Synthesis and evaluation of hydrophobically modified fenugreek gum for potential hepatic drug delivery

Abstract

The objective of this study was to hydrophobically modify fenugreek gum (FG) and to further evaluate the potential application of the obtained derivative in liver-targeted drug delivery system. Stearic acid (C 18 ) was conjugated with FG (FG-C 18 ) by a simple esterification reaction. The obtained FG-C 18 was then characterized on its chemical structure by Fourier transform infrared spectroscopy and 1 H-nuclear magnetic resonance. The self-assembled nanomicelles (NMs) of FG-C 18 in water were prepared by an ultrasonication method. The average diameter and zeta potential of FG-C 18 NMs were 196.70 ± 6.12 nm and À31.79 ± 1.58 mV, respectively. FG-C 18 NMs appeared as spherical particles under transmission electron microscopy and possessed a critical micellar concentration of 0.042 mg/ml by pyrene fluorescence probe method. A low toxicity of FG-C 18 was revealed on both HepG2 and MCF-7 cells at 0.1-100 mg/ ml. Haemolysis of FG-C 18 was less than 5%. Cellular uptake of coumarin-6 into HepG2 cells was enhanced by treating with C6-loaded FG-C 18 NMs compared to free coumarin-6. These results suggest that FG-C 18 have a potential application for a liver targeted drug delivery. ARTICLE HISTORY

Hepatic targeting of glycyrrhetinic acid via nanomicelles based on stearic acid-modified fenugreek gum

“…Moreover, many studies have demonstrated that galactosylated copolymers or grafted polysaccharides containing galactose residues on the surfaces of nanoparticles could enhance the drug level in the liver via the recognition of nanoparticles by ASGP-R [17,24]. The previous cellular uptake experiment [12] and the cytotoxicity assay performed in this study also indicated that GA/FG-C 18 NMs were first internalised into HepG2 cells, followed by GA release into the cytoplasm, which inhibited the growth of cells. The specific recognition between ligand and ASGP-R receptor was competed by the galactose solution.…”

“…Preparation of glycyrrhetinic acid-loaded nanomicelles FG-C 18 was successfully synthesised and characterised according to its physicochemical properties in our previous report [12]. GA/FG-C 18 NMs were prepared by an ultrasonication dispersion method.…”

“…FG has been widely applied in the food field [10], but few reports of FG as a nanocarrier have been made because its high swelling and hydrophilic characteristics resulted in low encapsulation efficiency for poorly water-soluble drugs [11]. In our previous study, FG was successfully modified with the hydrophobic chain of stearic acid (C 18 ) [12]. The obtained amphiphilic derivative showed a favourable self-assembly ability in water and good biocompatibility.…”

Natural Gums in Drug-Loaded Micro- and Nanogels

“…As the inner area of the particle is hydrophobic, the obtained systems may be useful in the delivery of active ingredients revealing low polarity [ 57 , 58 , 59 ]. In hydrophobic modifications, cholesterol [ 60 ], fatty acids [ 61 ] and other compounds [ 57 , 59 , 62 ] can be used. Parameters such as the particle diameter, the zeta potential and the loading efficiency can be modulated by adjusting the polymer chain length and the size of the hydrophobic residues [ 39 ].…”

Fenugreek (Trigonella foenum graecum) gum: A functional ingredient with promising properties and applications in food and pharmaceuticals—A review

“…In one another modification, fenugreek gum was hydrophobically modified and stearic acid was conjugated with fenugreek gum by a simple esterification reaction. The results suggested that the resultant conjugate can be successfully employed for a liver‐targeted drug delivery (Zhou et al, 2019). Fenugreek gum can be chemically modified by cyanoethylation using acrylonitrile or oxidation (using sodium chlorite).…”