Synthesis and Coordination Properties of a Water-Soluble Material by Cross-Linking Low Molecular Weight Polyethyleneimine with Armed Cyclotriveratrilene

Abstract

In this study, a full organic and water-soluble material was synthesized by coupling low molecular weight polyethylenimine (PEI-800) with cyclotriveratrilene (CTV). The water-soluble cross-linked polymer contains hydrophobic holes with a high coordination capability towards different organic drug molecules. The coordinating capability towards hydrophilic drugs (doxorubicin, gatifloxacin and sinomenine) and hydrophobic drugs (camptothecin and celastrol) was analyzed in an aqueous medium by using NMR, UV-Vis and emission spectroscopies. The coordination of drug molecules with the armed CTV unit through hydrophobic interactions was observed. In particular, celastrol exhibited more ionic interactions with the PEI moiety of the hosting system. In the case of doxorubicin, the host–guest detachment was induced by the addition of ammonium chloride, suggesting that the intracellular environment can facilitate the release of the drug molecules.

Acid and Glutathione Dual-Responsive, Injectable and Self-Healing Hydrogels for Controlled Drug Delivery

“…In Figure b, the UV–vis absorbed peak of CPT in PEI-CPT is observed at ∼370 nm, whereas in the UV–vis spectrum of free CPT, the absorption peak is evident around 365 nm, indicating a red shift in the position of the CPT absorption peak. Similarly, the fluorescence emission peak of CPT in PEI-CPT undergoes a red shift from 428 to 458 nm, consistent with previously reported literature …”

“…Similarly, the fluorescence emission peak of CPT in PEI-CPT undergoes a red shift from 428 to 458 nm, consistent with previously reported literature. 53 OSA-IR780 was synthesized through the Schiff base reaction involving IR780 with amine groups (IR780-NH 2 ) and OSA with aldehyde groups (Scheme S2). The straightforward preparation of OSA involved a peri-iodate oxidation ringopening reaction of sodium alginate (SA).…”