Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

Abstract

A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of α-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

Novel Polyphenols That Inhibit Colon Cancer Cell Growth Affecting Cancer Cell Metabolism

“…Serinol (55 mg, 0.60 mmol) was treated with 9-octadecenoyl chloride (oleoyl chloride) (198.6 mg, 0.66 mmol) and triethylamine (0.1 ml) to give the title compound (149 mg, 70%) as an amorphous white solid. Characterization of this compound is consistent with those found in the literature (Bieberich et al, 2002a;Osornio et al, 2012;Landau and Siegel, 2014). .…”

“…Selective N-acylation of 2-amino-1,3-propanediol (serinol, 1) was undertaken by reaction of the commercially available serinol with the corresponding acyl chlorides in the presence of triethylamine at 220°C to afford compounds 2-6 in good yields (70%-81%). It should be mentioned that the synthesis of these compounds was previously described in the literature following different procedures (Oette and Tschung, 1980;Bieberich et al, 2002a,b;Schulz and Robins, 2004;Osornio et al, 2012;Landau and Siegel, 2014;Merg et al, 2015). In our case, a unique procedure that implies the use of acyl chlorides and triethylamine has been followed for all of them.…”

Thixotropic stiff hydrogels from a new class of oleoyl-d-glucamine-based low-molecular-weight gelators

“…The alkyloylamino acids used in the above condensation are synthesised from the appropriate amino acid and the alkyloyl chloride in aqueous NaOH. 16 The hydrogelation ability of these new compounds are examined at various pH values and in the presence of salts to obtain the critical gelation concentration (CGC) (Fig. 1, S1, S2, ESI † and Table 1).…”

“…Oleoyl amino acids were synthesized following the reported method. 15,16 Oleoyl chloride (13.29 mmol) in absolute THF (20 mL) was added slowly under N 2 atmosphere over a 30 min period, with a dropping funnel, in an aqueous NaOH (2 M) solution (40 mL) of amino acid (19.94 mmol), which was immersed in ice bath. The solution, along with the generated white precipitate, was stirred in an ice bath for an additional hour, and then at rt for 12 h. Subsequently, water (10 mL) was added to dissolve the precipitate, and then aq.…”

Computational and Biochemical Design of a Nanopore Cleavable by a Cancer‐Secreted Enzyme

“…The amphipathic doxorubicin (calculated van der Waals dimensions of ∼6×12×17 Å) is slowly released by an as yet unknown mechanism 59. 60 Here we engineered a channel protein for potential improvement of drug release in liposomal delivery systems or nanoparticles with lipid bilayer arrays,61, 62 by enabling enzymatic cleavage of the channel's constriction loop. We hypothesize that cleavage of the pore constriction might increase the rate of drug release, although we do not know yet to what extent the cleavage would increase the diameter of the eyelet seen in WT OprD's constriction (Figure 1 C; 3 Å as measured in the crystal structure by using MOLE 2.0) 63…”