Formulation of water-dispersible hydrophobic compound nanocomplexes with polypeptides via a supramolecular approach using a high-speed vibration milling technique

Abstract

Polypeptides were used to solubilize functional hydrophobic molecules via a high-speed vibrational milling method.

“On‐Off” Switching of Functional Guest Molecules via Exchange of Natural Product Solubilizing Agents

“…Polysaccharides, such as β-(1,3-1,6)-D-glucan (GL), λ-carrageenan (CGN), tamarind gum, pullulan, arabinogalactan, and sodium hyaluronate, and polypeptides, e. g., poly-L-lysine, polyγ-glutamic acid, and collagen could incorporate porphyrin derivatives, affording complexes that were stable in water for at least one week. [68][69][70] When GL-Por derivative complexes of 9, 10, 11, 13, and 14 were prepared using the HSVM apparatus, the concentrations of the porphyrin compounds in the GL complexes were 0.34, 0.18, 0.78, 0.21, and 0.46 mM, respectively, by the absorbance after lyophilization and dissolution in DMSO. [69] Although these derivatives were completely incorporated into the GL complexes, 12 was partly released in bulk water due to its water solubilization.…”

“…Water solubilization of hydrophobic guest molecules is important to realize their functionalization and application in the fields of material chemistry and medicinal chemistry. [1][2][3][4][5][6][7][8][9][10][11][12] To this aim, the use of solubilizing agents helps reduce time and costs and broadens potential applications. Especially, using natural products as solubilizing agents leads to an excellent biocompatibility and a low environmental burden.…”

“…Similarly, polysaccharides and polypeptides can include a large amount and variety of guest molecules (Figure 1). [7][8][9][10][11][12][13] However, the preparation of complexes of CDxs, polysaccharides, and polypeptides with guest molecules via traditional solid-liquid extraction methods using sonication or heating requires long reaction times and affords aqueous solutions with relatively low concentrations of guest molecules. In contrast, these complexes can be rapidly and conveniently prepared using a mechanochemical high-speed vibration milling (HSVM) apparatus (Scheme 1a).…”

“…In contrast, these complexes can be rapidly and conveniently prepared using a mechanochemical high-speed vibration milling (HSVM) apparatus (Scheme 1a). [12][13][14] In this context, the incorporation of hydrophobic guest molecules in the lipid membrane of liposomes consisting of phospholipids (Figure 1) attracts considerable attention in the field of delivery systems. [15][16][17][18][19][20] Lipid-membrane-incorporated guest molecules (LMIGs) can be prepared using the organic solution injection method with a polar solvent such as methanol or dimethylsulfoxide (DMSO) or via a premixing method involving dissolution of lipids and guest molecules in an organic solvent followed by concentration and extraction with water.…”

“…Transfer of [60] and [70]fullerenes from cyclodextrin to liposomes Figure 2 shows the structures of [60] and [70]fullerenes (C 60 and C 70 ), which can dissolve in water upon the formation of a complex comprising a fullerene derivative sandwiched by two γ-CDxs (Figure 1). These γ-CDx-C 60 and γ-CDx-C 70 complexes were prepared using an HSVM apparatus (Scheme 1a).…”