Category: 96345-79-8

Kilcoyne, Michelle published the artcileSurface chemistry and linker effects on lectin-carbohydrate recognition for glycan microarrays, Synthetic Route of 96345-79-8, the publication is Analytical Methods (2012), 4(9), 2721-2728, database is CAplus.

Glycan microarrays are an increasingly utilized tool for anal. of protein-carbohydrate interactions and a variety of glycan-containing mols. and slide chemistries have been used to array carbohydrates on microarray surfaces. Slide surface chem. can have significant impact on the ligand presentation, background noise, spot size and morphol. and reproducibility of the arrayed mols., which in turn impacts upon lectin-carbohydrate recognition. The linker used to attach the carbohydrate to the mol. scaffold is another variable in ligand presentation. To evaluate these effects, three different microarray surface chemistries were arrayed with the same mono- and di-saccharide neoglycoconjugates and natural glycoproteins and incubated with four well-characterized plant lectins. Analogs of three monosaccharide neoglycoconjugates, with two common linkers each, were included in the test group to evaluate the linker effect on lectin recognition. Based on lowest background noise, expected lectin-ligand interaction, good spot morphol. and best reproducibility, the three-dimensional hydrogel slide surface proved most suitable for lectin interrogation of carbohydrate ligands, and the more flexible phenylisothiocyanate linker afforded greater recognition of the carbohydrates by the relevant lectins.

Analytical Methods published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Synthetic Route of 96345-79-8.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kinzel, Olaf published the artcileSynthesis of a functionalized high affinity mannose receptor ligand and its application in the construction of peptide-, polyamide- and PNA-conjugates, Safety of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Journal of Peptide Science (2003), 9(6), 375-385, database is CAplus and MEDLINE.

The synthesis of a high affinity mannose receptor ligand, appropriately functionalized for chemoselective ligation with an antigen or DNA-binding moieties is described. By a combination of solid- and solution-phase chem. a versatile synthesis of the target structure was accomplished. Examples of subsequent ligation reactions are described.

Journal of Peptide Science published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Safety of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Mahor, Sunil published the artcileMannosylated Polyethyleneimine-Hyaluronan Nanohybrids for Targeted Gene Delivery to Macrophage-Like Cell Lines, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Bioconjugate Chemistry (2012), 23(6), 1138-1148, database is CAplus and MEDLINE.

Nonviral gene delivery systems have a number of limitations including low transfection efficiency, specificity, and cytotoxicity, especially when the target cells are macrophages. To address these issues, the hypothesis tested in this study was that mannose functionalized nanohybrids composed of synthetic and natural polymers will improve transfection efficiency, cell viability, and cell specificity in macrophages. Robust nanohybrids were designed from hyaluronic acid (HA) and branched polyethyleneimine (bPEI) using carbodiimide chem. The reaction product, i.e., branched polyethyleneimine-hyaluronic acid (bPEI-HA) copolymer was subsequently functionalized with mannose at the terminal end of the copolymer to obtain mannosylated-bPEI-HA (Man-bPEI-HA) copolymer. UV spectroscopy and gel retardation studies confirmed the formation of polyplexes at polymer to DNA weight ratio ≥2. Alamar Blue and MTT assay revealed that the cytotoxicity of the developed nanohybrids were significantly (P < 0.05) lower than that of unmodified bPEI. Mannose functionalization of these nanohybrids showed specificity for both murine and human macrophage-like cell lines RAW 264.7 and human acute monocytic leukemia cell line (THP1), resp., with a significant level (P < 0.05) of expression of gaussia luciferase (GLuc) and green fluorescent reporter plasmids. Internalization studies indicate that a mannose mediated endocytic pathway is responsible for this higher transfection rate. These results suggest that hyaluronan-based mannosylated nanohybrids could be used as efficient carriers for targeted gene delivery to macrophages.

Bioconjugate Chemistry published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Woller, Eric K. published the artcileMannose Functionalization of a Sixth Generation Dendrimer, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biomacromolecules (2001), 2(3), 1052-1054, database is CAplus and MEDLINE.

