A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

Wang, Zerong Daniel; Mo, Yirong; Chiou, Chiao Lun; Liu, Minghong

doi:10.3390/molecules15010374

Cited by 11 publications

(6 citation statements)

References 18 publications

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“…At 21.5 min (Figure 3-4) a peak was observed relating to the final product (2) without one acetyl group. This was also reported by Wang et al and was explained to be related to the thermolytic condition of the BF3 reaction [233]. Previous studies have also reported 18 h reactions using the same reaction conditions described here (BF3.Et2O, DCM, RT, Fmoc-ser-OH) generating a pure yield of 5% [230].…”

Section: Design and Synthesis Of Mannosylated Building Blockssupporting

confidence: 64%

“…Further, Lewis acid reaction (Figure 3-2) was chosen due to the ease of access to starting materials and shorter reaction times regarding the steps taken compared to other methods available for preparation of a mannose-serine building block. (acetylated mannosyl donor) to Fmoc-Ser-OH using BF3.Et2O in DCM at RT for 4 h generated 2 (Fmoc-serine mannosylated amino acid building blocks) as a mixture of α and β due to attack of the Lewis acid from both below (β, 25.44%) and above (α, 74.55%) [233]. For synthesis details see Chapter 2, Section 2.1.2.…”

Section: Design and Synthesis Of Mannosylated Building Blocksmentioning

confidence: 99%

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Mannosylated lipopetides as model vaccines for targeting the mannose receptor

Sedaghat¹

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The mannose receptor (MR) is an important component of the immune system and understanding the structural and conformational characteristics of this receptor is a key aspect of targeted vaccine design. Improved understanding of the role of carbohydrate recognition domains (CRDs) 4-7 in recognising glycosylated ligands present on the surface of pathogens such as C. albicans, P. carinii, L. donovani, and M. tuberculosis has given new insight into MR vaccine development. Initial studies identified mannan and its derivatives to be important ligands in MR targeting, providing essential knowledge about structural properties of the MR. During the last decade many attempts have been made to target this receptor for applications including vaccine and drug development.In the present study, a library of vaccine constructs comprising fluorescently-labelled mannosylated lipid dendrimers that contained the ovalbumin CD4 + epitope, OVA323-339, as the model peptide antigen were synthesised using fluorenylmethyloxycarbonyl (Fmoc) solid phase peptide synthesis (SPPS). The vaccine constructs were designed with an alanine spacer between the O-linked mannose moieties to investigate the impact of distance between the mannose units on receptor-mediated uptake and/or binding in antigen presenting cells.Mannosylated building blocks were prepared with a Lewis acid reaction and the reaction was successfully modified and monitored for a better yield. This was followed by solid phase synthesis of mannosylated peptides with an azide functional group and a fluorescent tag. Considering the presence of multi-components on the designed mannosylated peptide, different methods of preparation was used and a high yield of the final mannosylated peptides with an azide functional group and a fluorescent tag were prepared. Further, OVA323-339 lipopeptides with an alkyne functional group were prepared using microwave assisted peptide synthesis. Final vaccine structures were prepared by attaching azide and alkyne functional groups using click chemistry. The same methods were applied for the preparation of a library of control vaccine structures.In vitro uptake studies performed on macrophage (F4/80 + ) and dendritic (CD11c + ) cells showed significant uptake and/or binding for vaccine constructs containing mannose and lipid, and also for the lipopeptide vaccine construct without mannose when compared to the controls (containing no lipid, no mannose and no mannose or lipid). Further, in vitro mannan competition assays demonstrated that uptake of the mannosylated and lipidated vaccine constructs was MR mediated. To address the specificity of receptor uptake, surface plasmon resonance (SPR) was performed usingBiacore technology which confirmed a high affinity of the mannosylated and lipidated vaccine constructs towards the human recombinant MR in vitro when compared with vaccine constructs without mannose. These studies also confirmed that both mannose and lipid moieties play significant II roles in receptor-mediated uptake on APCs, potentially faci...

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Section: Design and Synthesis Of Mannosylated Building Blockssupporting

confidence: 64%

Section: Design and Synthesis Of Mannosylated Building Blocksmentioning

confidence: 99%

Mannosylated lipopetides as model vaccines for targeting the mannose receptor

Sedaghat¹

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“…The solvent residue was removed by distillation. The obtained product was allowed to treat with methanol to obtain final product [18]. The product was crystallized by using ethanol.…”

Section: Synthesis Of Acetylated Nucleoside From Glucosementioning

confidence: 99%

Synthesis and Schematic Mechanism of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-b-Dglucopyranosylimino- 1,2,4-dithiazolidines and Its De-acetylated Nucleoside

Hardas¹,

Tayade²

2018

Asian J. Chem.

