89194-85-4

Upstream product

• 109-73-9 N-butylamine 
• 7790-39-8 platinum(II) iodide 
• 10025-99-7 potassium tetrachloroplatinate(II) 
• 7681-11-0 potassium iodide 
• 110365-47-4 {PtBua₃I}I 

Relevant academic research and scientific papers

In vitro activity, stability, and lipophilicity changes of cisplatin through substitution of different amine ligands

In this study, several cisplatin analogs were designed to investigate the antitumor activity and lipophilicity effects in amine change. The amines of the cisplatin molecule were substituted with aliphatic amines in different analogs. The cytotoxicity of analogs against human colon cancer (HCT116) was investigated using MTT assay, and spectroscopic methods were used to determine the DNA binding mode. Cytotoxicity studies revealed cis-dichloro-dimethylamine-platinum has a lower IC50 (48.87?μM) than carboplatin (68.46?μM) and more than cisplatin (21?μM) against human colon cancer cells (HCT116), respectively. DNA denaturation study indicated that the stability of DNA in the presence of these compounds diminished and substitution of propylamine and methylamine groups increased DNA denaturation. Further, the interaction of the desired compounds with DNA proved to be a spontaneous process. Tm analysis also revealed that cisplatin, cis-dichloro-dimethylamine-platinum, and cis-dichloro-dipropylamine-platinum complexes made DNA double helix unstable via covalent bond, while cis-dichloro-dibutylamine-platinum and cis-dichloro-diisobutylamine-platinum stabilized DNA via electrostatic binding to DNA. The results of fluorescence studies showed that the quenching nature of cisplatin and methyl and propyl systems was dynamic, while the static quenching was observed in the presence of cis-dichloro-dibutylamine-platinum and cis-dichloro-diisobutylamine-platinum. The molecular docking simulations and DFT analysis were performed to investigate the binding sites and chemical behavior of cisplatin analogs, respectively. Molecular docking demonstrated that except cis-dichloro-diisobutylamine-platinum, other complexes had higher negative docking energy than cisplatin for interaction with DNA, and methyl and propyl complexes may be good candidates for anticancer drugs. Graphical abstract: Some anticancer Pt(II) complexes as cisplatin analogs were synthesized with aliphatic amines to investigate the lipophilicity effects. In vitro cytotoxicity effects were tested against human colon cancer (HCT116). Moreover, the modes of DNA binding with synthesized compounds were investigated using fluorescence spectra, DFT and molecular docking. [Figure not available: see fulltext.]

Syntheses, crystal structures and copper-binding capabilities of amidate-hanging platinum mononuclear complexes containing alkylamine moieties

As analogs of cis-[Pt(piam)2(NH3)2] ·2H2O (1, piam = pivalamidate), two kinds of platinum mononuclear complexes, cis-[Pt(piam)2(NH2C 3H7)2]·H2O (2) and cis-[Pt(piam)2(NH2C4H9) 2] (3), have been synthesized and characterized by single-crystal X-ray analyses. The square-planar complexes 2 and 3 contain propyl and butyl moieties, respectively, enhancing the hydrophobicity. Both compounds have non-coordinated oxygen atoms in the piam ligands that can bind to a second metal, such as the Cu2+ ion, to afford trinuclear Pt-Cu-Pt complexes. UV-Vis and electron paramagnetic resonance spectra of the reaction of 2 and 3 with the Cu2+ ion show that both compounds form dinuclear Pt-Cu complexes as intermediates.

Synthesis and characterization of complexes of the type [Pt(amine)4]I2 and trans-[Pt(CH3NH2)2(H3C{single bond}N{double bond, long}C(CH3)2)2]I2 by crystallography and multinuclear magnetic resonance spectroscopy

Complexes of the type [Pt(amine)4]I2 were synthesized and characterized mainly by multinuclear (195Pt, 1H and 13C) magnetic resonance spectroscopy. The compounds were prepared with different primary amines, but not with bulky amines, due to steric hindrance. In 195Pt NMR, the signals were observed between -2715 and -2769 ppm in D2O. The coupling constant 3J(195Pt-1H) for the MeNH2 complex is 42 Hz. In 13C NMR, the average values of the coupling constants 2J(195Pt-13C) and 3J(195Pt-13C) are 18 and 30 Hz, respectively. The crystal structure of [Pt(EtNH2)4]I2 was determined by X-ray diffraction methods. The Pt atom is located on an inversion center. The structure is stabilized by H-bonding between the amines and the iodide ions. The compound with n-BuNH2 was found by crystallographic methods to be [Pt(n-BuNH2)4]2I3(n-BuNHCOO). The crystal contains two independent [Pt(CH3NH2)4]2+ cations, three iodide ions and a carbamate ion formed from the reaction of butylamine with CO2 from the air. When the compound [Pt(CH3NH2)4]I2 was dissolved in acetone, crystals identified as trans-[Pt(CH3NH2)2(H3C{single bond}N{double bond, long}C(CH3)2)2]I2 were isolated and characterized by crystallographic methods. Two trans bonded MeNH2 ligands had reacted with acetone to produce the two N-bonded Schiff base Pt(II) compound.

Multinuclear NMR study and crystal structures of complexes of the types cis- and trans-Pt(amine)2I2

Complexes of the types cis- and trans-Pt(amine)2I2 were studied by spectroscopic methods, especially by multinuclear NMR spectroscopy. In 195Pt NMR, the cis diiodo compounds with primary amines were observed between -3342 and -3357 ppm in acetone, while the trans compounds were found between -3336 and -3372 ppm. For the secondary amines, the chemical shifts were observed at lower fields. In 1H NMR, the trans complexes were observed at higher fields than the cis compounds, while in 13C NMR, the reverse was observed. The 2J( 195Pt-1H) and 3J(195Pt- 1H) coupling constants are larger for the cis compounds (ave. 67 and 45 Hz, respectively) than for the trans isomers (ave. 59 and 38 Hz). In 13C NMR, the values of 2J(195Pt-13C) and 3J(195Pt-13C) were also found to be larger for the cis complexes (ave. 17 and 39 Hz versus 11 and 28 Hz). There seems to be a slight dependence of the pKa values of the protonated amines or the proton affinity in the gas phase with the δ(Pt) chemical shifts. The crystal structures of eight diiodo complexes were determined. These compounds are cis-Pt(CH3NH2)2I2, cis-Pt(n-C4H9NH2)2I2, cis-Pt(Et2NH)2I2, trans-Pt(n-C 3H7NH2)2I2, trans-Pt(iso-C3H7NH2)2I 2, trans-Pt(n-C4H9NH2) 2I2, trans-Pt(t-C4H9NH 2)2I2 and trans-Pt(Me2NH) 2I2. The Pt-N bond distances located in trans position to the iodo ligands were compared to those located in trans position to the amines. The Pt-N bond in cis-Pt(Et2NH)2I2 are much longer than the others, probably caused by the steric hindrance of the two very bulky ligands located in cis positions.