Studies on the Uptake of Glucose Derivatives by Red Blood Cells

Abstract

Erythrocytes express the same glucose transporter (GLUT‐1) as is present in the blood‐brain barrier. With the aim of testing the viability of using this transport system to deliver glucosyl drug derivatives to the brain, the uptake of several dopamine–glucose conjugates and a few structurally related analogues by erythrocytes was studied with HPLC and 1H MAS NMR spectroscopy. The results showed that slight structural changes determine the uptake of glycoconjugates by red blood cells. However, experiments in the presence of glucose transport inhibitors showed that none of the conjugates that efficiently crossed the cell membrane were transported by GLUT‐1.

Small Molecule Ice Recrystallization Inhibitors Enable Freezing of Human Red Blood Cells with Reduced Glycerol Concentrations

“…However, the uptake of glucose (and glucose derivatives) is dependant upon the structure of the pyranose ring (ie. axial vs. equatorial positioning of hydroxyl groups) and ultimately the “shape” of the molecule 61 62 . The data from the two-step interrupted freezing experiment presented in the previous section suggests that β-PMP-Glc may be conferring protection against cryo-injury by interacting with RBC membrane and/or penetrating the cell.…”

Synthesis of difluoroaryldioxoles using BrF3

“…Prepared from tert-butyl 3,4-dihydroxyphenethylcarbamate ( 16) 23 (1.6 g), as described above, in 95% yield: 1.8 g, white crystals, m.p. = 142.7-143.1 • C; 1 H NMR 7.29 -7.21 (3 H, m), 4.67 (1 H, s br), 3.42 (2 H, t, J = 7 Hz), 2.92 (2 H, t, J = 7 Hz), 1.47 ppm (9 H, s); 13 C NMR 184.9, 156.6, 146.7, 145.3, 138.5, 126.8, 111.3, 110.8, 80.3, 42.5, 36.9, 29.1 ppm.…”

Synthesis ofN-Boc-C1 Vinyl Tetrahydroisoquinoline via Zn-Mediated Intramolecular Cyclization ofN-Boc Protected Iodo Acetonide

“…We began the synthesis of 2 with known carbamate 3 [6] (Scheme 1), which was prepared by N-Boc protection of commercially available 3,4-dimethoxyphenylethylamine in 92% yield. Regioselective iodination of 3 was achieved by using I 2 and CF 3 CO 2 Ag in dry CHCl 3 to afford iodocarbamate 4 in excellent yield (97%).…”

“…N-(tert-Butoxycarbonyl)-3,4-dimethoxyphenyl)ethylamine (3) [6] Et 3 N (2.0 mL, 14.3 mmol) was added to a stirred solution of 3,4-dimethoxyphenylethylamine (2.0 g, 11.0 mmol) in dry CH 2 Cl 2 (25 mL) was added followed by (Boc) 2 O (2.8 mL, 12.1 mmol) at 0 C. The resulting mixture was stirred at the same temperature for 20 min and then at room temperature for 6 h. Water was added to this and extracted with CH 2 Cl 2 (3 Â 20 mL). The combined organic layer was washed with brine, dried over anhydrous NaSO 4 , and concentrated under reduced pressure.…”