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Int. J. Mol. Sci. 2016, 17(6), 747;

Synthesis, Biological Activity, and Apoptotic Properties of NO-Donor/Enmein-Type ent-Kauranoid Hybrids

Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, and School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
State Key Laboratory of New-Tech for Chinese Medicine Pharmaceutical Processes, and National Post-Doctoral Research Workstation, Jiangsu Kanion Pharmaceutical Co., Ltd., Lianyungang 222001, China
State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, and School of Chemistry and Pharmacy, Guangxi Normal University, Guilin 541004, China
Department of Medicinal Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China
Authors to whom correspondence should be addressed.
Academic Editor: Ge Zhang
Received: 26 February 2016 / Revised: 2 May 2016 / Accepted: 6 May 2016 / Published: 24 May 2016
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Herein, we reported on a series of synthetic nitric oxide-releasing enmein-type diterpenoid hybrids (9ai). All the target compounds showed potent antibacterial activity against selected Gram-positive bacteria S. aureus and B. subtilis. The antiproliferative activity against human tumor K562, MGC-803, CaEs-17 and Bel-7402 cells, and human normal liver cells L-02 was tested and the structure activity relationships (SARs) were also concluded. Compounds 9b and 9d showed the best activity against S. aureus and B. subtilis with the same minimal inhibitory concentrations (MICs) of 4 and 2 μg/mL, respectively. The derivative 9f displayed IC50 values of 1.68, 1.11, 3.60 and 0.72 μM against the four cancer cell lines above and 18.80 μM against normal liver cells L-02; meanwhile, 9f also released a high level of NO at the time point of 60 min of 22.24 μmol/L. Furthermore, it was also found that 9f induced apoptosis via the mitochondria-related pathway and arrested cell cycle of Bel-7402 cells at S phase. These findings might be important to explore new chemical entities for the main causes of in-hospital mortality of S. aureus infection, combined with a solid tumor. View Full-Text
Keywords: NO-donor; enmein-type; ent-kauranoid; antiproliferative; apoptosis NO-donor; enmein-type; ent-kauranoid; antiproliferative; apoptosis

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Li, D.; Hu, X.; Han, T.; Xu, S.; Zhou, T.; Wang, Z.; Cheng, K.; Li, Z.; Hua, H.; Xiao, W.; Xu, J. Synthesis, Biological Activity, and Apoptotic Properties of NO-Donor/Enmein-Type ent-Kauranoid Hybrids. Int. J. Mol. Sci. 2016, 17, 747.

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