1026064-38-9Relevant academic research and scientific papers
Enediynes bearing polyfluoroaryl sulfoxide as new antiproliferative agents with dual targeting of microtubules and DNA
Borie, Cyril,Mondal, Shovan,Arif, Tanzeel,Briand, Manon,Lingua, Hugo,Dumur, Frédéric,Gigmes, Didier,Stocker, Pierre,Barbarat, Bernadette,Robert, Viviane,Nicoletti, Cendrine,Olive, Daniel,Maresca, Marc,Nechab, Malek
, p. 306 - 313 (2018/02/21)
A novel series of enediynes possessing pentafluorophenylsulfoxide have been developed. The innovative compounds possess antiproliferative activity against a broad panel of human cancer cells originating from breast, blood, lung, kidney, colon, prostate, pancreas or skin with IC50 ranging from 0.6 to 3.4 μM. The antiproliferative activity of enediynes in darkness is associated to their ability to compromise microtubule network. In addition, exposure to UV leads to double-stranded DNA cleavage caused by the newly synthesized molecules reducing further their IC50 in nanomolar range against human tumor cells, including chemo-resistant pancreatic cancer cells. Taken together, the examined data demonstrate that enediynes possessing pentafluorosulfoxide are promising molecules in the cancer therapy.
Synthesis and reactivity of enediyne-nucleobase hybrids: Effect of intramolecular π-stacking
Roy, Snigdha,Bag, Subhendu Sekhar,Basak, Amit
, p. 8600 - 8611 (2012/10/29)
Three distinct classes of nucleobase-containing enediynes 1-9 with varying nature of the linker have been synthesized to explore the effect of π-stacking interaction in accelerating the rate of Bergman cyclization (BC). Chemical reactivity study, both experimental and computations demonstrated the important role that aromatic π-stacking interactions between the appended nucleobases within an enediyne frame play in lowering the activation barrier of Bergman cyclization.
The effect of charge-transfer complexation/π-stacking interactions in lowering the activation barrier of the Bergman cyclization
Basak, Amit,Bag, Subhendu Sekhar,Das, Amit K.
, p. 1239 - 1245 (2007/10/03)
To elaborate the concept of weak interactions and their effect on Bergman Cyclization (BC), several 1,2-dikynyl benzenes incorporating various combinations of donor and acceptor units in the two arms of the enediynes were designed and synthesized, and the
Allene-eneyne Related Cycloaromatization: Design and Synthesis of New DNA-cleaving Compounds
Wu, Ming-Jung,Lin, Chi-Fong,Jing, Pao-Tzu,Chang, Li-Juan,Duh, Tsai-Hui,Lee, Fang-Chen,Chen, Huey-Ting
, p. 475 - 479 (2007/10/03)
(Z)-7-Sulfonyl-3-hexen-1,5-diyne containing molecules are stable at room temperature and isomerized to eneyne-allene-sulfones under alkaline conditions. These eneyne-allene-sulfones were not isolable, spontaneously cyclized to form biradical intermediates under mild conditions, and exhibited good DNA-cleaving and human tumor cell line growth inhibition properties. Further studies indicated that compounds bearing on aromatic ring at C(3) and C(4), such as 25, proved to be more active against those tumor cell lines. ReEndocrinology moval of acetylene unit at C(1) and C(2), made the resulting compound less active. A related compound, (Z,Z)-12-(2-tetrahydropyranyl)oxy-1-phenylsulfonyldodeca-4,8-diene-2,6,10-triyne (37), was synthesized. Upon treatment of triethylamine at refluxing benzene, this compound undergoes double cycloaromatization to form a naphalene adduct, which possesses excellent DNA-cleaving activity.
Chemical synthesis, DNA cleavage and antitumor activity of molecules with (Z)-7-sulfonyl-3-hexene-1,5-diyne functionalities
Wu, Ming-Jung,Lin, Chi-Fong,Ong, Chi-Wi
, p. 675 - 678 (2007/10/03)
Compounds 20a-d, 21a, 21d and 22 were synthesized from the corresponding (Z)-1,2-dichloroethylene, 1,2-diiodobenzene and 2,3 naphthylene bistriflate respectively and exhibited DNA cleaving properties at 37°C in pH 8.0 as well as potent cytotoxicity against human carcinoma cells with no additive.
