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Synthesis and Cytotoxic Properties of Chalcones: An Interactive and Investigative Undergraduate Laboratory Project at the Interface of Chemistry and Biology

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John Dickson , Lloyd Flores , Michelle Stewart , Regan LeBlanc , Hari N. Pati and Moses Lee

Department of Chemistry, Furman University, Greenville, SC 29613

Herman Holt

Department of Chemistry, University of North Carolina at Asheville, Asheville, NC 28804

J. Chem. Educ., 2006, 83 (6), p 934

DOI: 10.1021/ed083p934

Publication Date (Web): June 1, 2006

Section:

History, Education, and Documentation

Abstract

A highly integrated laboratory project that emphasizes techniques of chemistry and biology is described. Laboratory exercises of this nature are becoming increasingly important as interdisciplinary scientific research improves our ability to meet some of the grand challenges in chemistry laid out by the National Research Council in 2003. This project combines the synthesis of a small library of 30 appropriately substituted chalcones, the measurement of their cytotoxic properties, and the study of their structure–activity relationships using computational chemistry. In the synthesis portion of the sequence, students will learn basic organic laboratory techniques such as vacuum filtration, recrystallization, thin-layer chromatography (TLC), melting point determination, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and ultraviolet–visible (UV–vis) spectroscopy. For the biology component, the instructor should partner with a cell biologist to assist in conducting the experiments. The instructor should decide how involved the students would be in conducting the cytotoxicity studies. The molecular modeling aspect of this laboratory sequence will provide students with experience building molecules within the modeling program and optimizing the structure and conformation of the molecules using molecular mechanics and molecular dynamics.