Soft nanocarriers for new poorly soluble conjugate of pteridine and benzimidazole: Synthesis and cytotoxic activity against tumor cells

Nanocarriers for Biomedicine: From Lipid Formulations to Inorganic and Hybrid Nanoparticles

“…Research activity of our group focuses on self-assembling amphiphilic systems, with their design, aggregation ability and functionality as drug delivery systems emphasized [2,37,38]. Recently, much attention has been paid to non-covalent modification of liposomes with surfactants [37][38][39][40], with cationic liposomes attracting special interest [41][42][43][44][45][46][47]. Main types of lipid-and silicon-containing nanoparticles, comprising many kinds of nanocarriers that can be used to achieve the best medical performance.…”

“…Research activity of our group focuses on self-assembling amphiphilic systems, with their design, aggregation ability and functionality as drug delivery systems emphasized [2,37,38]. Recently, much attention has been paid to non-covalent modification of liposomes with surfactants [37][38][39][40], with cationic liposomes attracting special interest [41][42][43][44][45][46][47]. In [39,40] lipid nanoformulations based on L-α-phosphatidylcholine (PC), cholesterol (CHO) and hybrid amphiphilic ligands-quaternary ammonium salts with a sterically hindered phenolic (SHP) moiety with benzyl (SHP-2-Bn) and alkyl tails (SHP-2-R, where R=C n H 2n+1 , n = 8, 10, 12, 16) were obtained and characterized.…”

“…In the latter ca higher Pearson coefficient occurs for Im versus TPP-based ligand. Im-modified liposomes exhibit excellent long-term stability and high loading capacity toward a variety of drugs and spectral probes [44][45][46]. The authors of [44] obtained 70-100 nm sized liposomal formulations based on DPPC and Im-based amphiphiles with various length of hydrophobic tail for the encapsulation of a drug metronidazole.…”

“…Two types of nanocontainers, micellar and liposomal, were prepared in [45] for conjugated derivative of pteridine and benzimidazole with antitumor activity. For micellar systems, an increase in solubility of the hydrophobic bioactive compound occurs in the series Tween 80 < CTAB < Im-16 surfactants.…”

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

“…Pegylated cationic liposomes modified with a new arginine surfactant were described in [220], which were used to increase the bioavailability of new 2-benzimidazolylquinoxalines derivatives poorly soluble in water and showed highly selective cytotoxicity against a cervical cancer cell line (HeLa). Another benzimidazole derivative, 7-(benzimidazol-2-yl)-6-(2,4-dichlorophenyl)-2-thioxo-2,3dihydropteridin-4(1H)-one, when encapsulated in imidazolium surfactant-modified liposomes shows a sharp decrease in viability of diseased cells (HeLa) and increase of viability of normal cells (Chang liver) [221]. Cationic liposomes based on 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and alkyltriphenylphosphonium bromides were obtained by non-covalent surface modification with amphiphiles using varying hydrocarbon tail lengths and lipid/surfactant ratio and In the formation of modified liposomes, the degree of oligomerization of a cationic surfactant (monomeric, gemini or trimeric) and the ratio of lipid to surfactant are crucial factors, since only at a low surfactant concentration the incorporation of surfactant into the lipid bilayer of liposomes is possible, while after a certain threshold value complete destruction of the lipid bilayer and the formation of mixed surfactant-lipid micelles are observed [217][218][219].…”