Category: 5505-63-5

Chinoy, Zoeisha S.; Bodineau, Clement; Favre, Camille; Moremen, Kelley W.; Duran, Raul V.; Friscourt, Frederic published the artcile< Selective Engineering of Linkage-Specific α2,6-N-Linked Sialoproteins Using Sydnone-Modified Sialic Acid Bioorthogonal Reporters>, Electric Literature of 5505-63-5, the main research area is sialoprotein engineering sydnone sialic acid bioorthogonal chem; click chemistry; enzymes; fluorescent probes; glycobiology; sialic acids.

The metabolic oligosaccharide engineering (MOE) strategy using unnatural sialic acids has recently enabled the visualization of the sialome in living systems. However, MOE only reports on global sialylation and dissected information regarding subsets of sialosides is missing. Described here is the synthesis and utilization of sialic acids modified with a sydnone reporter for the metabolic labeling of sialoconjugates. The positioning of the reporter on the sugar significantly altered its metabolic fate. Further in vitro enzymic assays revealed that the 9-modified neuraminic acid is preferentially accepted by the sialyltransferase ST6Gal-I over ST3Gal-IV, leading to the favored incorporation of the reporter into linkage-specific α2,6-N-linked sialoproteins. This sydnone sugar presents the possibility of investigating the roles of specific sialosides.

Angewandte Chemie, International Edition published new progress about Bioorthogonal reaction. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Electric Literature of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Wang, Feifei; Kong, Hao; Meng, Xiangfeng; Tian, Xiao; Wang, Changjiang; Xu, Lei; Zhang, Xiang; Wang, Lei; Xie, Ran published the artcile< A light-initiated chemical reporter strategy for spatiotemporal labeling of biomolecules>, Electric Literature of 5505-63-5, the main research area is biomol spatiotemporal labeling light initiated chem reporter strategy.

The emergence of optochem. approaches has had a diverse impact over a broad range of biol. research due to spatiotemporal regulation. Herein, we integrate this feature into the bioorthogonal chem. reporter strategy, which enables visible light-controlled spatiotemporal labeling of cell-surface glycans, lipids, and proteins. The metabolic precursors were first incorporated into live cells, and next the bioorthogonal reaction converted the azide/alkyne into a photo-active functional group, which allowed for subsequent photo-click reaction. We demonstrated this strategy by specifically labeling sialome, mucin-type O-glycome, phospholipids and newly-synthesized membrane proteins, resp. The sequential photoirradiation-orthogonal reporter tagging (SPORT) should facilitate the probing of biomols. in complex biol. systems with high spatiotemporal precision.

RSC Chemical Biology published new progress about Affinity labeling. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Electric Literature of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Bhatta, Rimsha; Han, Joonsu; Zhou, Jingyi; Li, Haoyu; Wang, Hua published the artcile< Recyclable cell-surface chemical tags for repetitive cancer targeting>, Application of C6H14ClNO5, the main research area is recyclable cell surface chem tag repetitive cancer targeting; Cell targeting; Chemotherapy; Click chemistry; Metabolic glycan labeling; cancer.

Metabolic glycan labeling provides a facile yet powerful tool to install chem. tags to the cell membrane via metabolic glycoengineering processes of unnatural sugars. These cell-surface chem. tags can then mediate targeted conjugation of therapeutic agents via efficient chemistries, which has been extensively explored for cancer-targeted treatment. However, the commonly used in vivo chemistries such as azide-cyclooctyne and tetrazine-cyclooctene chemistries only allow for one-time use of cell-surface chem. tags, posing a challenge for long-term, continuous cell targeting. Here we show that cell-surface ketone groups can be recycled back to the cell membrane after covalent conjugation with hydrazide-bearing mols., enabling repetitive targeting of hydrazide-bearing agents. Upon conjugation to ketone-labeled cancer cells via a pH-responsive hydrazone linkage, Alexa Fluor 488-hydrazide became internalized and entered endosomes/lysosomes where ketone-sugars can be released and recycled. The recycled ketone groups could then mediate targeted conjugation of Alexa Fluor 647-hydrazide. We also showed that doxorubicin-hydrazide can be targeted to ketone-labeled cancer cells for enhanced cancer cell killing. This study validates the recyclability of cell-surface chem. tags for repetitive targeting of cancer cells with the use of a reversible chem., which will greatly facilitate future development of potent cancer-targeted therapies based on metabolic glycan labeling.

