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Article

Thiazolidinedione-Conjugated Lupeol Derivatives as Potent Anticancer Agents Through a Mitochondria-Mediated Apoptotic Pathway

by
Siqi Deng
1,
Yinxu Zhao
1,
Xiaoshan Guo
1,
Xian Hong
2,
Gang Li
2,
Yuchun Wang
1,
Qingyi Li
1,
Ming Bu
1,* and
Ming Wang
1,*
1
College of Pharmacy, Qiqihar Medical University, Qiqihar 161006, China
2
Research Institute of Medicine & Pharmacy, Qiqihar Medical University, Qiqihar 161006, China
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(20), 4957; https://doi.org/10.3390/molecules29204957
Submission received: 30 August 2024 / Revised: 13 October 2024 / Accepted: 18 October 2024 / Published: 20 October 2024
(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)
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Abstract

To improve the potential of lupeol against cancer cells, a privileged structure, thiazolidinedione, was introduced into its C-3 hydroxy group with ester, piperazine-carbamate, or ethylenediamine as a linker, and three series of thiazolidinedione-conjugated compounds (6a–i, 9a–i, and 12a–i) were prepared. The target compounds were evaluated for their cytotoxic activities against human lung cancer A549, human breast cancer MCF-7, human hepatocarcinoma HepG2, and human hepatic LO2 cell lines, and the results revealed that most of the compounds displayed improved potency over lupeol. Compound 12i exhibited significant activity against the HepG2 cell line, with an IC50 value of 4.40 μM, which is 9.9-fold more potent than lupeol (IC50 = 43.62 μM). Mechanistic studies suggested that 12i could induce HepG2 cell apoptosis, as evidenced by AO/EB staining and annexin V-FITC/propidium iodide dual staining assays. Western blot analysis suggested that compound 12i can upregulate Bax expression, downregulate Bcl-2 expression, and activate the mitochondria-mediated apoptotic pathway. Collectively, compound 12i is worthy of further investigation to support the discovery of effective agents against cancer.
Keywords: triterpenoid; lupeol; thiazolidinedione; hybrids; antitumor; apoptotic triterpenoid; lupeol; thiazolidinedione; hybrids; antitumor; apoptotic
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MDPI and ACS Style

Deng, S.; Zhao, Y.; Guo, X.; Hong, X.; Li, G.; Wang, Y.; Li, Q.; Bu, M.; Wang, M. Thiazolidinedione-Conjugated Lupeol Derivatives as Potent Anticancer Agents Through a Mitochondria-Mediated Apoptotic Pathway. Molecules 2024, 29, 4957. https://doi.org/10.3390/molecules29204957

AMA Style

Deng S, Zhao Y, Guo X, Hong X, Li G, Wang Y, Li Q, Bu M, Wang M. Thiazolidinedione-Conjugated Lupeol Derivatives as Potent Anticancer Agents Through a Mitochondria-Mediated Apoptotic Pathway. Molecules. 2024; 29(20):4957. https://doi.org/10.3390/molecules29204957

Chicago/Turabian Style

Deng, Siqi, Yinxu Zhao, Xiaoshan Guo, Xian Hong, Gang Li, Yuchun Wang, Qingyi Li, Ming Bu, and Ming Wang. 2024. "Thiazolidinedione-Conjugated Lupeol Derivatives as Potent Anticancer Agents Through a Mitochondria-Mediated Apoptotic Pathway" Molecules 29, no. 20: 4957. https://doi.org/10.3390/molecules29204957

APA Style

Deng, S., Zhao, Y., Guo, X., Hong, X., Li, G., Wang, Y., Li, Q., Bu, M., & Wang, M. (2024). Thiazolidinedione-Conjugated Lupeol Derivatives as Potent Anticancer Agents Through a Mitochondria-Mediated Apoptotic Pathway. Molecules, 29(20), 4957. https://doi.org/10.3390/molecules29204957

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