ChemInform Abstract: Superactive Iodination Reagent on a Base of Iodine Chloride and Silver Sulfate.

Chaikovski, Vitold K.; Kharlova, T. S.; Филимонов, В. Д.; Saryucheva, Tamara A.

doi:10.1002/chin.199934085

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, reaction of the commercially available quercetin with iodomethane afforded the known full methylated product (1) [ 39 ]. The product were iodinated with ICl in dry DMSO to yield compound 2 [ 40 ]. The product 2 was then reacted with the trifluoromethyl reagent (methyl fluorosulfonyldifluoroacetate) under nitrogen protection in the presence of CuI/DMF/HMPA afforded the desired compound 3 after purification by prep-HPLC [ 41 ].…”

Section: Resultsmentioning

confidence: 99%

A novel synthetic derivative of quercetin, 8-trifluoromethyl-3,5,7,3′,4′-O-pentamethyl-quercetin, inhibits bladder cancer growth by targeting the AMPK/mTOR signaling pathway

Tao

Deng

et al. 2017

Oncotarget

View full text Add to dashboard Cite

Quercetin is a naturally existing compound and shows attractive anticancer properties for a variety of solid tumors including glioma, bladder cancer, hepatocellular carcinoma, breast cancer, hematological malignancies and prostate carcinoma. However, these anticancer properties have not been clinically approved due to unclear mechanistic information and its low bioactivity. In our previous study, we elucidated that quercetin activates AMPK pathway which is the major mechanism for its unique anticancer effect in bladder cancer. In the present study, we are trying to enhance its bioactivity by chemical modification using fluorination approach to prepare novel chemical entities, based on the principle of intermediate derivative method (IDM). The compound we obtained is named 8-trifluoromethyl-3,5,7,3′,4′-O-pentamethyl- quercetin (TFQ), characterized by NMR spectra and mass spectrum (MS). The results from MTT and cologenic assay in two human and one murine bladder cancer cell lines showed that TFQ exhibits more potent inhibition on the three bladder cancer cell lines than quercetin (Que) although this enhanced effects is not very dramatic. Furthermore, we found that the survival of normal bladder cells PEBC was not significantly suppressed by TFQ compared with Que. Western blot analysis showed that TFQ possess more potent AMPK activation than Que. The downstream of AMPK was further examined by western blot. TFQ treatment is able to inactivate mTOR signaling pathway with the regulation of mTOR, 4EBP1 and P70S6K. These results demonstrated that the fluorinated quercetin derivative TFQ inhibits bladder cancer cell growth through the AMPK/mTOR pathway. Altogether, our findings suggest that TFQ could serve as a new potential therapeutic agent for bladder cancer more effective than Que.

show abstract

Section: Resultsmentioning

confidence: 99%