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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. 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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
ffa0b49d-b749-44bd-85f4-ce5b4d5c7604
e90f77c2-9a4c-4229-a09e-e1778f85a248
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Reactions Reactions of the melatonin metabolite N1.pdf (270 Kb)
Publication type
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.
Keywords
ABTS cation radical
Identifier http://uyr.uy.edu.mm/handle/123456789/108
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