Category: 5505-63-5

Cui, Xinxin; Du, Kunda; Yuan, Xiaoyin; Xiao, Wen; Tao, Yayu; Xu, Defeng; Hu, Hang published the artcile< A comparative study of the in vitro antitumor effect of mannose-doxorubicin conjugates with different linkers>, Synthetic Route of 5505-63-5, the main research area is doxorubicin mannose conjugate antitumor agent drug delivery system; conjugate; doxorubicin; mannose.

In this work, five Man-DOX conjugates with different linkers were developed for targeted DOX delivery. The five Man-DOX conjugates with different linkers were characterized by 1H NMR, HRMS, HPLC, UV-vis, and fluorescence spectroscopy. Man-Suc-DOX, Man-TDG-DOX, and Man-DG-DOX can self-assemble into near-spherical nanoparticles with hydrodynamic diameters of 150-200 nm and neg. ζ potentials in deionized water, whereas Man-SS-DOX and Man-SeSe-DOX are hardly dispersed in deionized water. The self-assembly behaviors of Man-Suc-DOX, Man-TDG-DOX, and Man-DG-DOX were studied by dissipative particle dynamics simulation and the results show that Man-Suc-DOX, Man-TDG-DOX, and Man-DG-DOX all self-assemble into spherical particles with Man and linkers on the surfaces and DOX in the interiors. The in vitro drug release study shows that Man-Suc-DOX, Man-TDG-DOX, and Man-DG-DOX exhibit limited drug release, while Man-SS-DOX and Man-SeSe-DOX exhibit glutathione-responsive drug release. The cellular uptake study shows that Man-DG-DOX exhibits the highest cellular uptake amount on HepG2 cells. Finally, Man-DG-DOX exhibits the best in vitro antitumor effect against HepG2 cells among the five Man-DOX conjugates with different linkers. Although the in vitro antitumor activity of Man-DG-DOX is still lower than free DOX, Man-DG-DOX shows significant selectivity toward HepG2 cells. Man-DG-DOX might achieve selective DOX delivery for mannose receptor overexpressed tumors.

Drug Development Research published new progress about Antitumor agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Synthetic Route of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chen, Maohua; He, Jie; Xie, Songzhi; Wang, Tao; Ran, Pan; Zhang, Zhanlin; Li, Xiaohong published the artcile< Intracellular bacteria destruction via traceable enzymes-responsive release and deferoxamine-mediated ingestion of antibiotics>, Reference of 5505-63-5, the main research area is deferoxamine ciprofloxacin mPET nanoparticle intracellular enzyme antibiotic; Antibiotic-siderophore complex; Enzyme-responsive release; Intracellular bacteria; Self-indicating nanoparticle; Traceable release.

Intracellular bacteria (ICBs) are among the most life-threatening causes of drug resistance. Challenges remains in the intracellular drug release specific to ICB-infected cells and efficient uptake into ICBs. In this study, mannose-grafted polymers containing enzymes-responsive and tetraphenylethylene segments (mPET) are assembled into nanoparticles with loading complexes of deferoxamine-ciprofloxacin conjugates with Fe3+ (DFeC). The aggregation-induced emission (AIE) of tetraphenylethylene segments is overlapped with DFeC absorptions, leading to fluorescence resonance energy transfer (FRET)-caused quenching of mPET@DFeC nanoparticles. Nanoparticles are efficiently acquired by infected macrophages via mannose mediation, and the DFeC release is triggered by intracellular lipase and alk. phosphatase specific to ICB-engulfed macrophages, followed by deferoxamine-mediated ingestion of ciprofloxacin into ICBs. The gradual alleviation of FRET effect and the concurrent restoration of AIE activity demonstrate capabilities of dynamically tracking the drug release and ICB treatment outcome. The mPET@DFeC treatment inhibits the hematol., hepatic and nephric toxicities caused by ICB infections, and all the infected mice survive with dramatic reductions of bacterial levels in livers (over 430 folds), spleens (over 240 folds) and kidneys (5.6 × 104 folds). Thus, this study has provided a feasible strategy to achieve intracellular enzymes-responsive and traceable release of antibiotics and then deferoxamine-mediated bacterial ingestion for ICB destruction.

