4877-14-9Relevant articles and documents
Synthesis and evaluation of mono- and multi-hydroxyl low toxicity pH-sensitive cationic lipids for drug delivery
Zhao, Zheng,Yao, Weihe,Wang, Ning,Liu, Chenyu,Zhou, Hengjun,Chen, Hailiang,Qiao, Weihong
, p. 69 - 78 (2019)
Cationic lipids can easily assemble into spherical liposomes in aqueous phase which showed unique superiority in drug and gene delivery. However, the toxicity of cationic lipids is still an obstacle to application. To develop low toxicity cationic lipids, we designed two cationic lipids contained different number of hydroxyl groups. Biocompatible mono-hydroxyl and multi-hydroxyl galactose head group was respectively modified to a biodegradable quaternary amine lipid, and two novel hydroxyl cationic lipids were synthesized and characterized by MS, 1H NMR and 13C NMR. Two lipids showed good surface activity and both of them can assemble to about 80 nm stable small unilamellar vesicles (SUVs) with cholesterol in aqueous phase. Both of lipids showed relatively lower toxicity than the well-known cationic lipid 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP). In vitro 24 h IC50 of two assemblies were more than 50 μg/mL, which were about 10 μg/mL higher than the IC50 of DOTAP. Multi-hydroxyl galactose lipids group showed much lower toxicity than mono-hydroxyl lipids group. Moreover, Both of the assemblies with lower hemolysis were nearly non-hemolytic risk under the concentration of 30 μg/mL. Transmission electron microscopy (TEM) and dynamic light scattering (DLS) showed that the average sizes of both doxorubicin (DOX) loaded liposomes were about 110 nm. The DOX entrapment efficiencies of galactose liposome and mono-hydroxyl liposome were 58% and 91%, respectively. Both of the DOX loaded liposomes were stable after one month placed at room temperature. Two DOX loaded liposomes showed better anti-cancer effect than free DOX above 5 μg/mL, and they can be internalized into cells and produce more release of DOX inside MCF-7 cells and HepG2 cells at pH 5.0. These results suggested that synthesized lipids are suitable as potential low toxicity cationic drug delivery systems.
N-Guanidino Derivatives of 1,5-Dideoxy-1,5-imino-d-xylitol are Potent, Selective, and Stable Inhibitors of β-Glucocerebrosidase
Sev?ek, Alen,?rot, Luka,Rihter, Jakob,?elan, Ma?a,van Ufford, Linda Quarles,Moret, Ed E.,Martin, Nathaniel I.,Pieters, Roland J.
supporting information, p. 483 - 486 (2017/04/10)
A series of lipidated guanidino and urea derivatives of 1,5-dideoxy-1,5-imino-d-xylitol were prepared from d-xylose using a concise synthetic protocol. Inhibition assays with a panel of glycosidases revealed that the guanidino analogues display potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range. Related urea analogues of 1,5-dideoxy-1,5-imino-d-xylitol were also synthesized and evaluated in the same fashion and found to be selective for β-galactosidase from bovine liver. No inhibition of human recombinant β-glucocerebrosidase was observed for the urea analogues. Computational studies provided insight into the potent activity of analogues bearing the substituted guanidine moiety in the inhibition of lysosomal glucocerebrosidase (GBA).
Semicarbazides as gel forming agents for common solvents and liquid crystals
Deindoerfer, Pia,Geiger, Thomas,Schollmeyer, Dieter,Ye, Jian Hui,Zentel, Rudolf
, p. 351 - 358 (2007/10/03)
This paper describes the synthesis of 14 new gelling agents with semicarbazide groups as H-bonding motifs and alkyl- and/or azobenzene side groups. They gel solvents like decaline, 1,2-dichlorobenzene and toluene and liquid crystalline mixtures. X-Ray structure analysis shows that the semicarbazides are connected by H-bonds, each molecule to four neighbours. As a result a ribbon is formed with a core of H-bonded semicarbazide groups and alkyl chains sticking to the side. IR measurements show an unchanged H-bonding motif in large crystals and in the gel fibres, even in LC-mixture. During heating the gel melts (rheology), while the H-bonding motif of the crystal disappears (IR and DSC measurements). First experiments show that these gel-forming agents can be used to gel LC-phases and to stabilise the director pattern present during gel formation. The Royal Society of Chemistry 2006.
