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Pyridoxine
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
Pyridoxine is the 4-methanol form of vitamin Bs, an important water-soluble vitamin that is naturally present in many foods. As its classification as a vitamin implies, vitamin B6 (and pyridoxine) are essential nutrients required for normal functioning of many biological systems within the body. Pyridoxine is converted to pyridoxal phosphate, which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. Although pyridoxine and vitamin Bs are frequently used as synonyms, this practice is, according to some sources, erroneous (ChemIDPlus). In this database, it is stated that vitamin B6 refers to several picolines, especially pyridoxine, pyridoxal and pyridoxamine. Pyridoxine is indicated for the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy. In pharmaceutical products, pyridoxine is employed as pyridoxine hydrochloride (CAS number 58-56-0, EC number 200-386-2, molecular formula C8H12CINO3) (1).
Cisplatin and Related Anticancer Drugs: Recent Advances and Insights
Published in Astrid Sigel, Helmut Sigel, Metal Ions in Biological Systems, 2004
Katie R. Barnes, Stephen J. Lippard
Combinatorial synthesis was used to prepare over 3,600 platinum complexes, which were subsequently screened by using a transcription inhibition fluorescence-based assay [141]. Out of the 3,600 compounds prepared, four species showed promising activity, cis-[(isopropyl-amine)2-PtC12], cis- [ammine(cyclobutylamine)PtCl2], cis-[(cyclobuty 1-amine)2-PtC12], and cis,-[ammine(2-amino-3-picoline)PtCl2] [141]. All four compounds had previously been identified as cytotoxic cisplatin analogues. Furthermore, the picoline-containing platinum compound is quite similar to ZD0473, recently developed for use in the clinic [142]. The high-throughput methodology could potentially serve as a new route for discovery of active cisplatin analogues.
Bivalent non-human gal-α1-3-gal glycan epitopes in the Fc region of a monoclonal antibody model can be recognized by anti-Gal-α1-3-Gal IgE antibodies
Published in mAbs, 2023
Grayson Hatfield, Lioudmila Tepliakova, Jessica Tran, Huixin Lu, Michel Gilbert, Roger Y. Tam
Following palivizumab transglycosylation reactions, remodeled glycans were characterized using PNGase F (New England Biolabs, Cat # P0705S) to release glycans, followed by HPAEC-PAD analysis as detailed below. For analysis using capillary electrophoresis laser-induced fluorescence (CE-LIF), PNGase-released glycans were fluorescently labeled with 8-aminopyrene-1,3,6-trisulfonate (APTS) using the Sciex Fast Glycan Labeling and Analysis Kit (Sciex, Cat.# B94499PTO). Glycans were bound to hydrophilic magnetic beads using a 8:1 ratio of acetonitrile:water. A labeling mixture comprising 7.9 µL (40 mM APTS in 20% acetic acid), 1.6 µL 0.5% NP-40, 0.8 µL (1 M picoline borane in acetonitrile), and 0.8 µL maltotriose internal standard was then mixed with the glycan-containing magnetic beads for 1 h at 60°C. Unreacted APTS dye was washed off the beads using 160 µL of 8:1 ratio of acetonitrile:water. Analyses were performed as described below. For both CE-LIF and HPAEC-PAD analyses, samples comprising glycans released from intact cetuximab or palivizumab were included in each sequence to also serve as a retention time standard. For CE-LIF, an APTS labeling blank was also included in each sequence to monitor the effects of labeling, and for HPAEC-PAD, a blank comprising diluted buffer was used.
Synthesis and characterisation of thiobarbituric acid enamine derivatives, and evaluation of their α-glucosidase inhibitory and anti-glycation activity
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
M. Ali, Assem Barakat, Ayman El-Faham, Hessa H. Al-Rasheed, Kholoud Dahlous, Abdullah Mohammed Al-Majid, Anamika Sharma, Sammer Yousuf, Mehar Sanam, Zaheer Ul-Haq, M. Iqbal Choudhary, Beatriz G. de la Torre, Fernando Albericio
Compound 3c was synthesised from 2a and 2-amino-4-picoline following the general procedure, affording the product as a light yellow powder in 87% yield; mp 175 °C; IR (KBr, cm−1) 3215, 3157, 3045, 2958, 2908, 2866, 1614, 1598, 1544, 1463; 1H-NMR (CDCl3δ, ppm):12.25 (d, 1H, J = 13.2 Hz, NH), 9.40 (d, 1H, J = 13.2 Hz, CH=), 8.27 (d, 1H, J = 5.2 Hz, Ar-H), 6.98 (d, 1H, J = 5.2 Hz, Ar-H), 6.86(s, 1H, Ar-H), 4.55 (m, 4H, 2CH2), 2.38 (s, 3H, CH3), 1.29 (m, 6H, 2CH3); 13C-NMR (CDCl3δ, ppm):179.1, 163.3, 160.7, 152.5, 150.7, 149.6, 149.0, 122.9, 113.6, 95.8, 43.2, 42.5, 21.2, 12.5, 12.4; LC/MS (ESI): 319.40 [M + 1]+; Anal. Calcd for C15H18N4O2S: C, 56.59; H, 5.70; N, 17.60; Found: C, 56.81; H, 5.78; N, 17.79.
Glycan modification of glioblastoma-derived extracellular vesicles enhances receptor-mediated targeting of dendritic cells
Published in Journal of Extracellular Vesicles, 2019
Sophie A. Dusoswa, Sophie K. Horrevorts, Martino Ambrosini, Hakan Kalay, Nanne J. Paauw, Rienk Nieuwland, Michiel D. Pegtel, Tom Würdinger, Yvette Van Kooyk, Juan J. Garcia-Vallejo
LeY-glycolipid (LeY-hexadecanehydrazide) was prepared from LeY pentasaccharide (Elicityl) and palmitic anhydride (Sigma-Aldrich), the latter undergoing two subsequent chemical transformations, first to tert-butyl N-(hexadecanoylamino) carbamate, then to palmitic hydrazide through common reactivity. Palmitic hydrazide was coupled to LeY through a reductive amination reaction. Briefly, palmitic hydrazide (2 eq., Sigma-Aldrich) and picoline borane (10 eq., Sigma-Aldrich) were dissolved in DMSO/AcOH/CHCl3 (8:2:1, 200 μl). The mixture was added to LeY (1 eq.) and the reaction was stirred for 2.5 h at 65°C. Addition of CHCl3/MeOH/H2O at 8:1:8 v/v ml ratio allowed the extraction of LeY-glycolipid as white slurry at the interphase. The mixture was centrifuged at 4600 rpm for 20 min, then the aqueous and organic layers were carefully removed, and the washing step was repeated once more. The slurry was freeze-dried (methanol/water) to remove residual solvent. Glycan derivatization was confirmed by ESI-MS (LCQ-Deca XP Ion trap mass spectrometer in positive mode; Thermo Scientific) using nanospray capillary needle. LeY-glycolipid was post-inserted into the EVs by adding 1 ml of EV suspension to 0.75 mg of glycolipid, previously dissolved in 15 μl of methanol. After 15 min of vigorous stirring and overnight at 4°C, the EVs were and purified by SEC.