Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells

Sanhueza, Carlos; Mayato, Carlos; García-Chicano, María; Díaz-Peñate, Raquel; Dorta, Rosa L.; Vázquez, Jesús T.

doi:10.1016/j.bmcl.2006.05.079

Cited by 14 publications

(11 citation statements)

References 21 publications

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“…Partially benzylated C-glucopyranosyl benzene 891 showed activity against human promyelocytic leukemia cell line (HL60), although several aliphatic C-glucosyl (but no galacto-or mannopyranosyl) derivatives were 3−6-fold more active and some of the latter type also induced apoptosis. 470 Compound 891 proved inactive against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines, while aliphatic counterparts had low micromolar efficiencies (IC 50 1− 10 μM). 471 Unprotected C-glycosyl naphthoquinones 892 (R = H) were ineffective toward human melanoma cells (A375); however, with O-peracetyl as well as 2,3,4-tri-O-acetyl-6-Obenzoyl protection, they showed in vitro cytotoxicity, which was independent of the sugar configuration.…”

Section: Miscellaneous Biological Studiesmentioning

confidence: 99%

“…Several C -glycosyl (het)arenes were studied against malignant cells (Figure ). Partially benzylated C -glucopyranosyl benzene 891 showed activity against human promyelocytic leukemia cell line (HL60), although several aliphatic C -glucosyl (but no galacto- or mannopyranosyl) derivatives were 3–6-fold more active and some of the latter type also induced apoptosis . Compound 891 proved inactive against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines, while aliphatic counterparts had low micromolar efficiencies (IC 50 1–10 μM) .…”

Section: Biological Effects Of C-glycosyl (Het)arenesmentioning

confidence: 99%

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C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

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This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes. A classification of the preparative routes to these synthetic targets according to methodologies and compound categories is provided. Several of these compounds, regardless of their natural or synthetic origin, display antidiabetic properties due to enzyme inhibition (glycogen phosphorylase, protein tyrosine phosphatase 1B) or by inhibiting renal sodium-dependent glucose cotransporter 2 (SGLT2). The latter class of synthetic inhibitors, very recently approved as antihyperglycemic drugs, opens new perspectives in the pharmacological treatment of type 2 diabetes. Various compounds with the C-glycopyranosyl (het)arene motif were subjected to biological studies displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.

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Section: Miscellaneous Biological Studiesmentioning

confidence: 99%

Section: Biological Effects Of C-glycosyl (Het)arenesmentioning

confidence: 99%

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

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“…Therefore, it's a challenge for the development of novel, effective, and environmentally safe antiviral agent. 5 Glycoside, widely distributed in plants, has increasingly aroused attention because of its various pharmacological effects, 6 such as anticancer, 7 antiviral, 8 antiproliferative, 9 anti-HBV, 10 anti-HIV, 11 antihyperglycemic, 12 antimicrobial, 13 antioxidant, 14 and cytotoxic 14 activities. Recently, a large number of natural glycosides were found to exhibit outstanding antiviral activities against TMV.…”

Section: Introductionmentioning

confidence: 99%

Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives

Chen

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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“…366−375 However, other Grignard reagents (e.g., butenyl magnesium chloride, acetal magnesium chloride, and phenyl magnesium chloride) under similar conditions afforded a mixture of αand β-C-glucosides 430−432 (α/β = 1:1). 366,370,371 It was found that the reaction temperature was a key factor in modulating the stereoselectivity.…”

Section: C-glycosylation With Glycosyl Acetates Through Glycosyl Anio...mentioning

confidence: 99%

Recent Advances in the Chemical Synthesis of C-Glycosides

2017

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Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg-Bäcklund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted.

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Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells

Cited by 14 publications

References 21 publications

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives

Recent Advances in the Chemical Synthesis of C-Glycosides

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