1235-74-1Relevant articles and documents
A novel dehydroabietic acid-based AIE-active fluorescent probe for rapid detection of Hg2+ and its environmental and biological applications
Chen, Lin-lin,Gu, Wen,Liu, Qing-song,Sun, Lu,Sun, Xue-bao,Sun, Yue,Wang, Zhong-long,Yang, Zi-hui
, (2021/10/20)
A highly sensitive AIE fluorescent probe (DBAQ) containing quinoxaline moiety was designed based on the natural diterpene dehydroabietic acid. This probe was synthesized and manifested via the analysis of FT-IR, 1H NMR, 13C NMR, and ESI-MS spectra. The probe DBAQ was utilized to selectively recognize Hg2+ against other competitive metal ions with the detection limit of 10.3 nM in MeCN/H2O solution (v/v = 1/9, pH = 7.5). In particular, DBAQ (λex/em = 425/600 nm) possessed a large Stokes shift (175 nm), short response time (10 s), and a wide pH range for Hg2+ detection (5 ～ 10). Job's plot method was used to determine the stoichiometry ratio of DBAQ-Hg2+ complexes as 1:2, which was confirmed by FT-IR. The binding mechanisms of DBAQ with Hg2+ were confirmed by 1H NMR titration. Meanwhile, DBAQ exhibited satisfied detection performance in seafood and environmental water samples. Furthermore, DBAQ revealed the considerably low cytotoxic effects to MCF-7 cells (IC50 > 100 μM), and it could be utilized as an outstanding imaging agent for the determination of Hg2+ both in living cells and zebrafish.
A novel dehydroabietic acid-based turn-on fluorescent probe for the detection of bisulfite and its application in live-cell and zebrafish imaging
Li, A-Liang,Wang, Zhong-Long,Wang, Wen-Yan,Liu, Qing-Song,Sun, Yue,Gu, Wen
, p. 16822 - 16832 (2021/09/28)
In this paper, a turn-on fluorescent probe (DBE) was designed and synthesized for probing bisulfite (HSO3?) by coupling dehydroabietic acid-based benzimidazole derivatives with ethyl cyanoacetate moiety. The structure of the compound was characterized using its UV-Vis,1H-NMR,13C-NMR and HRMS spectra. The probe showed significant selectivity and sensitivity towards HSO3?compared to other analytes in DMF/PBS buffer (3/7, v/v, 10 mM, pH = 7.4), and exhibited a detection limit at the nanomolar level (3.2 nM), fast response time (140 s) and good pH stability (6-10) in living systems. Furthermore, this probe was successfully utilized for the fluorescence imaging of HSO3?in living zebrafish and MCF-7 cells with remarkable lysosome-targeting properties.
Synthesis and anticancer evaluation of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid as PI3Kα inhibitors
Chen, Hao,Gu, Wen,Liu, Qing-Song,Sun, Yue,Yang, Ya-Qun
, (2020/04/27)
Phosphatidylinositol 3-kinase (PI3K) is one of the most attractive therapeutic targets for cancer treatment. In this study, a series of new 2-arylthio- and 2-arylamino-1H-benzo[d]imidazole derivatives of dehydroabietic acid were designed, synthesized and characterized by 1H NMR, 13C NMR, IR and MS spectra analyses. In the in vitro anticancer assay, some title compounds showed significant inhibitory activities against four cancer cell lines (HCT-116, MCF-7, HeLa and HepG2). Among them, compound 9g exhibited the most potent activity with IC50 values of 0.18 ± 0.03, 0.43 ± 0.05, 0.71 ± 0.08 and 0.63 ± 0.09 μM against four cancer cell lines, and considerably lower cytotoxicity to human gastric mucosal cell line Ges-1 (IC50: 21.95 ± 0.73 μM). Besides, compound 9g displayed a certain selective activity to PI3Kα (IC50 = 0.012 ± 0.002 μM) over PI3Kβ, γ and δ, and meanwhile, it can remarkably decrease the expression level of p-Akt (Ser473). In addition, compound 9g could increase intracellular reactive oxygen species level, decrease mitochondrial membrane potential, upregulate Bax and cleaved caspase-3/9 levels, downregulate Bcl-2 level and thus induce the apoptosis of HCT-116 cells in a dose-dependent manner. The results suggested that compound 9g could be considered as a promising PI3Kα inhibitor.
