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Effects of Terminal...
Effects of Terminal Dimethylation and Metal Coordination of Proline-2-formylpyridine Thiosemicarbazone Hybrids on Lipophilicity, Antiproliferative Activity, and hR2 RNR Inhibition
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Bacher, Felix (author)
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Doemoetoer, Orsolya (author)
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Kaltenbrunner, Maria (author)
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Mojovic, Milos (author)
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Popovic-Bijelic, Ana (author)
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- Gräslund, Astrid (author)
- Stockholms universitet,Institutionen för biokemi och biofysik
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Ozarowski, Andrew (author)
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Filipovic, Lana (author)
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Radulovic, Sinisa (author)
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Enyedy, Eva A. (author)
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Arion, Vladimir B. (author)
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(creator_code:org_t)
- 2014-11-12
- 2014
- English.
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In: Inorganic Chemistry. - : American Chemical Society (ACS). - 0020-1669 .- 1520-510X. ; 53:23, s. 12595-12609
- Related links:
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http://real.mtak.hu/...
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
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- The nickel(II), copper(II), and zinc(II) complexes of the proline-thiosemicarbazone hybrids 3-methyl-(S)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazone (l-Pro-FTSC or (S)-H2L1) and 3-methyl-(R)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazone (d-Pro-FTSC or (R)-H2L1), as well as 3-methyl-(S)-pyrrolidine-2-carboxylate-2-formylpyridine 4,4-dimethyl-thiosemicarbazone (dm-l-Pro-FTSC or (S)-H2L2), namely, [Ni(l-Pro-FTSC-2H)](2) (1), [Ni(d-Pro-FTSC-2H)](2) (2), [Ni(dm-l-Pro-FTSC-2H)](2) (3), [Cu(dm-l-Pro-FTSC-2H)] (6), [Zn(l-Pro-FTSC-2H)] (7), and [Zn(d-Pro-FTSC-2H)] (8), in addition to two previously reported, [Cu(l-Pro-FTSC-2H)] (4), [Cu(d-Pro-FTSC-2H)] (5), were synthesized and characterized by elemental analysis, one- and two-dimensional (1)H and (13)C NMR spectroscopy, circular dichroism, UV-vis, and electrospray ionization mass spectrometry. Compounds 1-3, 6, and 7 were also studied by single-crystal X-ray diffraction. Magnetic properties and solid-state high-field electron paramagnetic resonance spectra of 2 over the range of 50-420 GHz were investigated. The complex formation processes of l-Pro-FTSC with nickel(II) and zinc(II) were studied in aqueous solution due to the excellent water solubility of the complexes via pH potentiometry, UV-vis, and (1)H NMR spectroscopy. The results of the antiproliferative activity in vitro showed that dimethylation improves the cytotoxicity and hR2 RNR inhibition. Therefore, introduction of more lipophilic groups into thiosemicarbazone-proline backbone becomes an option for the synthesis of more efficient cytotoxic agents of this family of compounds.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
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- ref (subject category)
- art (subject category)
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- By the author/editor
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Bacher, Felix
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Doemoetoer, Orso ...
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Kaltenbrunner, M ...
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Mojovic, Milos
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Popovic-Bijelic, ...
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Gräslund, Astrid
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show more...
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Ozarowski, Andre ...
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Filipovic, Lana
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Radulovic, Sinis ...
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Enyedy, Eva A.
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Arion, Vladimir ...
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show less...
- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
- Articles in the publication
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Inorganic Chemis ...
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Stockholm University