Saccharide functionalization of fourth through sixth generation PAMAM dendrimers was carried out using a thiourea linkage occurs in high yield (77-92 %) with 85% incorporation of sugar residues. Reaction of 4-isothiocyanatophenyl α-D-mannopyranoside with amine-terminated G(4)-, G(5)-, and G(6)-PAMAMs afforded mannosylated dendrimers. Only a slight excess of the isothiocyanate (≤1.1 equiv/amine) was used. Protection of the mannose hydroxy groups was not necessary as isothiocyanates react selectively with primary amines. Dialysis against a water/ DMSO mixture using a cellulose tube (MW cutoff of 1000 g/mol) afforded the functionalized dendrimers in purified form. A widely applicable MALDI-TOF MS procedure was used for the anal. of the degree of dendrimer surface functionalization achieved.

Biomacromolecules published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C8H5F3O2S, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Arima, Hidetoshi published the artcileEnhancement of gene transfer activity mediated by mannosylated dendrimer/α-cyclodextrin conjugate (generation 3, G3), Product Details of C13H15NO6S, the publication is Journal of Controlled Release (2006), 116(1), 64-74, database is CAplus and MEDLINE.

To enhance gene transfer activity of dendrimers, we prepared its conjugate (generation 3, G3) with α-cyclodextrin bearing mannose (Man-α-CDE conjugates) with various degrees of substitution of the mannose moiety (DSM5, 10, 13, 20) and compared their cytotoxicity and gene transfer activity, and elucidated the enhancing mechanism for the activity. Of the various carriers used here, Man-α-CDE conjugate (G3, DSM10) provided the highest gene transfer activity in NR8383, A549, NIH3T3 and HepG2 cells, being independent of the expression of mannose receptors. Gene transfer activity of Man-α-CDE conjugate (G3, DSM10) was not decreased by the addition of 10% serum in A549 cells. Cytotoxicity of the polyplex with Man-α-CDE conjugates (G3, DSM10) was not observed in A549 and NIH3T3 cells up to the charge ratio of 200/1 (carrier/pDNA). The gel mobility and particle size of polyplex with Man-α-CDE conjugate (G3, DSM10) were relevant to those with α-CDE conjugate (G3), but ζ-potential, DNase I stability, pDNA condensation of the former polyplex were somewhat different from those of the latter one. Cellular association of polyplex with Man-α-CDE conjugate (G3, DSM10) was almost comparable to that with dendrimer (G3) complex and α-CDE conjugate (G3). The addition of mannan and mannose attenuated gene transfer activity of Man-α-CDE conjugate (G3, DSM10) in A549 cells. Alexa-pDNA complex with TRITC-Man-α-CDE conjugate (G3, DSM10), but not the complex with TRITC-α-CDE conjugate (G3), was found to translocate to nucleus at 24 h after incubation in A549 cells. HVJ-E vector including mannan, but neither the vector alone nor the vector including dextran, suppressed the nuclear localization of TRITC-Man-α-CDE conjugate (G3, DSM10) to a striking degree after 24 h incubation in A549 cells. These results suggest that Man-α-CDE conjugate (G3, DSM10) has less cytotoxicity and prominent gene transfer activity through not only its serum resistant and endosome-escaping abilities but also nuclear localization ability.

Journal of Controlled Release published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Product Details of C13H15NO6S.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gao, Jieming published the artcileNovel Monodisperse PEGtide Dendrons: Design, Fabrication, and Evaluation of Mannose Receptor-Mediated Macrophage Targeting, Category: alcohols-buliding-blocks, the publication is Bioconjugate Chemistry (2013), 24(8), 1332-1344, database is CAplus and MEDLINE.

