Category: 96345-79-8

Bonfils, Edwige published the artcileUptake by macrophages of a biotinylated oligo-α-deoxythymidylate by using mannosylated streptavidin, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Bioconjugate Chemistry (1992), 3(4), 277-84, database is CAplus and MEDLINE.

Streptavidin substituted with mannose residues increased by 20-fold the intracellular concentration of a biotinylated dodecakis(α-deoxythymidylate) in macrophages by comparison with the uptake of free oligodeoxynucleotide. Streptavidin, the bacterial homolog of the very basic avidin, which does not contain any carbohydrate moieties and is a neutral protein, was substituted with 12 mannose residues in order to be recognized and internalized by mannose-specific lectins on the surface of macrophages. A 3′-biotinylated 5′-fluoresceinylated dodecakis(α-deoxythymidylate) was synthesized and bound onto mannosylated streptavidin. The conjugate was isolated, and by using flow cytometry, it was shown that the uptake of fluoresceinylated oligodeoxynucleotides bound to mannosylated streptavidin by macrophages is 20-fold higher than that of free oligodeoxynucleotides and that the uptake was competitively inhibited by mannosylated serum albumin. Glycosylated streptavidin conjugates recognizing specific membrane lectins on different cells provide the possibility to target biotinylated antisense oligodeoxynucleotides and to increase the biol. effect of these chemotherapeutic agents.

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

Cavallaro, Gennara published the artcileGlycosilated macromolecular conjugates of antiviral drugs with a polyaspartamide, Related Products of alcohols-buliding-blocks, the publication is Journal of Drug Targeting (2004), 12(9-10), 593-605, database is CAplus and MEDLINE.

Two new polymeric conjugates for specific liver targeting were prepared by conjugation of sugar moieties and antiviral drugs to α, β-poly[N-2-(hydroxyethyl)-dl-aspartamide] (PHEA). PHEA-galactopyranosylphenylthiocarbamide-mono-O-succinylganciclovir (conjugate 7) and PHEA-mannopyranosylphenylthiocarbamide-O-succinylacyclovir (conjugate 8) were synthesized according to a multi-step procedure which allowed for obtaining high product yield and process standardization. Conjugate 7 contained 7.5 and 8.5% of galactose and ganciclovir (substituent/repeating unit, mol/mol), resp., and conjugate 8 contained 14.2 and 10.8% of mannose and acyclovir, resp. In vitro studies demonstrated that both acyclovir and ganciclovir were released from the polymeric adducts at a release rate depending on the incubation medium. Though a detailed study evidenced that the two bioconjugates undergo different hydrolysis pathways, in both cases high drug release rate was found in plasma, while the glycosidic moiety was not released. Pharmacokinetic studies carried out by i.v. administration of the bioconjugates to Balb/c mice demonstrated that the conjugation of glycosidic moieties promoted the disappearance of the polymer from the blood stream. The two derivatives displayed a different pharmacokinetic profile. In particular, the mannosyl conjugation promoted the rapid disposition of the macromol. in the kidneys and in the liver, while prevented the accumulation in the spleen. On the contrary, the galactosyl derivative was found to dispose in the liver at the same extent of the naked polymer. Few considerations on the different behavior of the conjugates were reported.

Journal of Drug Targeting 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, Related Products of alcohols-buliding-blocks.

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

Shao, Jun published the artcileCharacterization of a mannosylphospholipid liposome system for drug targeting to alveolar macrophages, Quality Control of 96345-79-8, the publication is Drug Delivery (1997), 4(1), 43-48, database is CAplus.

The potential that mannose receptors on alveolar macrophages (AMs) may be targeted using mannose-conjugated liposomes for intracellular drug delivery to AMs was investigated. A mannosylphospholipid was synthesized via the reaction of α-D-mannopyranosylphenylisothiocyanate with dipalmitoyl phosphatidylethanolamine, and the product was identified using thin-layer chromatog. and NMR spectroscopy. Liposomes containing this mannosylated phospholipid were made using a high-pressure homogenization method and analyzed using freeze-etch electron transmission microscopy. These liposomes were shown to exhibit unilamellar structure with a mean diameter of 140 ± 59 nm. The uptake of liposomes by rat alveolar macrophages, by measurement of internalized, liposome-encapsulated fluorescein, was found to be both dose and time dependent. The uptake of liposomes containing 40% mannosylphospholipid was 3.6-fold higher than that of liposomes without the mannosylated lipid (16% to 4.5%). Fluorescein in solution was not internalized by AMs. The enhancement of uptake by conjugation of mannose onto the liposome surface was markedly inhibited by the addition of free mannose at various concentrations, indicating an uptake process involving mannose receptor-mediated endocytosis.

