Synthesis and anti-cancer activities of glycosides and glycoconjugates of diterpenoid isosteviol

Sharipova, R. R.; Belenok, M. G.; Garifullin, B. F.; Sapunova, Аnastasiia S.; Voloshina, Alexandra D.; Andreeva, O. V.; Strobykina, I. Yu.; Skvortsova, Polina V.; Zuev, Yu. F.; Катаев, В. Е.

doi:10.1039/c9md00242a

Cited by 18 publications

(4 citation statements)

References 42 publications

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“…Cytotoxic effects of samples on human cancer and normal cells were estimated by means of the multifunctional Cytell Cell Imaging system (GE Health Care Life Science, Uppsala, Sweden) using the Cell Viability Bio App (version 3.6.7.19) which precisely counts the number of cells and evaluates their viability from fluorescence intensity data [31]. The M-HeLa clone 11 human, epithelioid cervical carcinoma, strain of HeLa, clone of M-HeLa; WI-38 VA-13 cell culture, subline 2RA (human embryonic lung), from the Type Culture Collection of the Institute of Cytology (Russian Academy of Sciences, Moscow, Russia); and Chang Liver cell line (Human liver cells) from N. F. Gamaleya Research Center of Epidemiology and Microbiology were used in the experiments.…”

Section: Methodsmentioning

confidence: 99%

Silica-Supported Assemblage of CuII Ions with Carbon Dots for Self-Boosting and Glutathione-Induced ROS Generation

et al. 2022

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The present work introduces coordinative binding of CuII ions with both amino-functionalized silica nanoparticles (SNs) and green-emitting carbon dots (CDs) as the pregrequisite for the CuII-assisted self-assembly of the CDs at the surface of the SNs. The produced composite SNs exhibit stable in time stimuli-responsive green fluorescence derived from the CuII-assisted assemblage of CDs. The fluorescence response of the composite SNs is sensitive to the complex formation with glutathione (GSH), enabling them to detect it with the lower limit of detection of 0.15 μM. The spin-trap-facilitated electron spin resonance technique indicated that the composite SNs are capable of self-boosting generation of ROS due to CuII→CuI reduction by carbon in low oxidation states as a part of the CDs. The intensity of the ESR signals is enhanced under the heating to 38 °C. The intensity is suppressed at the GSH concentration of 0.35 mM but is enhanced at 1.0 mM of glutathione, while it is suppressed once more at the highest intracellular concentration level of GSH (10 mM). These tendencies reveal the concentrations optimal for the scavenger or reductive potential of GSH. Flow cytometry and fluorescence and confocal microscopy methods revealed efficient cell internalization of SNs-NH2-CuII-CDs comparable with that of “free” CDs.

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Section: Methodsmentioning

confidence: 99%

Silica-Supported Assemblage of CuII Ions with Carbon Dots for Self-Boosting and Glutathione-Induced ROS Generation

et al. 2022

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“…Molecules 2023, 28, 4951 2 of 24 thereby inducing apoptosis and cell cycle arrest in the G 2 /M phase [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]. Since previous work also indicated an effect on mitochondrial permeability transition [35], it was natural to transfer our own previous findings on pentacyclic triterpenes to the diterpene isosteviol.…”

Section: Introductionmentioning

confidence: 99%

“…Isosteviol has been reported to be a suppressor of human DNA topoisomerase II [ 18 ] and of mammalian DNA polymerases, thus explaining its antitumor activity [ 19 , 20 ]. Parent stevioside was reported to have minor cytotoxic effects on several human cancer cell lines, thereby inducing apoptosis and cell cycle arrest in the G 2 /M phase [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ]. Since previous work also indicated an effect on mitochondrial permeability transition [ 35 ], it was natural to transfer our own previous findings on pentacyclic triterpenes to the diterpene isosteviol.…”

Section: Introductionmentioning

confidence: 99%

The Finally Rewarding Search for A Cytotoxic Isosteviol Derivative

et al. 2023

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Acid hydrolysis of stevioside resulted in a 63% yield of isosteviol (1), which served as a starting material for the preparation of numerous amides. These compounds were tested for cytotoxic activity, employing a panel of human tumor cell lines, and almost all amides were found to be non-cytotoxic. Only the combination of isosteviol, a (homo)-piperazinyl spacer and rhodamine B or rhodamine 101 unit proved to be particularly suitable. These spacered rhodamine conjugates exhibited cytotoxic activity in the sub-micromolar concentration range. In this regard, the homopiperazinyl-spacered derivatives were found to be better than those compounds with piperazinyl spacers, and rhodamine 101 conjugates were more cytotoxic than rhodamine B hybrids.

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“…Glycosides are well-known to exhibit important pharmacological activities. [2][3][4] Pertinent examples include inhibitors of various glycoproteins, 5 glycosides with anticarcinogenic activities, 6 novel glycosidic flavonoids acting as antioxidant and antibiotic agents, 7 compounds that regulate body fluid, etc. 8 Some examples of commercial drugs with glycosidic linkages are illustrated in Figure 2.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

Mukherjee,

Kundu,

Das

et al. 2023

Synthesis

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The development of stereoselective synthetic routes for C-glycosides has attracted immense attention from carbohydrate chemists in the last two decades. In this review, progress made in the last decade towards the synthesis of C-glycosides using glycals as a precursor are discussed. Glycals have been extensively manipulated to generate oxocarbenium cation or glycosyl anion to form C-C bond at the anomeric position through attack with C-nucleophiles or transition metal catalyzed coupling reactions. Recent reports on carbon Ferrier, intramolecular Cope, Claisen rearrangements, various coupling reactions in the presence or absence of directing groups are deliberated herein. Contemporary applications of these reactions in the syntheses of natural products, drugs and scaffolds with bioactive potential are briefly discussed.

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Synthesis and anti-cancer activities of glycosides and glycoconjugates of diterpenoid isosteviol

Abstract: A series of glycosides and glycoconjugates of diterpenoid isosteviol with various monosaccharide residues were synthesized. Most of them showed moderate to significant cytotoxicity against human cancer cell lines M-HeLa and MCF-7.

Cited by 18 publications

References 42 publications

Silica-Supported Assemblage of CuII Ions with Carbon Dots for Self-Boosting and Glutathione-Induced ROS Generation

Silica-Supported Assemblage of CuII Ions with Carbon Dots for Self-Boosting and Glutathione-Induced ROS Generation

The Finally Rewarding Search for A Cytotoxic Isosteviol Derivative

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

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