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

Adamus-Grabicka, Angelika A.; Markowicz-Piasecka, Magdalena; Ponczek, Michał B.; Kusz, Joachim; Małecka, Magdalena; Krajewska, Urszula; Budzisz, Elzbieta

doi:10.3390/molecules23123172

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

Angelika A. Adamus-Grabicka

¹,

Magdalena Markowicz-Piasecka

⁴,

⁵,

⁶ and

^1,*

Department of Cosmetic Raw Materials Chemistry, Faculty of Pharmacy, Medical University of Lodz, ul Muszynskiego 1, 90-151 Lodz, Poland

Laboratory of Bioanalysis, Department of Pharmaceutical Chemistry, Drug Analysis and Radiopharmacy, Medical University of Lodz, Muszyńskiego1, 90-151 Lodz, Poland

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.

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

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

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MDPI and ACS Style

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. https://doi.org/10.3390/molecules23123172

AMA Style

Adamus-Grabicka AA, Markowicz-Piasecka M, Ponczek MB, 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(12):3172. https://doi.org/10.3390/molecules23123172

Chicago/Turabian Style

Adamus-Grabicka, Angelika A., Magdalena Markowicz-Piasecka, Michał B. Ponczek, Joachim Kusz, Magdalena Małecka, Urszula Krajewska, and Elzbieta Budzisz. 2018. "Interaction of Arylidenechromanone/Flavanone Derivatives with Biological Macromolecules Studied as Human Serum Albumin Binding, Cytotoxic Effect, Biocompatibility Towards Red Blood Cells" Molecules 23, no. 12: 3172. https://doi.org/10.3390/molecules23123172

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

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