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

András Keglevich; Leonetta Dányi; Alexandra Rieder; Dorottya Horváth; Áron Szigetvári; Miklós Dékány; Csaba Szántay; Ahmed  Dhahir Latif; Attila Hunyadi; István Zupkó; Péter Keglevich; László Hazai

doi:10.3390/molecules25041010

Molecules (Feb 2020)

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

András Keglevich,
Leonetta Dányi,
Alexandra Rieder,
Dorottya Horváth,
Áron Szigetvári,
Miklós Dékány,
Csaba Szántay,
Ahmed Dhahir Latif,
Attila Hunyadi,
István Zupkó,
Péter Keglevich,
László Hazai

Affiliations

András Keglevich: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4., H-1111 Budapest, Hungary
Leonetta Dányi: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4., H-1111 Budapest, Hungary
Alexandra Rieder: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4., H-1111 Budapest, Hungary
Dorottya Horváth: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4., H-1111 Budapest, Hungary
Áron Szigetvári: Spectroscopic Research Department, Gedeon Richter Plc., P. O. Box 27, H-1475 Budapest 10, Hungary
Miklós Dékány: Spectroscopic Research Department, Gedeon Richter Plc., P. O. Box 27, H-1475 Budapest 10, Hungary
Csaba Szántay: Spectroscopic Research Department, Gedeon Richter Plc., P. O. Box 27, H-1475 Budapest 10, Hungary
Ahmed Dhahir Latif: Institute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary
Attila Hunyadi: Institute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary
István Zupkó: Department of Pharmacodynamics and Biopharmacy, Interdisciplinary Excellence Centre, University of Szeged, Eötvös u. 6., H-6720 Szeged, Hungary
Péter Keglevich: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4., H-1111 Budapest, Hungary
László Hazai: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Gellért tér 4., H-1111 Budapest, Hungary

DOI: https://doi.org/10.3390/molecules25041010
Journal volume & issue: Vol. 25, no. 4
p. 1010

Abstract

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New Vinca 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 IC50 values in the low micromolar concentration range.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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