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Open AccessArticle

Design, Synthesis, and Biological Evaluation of Artemisinin-Indoloquinoline Hybrids as Potent Antiproliferative Agents

1
Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
2
Institute of Immunology and Experimental Therapy, Polish Academy of Science, 12, R. Weigl Street, Wroclaw 53-114, Poland
3
Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, Ridai-cho, Kita-ku, Okayama, Japan
*
Authors to whom correspondence should be addressed.
Present Addresses: Pharmacy Department, Luzhou Medical College, Lu zhou 646000, China.
Molecules 2014, 19(11), 19021-19035; https://doi.org/10.3390/molecules191119021
Received: 13 August 2014 / Revised: 10 November 2014 / Accepted: 12 November 2014 / Published: 18 November 2014
A series of artemisinin-indoloquinoline hybrids were designed and synthesized in an attempt to develop potent and selective anti-tumor agents. Compounds 7a7f, 8 and 9 were prepared and characterized. Their antiproliferative activities against MV4-11, HCT-116, A549, and BALB/3T3 cell lines in vitro were tested. Nearly all of the tested compounds (79, except for compounds 7d and 7e against HCT-116) showed an increased antitumor activity against HCT-116 and A549 cell lines when compared to the dihydroartemisinin control. Especially for the artemisinin-indoloquinoline hybrid 8, with an 11-aminopropylamino-10H-indolo[3,2-b]quinoline substituent, the antiproliferative activity against the A549 cell line had improved more than ten times. The IC50 value of hybrid 8 against A549 cell lines was decreased to 1.328 ± 0.586 μM, while dihydroartemisin showed IC50 value of >20 µM in the same cell line. Thus, these results have proven that the strategy of introducing a planar basic fused aromatic moiety, such as the indoloquinoline skeleton, could improve the antiproliferative activity and selectivity towards cancer cell lines. View Full-Text
Keywords: artemisinin; indoloquinoline; hybrid; antiproliferative activity; cytotoxicity artemisinin; indoloquinoline; hybrid; antiproliferative activity; cytotoxicity
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MDPI and ACS Style

Wang, L.; Świtalska, M.; Wang, N.; Du, Z.-J.; Fukumoto, Y.; Diep, N.K.; Kiguchi, R.; Nokami, J.; Wietrzyk, J.; Inokuchi, T. Design, Synthesis, and Biological Evaluation of Artemisinin-Indoloquinoline Hybrids as Potent Antiproliferative Agents. Molecules 2014, 19, 19021-19035. https://doi.org/10.3390/molecules191119021

AMA Style

Wang L, Świtalska M, Wang N, Du Z-J, Fukumoto Y, Diep NK, Kiguchi R, Nokami J, Wietrzyk J, Inokuchi T. Design, Synthesis, and Biological Evaluation of Artemisinin-Indoloquinoline Hybrids as Potent Antiproliferative Agents. Molecules. 2014; 19(11):19021-19035. https://doi.org/10.3390/molecules191119021

Chicago/Turabian Style

Wang, Li; Świtalska, Marta; Wang, Ning; Du, Zhen-Jun; Fukumoto, Yuta; Diep, Nguyen K.; Kiguchi, Ryo; Nokami, Junzo; Wietrzyk, Joanna; Inokuchi, Tsutomu. 2014. "Design, Synthesis, and Biological Evaluation of Artemisinin-Indoloquinoline Hybrids as Potent Antiproliferative Agents" Molecules 19, no. 11: 19021-19035. https://doi.org/10.3390/molecules191119021

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