| Tartalom: |
http://dx.doi.org/10.1016/j.jorganchem.2015.07.012 |
| Archívum: |
MTA Könyvtár |
| Gyűjtemény: |
Status = Published
Type = Article
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| Cím: |
Synthesis and anticancer activity studies of ferrocenyl-thymine-3,6-dihydro-2H-thiopyranes ? a new class of metallocene-nucleobase derivatives
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| Létrehozó: |
Skiba, Joanna
Karpowicz, Rafał
Szabó, Ildikó
Therrien, Bruno
Kowalski, Konrad
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| Dátum: |
2015-10-01
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| Téma: |
QD04 Organic chemistry / szerves kémia
QP Physiology / élettan
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| Tartalmi leírás: |
A convenient synthesis of ferrocenyl-4-thiothymine-3,6-dihydro-2H-thiopyrane (3) and ferrocenyl-thymine-3,6-dihydro-2H-thiopyrane (4) by a hetero-Diels-Alder cycloaddition reaction is reported. These complexes represent new class of ferrocenyl nucleobase derivatives. The 2H-thiopyrane ring mimics the sugar subunit present in natural nucleosides and nucleotides. The X-ray crystal structure analysis of the precursor thioketone (1) showed that individual molecules of 1 form H-bonded dimers in the solid state. Compounds 3 and 4 were tested in vitro for their antiproliferative activity against human colon carcinoma HT-29, estrogen receptor-responsive human breast adenocarcinoma MCF-7, estrogen-negative human breast adenocarcinoma MDA-MB-231, human promyelocytic leukemia HL-60 and human monocytic MonoMac6 cancer cells. Ferrocenyl-4-thiothymine-3,6-dihydro-2H-thiopyrane 3 showed a cytostatic effect on MonoMac6, MCF-7 and HL-60 cell lines, but was devoid of activity on MDA-MB-231 and HT-29 cells. In contrast, all cell lines tested were sensitive toward thymine derivative 4. Proapoptic activity of 3 and 4 was confirmed by means of acridine orange/ethidium bromide (AO/EB) double-staining assay.
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| Típus: |
Article
PeerReviewed
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| Formátum: |
text
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| Azonosító: |
Skiba, Joanna and Karpowicz, Rafa? and Szabó, Ildikó and Therrien, Bruno and Kowalski, Konrad (2015) Synthesis and anticancer activity studies of ferrocenyl-thymine-3,6-dihydro-2H-thiopyranes ? a new class of metallocene-nucleobase derivatives. Journal of Organometallic Chemistry, 794. pp. 216-222. ISSN 0022-328X
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