent radical scavenger, was oxidized using the ABTS cation radical [ABTS = 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonic acid)]. Several new oxidation products were obtained, which were separated by repeated chromatography and characterized by spectroscopic methods such as mass spectrometry (ESI-MS and ESI-HRMS), 1 H-NMR and 13C-NMR, HMBC, HSQC, H,H COSY correlations and IR spectroscopy. The main products were oligomers of 1 (3 dimers, 1 trimer and 2 tetramers). In all cases, the amino group N2 was involved in the reactions. Two of the dimers turned out to be cis (2a) and trans (2b) isomers containing an azo bond. In the other dimer (3a), the nitrogen atom N2 was attached to atom C5 of the second aromatic amine, with loss of the methoxy group. In the trimer (5), one N2 formed a bridge to C5 of unit B, as in the respective dimer, while this one of C had bridged to C6 of B. One of the tetramers (6) was composed of a trimer 5 attached to N2 of a fourth 1 molecule via an azo bond as in 2a/b. In the other tetramer (7), an additional C–C bond between rings B and C in 6 is assumed. Although oligomers of AMK may only attain low in vivo concentrations, the types of reactions observed shed light on the physiologically possible metabolism of AMK once reacted with a free radical. The displacement of a methoxy group, rarely seen in the oxidation of methoxylated biomolecules, underlines the reactivity of AMK (1). Preliminary data show that, in the presence of ABTS cation radicals, AMK (1) can interact with side chains of aromatic amino acids, a finding which may be crucial for understanding to date unidentified protein modification by a melatonin metabolite detected earlier in experiments with radioactively labeled melatonin. |
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Keywords | ||||||
ABTS cation radical | ||||||
Identifier | http://uyr.uy.edu.mm/handle/123456789/108 | |||||
Journal articles | ||||||
Conference papaers | ||||||
Books/reports/chapters | ||||||
Thesis/dissertations |