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Molecules 2018, 23(12), 3172; https://doi.org/10.3390/molecules23123172

Interaction of Arylidenechromanone/Flavanone Derivatives with Biological Macromolecules Studied as Human Serum Albumin Binding, Cytotoxic Effect, Biocompatibility Towards Red Blood Cells

1
Department of Cosmetic Raw Materials Chemistry, Faculty of Pharmacy, Medical University of Lodz, ul Muszynskiego 1, 90-151 Lodz, Poland
2
Laboratory of Bioanalysis, Department of Pharmaceutical Chemistry, Drug Analysis and Radiopharmacy, Medical University of Lodz, Muszyńskiego1, 90-151 Lodz, Poland
3
Department of General Biochemistry, Faculty of Biology and Environmental Protection, University of Lodz, Pomorska 141/143, 90-236 Lodz, Poland
4
Institute of Physics, University of Silesia, Uniwersytecka 4, 40-007 Katowice, Poland
5
Department of Physical Chemistry, Theoretical and Structural Chemistry Group, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland
6
Department of Pharmaceutical Biochemistry and Molecular Diagnostics, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland
*
Author to whom correspondence should be addressed.
Received: 25 October 2018 / Revised: 27 November 2018 / Accepted: 28 November 2018 / Published: 1 December 2018
(This article belongs to the Section Medicinal Chemistry)
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Abstract

The aim of this study was to determine the cytotoxic effect of 3-arylidenechromanone (1) and 3-arylideneflavanone (2) on HL-60 and NALM-6 cell lines (two human leukemia cell lines) and a WM-115 melanoma cell line. Both compounds exhibited high cytotoxic activity with higher cytotoxicity exerted by compound 2, for which IC50 values below 10 µM were found for each cell line. For compound 1, the IC50 values were higher than 10 µM for HL-60 and WM-115 cell lines, but IC50 < 10 µM was found for the NALM-6 cell line. Both compounds, at the concentrations close to IC50 (concentration range: 5–24 µM/L for compound 1 and 6–10 µM/L for compound 2), are not toxic towards red blood cells. The synthesized compounds were characterized using spectroscopic methods 1H- and 13C-NMR, IR, MS, elemental analysis, and X-ray diffraction. The lipophilicity of both synthesized compounds was determined using an RP-TLC method and the logP values found were compared with the theoretical ones taken from the Molinspiration Cheminformatics (miLogP) software package. The mode of binding of both compounds to human serum albumin was assessed using molecular docking methods. View Full-Text
Keywords: synthesis; crystal structure; cytotoxic effect; benzoflavanone/chromanone derivatives; erythrotoxicity synthesis; crystal structure; cytotoxic effect; benzoflavanone/chromanone derivatives; erythrotoxicity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Adamus-Grabicka, A.A.; Markowicz-Piasecka, M.; Ponczek, M.B.; Kusz, J.; Małecka, M.; Krajewska, U.; Budzisz, E. Interaction of Arylidenechromanone/Flavanone Derivatives with Biological Macromolecules Studied as Human Serum Albumin Binding, Cytotoxic Effect, Biocompatibility Towards Red Blood Cells. Molecules 2018, 23, 3172.

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