3006-58-4Relevant articles and documents
Effects of cholesterol on the miscibility of synthetic glucosamine diesters in lipid bilayers and the entrapment of superoxide dismutase into the positively charged liposomes
Miyajima,Komatsu,Sun,Aoki,Handa,Xu,Fuji,Okada
, p. 1889 - 1894 (1993)
Methyl-D-glucosamine-3,6-dilauroyl, dimyristoyl, dipalmitoyl or distearoyl esters were synthesized as positively charged lipids. They were incorporated into phosphatidylcholine liposomal membranes and the entrapment of superoxide dismutase (SOD) into the liposomes was attempted. The efficiency of the SOD- entrapment into the positively charged multilamellar vesicles (MLVs), comprising egg yolk phosphatidylcholine and synthetic glucosamine diesters, was enhanced by the addition of cholesterol to the membranes. A differential scanning calorimetric study showed that the miscibility (solubility) of glucosamine diesters in phosphatidylcholine-bilayers increased on the addition of cholesterol to the membranes. Cholesterol assisted in the mixing of phosphatidylcholines with positively charged glucosamine diesters and increased the positive charges on the liposomal membranes. This was confirmed by incremental increases in the zeta-potential of liposomal membranes with an increase in the cholesterol content. Entrapment of SOD thus became more efficient due to the enhanced electrostatic attraction between the positively charged membranes and the negatively charged SOD, and/or the electrostatic repulsive interactions between positively charged membranes; the latter interactions induced a thickening of the water layer in MLVs.
Protected N-Acetyl Muramic Acid Probes Improve Bacterial Peptidoglycan Incorporation via Metabolic Labeling
Brown, Ashley R.,Wodzanowski, Kimberly A.,Santiago, Cintia C.,Hyland, Stephen N.,Follmar, Julianna L.,Asare-Okai, Papanii,Grimes, Catherine Leimkuhler
, p. 1908 - 1916 (2021/09/29)
Metabolic glycan probes have emerged as an excellent tool to investigate vital questions in biology. Recently, methodology to incorporate metabolic bacterial glycan probes into the cell wall of a variety of bacterial species has been developed. In order to improve this method, a scalable synthesis of the peptidoglycan precursors is developed here, allowing for access to essential peptidoglycan immunological fragments and cell wall building blocks. The question was asked if masking polar groups of the glycan probe would increase overall incorporation, a common strategy exploited in mammalian glycobiology. Here, we show, through cellular assays, that E. coli do not utilize peracetylated peptidoglycan substrates but do employ methyl esters. The 10-fold improvement of probe utilization indicates that (i) masking the carboxylic acid is favorable for transport and (ii) bacterial esterases are capable of removing the methyl ester for use in peptidoglycan biosynthesis. This investigation advances bacterial cell wall biology, offering a prescription on how to best deliver and utilize bacterial metabolic glycan probes.
COMPOUNDS AND METHODS TO ENHANCE THE ORAL AVAILABILITY OF GLYCOMIMETICS
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Page/Page column 63; 64, (2014/10/03)
Potent E-selecting antagonist compounds are described herein. In certain embodiments, compounds and methods are provided for enhancing the oral availability of glycomimetics. More specifically, in an embodiment, a glyeomimetic is modified to decrease the
