1235-74-1Relevant academic research and scientific papers
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.
Synthesis and antitumor evaluation of (aryl)methyl-amine derivatives of dehydroabietic acid-based B ring-fused-thiazole as potential PI3K/AKT/mTOR signaling pathway inhibitors
Chen, Nai-Yuan,Xie, Yu-Lan,Lu, Guo-Dong,Ye, Fang,Li, Xin-Yu,Huang, Yu-Wen,Huang, Ming-Li,Chen, Tie-Yu,Li, Cui-Ping
, p. 967 - 979 (2020/04/24)
Abstract: In an attempt to search for new natural product-based antitumor agents, a series of novel (aryl)methyl-amine derivatives of dehydroabietic acid-based B ring-fused-thiazole were designed and synthesized. The primary bioassay showed that compounds
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 of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
González-Cardenete, Miguel A.,Zaragozá, Ramón J.
, p. 15015 - 15022 (2020/04/27)
The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.
Synthesis, cytotoxicity and apoptosis-inducing activity of novel 1H-benzo[d]imidazole derivatives of dehydroabietic acid
Li, A-Liang,Yang, Ya-Qun,Wang, Wen-Yan,Liu, Qing-Song,Sun, Yue,Gu, Wen
, p. 1668 - 1678 (2020/07/30)
With the expectation of finding new and effective antitumor drugs, a series of novel N-(1H-benzo[d]imidazole-2-yl)-benzamide/benzenesulfonamide derivatives of dehydroabietic acid were synthesized and evaluated for cytotoxic activity against three human ca
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.
The synthesis of a DHAD/ZnAlTi-LDH composite with advanced UV blocking and antibacterial activity for skin protection
Duan, Wengui,Hu, Tingting,Liang, Ruizheng,Lin, Guishan,Liu, Xinlong,Wang, Xiu,Wei, Min,Zhu, Yu
, p. 9786 - 9790 (2020/03/23)
Skin wounds are particularly vulnerable and susceptible to bacterial infection. Unfortunately, the abuse of antibiotics has resulted in the emergence of a number of multidrug-resistant bacteria in the past few decades. Moreover, secondary damage of the fragile new tissue around the wound caused by high-energy ultraviolet (UV) radiation has been rarely noticed. To address these problems, herein, we present an alternative strategy to overcome drug-resistant bacteria and UV damage by taking advantage of dehydroabietic acid derivatives (DHADs) and layered double hydroxides (LDHs). DHAD, synthesized from dehydroabietic acid (DHA) through a series of reactions, was assembled with ZnAlTi-LDH to obtain a DHAD/ZnAlTi-LDH composite. The results showed that DHAD/ZnAlTi-LDH has a prominent reactive oxygen species (ROS) production capacity, and both Gram-negative and positive bacteria can be killed under visible light irradiation. At the same time, it can effectively shield the skin from UV rays. In vitro and vivo experiments confirmed that the composite has great promise for bactericidal applications, UV blocking and wound healing.
Dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and preparation method and application thereof
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Paragraph 0030-0035, (2020/09/30)
The invention discloses a dehydroabietic acid-based 2,4-diarylbenzimidazole fluorescent probe for ferric ions and mercury ions, and a preparation method and application thereof. The preparation methodcomprises the following steps: subjecting dehydroabieti
Synthesis and Antibacterial Activity of Benzenesulfonylhydrazone Derivatives of Methyl Dehydroabietate
Zhou, Zhi,Wang, Xiang,Zhou, Tingting
, p. 819 - 823 (2019/06/27)
Six benzenesulfonylhydrazone derivatives of methyl dehydroabietate are synthesized via esterification, benzylic oxidation, condensation with hydrazine hydrate, and following nucleophilic substitution reaction with a variety of substituted benzenesulfonyl chloride. The structures of the synthesized compounds are characterized by 1H NMR and MS spectra. Antibacterial activity of the target compounds is evaluated by disk diffusion method against E. coli, S. aureus, and B. subtilis. The results demonstrate that benzenesulfonylhydrazone derivatives of methyl dehydroabietate exhibit inhibitory activity. Among the six compounds, p-fluorobenzenesulfonylhydrazone of methyl dehydroabietate exhibits the highest antibacterial activity with the zone of inhibition of 17.3 mm against B. subtilis and 16.5 mm against S. aureus.
Synthesis and biological evaluation of novel N-(piperazin-1-yl)alkyl-1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential MEK inhibitors
Chen, Hao,Qiao, Chao,Miao, Ting-Ting,Li, A-Liang,Wang, Wen-Yan,Gu, Wen
, p. 1544 - 1561 (2019/08/28)
In this paper, a series of novel 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid bearing different N-(piperazin-1-yl)alkyl side chains were designed, synthesised and evaluated for their in vitro anticancer activities against three human hepato
