Abstract
Synthesis of a novel theranostic molecule for targeted cancer intervention. A reaction between curcumin and lawsone was carried out to yield the novel curcumin naphthoquinone (CurNQ) molecule (2,2′-((((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl) bis(2-methoxy-4,1-phenylene))bis(oxy))bis(naphthalene-1,4-dione). CurNQ’s structure was elucidated and was fully characterized. CurNQ was demonstrated to have pH specific solubility, its saturation solubility increased from 11.15 µM at pH 7.4 to 20.7 µM at pH 6.8. This pH responsivity allows for cancer targeting (Warburg effect). Moreover, CurNQ displayed intrinsic fluorescence, thus enabling imaging and detection applications. In vitro cytotoxicity assays demonstrated the chemotherapeutic properties of CurNQ as CurNQ reduced cell viability to below 50% in OVCAR-5 and SKOV3 ovarian cancer cell lines. CurNQ is a novel theranostic molecule for potential targeted cancer detection and treatment.
Highlights
Natural compounds provide a significant database of potential drug candidates and play a pivotal role in drug discovery [1,2]
The desired molecule was synthesized through a Williamson ether desired molecule
The desired molecule was synthesized through a Williamson ether synthesis synthesis reaction between CUR and BrNQ (Figure 1)
Summary
Natural compounds provide a significant database of potential drug candidates and play a pivotal role in drug discovery [1,2]. Phytochemicals are naturally occurring compounds and have been used for centuries to treat and prevent many illnesses [3]. An interesting concept of late in anticancer interventions are theranostic systems (i.e., combining diagnostic and therapeutic elements in a single platform) in which chemically modified phytochemicals could play a significant role [6,7]. Theranostic agents are highly advanced systems that can function to monitor the accumulation of various compounds (including nanomedicines) at target sites, quantify triggered drug release, and detect malignant cells in order to deliver a chemotherapeutic agent to the targeted site [7,8]. The ability to simultaneously detect and treat cancer reduces patient mortality as a result of early disease detection and immediate treatment [9]
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