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Broadly speaking nucleosides are glycosylamine which can be converted to nucleotides i.e. having phosphate group [1]. The major constituents of nucleoside are nitrogenous base and ribose or de-oxyribose. The base in nucleoside is connected to ribose or de-oxyribose through β-glycosidic linkage [2]. Some naturally occurring nucleosides are cytidine, uridine, adenosine, guanosine, thymidine and inosine etc. [3,4]. However, there is need of synthetic nucleoside analogues in order to arrest viral growth, cancer cell growth and for some other related medicinal issues. The benefit of using synthetic nucleoside is that, these compounds after administration get activated in cells and get converted into its active nucleotides. Usually nucleotides are charged and don't cross the cell membrane easily, which can be easily done by using nucleoside [5]. These synthetic nucleosides also work as sugar backbone and does not hydrolyse as easy as RNA, hence, provides the stability in such cases [6]. Synthesis and Schematic Mechanism of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-β β β β β-Dglucopyranosylimino-1,2,4-dithiazolidines and Its De-acetylated Nucleoside ARUNA HARDAS 1 and PRITI TAYADE (GOSAVI) 2,*

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“…In this regard, aminoglycosides showed the primary advancement regarding their demand and utilisation as anticancer drugs. Monosaccharides increase tumor consumption compared to normal cells, resulting in increased intracellular uptake of tumor cells [8,9]. Activation and release of glycogen-mediated drugs to the target site can be accelerated by a glycoside attached to a specific antibody.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of New Derivatives of Busulfan as an Anti-carcinogenic Drug against k562 Cancer Cells Using the AO / PI Method

Jabbari¹,

Khosravi²,

Azimi³

2022

TOMCJ

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Background: Busulfan is a DNA alkylating drug used to treat chronic myeloid leukemia (CML). This type of leukemia affects bone marrow cells or myocytes, which make up bone marrow tissue having a chronic process. Leukemia is a progressive and malignant disease of the body's hematopoietic organs. The disease is caused by the underdevelopment and proliferation of white blood cells and their precursors in the blood and bone marrow. Objective: The synthesis of Busulfan drug and the conjugation of Busulfan from the anomeric position of acetylated galactose as a new derivative of Busulfan and its anti-cancer effect on K562 cancer cells are among the most important objectives of this study. Methods: In this work, galactose was acetylated with acetic anhydride in the presence of sodium acetate, then the anomeric position of acetylated carbohydrate deacetylated using imidazole to obtain the final product through the reaction of Busulfan. Anti-cancer activity of the product was evaluated against K562 cancer cells. The proliferation and survival of K562 cancer cells and PBMCs (peripheral blood mononuclear cells) using the AO/PI method were studied. Furthermore, 1- (2, 3, 4, 6-tetra-O-acetyl-Iβ-D-galactopyranosyl) -4- (methyl sulfonyl oxy) butane was evaluated against cancer cells as a new derivative. Results: In this study, the Acridine Orange / Propidium Iodide (AO/PI) method was performed using fluorescence microscopy to evaluate the efficacy of a synthesized product. The effective dose of 0.02 mg/L of 1- (2, 3, 4, 6-tetra-O-acetyl-Iβ-D-galactopyranosyl) -4- (methyl sulfonyl oxy) butane was observed to cause 96% of cancer cells necrosis. Conclusion: 1- (2, 3, 4, 6-tetra-O-acetyl-Iβ-D-galactopyranosyl) -4- (methyl sulfonyl oxy) butane as a new derivative of Busulfan acts non-specifically in the cell cycle by inhibiting DNA activity by alkylation and binding to the DNA strand. Alkylating agents usually bind an alkyl group to the number seven nitrogen atom in the guanine nucleotide in a DNA molecule.

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A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

Cited by 11 publications

References 18 publications

Mannosylated lipopetides as model vaccines for targeting the mannose receptor

Mannosylated lipopetides as model vaccines for targeting the mannose receptor

Synthesis and Schematic Mechanism of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-b-Dglucopyranosylimino- 1,2,4-dithiazolidines and Its De-acetylated Nucleoside

Synthesis and Evaluation of New Derivatives of Busulfan as an Anti-carcinogenic Drug against k562 Cancer Cells Using the AO / PI Method

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