Journal of Controlled Release published new progress about Antibacterial agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Reference of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Lin, Jieye; Oliver, Allen G.; Serianni, Anthony S. published the artcile< D-Mannosamine hydrochloride (2-amino-2-deoxy-D-mannose hydrochloride): ionic hydrogen bonding in saccharides involving chloride and aminium ions>, SDS of cas: 5505-63-5, the main research area is mannosamine hydrochloride ionic hydrogen bonding saccharide; 2-amino-2-deoxy-d-mannose hydrochloride; anomeric disorder; crystal structure; d-mannosamine hydrochloride; ionic hydrogen bonding.

D-Mannosamine hydrochloride (2-amino-2-deoxy-D-mannose hydrochloride), C6H14NO5+·Cl-, (I), crystallized from a methanol/ethyl acetate/n-hexane solvent mixture at room temperature in a 4C1 chair conformation that is slightly distorted towards the C3,O5B form. A comparison of the structural parameters of (I) with the corresponding parameters in α-D-glucosamine hydrochloride, (II), and β-D-galactosamine hydrochloride, (III)/(III’), was undertaken to evaluate the effects of ionic hydrogen bonding on structural properties. Three types of ionic hydrogen bonds are present in the crystals of (I)-(III)/(III’), i.e. N+-H···O, N+-H···Cl-, and O-H···Cl-. The exocyclic structural parameters in (I), (II), and (III)/(III’) appear to be most influenced by this bonding, especially the exocyclic hydroxy groups, which adopt eclipsed conformations enabled by ionic hydrogen bonding to the chloride anion. Anomeric disorder was observed in crystals of (I), with an α:β ratio of 37:63. However, anomeric configuration appears to exert minimal structural effects; i.e., bond lengths, bond angles, and torsion angles are essentially identical in both anomers. The observed disorder at the anomeric C atom of (I) appears to be caused by the presence of the chloride anion and atom O3 or O4 in proximal voids, which provide opportunities for hydrogen bonding to atom O1 in both axial and equatorial orientations.

Acta Crystallographica, Section C: Structural Chemistry published new progress about Crystallization. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, SDS of cas: 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hassenrueck, Jessica; Wittmann, Valentin published the artcile< Cyclopropene derivatives of aminosugars for metabolic glycoengineering>, Quality Control of 5505-63-5, the main research area is cyclopropene aminosugar metabolic glycoengineering; bioorthogonal chemistry; carbohydrates; cyclopropenes; inverse electron-demand Diels–Alder reaction; metabolic engineering.

Cyclopropenes have been proven valuable chem. reporter groups for metabolic glycoengineering (MGE). They readily react with tetrazines in an inverse electron-demand Diels-Alder (DAinv) reaction, a prime example of a bioorthogonal ligation reaction, allowing their visualization in biol. systems. Here, we present a comparative study of six cyclopropene-modified hexosamine derivatives and their suitability for MGE. Three mannosamine derivatives in which the cyclopropene moiety is attached to the sugar by either an amide or a carbamate linkage and that differ by the presence or absence of a stabilizing Me group at the double bond have been examined We determined their DAinv reaction kinetics and their labeling intensities after metabolic incorporation. To determine the efficiencies by which the derivatives are metabolized to sialic acids, we synthesized and investigated the corresponding cyclopropane derivatives because cyclopropenes are not stable under the anal. conditions. From these experiments, it became obvious that N-(cycloprop-2-en-1-ylcarbonyl)-modified (Cp-modified) mannosamine has the highest metabolic acceptance. However, carbamate-linked N-(2-methylcycloprop-2-en-1-ylmethyloxycarbonyl)-modified (Cyoc-modified) mannosamine despite its lower metabolic acceptance results in the same cell-surface labeling intensity due to its superior reactivity in the DAinv reaction. Based on the high incorporation efficiency of the Cp derivative we synthesized and investigated two new Cp-modified glucosamine and galactosamine derivatives Both compounds lead to comparable, distinct cell-surface staining after MGE. We further found that the amide-linked Cp-modified glucosamine derivative but not the Cyoc-modified glucosamine is metabolically converted to the corresponding sialic acid.

Beilstein Journal of Organic Chemistry published new progress about Amino sugars Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Quality Control of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Shen, Li; Cai, Kaimin; Yu, Jin; Cheng, Jianjun published the artcile< Facile Click-Mediated Cell Imaging Strategy of Liposomal Azido Mannosamine Lipids via Metabolic or Nonmetabolic Glycoengineering>, Reference of 5505-63-5, the main research area is fluorescence imaging liposome azido mannosamine lipid.

Two Ac4ManNAz (AAM) derivatives with octadecanoic ester (C18 ester) and octadecyl ether (C18 ether) attached to the anomeric hydroxyl groups were synthesized and used in preparation of liposomes. Both liposomes show strong cell-labeling efficiencies on MDA-MB-231 cancer cells. The cell surface-anchored azide group can react with DBCO-Cy5 via Cu-free click chem. The two liposomes exhibit different azide placement mechanisms; C18-ether-AAM-treated cells have azido placement through direct insertion, while C18-ester-AAM-treated cells express azido more through metabolic glycoengineering.

ACS Omega published new progress about Confocal laser scanning microscopy. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Reference of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Pollastri, Sara; Delaunay, Clara; Thepaut, Michel; Fieschi, Franck; Bernardi, Anna published the artcile< Glycomimetic ligands block the interaction of SARS-CoV-2 spike protein with C-type lectin co-receptors>, Category: alcohols-buliding-blocks, the main research area is glycomimetic ligand synthesis L SIGN SARSCoV2 coronavirus spike protein.

The C-type lectin receptors DC-SIGN and L-SIGN bind to glycans on the SARS-CoV-2 spike glycoprotein and promote trans-infection of ACE2-expressing cells. We tested C2 triazole-modified mono- and pseudo-di-mannosides as inhibitors of DC/L-SIGN binding to a model mannosylated protein (Man-BSA) and to SARS-CoV2 spike, finding that they inhibit the interaction of both lectins with the spike glycoprotein in a Surface Plasmon Resonance (SPR) assay and are more potent than mannose by up to 36-fold (DC-SIGN) and 10-fold (L-SIGN). The mols. described here are the first known glycomimetic ligands of L-SIGN.

Chemical Communications (Cambridge, United Kingdom) published new progress about Anticoronaviral agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Category: alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Shen, Li; Cai, Kaimin; Yu, Jin; Cheng, Jianjun published the artcile< Novel Liposomal Azido Mannosamine Lipids on Metabolic Cell Labeling and Imaging via Cu-Free Click Chemistry>, Reference of 5505-63-5, the main research area is liposomal azido mannosamine lipid metabolic cell labeling imaging.

In comparison with the popular Ac4ManNAz applied as cell labels via Cu-free click chem., two novel azido mannosamine lipids with C6 and C12 esters on anomeric hydroxyl groups were prepared and encapsulated in a liposome delivery system, which enhanced chem. stabilities and showed good cell-metabolizable labeling efficiency on MDA-MB-231 cells with strong fluorescence after the treatment of DBCO-Cy5 by triazole formation via click chem.

Bioconjugate Chemistry published new progress about Confocal microscopy. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Reference of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Wang, Hua; Bo, Yang; Liu, Yang; Xu, Ming; Cai, Kaimin; Wang, Ruibo; Cheng, Jianjun published the artcile< In vivo cancer targeting via glycopolyester nanoparticle mediated metabolic cell labeling followed by click reaction>, Name: (2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride, the main research area is cancer targeting glycopolyester nanoparticle metabolic cell labeling; Cancer targeting; Cell labeling; Click chemistry; Drug design; Sugar.

We developed glycopolyesters (GPs) via azido-sugar initiated ring-opening polymerization of O-carboxyanhydrides (OCAs) and achieved efficient in vivo cancer targeting via GP-nanoparticle (GP-NP) mediated metabolic cell labeling followed by Click reaction. GP-NP shows controlled release of azido-sugars and can efficiently label LS174T colon cancer cells with azido groups in tumor-bearing mice. The exogenously introduced azido groups render excellent in vivo cancer targeting and retention of dibenzocyclooctyne-Cy5 (DBCO-Cy5) with an increasing tumor retention enhancement over time (68% at 6 h, 105% at 24 h, and 191% at 48 h) compared to control mice without azido labeling. The tumor accumulation of DBCO-doxorubicin is also significantly enhanced in GP-NP pretreated mice, resulting in improved in vivo anticancer efficacy. This study, for the first time, proposes the use of azido-sugar initiated polymerization of OCAs to form sugar delivery vehicles with high stability and controlled release, and demonstrates the increasing tumor targeting effect of DBCO-cargo over time by azido-modified tumor cells.

Biomaterials published new progress about Antitumor agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Name: (2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Li, Ye; Liang, Jun; Gao, Jia-Ning; Shen, Yu; Kuang, Hai-Xue; Xia, Yong-Gang published the artcile< Novel LC-MS/MS method for complete composition analysis of polysaccharides by aldononitrile acetate and multiple reaction monitoring>, Name: (2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride, the main research area is plant polysaccharide composition liquid chromatog tandem mass spectrometry; Aldononitrile acetate derivatization; LC-MS/MS; Monosaccharide compositions; Polysaccharides.

Carbohydrate anal. has always been a challenging task due to the occurrence of high polarity and multiple isomers. Aldoses are commonly analyzed by gas liquid chromatog. (GLC) following aldononitrile acetate derivatization (AND). However, the GLC technique cannot be applied for the simultaneous determination of aldoses, ketoses, and uronic acids. In this study, a new method based on the combination of liquid chromatog.-tandem mass spectrometry (LC-MS/MS) and AND is developed for the complete characterization of monosaccharide composition (i.e., aldoses, ketoses, alditols, amino sugars, and uronic acids) in plant-derived polysaccharides. In addition to discussing the possible byproducts, the study optimizes the multiple reaction monitoring (MRM) parameters and LC conditions. The final separation of 17 carbohydrates is performed on a BEH Shield RP18 column (150 mm x 2.1 mm, 1.7μm) within 25 min, without using any buffer salt. Notably, the complex polysaccharides extracted from Ligusticum chuanxiong, Platycodon grandiflorum, Cyathula officinalis Kuan, Juglans mandshurica Maxim, and Aralia elata (Miq.). Seem bud can be successfully characterized using the developed method. Overall, the results demonstrated that the newly established LC-MS/MS MRM method is more effective and powerful than the GLC-based methods reported previously, and it is more suitable for the anal. of highly complex natural polysaccharides, including complex pectins, fructosans, and glycoproteins.

Carbohydrate Polymers published new progress about Alditols Role: ANT (Analyte), ANST (Analytical Study). 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Name: (2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Medve, Laura; Achilli, Silvia; Guzman-Caldentey, Joan; Thepaut, Michel; Senaldi, Luca; Le Roy, Aline; Sattin, Sara; Ebel, Christine; Vives, Corinne; Martin-Santamaria, Sonsoles; Bernardi, Anna; Fieschi, Franck published the artcile< Enhancing Potency and Selectivity of a DC-SIGN Glycomimetic Ligand by Fragment-Based Design: Structural Basis>, Safety of (2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride, the main research area is pseudo dimannoside design synthesis DCSIGN ligand selective antagonist; DC-SIGN; carbohydrates; glycomimetics; ligand design; virtual screening.

Chem. modification of pseudo-dimannoside ligands guided by fragment-based design allowed for the exploitation of an ammonium-binding region in the vicinity of the mannose-binding site of DC-SIGN, leading to the synthesis of a glycomimetic antagonist, I, of unprecedented affinity and selectivity against the related lectin langerin. Here, the computational design of pseudo-dimannoside derivatives as DC-SIGN ligands, their synthesis, their evaluation as DC-SIGN selective antagonists, the biophys. characterization of the DC-SIGN/I complex, and the structural basis for the ligand activity are presented. On the way to the characterization of this ligand, an unusual bridging interaction within the crystals shed light on the plasticity and potential secondary binding sites within the DC-SIGN carbohydrate recognition domain.

Chemistry – A European Journal published new progress about Alkynes, α- Role: RCT (Reactant), RACT (Reactant or Reagent). 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Safety of (2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts