Synthesis and Anticancer Evaluation of 4-Anilinoquinolinylchalcone Derivatives

Cheng-Yao Yang; Min-Yu Lee; Yeh-Long Chen; Jun-Ping Shiau; Yung-Hsiang Tsai; Chia-Ning Yang; Hsueh-Wei Chang; Chih-Hua Tseng

doi:10.3390/ijms24076034

Synthesis and Anticancer Evaluation of 4-Anilinoquinolinylchalcone Derivatives

Int J Mol Sci. 2023 Mar 23;24(7):6034. doi: 10.3390/ijms24076034.

Authors

Cheng-Yao Yang¹, Min-Yu Lee², Yeh-Long Chen¹, Jun-Ping Shiau³, Yung-Hsiang Tsai⁴, Chia-Ning Yang⁵, Hsueh-Wei Chang^{6

7}, Chih-Hua Tseng^{8

9

10

11

12}

Affiliations

¹ Department of Medicinal and Applied Chemistry, College of Life Science, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan.
² Graduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
³ Division of Breast Oncology and Surgery, Department of Surgery, Kaohsiung Medical University Hospital, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁴ Department of Seafood Science, National Kaohsiung University of Science and Technology, Kaohsiung 811213, Taiwan.
⁵ Institute of Precision Medicine, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
⁶ Department of Biomedical Science and Environmental Biology, College of Life Science, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁷ Center for Cancer Research, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
⁸ Department of Fragrance and Cosmetic Science, College of Pharmacy, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan.
⁹ School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung City 80708, Taiwan.
¹⁰ Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung City 80708, Taiwan.
¹¹ Department of Pharmacy, Kaohsiung Municipal Ta-Tung Hospital, Kaohsiung City 80145, Taiwan.
¹² College of Professional Studies, National Pingtung University of Science and Technology, Pingtung County 912301, Taiwan.

Abstract

A series of 4-anilinoquinolinylchalcone derivatives were synthesized and evaluated for antiproliferative activities against the growth of human cancer cell lines (Huh-7 and MDA-MB-231) and normal lung cells (MRC-5). The results exhibited low cytotoxicity against human lung cells (MRC-5). Among them, (E)-3-{4-{[4-(benzyloxy)phenyl]amino}quinolin-2-yl}-1-(4-methoxyphenyl) prop-2-en-1-one (4a) was found to have the highest cytotoxicity in breast cancer cells and low cytotoxicity in normal cells. Compound 4a causes ATP depletion and apoptosis of breast cancer MDA-MB-231 cells and triggers reactive oxygen species (ROS)-dependent caspase 3/7 activation. In conclusion, it is worth studying 4-anilinoquinolinylchalcone derivatives further as new potential anticancer agents for the treatment of human cancers.

Keywords: 4-anilinoquinolinylchalcone; apoptosis; cytotoxicity; lapatinib; reactive oxygen species.

MeSH terms

Antineoplastic Agents* / therapeutic use
Apoptosis
Breast Neoplasms* / metabolism
Cell Line, Tumor
Cell Proliferation
Drug Screening Assays, Antitumor
Female
Humans
Molecular Structure
Reactive Oxygen Species / pharmacology
Structure-Activity Relationship

Substances

Reactive Oxygen Species
Antineoplastic Agents

Abstract

MeSH terms

Substances

Grants and funding