Novel PEGtide dendrons of generations 1 through 5 (G1.0-5.0) containing alternating discrete poly(ethylene glycol) (dPEG) and amino acid/peptide moieties were designed and developed. To demonstrate their targeting utility as nanocarriers, PEGtide dendrons functionalized with mannose residues were developed and evaluated for macrophage targeting. PEGtide dendrons were synthesized using 9-fluorenylmethyloxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) protocols. The N-α-Fmoc-N-ε-(5-carboxyfluorescein)-l-lysine (Fmoc-Lys(5-FAM)-OH) and monodisperse Fmoc-dPEG₆-OH were sequentially coupled to Fmoc-β-Ala-resin to obtain the resin-bound intermediate Fmoc-dPEG₆-Lys(5-FAM)-β-Ala (1). G1.0 dendrons were obtained by sequentially coupling Fmoc-Lys(Fmoc)-OH, Fmoc-β-Ala-OH, and Fmoc-dPEG₆-OH to 1. Dendrons of higher generation, G2.0-5.0, were obtained by repeating the coupling cycles used for the synthesis of G1.0. Dendrons containing eight mannose residues (G3.0-mannose₈) were developed for mannose receptor (MR) mediated macrophage targeting by conjugating α-d-mannopyranosylphenyl isothiocyanate to G3.0 dendrons. In the present study PEGtide dendrons up to G5.0 were synthesized. The mol. weights of the dendrons determined by MALDI-TOF were in agreement with calculated values. The hydrodynamic diameters measured using dynamic light scattering (DLS) ranged from 1 to 8 nm. Cell viability in the presence of G3.0 and G3.0-mannose₈ was assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and was found to be statistically indistinguishable from that of untreated cells. G3.0-mannose₈ exhibited 12-fold higher uptake than unmodified G3.0 control dendrons in MR-expressing J774.E murine macrophage-like cells. Uptake was nearly completely inhibited in the presence of 10 mg/mL mannan, a mannose analog and known MR substrate. Confocal microscopy studies demonstrated the presence of significant intracellular punctate fluorescence colocalized with a fluid endocytosis marker with little surface fluorescence in cells incubated with G3.0-mannose₈. No significant cell-associated fluorescence was observed in cells incubated with G3.0 dendrons that did not contain the targeting ligand mannose. The current studies suggest that PEGtide dendrons could be useful as nanocarriers in drug delivery and imaging applications.

Bioconjugate Chemistry published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Peng, Huige published the artcileReprogramming Tumor-Associated Macrophages To Reverse EGFR^T790M Resistance by Dual-Targeting Codelivery of Gefitinib/Vorinostat, Synthetic Route of 96345-79-8, the publication is Nano Letters (2017), 17(12), 7684-7690, database is CAplus and MEDLINE.

Gefitinib is a first-line therapy in the EGFR-mutated nonsmall cell lung cancer (NSCLC). However, the development of drug resistance is almost unavoidable, thus leading to an unsustainable regimen. EGFR^T790M mutation is the major cause responsible for the mol.-targeting therapy failure in NSCLC. Although the recently approved osimertinib is effective for the EGFR^T790M-pos. NSCLC, the osimertinib-resistant EGFR mutation is rapidly developed, too. In this study, we proposed a tumor-associated macrophage (TAM) reprogramming strategy for overcoming the EGFR^T790M-associated drug resistance via a dual-targeting codelivery system of gefitinib/vorinostat that acted on both TAM with overexpression of mannose receptors and the HER-2 pos. NSCLC cells. The trastuzumab-modified, mannosylated liposomal system was able to repolarize the protumor M2 phenotype to the antitumor M1 and cause the elevating ROS in the cancer cells, consequently modulating the intracellular redox balance via ROS/NOX3/MsrA axis. The suppressed MsrA facilitated the EGFR^T790M degradation through 790M oxidation by ROS, thus resensitizing the EGFR^T790M-pos. cells to gefitinib. The dual-targeting codelivery and TAM-reprogramming strategies provided a potential method for rescuing the EGFR^T790M-caused resistance to tyrosine kinase inhibitor treatment.

Nano Letters published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Synthetic Route of 96345-79-8.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Murthy, Niren published the artcileBioinspired pH-Responsive Polymers for the Intracellular Delivery of Biomolecular Drugs, Product Details of C13H15NO6S, the publication is Bioconjugate Chemistry (2003), 14(2), 412-419, database is CAplus and MEDLINE.

