81575-48-6Relevant articles and documents
Identification of novel bivalent mimetics of annonaceous acetogenins via a scaffold-hopping strategy
Liu, Yanghan,Liu, Yongqiang,Li, Zhen,Zhou, Guang-Biao,Yao, Zhu-Jun,Jiang, Sheng
supporting information, p. 1650 - 1653 (2014/04/17)
A series of novel bivalent mimetics of annonaceous acetogenins have been designed, synthesized, and evaluated. Among these, compound 7 bearing a homopiperazine ring in the middle region exhibited more potent growth inhibitory activity and higher selectivity against cancer cells over normal cells by comparison with AA005. This work indicates that modification of the middle piperazine ring is a useful optimizing tool for the simplified acetogenin mimetics.
In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues
Ma, Wei,Zhou, Hao,Ying, Yi-Lun,Li, Da-Wei,Chen, Guo-Rong,Long, Yi-Tao,Chen, Hong-Yuan
, p. 5990 - 6000 (2011/09/19)
Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV-vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure-activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.
Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria
Duveau, Damien Y.,Arce, Pablo M.,Schoenfeld, Robert A.,Raghav, Nidhi,Cortopassi, Gino A.,Hecht, Sidney M.
experimental part, p. 6429 - 6441 (2010/10/03)
Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate.