7470-44-2Relevant articles and documents
Safrole oxide induces neuronal apoptosis through inhibition of integrin β4/SOD activity and elevation of ROS/NADPH oxidase activity
Su, Le,Zhao, BaoXiang,Lv, Xin,Wang, Nan,Zhao, Jing,Zhang, ShangLi,Miao, JunYing
, p. 999 - 1006 (2007)
Neuronal apoptosis is a very important event in the development of the central nervous system (CNS), but the underlying mechanisms remain to be elucidated. We have previously shown that safrole oxide, a small molecule, induces integrin β4 expression and promotes apoptosis in vascular endothelial cells. In this study, the effects of safrole oxide on cell growth and apoptosis have been examined in primary cultures of mouse neurons. Safrole oxide was found to significantly inhibit neuronal cell growth and to induce apoptosis. The inhibitory and apoptotic activities of safrole oxide followed a dose- and time-dependent manner. Interestingly, the expression of integrin β4 was significantly inhibited with safrole oxide treatment. Furthermore, safrole oxide dramatically increases the level of intracellular reactive oxygen species (ROS) and the activity of NADPH oxidase. Moreover, manganese-dependent superoxide dismutase (MnSOD) activity was decreased significantly with safrole oxide treatment. Our study thus demonstrates that safrole oxide induces neuronal apoptosis through integrin β4, ROS, NADPH, and MnSOD.
Utilization of catecholic functionality in natural safrole and eugenol to synthesize mussel-inspired polymers
Alhaffar, Mouheddin T.,Akhtar, Mohammad N.,Ali, Shaikh A.
, p. 21265 - 21277 (2019/07/22)
Naturally occurring safrole I upon epoxidation gave safrole oxide II, which underwent ring opening polymerization using a Lewis acid initiator/catalyst comprising of triphenylmethylphosphonium bromide/triisobutylaluminum to afford new polyether III in excellent yields. Epoxy monomer II and allyl glycidyl ether IV in various proportions have been randomly copolymerized to obtain copolymer V. A mechanism has been proposed for the polymerization reaction involving chain transfer to the monomers. A strategy has been developed for the deprotection of the methylene acetal of V using Pb(OAc)4 whereby one of the methylene protons is replaced with a labile OAc group to give VI. The pendant allyl groups in VI have been elaborated via a thiol-ene reaction using cysteamine hydrochloride and thioglycolic acid to obtain cationic VII and anionic VIII polymers, both containing a mussel-inspired Dopa-based catechol moiety. During aqueous work up, the protecting group containing OAc was deprotected under mild conditions. Cationic VII and anionic VIII were also obtained via an alternate route using epoxide IX derived from 3,4-bis[tert-butyldimethylsilyloxy]allylbenzene. Monomer IX was homo- as well as copolymerized with IV using Lewis acid initiator/catalyst system to obtain homopolymer X and copolymer X1. Copolymer XI was then elaborated using a thiol-ene reaction followed by F- catalysed silyl deprotection to obtain mussel inspired polymers VII and VIII, which by virtue of having charges of opposite algebraic signs were used to form their coacervate.
New safrole oxide derivatives: Synthesis and in vitro antiproliferative activities on A549 human lung cancer cells
Wang, Li-Ying,Wang, Xiu-Hua,Tan, Jia-Lian,Xia, Shuai,Sun, Heng-Zhi,Shi, Jin-Wen,Jiang, Ming-Dong,Fang, Liang,Zuo, Hua,Dupati, Gautam,Jang, Kiwan,Shin, Dong-Soo
, p. 3571 - 3575 (2013/01/16)
A number of novel small molecules, safrole oxide derivatives 4a-c, 6a-c, 9a-h, were synthesized by the reaction of safrole oxide with anilines 3 and 5, or its alkyl allyl ether derivative 7 with alkyl bromide 8 in moderate yields. The antiproliferative effects of all the target molecules on A549 cell growth were investigated and it was found that the 14 novel compounds could suppress A549 lung cancer cell growth. Among them, compound 6b was the most effective compound in inhibiting the proliferation of A549 cells.