N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes
The platinum(II) complexes trans-[PtCl2(Ln)2]∙xSolv 1–13 (Solv = H2O or CH3OH), involving N6-benzyladenosine-based N-donor ligands, were synthesized; Ln stands for N6-(2-methoxybenzyl)adenosine (L1, involved in complex 1), N6-(4-methoxy-benzyl)adenosine (L2, 2), N6-(2-chlorobenzyl)adenosine (L3, 3),...
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| Format: | Article |
| Language: | English |
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MDPI AG
2013-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/18/6/6990 |
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| author | Ján Vančo Zdeněk Trávníček Igor Popa Pavel Štarha |
| author_facet | Ján Vančo Zdeněk Trávníček Igor Popa Pavel Štarha |
| author_sort | Ján Vančo |
| collection | DOAJ |
| description | The platinum(II) complexes trans-[PtCl2(Ln)2]∙xSolv 1–13 (Solv = H2O or CH3OH), involving N6-benzyladenosine-based N-donor ligands, were synthesized; Ln stands for N6-(2-methoxybenzyl)adenosine (L1, involved in complex 1), N6-(4-methoxy-benzyl)adenosine (L2, 2), N6-(2-chlorobenzyl)adenosine (L3, 3), N6-(4-chlorobenzyl)-adenosine (L4, 4), N6-(2-hydroxybenzyl)adenosine (L5, 5), N6-(3-hydroxybenzyl)-adenosine (L6, 6), N6-(2-hydroxy-3-methoxybenzyl)adenosine (L7, 7), N6-(4-fluoro-benzyl)adenosine (L8, 8), N6-(4-methylbenzyl)adenosine (L9, 9), 2-chloro-N6-(3-hydroxy-benzyl)adenosine (L10, 10), 2-chloro-N6-(4-hydroxybenzyl)adenosine (L11, 11), 2-chloro-N6-(2-hydroxy-3-methoxybenzyl)adenosine (L12, 12) and 2-chloro-N6-(2-hydroxy-5-methylbenzyl)adenosine (L13, 13). The compounds were characterized by elemental analysis, mass spectrometry, IR and multinuclear (1H-, 13C-, 195Pt- and 15N-) and two-dimensional NMR spectroscopy, which proved the N7-coordination mode of the appropriate N6-benzyladenosine derivative and trans-geometry of the title complexes. The complexes 1–13 were found to be non-toxic in vitro against two selected human cancer cell lines (HOS and MCF7; with IC50 > 50.0 µM). However, they were found (by ESI-MS study) to be able to interact with the physiological levels of the sulfur-containing biogenic biomolecule L-methionine by a relatively simple 1:1 exchange mechanism (one Ln molecule was replaced by one L-methionine molecule), thus forming a mixed-nitrogen/sulfur-ligand dichlorido-platinum(II) coordination species. |
| first_indexed | 2024-12-23T19:55:12Z |
| format | Article |
| id | doaj.art-2147ba188f7f4437be293f9b83dbcbc2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T19:55:12Z |
| publishDate | 2013-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2147ba188f7f4437be293f9b83dbcbc22022-12-21T17:33:15ZengMDPI AGMolecules1420-30492013-06-011866990700310.3390/molecules18066990N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido ComplexesJán VančoZdeněk TrávníčekIgor PopaPavel ŠtarhaThe platinum(II) complexes trans-[PtCl2(Ln)2]∙xSolv 1–13 (Solv = H2O or CH3OH), involving N6-benzyladenosine-based N-donor ligands, were synthesized; Ln stands for N6-(2-methoxybenzyl)adenosine (L1, involved in complex 1), N6-(4-methoxy-benzyl)adenosine (L2, 2), N6-(2-chlorobenzyl)adenosine (L3, 3), N6-(4-chlorobenzyl)-adenosine (L4, 4), N6-(2-hydroxybenzyl)adenosine (L5, 5), N6-(3-hydroxybenzyl)-adenosine (L6, 6), N6-(2-hydroxy-3-methoxybenzyl)adenosine (L7, 7), N6-(4-fluoro-benzyl)adenosine (L8, 8), N6-(4-methylbenzyl)adenosine (L9, 9), 2-chloro-N6-(3-hydroxy-benzyl)adenosine (L10, 10), 2-chloro-N6-(4-hydroxybenzyl)adenosine (L11, 11), 2-chloro-N6-(2-hydroxy-3-methoxybenzyl)adenosine (L12, 12) and 2-chloro-N6-(2-hydroxy-5-methylbenzyl)adenosine (L13, 13). The compounds were characterized by elemental analysis, mass spectrometry, IR and multinuclear (1H-, 13C-, 195Pt- and 15N-) and two-dimensional NMR spectroscopy, which proved the N7-coordination mode of the appropriate N6-benzyladenosine derivative and trans-geometry of the title complexes. The complexes 1–13 were found to be non-toxic in vitro against two selected human cancer cell lines (HOS and MCF7; with IC50 > 50.0 µM). However, they were found (by ESI-MS study) to be able to interact with the physiological levels of the sulfur-containing biogenic biomolecule L-methionine by a relatively simple 1:1 exchange mechanism (one Ln molecule was replaced by one L-methionine molecule), thus forming a mixed-nitrogen/sulfur-ligand dichlorido-platinum(II) coordination species.http://www.mdpi.com/1420-3049/18/6/6990platinum(II) complexestransplatin derivativesN6-benzyladenosine derivativesmultinuclear NMRantitumor activity |
| spellingShingle | Ján Vančo Zdeněk Trávníček Igor Popa Pavel Štarha N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes Molecules platinum(II) complexes transplatin derivatives N6-benzyladenosine derivatives multinuclear NMR antitumor activity |
| title | N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes |
| title_full | N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes |
| title_fullStr | N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes |
| title_full_unstemmed | N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes |
| title_short | N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes |
| title_sort | n6 benzyladenosine derivatives as novel n donor ligands of platinum ii dichlorido complexes |
| topic | platinum(II) complexes transplatin derivatives N6-benzyladenosine derivatives multinuclear NMR antitumor activity |
| url | http://www.mdpi.com/1420-3049/18/6/6990 |
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