Synthesis and Cytotoxic Activity of New Vindoline Derivatives Coupled to Natural and Synthetic Pharmacophores

New alkaloid derivatives were synthesized to improve the biological activity of the natural alkaloid vindoline. To this end, experiments were performed to link vindoline with various structural units, such as amino acids, a 1,2,3-triazole derivative, morpholine, piperazine and N-methylpiperazine. Th...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2020-02, Vol.25 (4), p.1010
Hauptverfasser:	Keglevich, András, Dányi, Leonetta, Rieder, Alexandra, Horváth, Dorottya, Szigetvári, Áron, Dékány, Miklós, Szántay, Jr, Csaba, Latif, Ahmed Dhahir, Hunyadi, Attila, Zupkó, István, Keglevich, Péter, Hazai, László
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino acids Amino Acids - chemistry anticancer drugs Antineoplastic Agents, Phytogenic - chemical synthesis Antineoplastic Agents, Phytogenic - pharmacology Biological activity Cancer Cell Line, Tumor Cell Survival - drug effects Chemistry Techniques, Synthetic Cytotoxicity Cytotoxins - chemical synthesis Cytotoxins - pharmacology Dose-Response Relationship, Drug Gynecological cancer HeLa Cells Humans ic50 values Inhibitory Concentration 50 Magnetic resonance spectroscopy Mass spectrometry Mass spectroscopy MCF-7 Cells Molecular Structure Morpholine Morpholines - chemistry NMR NMR spectroscopy Nuclear magnetic resonance organic synthesis Pharmacophores Piperazine Piperazines - chemistry Structure-Activity Relationship Triazoles Triazoles - chemistry Tumor cell lines Vinblastine - analogs & derivatives Vinblastine - chemistry vinca alkaloids Vindoline
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Beschreibung
Zusammenfassung:	New alkaloid derivatives were synthesized to improve the biological activity of the natural alkaloid vindoline. To this end, experiments were performed to link vindoline with various structural units, such as amino acids, a 1,2,3-triazole derivative, morpholine, piperazine and N-methylpiperazine. The structure of the new compounds was characterized by NMR spectroscopy and mass spectrometry (MS). Several compounds exhibited in vitro antiproliferative activity against human gynecological cancer cell lines with IC values in the low micromolar concentration range.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules25041010