Journal of Drug Delivery Science and Technology 59 (2020) 101872 Available online 9 July 2020 1773-2247/© 2020 Elsevier B.V. All rights reserved. Stearoylcholine and oleoylcholine: Synthesis, physico-chemical characterization, nanoparticle formation, and toxicity studies Maryam Saadat a, b , Sevda Jafari d , Parvin Zakeri-Milani c , Javid Shahbazi-Mojarrad b , Hadi Valizadeh b, * a Student Research Committee, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran b Drug Applied Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran c Liver and Gastrointestinal Diseases Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran d Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran A R T I C L E INFO Keywords: Alkanoylcholines Stearoylcholine Oleoylcholine Cytotoxicity Breast cancer Lung cancer Nanoparticles ABSTRACT Surfactants are used frequently as a component of pharmaceutical products. Cationic surfactants used to the formation of cationic nanoparticles (NPs) those present enhanced cellular uptake. With this purpose, frst cationic surfactants, Stearylcholine (SC), and Oleylcholine (OC) were synthesized and then their characterization such as critical micelle concentration (CMC), Krafft temperature, and hydrophilic lyophilic balance (HLB) were evaluated. Cationic solid lipid nanoparticles (SLNs) were prepared through the emulsifcation method. The particle size and Zeta potential (ZP) of SC-SLNs were 93 � 0.1 nm and þ38.3 mV. OC-SLNs showed the particle size of 718 � 0.1 nm and ZP of þ39.9 mV. Cytotoxicity studies of SLNs and synthesized materials were assessed on human normal HFFF-2 and A549 lung cancer cells. Resultant SLNs showed no cytotoxic effects on HFFF-2 cells. SLNs and synthetic materials showed toxic effects on A549 lung cancer cells. 1. Introduction Surfactants are organic compositions which contain hydrophobic tail and hydrophilic head groups. They decrease the interfacial tension be- tween two phases including: emulsions (liquid-liquid) or suspensions (liquid-solid), to make a monophasic media. These components are being used frequently as emulsifers, dispersants, foaming agents, wet- ting agents, and detergents [1]. Surfactants usually are classifed into four main groups including non‒ionic, zwitterionic, anionic, and cationic surfactants. Cationic surfactants are derivations of amines in- cludes primary, secondary, tertiary, and quaternary ammonium. Qua- ternary ammonium salts carry cationic charge in all ranges of pH, so they are pH-independent components. These kinds of materials are degradable under anaerobic [2,3] and aerobic conditions [4,5]. How- ever, some documents reported that these materials represent partial or no biodegradability under anaerobic situations [6–8]. Also, they show high sorption effcacy to the environmental relevance components [9, 10]. Quaternary ammonium salts could disrupt cell membranes and exhibit antimicrobial behavior over bacteria, fungi, and some viruses [10,14]. The affnity of these compounds to most biologic membranes causes low selectivity and damaging mammalian cells when exposed for a long time [11]. To decrease the side effects of these compounds cleavable moiety such as ester bound was introduced into the molecule, which is more labile and hydrolytic degradable [12]. These kinds of surfactants were named ester quaternary ammonium compounds. In which choline esters or alkanoylcholines are common due to their biocompatibility [13]. They are the product of ester linkage between fatty acids and choline. Choline, (2-hydroxyethyl) trimethylammonium salt, is a natural compound that exists in the human body as membrane constituents and precursor of neurotransmitters [14,15]. It is biodegradable and biocompatible in the environment and living organisms [16,17]. So, its derivatives are suitable candidates to make eco-friendly compounds. As a result, choline was utilized as counter-ion in ionic liquids to reducing their melting points [18] and using as an additive for eutectic solvents [19]. Rengestl and et al. investigated the lyotropic behavior of these materials in detail [20]. Surfactants based on choline esters are a branch of quaternary ammonium compounds (QACs) known as alkanoylcholines. Alkanoylcholines are cationic lipids that are recognized ordinarily as * Corresponding author. Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, 51664, Iran. E-mail address: valizadeh@tbzmed.ac.ir (H. Valizadeh). Contents lists available at ScienceDirect Journal of Drug Delivery Science and Technology journal homepage: www.elsevier.com/locate/jddst https://doi.org/10.1016/j.jddst.2020.101872 Received 23 March 2020; Received in revised form 30 May 2020; Accepted 14 June 2020