A folate-functionalized degradable amphiphilic dendrimer-like star polymer (FA-DLSP) with a well-defined poly(L-lactide) (PLLA) star polymer core and six hydrophilic polyester dendrons based on 2,2-bis(hydroxymethyl) propionic acid was successfully synthesized to be used as a nanoscale carrier for cancer cell-targeted drug delivery. This FA-DLSP hybrid formed unimolecular micelles in the aqueous solution with a mean particle size of ca. 15 nm as determined by dynamic light scattering and transmission electron microscopy. To study the feasibility of FA-DLSP micelles as a potential nanocarrier for targeted drug delivery, we encapsulated a hydrophobic anticancer drug, doxorubicin (DOX), in the hydrophobic core, and the loading content was determined by UV-vis analysis to be 4 wt %. The DOX-loaded FA-DLSP micelles demonstrated a sustained release of DOX due to the hydrophobic interaction between the polymer core and the drug molecules. The hydrolytic degradation in vitro was monitored by weight loss and proton nuclear magnetic resonance spectroscopy to gain insight into the degradation mechanism of the FA-DLSP micelles. It was found that the degradation was pH-dependent and started from the hydrophilic shell gradually to the hydrophobic core. Flow cytometry and confocal microscope studies revealed that the cellular binding of the FA-DLSP hybrid against human KB cells with overexpressed folate-receptors was about twice that of the neat DLSP (without FA). The in vitro cellular cytotoxicity indicated that the FA-DLSP micelles (without DOX) had good biocompatibility with KB cells, whereas DOX-loaded micelles exhibited a similar degree of cytotoxicity against KB cells as that of free DOX. These results clearly showed that the FA-DLSP unimolecular micelles could be a promising nanosize anticancer drug carrier with excellent targeting property.

We report the synthesis and functionalization of amphiphilic dendrimer-like star polymers (DLSPs) with a hydrophobic star-shaped poly(l-lactide) (PLLA) core and a hydrophilic poly(amidoamine) (PAMAM) dendron shell. First, carboxylic acid-functionalized PLLA star polymer was synthesized by ring-opening polymerization of l-lactide followed by functionalization with succinic anhydride. Second, 1-, 2-, and 3-generation PAMAM dendrons with a primary amine at the dendron root and benzyl ester protections at the periphery were prepared via a divergent method. By amide coupling between the carboxylic acid-terminated PLLA star polymer and six PAMAM dendrons, amphiphilic DLSPs were successfully synthesized. To enhance bioactivity and bioconjugation capability, the benzyl ester surface groups in these DLSPs were converted to carboxylic acid, primary amine, and triethylene glycol functional groups, respectively. Nuclear magnetic resonance spectroscopy and size-exclusion chromatography were used to confirm quantitative functionalization. These functional DLSPs exhibited a unique unimolecular micelle (14−28 nm) behavior in aqueous solution with a small amount of aggregation (205−344 nm), as studied by dynamic light scattering. In addition, they also exhibited large differences in thermal behaviors depending on the nature of different surface groups. Experimental results showed that these DLSPs had good solubility in aqueous solutions (ca. 10−25 mg/mL) and could greatly enhance the water solubility of hydrophobic drugs. Therefore, these amphiphilic DLSPs are promising candidates for controlled hydrophobic drug delivery.

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By coupling a well-defined PLLA star polymer with six carboxylic acid-terminated polyester dendrons based on 2,2-bis(hydroxymethyl)propionic acid, a biodegradable dendrimer-like star polymer (DLSP) with multiple carboxylic acid groups at the outer surface was successfully synthesized. Conjugation of amine-functionalized folic acids (FA) onto the DLSP yielded a folate-DLSP hybrid as a carrier for targeted drug delivery. The chemical structures were proven by proton nuclear magnetic resonance and size exclusion chromatography. The DLSPs could form unimolecular micelles with a mean particle size of about 18 nm, as determined by dynamic light scattering. Flow cytometry and confocal microscope studies revealed that the cellular uptake of the folate-DLSP hybrid against KB cells (overexpressed folate-receptor) was much higher than that of the neat DLSP (without FA) due to the folate receptor-mediated binding.

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It is difficult for existing filtrate reducer to meet oilfield application requirements. Based on the molecular structure design principle of temperature-resistant vinyl copolymer, a quaternary copolymer filtrate reducer has been developed with VCAP, AMPS, DMDAAC and AM as monomers through water solution copolymerization using redox initiation system. The optimum synthesis conditions were as follows: the mole ratio of monomer was VCAP/AMPS/DMDAAC/AM=1:1:1:9, reaction temperature was 70°C, reaction time was 6 h, initiator mass ratio was 0.2% and total monomer mass ratio was 20%. The filtration loss of base slurry with 1wt% optimum synthetic product after aging at 150 °C for 16 h was 5.2 mL.