Synthesis of artemisinic acid derived glycoconjugates and their anticancer studies

Kotammagari, Tharun K.; Paul, Sayantan; Barik, Ganesh Kumar; Santra, Manas Kumar; Bhattacharya, Asish K.

doi:10.1039/d0ob00216j

Cited by 17 publications

(13 citation statements)

References 24 publications

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“…3) were synthesized as per reported literature methods and their spectral data were found to be consistent with the reported literature data. 15,20,21 The stereochemistries of the anomeric configurations of the azido sugars 5a-f were assigned as the β-configurations on the basis of comparison with reported data 20 as well as their coupling constants in the 1 H NMR (nuclear magnetic resonance) spectra. In general, the anomeric proton of the azido sugars appeared as a doublet integrated to one proton at 4.61-4.98 ppm in the 1 H NMR spectra with a coupling constant in the range of 8.5-8.8 Hz, which unequivocally proves that the azide groups are β-oriented.…”

Section: Synthesis and Characterization Of The Synthesized Compoundsmentioning

confidence: 99%

“…It has also been reported that the conjugation of a carbohydrate scaffold to naturally occurring bioactive molecules has led to enhanced bioactivity and manifestation of superior biological properties such as solubility, stability, and bioactivity compared to the parent molecule. [15][16][17] Therefore, glycoconjugates of bioactive natural products can be ideal candidates for efficacious therapeutic agents. The hypervalent nature of sugar assists the drug molecule to reach target cells, thus playing a major role in the drug delivery system.…”

Section: Introductionmentioning

confidence: 99%

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Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus

et al. 2022

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Section: Synthesis and Characterization Of The Synthesized Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus

et al. 2022

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“…Bhattacharya and co-workers produced a family of O -artemisinic acid and N- artemisinic acid glycohybrids via CuAAC coupling of individual sugar azides with propargyl O -artemisinic acid ester under standard click conditions in appreciable yields . The resulting glycohybrid analogues of artemisinic acid were evaluated for their anticancer activity.…”

Section: Application Of Carbo-cuaac Click Chemistry In Drug Discovery...mentioning

confidence: 99%

“…CuAAC click chemistry mediated artemisinic acid derived glycohybrids ( 1086 and 1087 ) with promising anticancer activities …”

Section: Application Of Carbo-cuaac Click Chemistry In Drug Discovery...mentioning

confidence: 99%

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology.

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“…Since the peroxide bridge present in artemisinins is the main pharmacophore responsible for both antiplasmodial In another study [65], glycoconjugate derivatives of artemisinic acid were synthesized and anticancer properties were studied. It was found that all artemisinic acid glycoconjugates were able to inhibit the growth of MCF7, however, showed moderate cytotoxicity (Fig.…”

Section: Modificationsmentioning

confidence: 99%

Antimalarial and anticancer properties of artesunate and other artemisinins: current development

Khanal

2021

Monatsh Chem

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Graphic abstract This review provides a recent perspective of artesunate and other artemisinins as antimalarial drugs and their uses in cancer therapy. Artesunate is an artemisinin derivative. Artemisinin is extracted from the plant Artemisia annua. Artemisinin and its derivatives have been the most useful drug for malarial treatment in human history. The artesunate has an advantage of a hydrophilic group over other artemisinins which makes it a more potent drug. On the industrial scale, artemisinins are synthesized in semisynthetic ways. The 1,2,4-endoperoxide bridge of artemisinins is responsible for the drug's antimalarial activity. There is the emergence of artemisinin resistance on Plasmodium falciparum and pieces of evidence suggest that it is mainly due to the mutation at Kelch13 protein of P. falciparum . Clinical trial data show that the artesunate is more favorable than quinine and other artemisinins to treat patients with severe malaria. Pieces of evidence indicate that artemisinins can be developed as anticancer drugs. The mechanism of actions on how artemisinins act as an anticancer drug involves oxidative stress, DNA damage and repair, and various types of cell deaths.

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Synthesis of artemisinic acid derived glycoconjugates and their anticancer studies

Abstract: Twenty-four artemisinic acid glycoconjugate hybrids were synthesized using click reaction and evaluated for their anticancer activities against the MCF7 cell line.

Cited by 17 publications

References 24 publications

Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus

Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

Antimalarial and anticancer properties of artesunate and other artemisinins: current development

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