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Moons, Sam J.; Rossing, Emiel; Heming, Jurriaan J. A.; Janssen, Mathilde A. C. H.; van Scherpenzeel, Monique; Lefeber, Dirk J.; de Jonge, Marien I.; Langereis, Jeroen D.; Boltje, Thomas J. published the artcile< Structure-Activity Relationship of Fluorinated Sialic Acid Inhibitors for Bacterial Sialylation>, Synthetic Route of 5505-63-5, the main research area is mannosamine fluorosialic acid synthesis antibacterial SAR Haemophilus influenzae sialylation.

Bacterial pathogens such as Nontypeable Haemophilus influenzae (NTHi) can evade the immune system by taking up and presenting host-derived sialic acids. Herein, we report a detailed structure-activity relationship of sialic acid-based inhibitors that prevent the transfer of host sialic acids to NTHi. We report the synthesis and biol. evaluation of C-5, C-8, and C-9 derivatives of the parent compound 3-fluorosialic acid (SiaNFAc). Small modifications are tolerated at the C-5 and C-9 positions, while the C-8 position does not allow for modification. These structure-activity relationships define the chem. space available to develop selective bacterial sialylation inhibitors.

Bioconjugate Chemistry published new progress about Antibacterial 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

Wei, Zhaohan; Zhang, Xiaoqiong; Yong, Tuying; Bie, Nana; Zhan, Guiting; Li, Xin; Liang, Qingle; Li, Jianye; Yu, Jingjing; Huang, Gang; Yan, Yuchen; Zhang, Zelong; Zhang, Bixiang; Gan, Lu; Huang, Bo; Yang, Xiangliang published the artcile< Boosting anti-PD-1 therapy with metformin-loaded macrophage-derived microparticles>, Application In Synthesis of 5505-63-5, the main research area is metformin programmed cell death therapy macrophage microparticle.

The main challenges for programmed cell death 1(PD-1)/PD-1 ligand (PD-L1) checkpoint blockade lie in a lack of sufficient T cell infiltration, tumor immunosuppressive microenvironment, and the inadequate tumor accumulation and penetration of anti-PD-1/PD-L1 antibody. Resetting tumor-associated macrophages (TAMs) is a promising strategy to enhance T-cell antitumor immunity and ameliorate tumor immunosuppression. Here, mannose-modified macrophage-derived microparticles (Man-MPs) loading metformin (Met@Man-MPs) are developed to efficiently target to M2-like TAMs to repolarize into M1-like phenotype. Met@Man-MPs-reset TAMs remodel the tumor immune microenvironment by increasing the recruitment of CD8+ T cells into tumor tissues and decreasing immunosuppressive infiltration of myeloid-derived suppressor cells and regulatory T cells. More importantly, the collagen-degrading capacity of Man-MPs contributes to the infiltration of CD8+ T cells into tumor interiors and enhances tumor accumulation and penetration of anti-PD-1 antibody. These unique features of Met@Man-MPs contribute to boost anti-PD-1 antibody therapy, improving anticancer efficacy and long-term memory immunity after combination treatment. Our results support Met@Man-MPs as a potential drug to improve tumor resistance to anti-PD-1 therapy.

