covalent technique, where they demonstrated that water soluble binding monomers such as

methacrylic acid (MAA) were quantitatively incorporated inside the nanoparticles, which is a

crucial condition for an efficient imprinting to take place.261 However, the density of the MAA

groups was probably higher in the outer shell of the nanoparticles, as previously described for

other miniemulsion polymerizations involving water soluble monomers.262 This probably led to

an increased binding efficiency, since the imprinted sites were mostly situated near the

nanoparticle surface and therefore more easily accessible for the template molecules during the

rebinding studies.

 In our molecularly imprinted nanoparticle synthesis, ethylene glycol dimethacrylate

(EGDMA) was used as the hydrophobic cross-linker, MAA as the binding monomer,

azobisi sobutyronitrile (AIBN) as the oil-soluble radical initiator, hexadecane as the highly

hydrophobic agent preventing Ostwald Ripening,83 ethyl butyrate (EB) as the hydrophobic

porogen, and amitriptyline as the template molecule. The relative molar amounts cross-

linker/monomer/template during the imprinting step ranged around 20/4/1 which are commonly

used ratios in molecular imprinting technology.263 It should be noticed that, to demonstrate the

ability of amitriptyline-based molecularly imprinted nanoparticles to be used as detoxification

agents, we deliberately chose to vary only the amounts of cross-linker, monomer, and template

as shown in Table 7-1. Amitriptyline has non-negligible water solubility which makes it able to

freely dissolve in aqueous systems such as in the blood stream. Nevertheless, amitriptyline is

highly hydrophobic with reported partition coefficient values of several thousands between 1-

octanol and water.264 Therefore, under our experimental miniemulsion polymerization

conditions, incorporation of amitriptyline in the miniemulsion oil core during polymerization can