Formation and properties of colloidal particles of cationic derivatives of chlorin e 6 in aqueous medium
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Formation and properties of colloidal particles of cationic derivatives of chlorin e6 in aqueous medium Dmitry Belykh1 · Inna Loukhina1 · Vasily Mikhaylov1 · Irina Khudyaeva1 Received: 22 July 2020 / Accepted: 4 November 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
Abstract We show that the colloidal particles formed by chlorin e 6 cationic derivatives have a positive charge and their stability decreases with decreasing chlorin concentration. The concentration at which colloid formation begins was found to be determined by the number of cationic groups in the molecule; moreover, as it should be expected, the more cationic groups, the higher this concentration. The formation of stable colloidal particles is facilitated by the presence of a cationic group distant from the macrocycle. Graphic abstract
Keywords Chlorin e6 derivatives · Electrokinetic potential · Aggregation · Colloidal particles Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01421-w) contains supplementary material, which is available to authorized users. * Dmitry Belykh belykh‑[email protected] * Inna Loukhina loukhina‑[email protected] Extended author information available on the last page of the article
Photodynamic therapy in a number of cases is an effective method of treatment of cancer, infectious and other diseases (Belik et al. 2017; Feofanov et al. 2004; Krasnovskii 2015; Mojzisova et al. 2009; Ormond and Freeman 2013; Parkhats et al. 2005, 2011; Stranadko 2015). Chlorin e 6 and many of its derivatives are effective photosensitizers with good spectral characteristics and relatively low dark toxicity; some of these compounds are already in use in clinical practice
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(Belik et al. 2017; Konan et al. 2002; Krasnovskii 2015; Nazarova et al. 2005; Nechaev and Mironov 2008; Ormond and Freeman 2013; Parkhats et al. 2005; Stranadko 2015; Zenkevich et al. 1996). In this regard, chlorin e 6 is a promising platform for the development of new photosensitizers for medical purposes. In particular, as shown in a number of works, the introduction of cationic groups on the periphery of the macrocycle of chlorin e 6 derivatives not only increases bioavailability, but also enhances photo-induced antibacterial activity (Berezin et al. 2018; Kustov et al. 2016, 2018, 2020; Otvagin et al. 2018; Tarabukina et al. 2015; Venediktov et al. 2017). Chlorin e6 derivatives with one (1), two (2), or three (3) cationic groups (Fig. 1) exhibit good photoinduced antibacterial activity (Kustov et al. 2018), therefore a number of properties of these compounds have been studied in detail (Batov et al. 2019; Berezin et al. 2017, 2018; Kustov et al. 2016; Venediktov et al. 2017). Due to the potential of using cationic chlorins (1–3) for medical purposes, the state of these compounds in aqueous media is of particular interest. As shown in (Batov et al. 2019), compounds (1–3) form colloidal particles in the aqueous medium that are destroyed in the pre
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