122210-01-9Relevant academic research and scientific papers
Allobetulin N-acetylglucosaminide. Synthesis and antimicrobial activity
Strobykina, I. Yu.,Garifullin,Strobykina,Voloshina,Sharipova,Kataev
, p. 890 - 893 (2017)
Allobetulin N-acetylglucosaminide has been synthesized and shown to exhibit selective bacteriostatic activity against Staphylococcus aureus ATCC 209p with a minimum inhibitory concentration of 15.5 μg/mL.
Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides
Ma?a, Patrycja,Pedersen, Christian Marcus
supporting information, p. 5685 - 5689 (2021/08/30)
N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i. e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.
Synthesis and cytotoxicity of the conjugates of diterpenoid isosteviol and N-acetyl-D-glucosamine
Garifullin, Bulat F.,Strobykina, Irina Yu.,Khabibulina, Leysan R.,Sapunova, Anastasiya S.,Voloshina, Aleksandra D.,Sharipova, Radmila R.,Khairutdinov, Bulat I.,Zuev, Yuriy F.,Kataev, Vladimir E.
, p. 1372 - 1378 (2019/08/22)
A series of conjugates of diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and N-acetyl-D-glucosamine was synthesised and their cytotoxicity against several human cancer cell lines (M-Hela, MCF-7, Hep G2, Panc-1, PC-3), as well as normal human cell lines (WI-38, Chang liver) was assayed. Most of the conjugates were found to be cytotoxic against the mentioned cancer cell lines in the range of IC50 values 13–89 μM. Two lead compounds 14a and 14b showed selective cytotoxicity against M-Hela (IC50 13 and 14 μM) that was two times as high as the cytotoxicity of the anti-cancer drug Tamoxifen in control (IC50 28 μM). It was found that cytotoxic activity of the lead compounds against M-Hela cells is due to induction of apoptosis.
Novel carbohydrate-based sulfonamide derivatives as selective carbonic anhydrase II inhibitors: Synthesis, biological and molecular docking analysis
Hou, Zhuang,Cai, Qiang,Cheng, Mao-sheng
, (2021/09/28)
A series of sulfonamides containing glucosamine moieties had been prepared and investigated for the inhibition of the zinc enzyme carbonic anhydrases (CAs, EC 4.2.1.1). Compared to their parent compound p-sulfamoylbenzoic acid, target compounds showed two order of magnitude improvement in their binding affinities against hCA II in vitro. Moreover, they also showed great selectivity toward hCA II enzyme with the ratios for inhibiting hCA II over hCA I in the range 20–96 and for inhibiting hCA II over hCA IX in the range 4.3–9. Due to the introduction of glucosamine moieties, all of compounds displayed good water solubility (in the range of 2.0–2.5%) and the pH values of the obtained solutions is neutral (7.0–7.2). Compared to the clinically available and relatively highly acidic dorzolamide (pH 5.5), target compounds are more likely to be less irritating to the eye when applied to topical glaucomatous drugs. Then, cytotoxicity evaluation suggested that all target compounds did not display any appreciable toxicity against human cornea epithelial cell. In addition, molecular docking studies elucidated the binding modes of those compounds toward hCA II. Collectively, these results suggest that target compounds represented a promising scaffold to treat glaucoma without major topical side effects.
Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
Andreeva, Olga V.,Garifullin, Bulat F.,Sharipova, Radmila R.,Strobykina, Irina Yu.,Sapunova, Anastasiya S.,Voloshina, Alexandra D.,Belenok, Mayya G.,Dobrynin, Alexey B.,Khabibulina, Leysan R.,Kataev, Vladimir E.
, p. 2367 - 2380 (2020/08/28)
Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.
Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group
Cai, Li,Emmanuel, Khalisha A.,Gao, Qi,Ge, Dongmian,Han, Ziyi,Li, Gen,McManus, Cynthia L.,Sui, Qiang,Xue, Jundi
, p. 1955 - 1962 (2020/10/02)
Lipid A, the hydrophobic domain of lipopolysaccharide (LPS), is a strong immunostimulator and therefore a valuable target for the development of novel immunomodulators. Various lipid A derivatives have been chemically synthesized in order to reduce toxicity while retaining the immunostimulatory activity. In this work, we describe a novel approach to the frequently problematic synthesis of monophosphorylated mono- and disaccharide lipid X using a combination of established chemistry and a novel 2-naphthyl-methyl ether (Nap) protecting group for “permanent” protection of hydroxy groups. Of particular note is the fact that the key Nap protecting group is able to remain in the molecule until the final global deprotection step. Our synthetic strategy is not only efficient in regards to the yield of the various chemical transformations, but also robust in regards to the potential application of this route to the production of other lipid A analogs.
Self-Adjuvanting Cancer Vaccines from Conjugation-Ready Lipid A Analogues and Synthetic Long Peptides
Reintjens, Niels R. M.,Tondini, Elena,De Jong, Ana R.,Meeuwenoord, Nico J.,Chiodo, Fabrizio,Peterse, Evert,Overkleeft, Herman S.,Filippov, Dmitri V.,Van Der Marel, Gijsbert A.,Ossendorp, Ferry,Codée, Jeroen D. C.
, p. 11691 - 11706 (2020/11/26)
Self-adjuvanting vaccines, wherein an antigenic peptide is covalently bound to an immunostimulating agent, have been shown to be promising tools for immunotherapy. Synthetic Toll-like receptor (TLR) ligands are ideal adjuvants for covalent linking to peptides or proteins. We here introduce a conjugation-ready TLR4 ligand, CRX-527, a potent powerful lipid A analogue, in the generation of novel conjugate-vaccine modalities. Effective chemistry has been developed for the synthesis of the conjugation-ready ligand as well as the connection of it to the peptide antigen. Different linker systems and connection modes to a model peptide were explored, and in vitro evaluation of the conjugates showed them to be powerful immune-activating agents, significantly more effective than the separate components. Mounting the CRX-527 ligand at the N-terminus of the model peptide antigen delivered a vaccine modality that proved to be potent in activation of dendritic cells, in facilitating antigen presentation, and in initiating specific CD8+ T-cell-mediated killing of antigen-loaded target cells in vivo. Synthetic TLR4 ligands thus show great promise in potentiating the conjugate vaccine platform for application in cancer vaccination.
LANGERIN+ CELL TARGETING
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, (2019/08/08)
The present invention relates to the use of a vehicle for specific molecular targeting of Langerin+ cells, wherein the vehicle is capable of specifically binding to a Langerin+ cell, said vehicle comprising (a) at least one carrier and (b) at least one sa
Convergent Synthesis of Sialyl LewisX- O-Core-1 Threonine
Sardar, Mohammed Y. R.,Mandhapati, Appi Reddy,Park, Simon,Wever, Walter J.,Cummings, Richard D.,Chaikof, Elliot L.
, p. 4963 - 4972 (2018/05/17)
Selectins are a class of cell adhesion molecules that play a critical role during the initial steps of inflammation. The N-terminal domain of P-selectin glycoprotein ligand-1 (PSGL-1) binds to all selectins, but with the highest affinity to P-selectin. Re
Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors
Lacey, Kristina D.,Quarels, Rashanique D.,Du, Shaofu,Fulton, Ashley,Reid, Nicholas J.,Firesheets, Austin,Ragains, Justin R.
supporting information, p. 5181 - 5185 (2018/09/12)
Two classes of thioglycoside, 4-(4-methoxyphenyl)-3-butenylthioglycosides (MBTGs) and 4-(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), undergo acid-catalyzed O-glycosylations with a range of sugar and nonsugar alcohols at 25 °C. Electron density at t
