1240724-54-2

Upstream product

• 110-15-6 succinic acid 
• 490-91-5 thymoquinone 
• 89-83-8 thymol 

Downstream Products

• 1353853-23-2 3-(3-hydroxypropyl)-2-methyl-5-(1-methylethyl)cyclohexa-2,5-diene-1,4-dione 
• 1240724-40-6 (-)-menthyl 3-(2-methyl-5-(1-methylethyl)-3,6-dioxocyclohexa-1,4-dienyl)propanoate 
• 1240724-47-3 C₂₃H₃₂O₄ 
• 1240724-45-1 C₂₃H₃₂O₄ 
• 1240724-50-8 C₂₃H₃₀O₄ 

Relevant academic research and scientific papers

Combination of 5-fluorouracil and thymoquinone targets stem cell gene signature in colorectal cancer cells

Cancer stem cells (CSCs) residing in colorectal cancer tissues have tumorigenic capacity and contribute to chemotherapeutic resistance and disease relapse. It is well known that the survival of colorectal CSCs after 5-fluorouracil (5-FU)-based therapy leads to cancer recurrence. Thus CSCs represent a promising drug target. Here, we designed and synthesized novel hybrid molecules linking 5-FU with the plant-derived compound thymoquinone (TQ) and tested the potential of individual compounds and their combination to eliminate colorectal CSCs. Both, Combi and SARB hybrid showed augmented cytotoxicity against colorectal cancer cells, but were non-toxic to organoids prepared from healthy murine small intestine. NanoString analysis revealed a unique signature of deregulated gene expression in response to the combination of TQ and 5-FU (Combi) and SARB treatment. Importantly, two principle stem cell regulatory pathways WNT/?-Catenin and PI3K/AKT were found to be downregulated after Combi and hybrid treatment. Furthermore, both treatments strikingly eliminated CD133+ CSC population, accompanying the depleted self-renewal capacity by eradicating long-term propagated 3D tumor cell spheres at sub-toxic doses. In vivo xenografts on chicken eggs of SARB-treated HCT116 cells showed a prominent nuclear ?-Catenin and E-cadherin staining. This was in line with the reduced transcriptional activity of ?-Catenin and diminished cell adhesion under SARB exposure. In contrast to 5-FU, both, Combi and SARB treatment effectively reduced the angiogenic capacity of the remaining resistant tumor cells. Taken together, combination or hybridization of single compounds target simultaneously a broader spectrum of oncogenic pathways leading to an effective eradication of colorectal cancer cells.

Thymoquinone derivative, intermediate, as well as preparation method and application of thymoquinone derivative

The invention discloses a thymoquinone derivative, an intermediate, as well as a preparation method and application of the thymoquinone derivative. The structure of the thymoquinone derivative disclosed by the invention is shown as a formula (I). The preparation method of the thymoquinone derivative provided by the invention has the advantages of use of cheap and readily-available raw materials, less reaction steps and high yield, is suitable for industrial production, and has a better prospect.

Thymoquinone derivative, and preparation method and applications thereof

The invention relates to a thymoquinone derivative, and a preparation method and applications thereof, and belongs to the technical field of organic synthesis. The molecular general formula of the novel thymoquinone derivative is disclosed in the invention. The novel thymoquinone derivative possesses obvious inhibition effect on cancer cells; the adopted raw materials are cheap; preparation is simple and convenient; reaction steps are few; yield is high; the preparation method is suitable for industrialized production; and the thymoquinone derivative is a medicine with promising prospect.

Terpene conjugates of the Nigella sativa seed-oil constituent thymoquinone with enhanced efficacy in cancer cells

Thymoquinone (TQ; 1) is a weak anticancer constituent of black seed oil. Derivatives bearing terpene-terminated 6-alkyl residues were tested in cells of human HL-60 leukemia, 518A2 melanoma, multidrug-resistant KB-V1/Vbl cervix, and MCF-7/Topo breast carcinomas, as well as in non-malignant human foreskin fibroblasts. Derivatives with a short four-atom spacer between quinone and cyclic monoterpene moieties were more antiproliferative than analogues with longer spacers. 6-(Menthoxybutyryl) thymoquinone (3a) exhibited single-digit micromolar IC50 (72 h) values in all four cell lines. It was seven times more active than TQ (1) in 518A2 melanoma cells and four times in KB-V1/Vbl cervix carcinoma cells, while only half as toxic in the fibroblasts. Compound 3a was also not a substrate for the Pgp and BCRP drug transporters of the resistant cancer cells. The caryophyllyl and germacryl conjugates 3e and 3f specifically inhibited the growth of the resistant MCF-7 breast carcinoma cells. Conjugation of TQ with the triterpene betulinic acid via the OH group as in 3g led to a loss in activity, while conjugation via the carboxylic acid afforded compound 4 with nanomolar IC50 (72 h) activity against HL-60 cells. All anticancer-active derivatives of TQ (1) induced apoptosis associated with DNA laddering, a decrease in mitochondrial membrane potential and a slight increase in reactive oxygen species.