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Synthesis and antip...
Synthesis and antiproliferative activity of two diastereomeric lignan amides serving as dimeric caffeic acid-l-DOPA hybrids
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- Magoulas, George E. (författare)
- University of Patras
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- Rigopoulos, Andreas (författare)
- University of Patras
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- Piperigkou, Zoi (författare)
- Institute of Chemical Engineering Sciences (FORTH/ICE-HT)
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- Gialeli, Chrysostomi (författare)
- Lund University,Lunds universitet,Proteinkemi, Malmö,Forskargrupper vid Lunds universitet,Protein Chemistry, Malmö,Lund University Research Groups,University of Patras
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- Karamanos, Nikos K. (författare)
- University of Patras,Institute of Chemical Engineering Sciences (FORTH/ICE-HT)
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- Takis, Panteleimon G. (författare)
- University of Ioannina
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- Troganis, Anastassios N. (författare)
- University of Ioannina
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- Chrissanthopoulos, Athanassios (författare)
- University of Patras
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- Maroulis, George (författare)
- University of Patras
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- Papaioannou, Dionissios (författare)
- University of Patras
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(creator_code:org_t)
- Elsevier BV, 2016
- 2016
- Engelska 13 s.
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Ingår i: Bioorganic Chemistry. - : Elsevier BV. - 0045-2068. ; 66, s. 132-144
- Relaterad länk:
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http://dx.doi.org/10...
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https://lup.lub.lu.s...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Two new diastereomeric lignan amides (4 and 5) serving as dimeric caffeic acid-l-DOPA hybrids were synthesized. The synthesis involved the FeCl3-mediated phenol oxidative coupling of methyl caffeate to afford trans-diester 1a as a mixture of enantiomers, protection of the catechol units, regioselective saponification, coupling with a suitably protected l-DOPA derivative, separation of the two diastereomers thus obtained by flash column chromatography and finally global chemoselective deprotection of the catechol units. The effect of hybrids 4 and 5 and related compounds on the proliferation of two breast cancer cell lines with different metastatic potential and estrogen receptor status (MDA-MB-231 and MCF-7) and of one epithelial lung cancer cell line, namely A-549, was evaluated for concentrations ranging from 1 to 256 μM and periods of treatment of 24, 48 and 72 h. Both hybrids showed interesting and almost equipotent antiproliferative activities (IC50 64-70 μM) for the MDA-MB-231 cell line after 24-48 h of treatment, but they were more selective and much more potent (IC50 4-16 μM) for the MCF-7 cells after 48 h of treatment. The highest activity for both hybrids and both breast cancer lines was observed after 72 h of treatment (IC50 1-2 μM), probably as the result of slow hydrolysis of their methyl ester functions.
Ämnesord
- NATURVETENSKAP -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
Nyckelord
- A-549
- Amides
- Antiproliferative activity
- l-DOPA
- Lignans
- MCF-7
- MDA-MB-231
- Phenol oxidative coupling
Publikations- och innehållstyp
- art (ämneskategori)
- ref (ämneskategori)
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