Protecting Groups

Boons, Geert‐Jan; Hale, Karl J.

doi:10.1002/9780470760321.ch2

Cited by 1 publication

(1 citation statement)

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“…For benzoylation reaction, 18 benzoyl chloride (55.8 μL, 0.48 mmol) was added dropwise at 0 °C to a stirred solution of neoandrographolide (48.0 mg, 0.1 mmol) in 1 mL dichloromethane and triethylamine (67 μL, 0.48 mmol). After the completion (3–4 h) of the reaction, it was concentrated under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Carbohydrate Modifications of Neoandrographolide for Improved Reactive Oxygen Species-Mediated Apoptosis through Mitochondrial Pathway in Colon Cancer

et al. 2019

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Modifications at the carbohydrate moiety of neoandrographolide, isolated from the medicinal plant Andrographis paniculata, result in more potent and less toxic derivatives, namely, 4′,6′-benzylidene neoandrographolide (2b) and 4′6′-p-methoxybenzylidene neoandrographolide (2c). These showed improved cytotoxicity against SW-620, PC-3, and A549 cancer cell lines. Nuclear morphology studies were conducted on compound 2b by 4′,6-diamidino-2-phenylidole staining and detection of intracellular reactive oxygen species (ROS) accumulation. It showed an increase in the generation of cellular and mitochondrial ROS level. The probable relation of B-cell lymphoma-2 (Bcl-2, an apoptosis inhibitor) to B-cell lymphoma-2-associated X protein (Bax, an apoptosis promoter) ratio with caspase-3 (apoptosis coordination enzyme) in the colon cancer cell line SW-620 was investigated, and it was discovered that upon 2b treatment, the expression of caspase-3 Bax increased remarkably. However, in 2b-treated cells, the expression of Bcl-2 was downregulated as compared to untreated cells.

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Section: Methodsmentioning

confidence: 99%