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Design, Synthesis and Characterization of Photoactive Carbon Monoxide Releasing Molecules from Mn(I) and Re(I) Tricarbonyl Complexes: Towards CO Delivery Tracking and Selective Cancer Eradication

  • Author(s): Jimenez, Jorge
  • Advisor(s): Mascharak, Pradip K
  • et al.
Abstract

Carbon monoxide (CO) has recently been shown to display various salutary effects in mammalian physiology. CO displays antiflammation, vasoregulatory, and anti-apoptotic properties toward normal cells. Interestingly, CO displays pro-apoptotic properties against cancer cells while showing minimum effects toward normal cells at similar concentrations. This has increased the interest in the design and synthesis of molecules capable of delivering CO to specific targets (CORMs). The effective application of these complexes is limited for the lack of controlled CO release from many of these CORMs. We have designed and synthesized CORMs able to release CO exclusively upon light exposure (photoCORMs). We have also utilized different ligands to impart specific chemical and physical properties to these complexes.

Chapter 2 describes the design and synthesis of Mn(I) tricarbonyl complexes capable of releasing CO upon visible light illumination. We also describe the utilization of 1,3,5-triazaadamant-7-amine derived ligands that impart water-solubility to the Mn(I) complexes. The Mn(I) complexes in these studies release the three CO ligands upon exposure to visible light.

Chapter 3 describes the desing and synthesis of six luminescent Re(I) tricarbonyl complexes. The highly luminescent properties of these complexes allow one to track their internalization in cellular systems. All complexes utilized in these studies are readily internalized in MDA-MB-231 cancer cells despite their lipophilicity or charge. One complex in particular was covalently attached to carboxymethyl chitosan (CMC) forming a composite (ReCMC). ReCMC internalizes in both MDA-MB-231 and HT-29 cancer cells and displays eradication in these cells in a concentration dependent manner.

Chapter 4 descibes the desing and synthesis of a luminescent Mn(I) tricarbonyl complex. The luminescent properties of this complex allows one to track its internalization in HT-29 cells. This is the first example of a Mn(I) tricarbonyl complex that is luminescent and can be tracked inside cells. This complex releases all three CO ligands upon exposure to visible light. It also displays eradication of the HT-29 cells upon exposure to visible light but no under dark conditions. However, this complex does not affect the viability of HEK-293 normal cells upon visible light exposure or under dark conditions.

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