Stereoselective synthesis of oxime containing Pd(ii) compounds: highly effective, selective and stereo-regulated cytotoxicity against carcinogenic PC-3 cells

Abstract

New palladium compounds [Pd{(1S,4R)-NOH^NH(R)}Cl2] (R = Ph 1a or Bn 1b), [Pd{(1S,4R)-NOH^NH(R)}{(1S,4R)-NO^NH(R)}][Cl] (R = Ph 2a or Bn 2b) and corresponding [Pd{(1R,4S)-NOH^NH(R)}Cl2] (R = Ph 1a’ or Bn 1b’) and...

Fluorescent Vitamin B12–Platinum(II) Derivatives as Potential Metallotheranostic Agents for the Treatment and Imaging of Tumors

“…The most diagnostic bands were assigned to vibrations involving the groups directly coordinated to the metal center, that is, the oxime and amino nitrogen donors. For instance, ν(OH) oxime (3307 cm −1 ) and ν(NH) amine (3205 cm −1 ) appear much sharper and resolved than in the free ligand, as reported in the literature [40], and ν(C=N) oxime , ν(Ph-N) amine , and ν(N-OH) oxime (at 1599, 1236, and 910 cm −1 , respectively) show a general shift to lower wavenumbers upon metal binding, which is in agreement with the data in the literature [48,49]. Additional information was obtained from the far-IR spectrum of Pt1 (Figure 4).…”

“…In this context, natural terpenes are enantiomerically pure, commercially available low-cost reagents that may be used as building blocks to prepare optically active metal derivatives through the exploitation of known stereoselective functionalization procedures [35]. Royo and coworkers previously reported on the use of chiral amino-oxime organic compounds derived from Rand S-limonene to prepare water-soluble, enantiopure Ru(II) [36,37], Ti(IV) [38,39], Pd(II) [40], and Pt(II) [41] derivatives with relevant antitumor properties. The rationale behind the aforementioned designing strategy relies on the fact that both amino and oxime functional groups are versatile building blocks for the design of soluble and stable metal compounds under physiological conditions [42,43].…”

“…The pure major epimer R N -Pt1 could be isolated by recrystallization from chloroform (89% yield). However, upon dissolution in various solvents, an epimerization process involving the coordinated amino moiety occurred [40,46,47], again leading to a final R N -Pt1:S N -Pt1 ratio of ca. 2.5:1 in both CDCl 3 (within 24 h) and CD 3 OD (within a few minutes), as estimated by 1 H NMR spectroscopy.…”

Cytotoxic Effects of New Palladium(II) Complexes with Thiazine or Thiazoline Derivative Ligands in Tumor Cell Lines

“…For this reason, several recent investigations have focused their efforts on the synthesis of organometallic compounds which include transition metals and chelates [ 4 ]. In this context, palladium compounds have been explored as alternatives for platinum compounds as antitumor drugs due to their structural and chemical similarities and their coordination capability [ 2 , 4 , 5 ]. However, from a thermodynamic and kinetic perspective, Pd(II) complexes are in general more unstable than Pt(II) ones, being around 10 5 times more reactive [ 6 ] and forming unsought chemical species before reaching their target.…”