Functionalization of Natural Compounds to Enhance the Bioactivity of Zerumbone in Cancer Chemotherapy

Authors

  • Ngoc Hung Truong Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 1H Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi, 100000, Vietnam.
  • Duc Anh Le Institute of Chemistry and Material, Academy of Military Science and Technology, 17 Hoang Sam Street, Cau Giay, Hanoi, 100000, Vietnam.
  • Thi Ha Vu Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 1H Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi, 100000, Vietnam.
  • Thi Inh Cam Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 1H Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi, 100000, Vietnam.
  • Huu Nghi Do Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 1H Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi, 100000, Vietnam.
  • Manh Cuong Nguyen Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 1H Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi, 100000, Vietnam.
  • Khac Vu Tran Hanoi University of Science and Technology, 1 Dai Co Viet Str., Hai Ba Trung Street, Hanoi 100000, Vietnam.
  • Hanh Nguyen Tran University of Science and Technology of Hanoi, A21 Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi 100000, Vietnam.
  • Van Chung Pham Applied Medicinal Chemistry and Pharmaceutical Technology JSC, 45/24 Dien Bien Phu Street, Ngo Quyen, Hai Phong 180000, Vietnam.
  • Van Chinh Luu Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 1H Building, 18 Hoang Quoc Viet Street, Cau Giay, Hanoi, 100000, Vietnam.

DOI:

https://doi.org/10.9734/bpi/rdcbr/v10/3608

Keywords:

Quinolines, molecular docing, anti-inflammatory, 8-hydroxyquinoline, derivatives, heterocyclic chemistry

Abstract

The alkylation reaction was employed to conjugate zerumbone with 3-substituted quinazolinone-4(3H)-ones and quinolines, resulting in the synthesis of 11 novel conjugates. These conjugates were thoroughly characterized using 1D-, 2D-NMR, and HRMS spectral data. Their enhanced bioactivity was evaluated through anti-inflammatory assays, specifically by inhibiting NO production in RAW 267.4 cells. Additionally, their cytotoxic activity was assessed against three human cancer cell lines: HepG2, SK-LU-1, and MCF-7. The results demonstrated that all 11 conjugates exhibited significantly potent cytotoxic activity, with IC50 values ranging from 1.01 to 9.86 µg/mL, surpassing the efficacy of the parent compound zerumbone. Furthermore, in silico studies, including EGFR inhibitory activity through docking and molecular dynamics simulations, were conducted to identify the most potent compounds. These studies highlighted the key interactions of zerumbone derivatives 16a-k with critical amino acids in the active site of the EGFR (PDB ID 4HJO) protein.

Downloads

Published

2025-01-09

How to Cite

Ngoc Hung Truong, Duc Anh Le, Thi Ha Vu, Thi Inh Cam, Huu Nghi Do, Manh Cuong Nguyen, … Van Chinh Luu. (2025). Functionalization of Natural Compounds to Enhance the Bioactivity of Zerumbone in Cancer Chemotherapy. Recent Developments in Chemistry and Biochemistry Research Vol. 10, 71–102. https://doi.org/10.9734/bpi/rdcbr/v10/3608

Issue

Recent Developments in Chemistry and Biochemistry Research Vol. 10

Section

Chapters