Nature Communications published new progress about Antitumor agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Application In Synthesis of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Green, Scott B.; Lanier, Robert J. Jr.; Carey, Shane M.; Morgan, David R.; Gracz, Hanna; Sherman, Julian; Rodriguez, Ana; D′Antonio, Edward L. published the artcile< Synthesis, biochemical, and biological evaluation of C2 linkage derivatives of amino sugars, inhibitors of glucokinase from Trypanosoma cruzi>, Category: alcohols-buliding-blocks, the main research area is glucosamine mannosamine galactosamine inhibitor glucokinase inhibitor parasite protozoan; amino sugar inhibitor glucokinase Trypanosoma cruzi glucosamine protozoan parasite; Amino sugars; Chagas’ disease; Glucokinase; Inhibitors; Neglected tropical diseases.

Eighteen amino sugar analogs were screened against Trypanosoma cruzi glucokinase (TcGlcK), a potential drug-target of the protozoan parasite in order to assess for viable enzyme inhibition. The analogs were divided into three amino sugar scaffolds that included D-glucosamine (D-GlcN), D-mannosamine (D-ManN), and D-galactosamine (D-GalN); moreover, all but one of these compounds were novel. TcGlcK is an important metabolic enzyme that has a role in producing G6P for glycolysis and the pentose phosphate pathway (PPP). The inhibition of these pathways via glucose kinases (i.e., glucokinase and hexokinase) appears to be a strategic approach for drug discovery. Glucose kinases phosphorylate D-glucose with co-substrate ATP to yield G6P and the formed G6P enters both pathways for catabolism. The compound screen revealed five on-target confirmed inhibitors that were all from the D-GlcN series, such as compounds 1, 2, 4, 5, and 6. Four of these compounds were strong TcGlcK inhibitors (1, 2, 4, and 6) since they were found to have micromolar inhibitory constant (Ki) values around 20 μM. Three of the on-target confirmed inhibitors amino sugars, e.g. I-III, revealed notable in vitro anti-T. cruzi activity with IC50 values being less than 50 μM. Compound 1 was benzoyl glucosamine (BENZ-GlcN), a known TcGlcK inhibitor that was the starting point for the design of the compounds in this study; in addition, TcGlcK – I inhibition properties were previously determined [D′Antonio, E. L. et al. (2015) Mol. Biochem. Parasitol. 204, 64-76]. As such, compounds II-III were further evaluated biochem., where formal Ki values were determined as well as their mode of TcGlcK inhibition. The Ki values determined for compounds II-III were 107 ± 4 μM and 15.2 ± 3.3 μM, resp., and both of these compounds exhibited the competitive inhibition mode.

Bioorganic & Medicinal Chemistry Letters published new progress about Drug discovery. 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

Song, Zilan; Liu, Bo; Peng, Xia; Gu, Wangting; Sun, Yiming; Xing, Li; Xu, Yi; Geng, Meiyu; Ai, Jing; Zhang, Ao published the artcile< Design, Synthesis, and Pharmacological Evaluation of Biaryl-Containing PD-1/PD-L1 Interaction Inhibitors Bearing a Unique Difluoromethyleneoxy Linkage>, Related Products of 5505-63-5, the main research area is difluoromethyleneoxy linkage PD1 PDL1 interaction inhibitor anticancer.

