New heteroleptic palladium(II) dithiocarbamates: synthesis, characterization, packing and anticancer activity against five different cancer cell lines

Abstract

Two new heteroleptic palladium(II) complexes have been synthesized by reacting equimolar quantities of palladium(II) chloride, sodium 4‐(2‐methoxyphenyl)piperazine‐1‐carbodithioate and diphenyl‐p‐tolylphosphine (1) or tri‐p‐tolylphosphine (2). Complexes 1 and 2 have been characterized using elemental analysis, Fourier transform infrared spectroscopy, multinuclear NMR (1H, 13C and 31P) spectroscopy and single‐crystal X‐ray analysis. The latter technique confirms a pseudo square‐planar geometry in which two adjacent positions are occupied by bidentate dithiocarbamate while chloro and substituted triphenylphosphine are present at the remaining two positions. The anticancer activity of both complexes against five different cancer cell lines (LU – human lung carcinoma, established at UIC, Department of Surgical Oncology; MCF7 – human breast adenocarcinoma, ATCC number HTB‐22™; MDA‐MB‐231 – human breast adenocarcinoma, ATCC number HTB‐26™; Hepa‐1c1c7 – mouse liver hepatoma, ATCC number CRL‐2026™; PC‐3 – human prostate adenocarcinoma, ATCC number CRL‐1435™) was determined by MTT assay, revealing 2 has higher activity than 1. A drug–calf thymus DNA binding study with UV–visible spectroscopy reveals a higher DNA binding affinity of 2 (3.511 × 104 M−1) than 1 (4.213 × 103 M−1). Density functional theory studies confirm the relatively more stable nature of 2 than 1. Copyright © 2016 John Wiley & Sons, Ltd.

Dithiocarbamates: Challenges, Control, and Approaches to Excellent Yield, Characterization, and Their Biological Applications

“…Aly et al, Nabipour et al, Manav et al, and Ghorbani-Vaghei et al identified numerous applications of dithiocarbamates in biological studies as anticancer [13], antifungal [13], antibacterial [99, 100], rodent repelling [101], growth depressing [102], and toxicity studies [18]. According to Khan et al, palladium(II) and platinum(II) coordination compounds of dithiocarbamates attracted a lot of attention due to their better anticancer, antitumour, and less toxic properties than cisplatin [103]. They further stated that the presence of nitrogen and sulfur (N and S) coordination modes in ligands used to synthesize platinum(II) complexes helped to lower the challenges linked with cisplatin's toxicity and its analogues.…”

An insight into the therapeutic potential of piperazine-based anticancer agents

“…The higher activity of compound 17 was possibly due to its higher stability as compared to 16, as determined by density functional theory. 40 Arjmand et al designed and synthesized tin iminodiacetate conjugated with piperazinediium cation 18 as a potential antitumor agent. Conjugate 18 showed significant cytotoxic activity versus HCT15, HOP62, MCF7, and SK-OV-3 cancer cell lines, having GI 50 values of less than 10 µg/mL.…”

From Recovered Palladium to Molecular and Nanoscale Catalysts

“…Complexes 3 and 4 were fully characterized by 1 H NMR, 13 C{ 1 H} and 31 P{ 1 H} NMR and IR spectroscopy as well as mass spectrometry and elemental analysis. The 1 H and 31 P{ 1 H} NMR spectra both showed an upfield shift in their resonances due to the electron back-donation from the palladium center to the dithiocarbamate ligand 26 and the σ-donation of the adjacent dithiocarbamate ligand. In addition to the new resonance observed at 30.5 ppm for both 3 and 4 in the 31 P{ 1 H} NMR spectra, the presence of the hexafluorophosphate counteranion was evidenced by a characteristic septet.…”