Cancer drug camptothecin-functionalized dipeptides have been shown to self-assemble into helical structures because of the solubility requirements of the molecule’s polar and non-polar regions. These structures hold potential to shuttle the cancer drug to tumor cells while preventing decomposition of the drug and protecting normal cells from unwanted exposure. In an effort to probe greater structural diversity in these compounds, eighty-seven students of Chemistry 2550 (Organic Chemistry Laboratory II) were given the opportunity to work with the Parquette Research Group to conduct ~350 chemical transformations in 36 hours to produce 42 new cancer drug-conjugated dipeptides. These preliminary results were confirmed, and this camptothecin-dipeptide library was ultimately expanded to 66 structures through the efforts of graduate and undergraduate students alike. These products were purified and characterized using HPLC methods, analyzed using ESI-MS, and their self-assembly properties were characterized using transmission electron microscopy (TEM). The investigation of new amino acids in this system may lead to nanostructures with optimal biocompatibility and cancer-targeting properties.

Self-assembly of camptothecin-linked dipeptides

253rd National Meeting (2017)

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