Blockade of immune checkpoint PD-1/PD-L1 has been a promising anticancer strategy; however, clin. available PD-1/PD-L1 small-mol. inhibitors are lacking. In view of the high potency of compound 2 (BMS-1002), structural fine tuning of the methoxy linkage together with diverse modification in the solvent interaction region was conducted. A series of novel derivatives featuring a difluoromethyleneoxy linkage were designed. Compound 43 was identified as the most promising PD-1/PD-L1 inhibitor with an IC50 value of 10.2 nM in the HTRF assay. This compound is capable of promoting CD8+ T cell activation through inhibiting PD-1/PD-L1 cellular signaling. Moreover, in the Hepa1-6 syngeneic mouse model, administration of compound 43 at 1 mg/kg dosage promoted CD8+ T cell activation and delayed the tumor growth with good tolerance. Notably, the tumor in one mouse of the compound 43-treated group was completely regressed. These results indicate that compound 43 is a promising candidate worthy of further investigation.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Related Products of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Song, Zilan; Liu, Bo; Peng, Xia; Gu, Wangting; Sun, Yiming; Xing, Li; Xu, Yi; Geng, Meiyu; Ai, Jing; Zhang, Ao published the artcile< Design, Synthesis, and Pharmacological Evaluation of Biaryl-Containing PD-1/PD-L1 Interaction Inhibitors Bearing a Unique Difluoromethyleneoxy Linkage>, Related Products of 5505-63-5, the main research area is difluoromethyleneoxy linkage PD1 PDL1 interaction inhibitor anticancer.

Blockade of immune checkpoint PD-1/PD-L1 has been a promising anticancer strategy; however, clin. available PD-1/PD-L1 small-mol. inhibitors are lacking. In view of the high potency of compound 2 (BMS-1002), structural fine tuning of the methoxy linkage together with diverse modification in the solvent interaction region was conducted. A series of novel derivatives featuring a difluoromethyleneoxy linkage were designed. Compound 43 was identified as the most promising PD-1/PD-L1 inhibitor with an IC50 value of 10.2 nM in the HTRF assay. This compound is capable of promoting CD8+ T cell activation through inhibiting PD-1/PD-L1 cellular signaling. Moreover, in the Hepa1-6 syngeneic mouse model, administration of compound 43 at 1 mg/kg dosage promoted CD8+ T cell activation and delayed the tumor growth with good tolerance. Notably, the tumor in one mouse of the compound 43-treated group was completely regressed. These results indicate that compound 43 is a promising candidate worthy of further investigation.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Related Products of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Weldu, Welday Desta; Wang, Cheng-Chung published the artcile< Selective Acetylation of Non-anomeric Groups of per-O-Trimethylsilylated Sugars>, Application In Synthesis of 5505-63-5, the main research area is TMSOTf catalyzed protecting group aminoglycoside preparation regioselective acetylation.

Selective modification of the hydroxyl groups of sugars has been a long-standing challenge due to their proximate relative reactivity. Herein, we report a TMSOTf-catalyzed selective acetylation of the non-anomeric hydroxyl groups of several per-O-TMS-protected sugar substrates while leaving their anomeric group unaffected. In addition to standing versatile by itself, the anomeric O-TMS group left intact can be functionalized to afford key sugar precursors such as imidate donors, which could otherwise be synthesized via a stepwise anomeric deprotection-functionalization procedure.

Journal of Organic Chemistry published new progress about Acetylation catalysts. 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Application In Synthesis of 5505-63-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Schafer, Rebecca J. B.; Monaco, Mattia R.; Li, Mao; Tirla, Alina; Rivera-Fuentes, Pablo; Wennemers, Helma published the artcile< The Bioorthogonal Isonitrile-Chlorooxime Ligation>, Product Details of C6H14ClNO5, the main research area is bioorthogonal isonitrile chlorooxime ligation.

Bioorthogonal reactions are valuable tools for the selective labeling and imaging of natural products and proteins. Here, we present the reaction between isonitriles and chlorooximes as a ligation that proceeds quickly (k ≈ 1 M-1 s-1) and with high chemoselectivity in an aqueous environment. Imaging of metabolically labeled cell surface glycans underlined the tolerance of the ligation to common functional groups in cellular systems. Live-cell dual-labeling experiments revealed that the isonitrile-chlorooxime ligation is orthogonal to the strain-promoted azide-alkyne cycloaddition

Journal of the American Chemical Society published new progress about Azide-alkyne 1,3-dipolar cycloaddition reaction (strain-promoted (SPAAC)). 5505-63-5 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H14ClNO5, Product Details of C6H14ClNO5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts