Chalcones: Potential Chemotherapeutic Compounds and Educational Tools for Closing the Loop in STEM

Area of Science:

• Medicinal Chemistry
• Organic Synthesis
• Cancer Biology

Background:

• Chalcones are natural products with documented anti-cancer properties, particularly against breast cancer.
• African-American women face higher rates of triple-negative breast cancer, highlighting a need for targeted therapies.
• Limited research existed on the antiproliferative effects of electron-withdrawing groups on chalcone structures.

Purpose of the Study:

• To synthesize halogenated chalcones as potential chemotherapeutics.
• To investigate the impact of electron-withdrawing groups (chlorine) on chalcone antiproliferative activity.
• To integrate synthetic and biological studies into undergraduate organic chemistry and molecular biology courses.

Main Methods:

• Chalcones synthesized via aldol condensation and purified from hot ethanol.
• Biological activity assessed using MTT assay to determine cell death and inhibition of proliferation.
• Comparison of antiproliferative effects of chlorinated chalcones versus unsubstituted chalcones.

Main Results:

• The synthesized compound (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one demonstrated dose-dependent inhibition of MDA-MB-231 breast cancer cell progression.
• The chlorinated chalcone outperformed the unsubstituted analogue (E)-1,3-diphenyl-2-propen-1-one in inhibiting cell progression.
• Educational integration facilitated understanding of translational science from synthesis to potential therapeutic application.

Conclusions:

• Introducing electron-withdrawing groups, like chlorine, enhances the antiproliferative potential of chalcones.
• Halogenated chalcones show promise as chemotherapeutic agents for breast cancer.
• This project successfully combined undergraduate education with meaningful research addressing health disparities.