Studies on the interaction of 2-amino-3-hydroxy-anthraquinone with surfactant micelles reveal its nucleation in human MDA-MB-231 breast adinocarcinoma cells

Abstract

Structural and spectroscopic studies on 2-amino-3-hydroxy-anthraquinone (AQ), an analogue of anthracycline drugs, were carried out using computational methods. The interactions of AQ with anionic surfactant sodium dodecyl sulphate (SDS) and cationic surfactant cetyltrimethylammonium bromide (CTAB) were investigated in aqueous solution at physiological pH (7.4) by UV-Vis spectroscopy, and compared with the well-known anthracycline drugs. The affinity of such molecule to surfactant micelles may mean it can act as a model system for a biological membrane–drug interaction, which is important in determining the biological action of this molecule. The binding constant, partition coefficient and Gibbs free energy for the binding and distribution of AQ between the bulk aqueous solution and surfactant micelles were determined for AQ–surfactant interactions. It was observed that hydrophobic interaction plays a crucial role in the binding of AQ to SDS micelles, while the hydrophilic interaction plays an important role in its interaction with CTAB micelles. These interactions also have a vital role in the distribution of AQ between surfactant micelle–water phases. This study gives an idea that the present molecule may successfully permeate biological membranes, so AQ was allowed to interact with human breast adinocarcinoma cell MDA-MB-231. Experimental findings established that AQ induces apoptosis by means of nucleation into these cells.