Drug Delivery 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 C11H8O3, Quality Control of 96345-79-8.

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

Wang, Ce published the artcileLymphatic-targeted cationic liposomes: A robust vaccine adjuvant for promoting long-term immunological memory, Name: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Vaccine (2014), 32(42), 5475-5483, database is CAplus and MEDLINE.

Although retaining antigens at the injection site (the so-called “depot effect”) is an important strategy for vaccine development, increasing evidence showed that lymphatic-targeted vaccine delivery with liposomes could be a promising approach for improving vaccine efficacy. However, it remains unclear whether antigen depot or lymphatic targeting would benefit long-term immunol. memory, a major determinant of vaccine efficacy. In the present study, OVA antigen was encapsulated with DOTAP cationic liposomes (LP) or DOTAP-PEG-mannose liposomes (LP-Man) to generate depot or lymphatic-targeted liposome vaccines, resp. The result of in vivo imaging showed that LP mostly accumulated near the injection site, whereas LP-Man not only effectively accumulated in draining lymph nodes (LNs) and the spleen, but also enhanced the uptake by resident antigen-presenting cells. Although LP vaccines with depot effect induced anti-OVA IgG more potently than LP-Man vaccines did on day 40 after priming, they failed to mount an effective B-cell memory response upon OVA re-challenge after three months. In contrast, lymphatic-targeted LP-Man vaccines elicited sustained antibody production and robust recall responses three months after priming, suggesting lymphatic targeting rather than antigen depot promoted the establishment of long-term memory responses. The enhanced long-term immunol. memory by LP-Man was attributed to vigorous germinal center responses as well as increased Tfh cells and central memory CD4⁺ T cells in the secondary lymphoid organs. Hence, lymphatic-targeted vaccine delivery with LP-Man could be an effective strategy to promote long-lasting immunol. memory.

Vaccine 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 C13H26N2, Name: (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

Layek, Buddhadev published the artcileAPC targeted micelle for enhanced intradermal delivery of hepatitis B DNA vaccine, HPLC of Formula: 96345-79-8, the publication is Journal of Controlled Release (2015), 143-153, database is CAplus and MEDLINE.

Chronic hepatitis B is a serious liver disease and puts people at high risk of death from cirrhosis and liver cancer. Although DNA vaccination has been emerged as a potential immunotherapeutic strategy for the treatment of chronic hepatitis B, the efficiencies were not adequate in clin. trials. Here we describe the design, synthesis, and evaluation of mannosylated phenylalanine grafted chitosan (Man-CS-Phe) as a DNA delivery vector for direct transfection of antigen presenting cells to improve cellular and humoral immunity to plasmid-coded antigen. The cationic Man-CS-Phe micelles condense plasmid DNA into nanoscale polyplexes and provide efficient protection of complexed DNA from nuclease degradation The mannose receptor-mediated enhanced cell uptake and high in vitro transfection efficiency of the polyplexes were demonstrated in RAW 264.7 and DC 2.4 cells using GFP-expressing plasmid DNA. Furthermore, intradermal immunization of BALB/c mice indicated that hepatitis B DNA vaccine/Man-CS-Phe polyplexes not only induced multi-fold higher serum antibody titer in comparison to all other formulations including FuGENE HD, but also significantly stimulated T-cell proliferation and skewed T helper toward Th1 polarization. These results illustrate that the Man-CS-Phe can serve as a promising DNA delivery vector to harness both cellular and humoral arms of immune system.

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, HPLC of Formula: 96345-79-8.

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

Kieburg, Christoffer published the artcileGlycodendrimer synthesis without using protecting groups, Quality Control of 96345-79-8, the publication is Tetrahedron Letters (1997), 38(22), 3885-3888, database is CAplus.

Oligoantennary neoglycoconjugates can act as powerful inhibitors of carbohydrate-protein interactions and thus serve as anti-adhesives in carbohydrate-based adhesion systems. They were obtained by a procedure that does not require protecting groups. Various unprotected NCS-functionalized saccharides were coupled with oligoamines in aqueous solution This versatile method is generally applicable to the synthesis of thiourea-bridged glycodendrimers.

Tetrahedron 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, Quality Control of 96345-79-8.

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

Studer, Peggy published the artcileSynthesis and Characterization of Poly(ethylene oxide)-block-poly(methylidene malonate 2.1.2) Block Copolymers Bearing a Mannose Group at the PEO Chain End, Application of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Bioconjugate Chemistry (2005), 16(1), 223-229, database is CAplus and MEDLINE.

A poly(ethylene oxide)-block-poly(methylidene malonate 2.1.2) block copolymer (PEO-b-PMM 2.1.2) bearing a mannose moiety at the poly(ethylene oxide) chain end was synthesized by sequential anionic polymerization of ethylene oxide (EO) and methylidene malonate 2.1.2 (MM 2.1.2), followed by a coupling reaction between its poly(ethylene oxide) amino- or aldehyde-end group and a sugar derivative Different coupling procedures, either in organic media or in aqueous micellar solutions, were examined in order to optimize the poly(ethylene oxide) end-glycosylation yield. The micellar size of the functionalized block copolymers was determined by dynamic light scattering.

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 C10H23N, Application 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

Grabosch, Carsten published the artcileGlycoarrays by a New Tandem Noncovalent-Covalent Modification of Polystyrene Microtiter Plates and their Interrogation with Live Cells, Recommanded Product: (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is ChemBioChem (2012), 13(13), 1874-1879, S1874/1-S1874/18, database is CAplus and MEDLINE.

Thiourea bridging was used for fabrication of glycoarrays on polystyrene microtiter plates, to allow assaying of carbohydrate recognition in a optimally easy and flexible way. For the noncovalent modification of polystyrene microtiter plates, dodecylamine and dodecyl isothiocyanate were selected. This first immobilization step was followed by thiourea bridging with a suitable carbohydrate derivative and subsequent carbohydrate-specific read out. For the testing system, mannose-specific bacterial adhesion was employed with green fluorescent protein (GFP)-tagged Escherichia coli bacteria (pPKLl 162). A selection of inhibitors of type 1 fimbriae-mediated bacterial adhesion was used. Tandem noncovalent-covalent modification of polystyrene microtiter plates led to stable glycoarrays that yield valuable and valid data in adhesion inhibition tests with live bacterial cells. Nonspecific adhesion to polystyrene is excluded in this protocol. In addition to polystyrene plates, polypropylene (PP) microtiter plates were tested by the same approach and showed results that were in good accordance with the assays on analogously modified polystyrene plates.

ChemBioChem 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

Grabosch, Carsten published the artcileA dual Click’ strategy for the fabrication of bioselective, glycosylated self-assembled monolayers as glycocalyx models, Quality Control of 96345-79-8, the publication is Organic & Biomolecular Chemistry (2013), 11(24), 4006-4015, database is CAplus and MEDLINE.

Solid surfaces decorated with specific saccharide patterns can serve as a model for the chem. and structurally highly complex glycocalyx of eukaryotic cells. Here we present an approach based on self-assembled monolayers on gold, which are built up in a three-step manner to provide a solid basis, a biorepulsive oligoethylene glycol part, and a specific glycoside terminus, e.g. I, in a modular way. Of the different reaction sequences, the one with two consecutive click reactions’ (the copper(I)-catalyzed 1,3-dipolar cycloaddition of alkynes with azides and the thiourea-bridging of isothiocyanates with amines) directly on SAM’ results in the densest layers, as demonstrated by IR absorption reflection spectroscopy and ellipsometry. As a real life’ test, the surfaces obtained this way were used for bacterial adhesion experiments Here the biorepulsivity of the middle part of the SAMs as well as specific binding to the carbohydrate termini could be clearly demonstrated.

Organic & Biomolecular 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, Quality Control of 96345-79-8.

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

Jiang, Hu-Lin published the artcileMannosylated chitosan-graft-polyethylenimine as a gene carrier for Raw 264.7 cell targeting, Application In Synthesis of 96345-79-8, the publication is International Journal of Pharmaceutics (2009), 375(1-2), 133-139, database is CAplus and MEDLINE.

Gene transfer using non-viral vectors is a promising approach for the safe delivery of therapeutic genes. Among non-viral vectors, chitosans have been proposed as alternative, biocompatible cationic polymers for non-viral gene delivery. However, the low transfection efficiency and low specificity of chitosan needs to be addressed prior to clin. application. In this study, mannosylated chitosan-graft-polyethylenimine (Man-CHI-g-PEI) copolymer was prepared by thiourea reaction between the isothiocyanate group of mannopyranosylphenylisothiocyanate and the amine groups of chitosan-graft-PEI (CHI-g-PEI) for targeting into antigen presenting cells (APCs) having mannose receptors. The composition and mol. weight were characterized using ¹H NMR and GPC, resp. The copolymer was complexed with plasmid DNA in various copolymer/DNA (N/P) charge ratios, and the complexes were characterized. Man-CHI-g-PEI showed good DNA binding ability and high protection of DNA from nuclease attack and had low cytotoxicity compared with PEI 25K. The transfection efficiency of Man-CHI-g-PEI/DNA complexes into the Raw 264.7 macrophage cell line, which has mannose receptors, was higher than CHI-g-PEI itself as well as PEI 25K, indicating Man-CHI-g-PEI can be used as an APCs’ targeting gene delivery carrier.

International Journal of Pharmaceutics 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