A range of derivatives has previously been synthesized in order to overcome the stability and pharmacokinetic hurdles that hinder the in vivo investigation of the natural product, curcumin. One such derivative, pyrazole 15, has been demonstrated to inhibit the independent prostate -proliferation of a highly metastatic androgencancer cell line (PC3). In this work, pyrazole analogues, 15 and 32 and the corresponding curcumin analogues, 30 and 31 were ty assisted technique. A stabili-synthesized using a microwavestudy, and in silico assessment, of curcumin 1 and thirteen pyrazole 42) was hindered by the poor solubility of -analogues (15,17, and 32these analogues, as a result of their hydrophobicities. An attempt guest -to improve the solubility of pyrazole 15, through hostCD) 46, -cyclodextrin (γ-complexation with three macromolecules, γsulfonatocalix[4]arene sCX[4] 48 and cucurbit[7]uril CB[7] 52, -pwas unsuccessful, presumably due to the lack of sufficient bonding interactions or the incompatibility of the pyrazole with the hydrophobic cavities in these molecules. Eight polymeric micelle (PM) formulations were then fabricated with the aim of generating sufficient hydrophobicity to entrap pyrazole 15; seven formulations of the Pluronic® F127 72 based PMs, via the thin film hydration PS polymer -b-method, and one formulation incorporating POEGAPMs 100), via the dialysis method. All the -PS-b-based PMs (POEGAempty PMs were shown to be stable, with particle sizes below 52 nm and polydispersity indexes (PDI) below 0.34, indicating PMs 93 were not able to -homogeneity and stability. F127accommodate pyrazole 15 (size 253.7 ± 25.4, PDI 0.63 ± 0.13, and lowest %DL 0.29 ± 0.01). Increasing the hydrophobicity of Pluronic® F127 72 by adding TPGS 73 in different ratios, as in the mixed PMs -PMs 96 and FT11-PMs 95, FT32-PMs 94, FT21-micelles FT4197, resulted in better stability, a higher degree of monodispersity and the encapsulation of the hydrophobic pyrazole 15 (particle 1.19). The -0.25, and %DL 1.08 -55 nm, PDIs 0.15 –sizes 30 LHRH 75, to give the -Lys6]-addition of the targeting moiety [DPMs 98, helped improve the adaptability for the drug -FLHRH(particle size 57.6 ± 13.7 nm, PDI 0.41 ± 0.17 and %DL 0.48 ± 0.01), but not to the same levels as the addition of the hydrophobic TPGS PMs 99, reduced the -73. Targeted mixed micelles FLHRHT32PMs 98 -particle size and the PDI, in comparison to targeted FLHRH(without TPGS 73), as a result of increasing the hydrophobicity increases the stability (particle size 22.0 ± 0.2 nm, PDI 0.28 ± 0.03, PMs 100 displayed good -PS-b-and %DL 0.64 ± 0.05). POEGAstability in comparison to the Pluronic® F127 72 based PMs (particle size of 54.0 ± 0.3 nm and PDI 0.15 ± 0.01). Finally, the