The biotechnol. and pharmaceutical industries have developed a wide variety of potential therapeutics based on the mols. of biol.: DNA, RNA, and proteins. While these therapeutics have tremendous potential, effectively formulating and delivering them have also been a widely recognized challenge. A variety of viruses and toxins have evolved multi-functional biomols. to solve this problem by directing cellular uptake and enhancing biomol. transport to the cytoplasm from the low pH endosomal compartment. In the study reported here, we have designed and synthesized bio-inspired, pH-responsive polymeric carriers, which we call “encrypted polymers”, that mimic the multi-functional design of biol. These encrypted polymers target and direct cellular uptake, as well as enhance cytosolic delivery by disrupting endosomal membranes in a pH-dependent fashion. We show that the encrypted polymeric carriers significantly enhance the delivery of oligonucleotides and peptides to the cytoplasm of cultured macrophages, demonstrating the potential of this approach for delivery of biotherapeutics and vaccines.

Bioconjugate Chemistry published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Product Details of C13H15NO6S.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gestwicki, Jason E. published the artcileInfluencing Receptor-Ligand Binding Mechanisms with Multivalent Ligand Architecture, Synthetic Route of 96345-79-8, the publication is Journal of the American Chemical Society (2002), 124(50), 14922-14933, database is CAplus and MEDLINE.

Multivalent ligands can function as inhibitors or effectors of biol. processes. Potent inhibitory activity can arise from the high functional affinities of multivalent ligand-receptor interactions. Effector functions, however, are influenced not only by apparent affinities but also by alternate factors, including the ability of a ligand to cluster receptors. Little is known about the mol. features of a multivalent ligand that determine whether it will function as an inhibitor or effector. We envisioned that, by altering multivalent ligand architecture, ligands with preferences for different binding mechanisms would be generated. To this end, a series of 28 ligands possessing structural diversity was synthesized. This series provides the means to explore the effects of ligand architecture on the inhibition and clustering of a model protein, the lectin Con A (Con A). The structural parameters that were varied include scaffold shape, size, valency, and d. of binding elements. We found that ligands with certain architectures are effective inhibitors, but others mediate receptor clustering. Specifically, high mol. weight, polydisperse polyvalent ligands are effective inhibitors of Con A binding, whereas linear oligomeric ligands generated by the ring-opening metathesis polymerization have structural properties that favor clustering. The shape of a multivalent ligand also influences specific aspects of receptor clustering. These include the rate at which the receptor is clustered, the number of receptors in the clusters, and the average inter-receptor distance. Our results indicate that the architecture of a multivalent ligand is a key parameter in determining its activity as an inhibitor or effector. Diversity-oriented syntheses of multivalent ligands coupled with effective assays that can be used to compare the contributions of different binding parameters may afford ligands that function by specific mechanisms.

Journal of the American Chemical Society published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Synthetic Route of 96345-79-8.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Chihara, Yuko published the artcileSerum-resistant Gene Transfer Activity of Mannosylated Dendrimer/α-Cyclodextrin Conjugate (G3), Application In Synthesis of 96345-79-8, the publication is Journal of Inclusion Phenomena and Macrocyclic Chemistry (2006), 56(1-2), 89-93, database is CAplus.

The purpose of this study is to evaluate in vitro gene transfer activity of polyamidoamine (PAMAM) starburst dendrimer (generation 3, G3) conjugate with α-cyclodextrin (α-CDE conjugate (G3)) bearing mannose (Man-α-CDE conjugate (G3)) with the degree of substitution of the mannose moiety 10 (DSM 10) as a novel non-viral vector in NIH3T3 and HepG2 cells. Man-α-CDE conjugate (G3) was found to have much higher gene transfer activity than dendrimer and α-CDE conjugate in NIH3T3 and HepG2 cells, which are independent of the expression of cell-surface mannose receptors. Gene transfer activity of Man-α-CDE conjugate (G3) was highly serum-resistant compared to that of dendrimer and α-CDE conjugate. No cytotoxicity after transfection of the complex of pDNA with Man-α-CDE conjugate (G3) was observed and the transfection activity was much higher than Lipofectin in NIH3T3 cells. These results suggest the potential use of Man-α-CDE conjugate (G3) as a non-viral vector.

Journal of Inclusion Phenomena and Macrocyclic Chemistry published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Application In Synthesis of 96345-79-8.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts