Synthesis and Cytotoxicity of Platinum(II) Complexes of a Physiologically Active Carrier Histamine

Abstract

A series of novel platinum(II) complexes involving a physiologically active carrier histamine as the carrier, cis-[Pt(histamine)X2] (X2=2Cl-, oxalate, malonate, 1,1-cyclobutanedicarboxylate (CBDCA), 3-hydroxy-1,1-cyclobutanedicarboxylate (HO-CBDCA)), have been synthesized and characterized by elemental analysis and spectroscopic data along with X-ray crystal structure for a representative complex cis-[Pt(histamine)Cl2]. The cytotoxicity of the complexes has also been assessed in the human cancer cell lines A549/ATCC, HT-29, and LNcap. One complex, cis-[Pt(histamine)Cl2], is more active than carboplatin against both the sensitive and resistant cells.

Synthesis and anticancer activity of [2-hydroxy-1,3-diaminopropane-κ2N,N′] platinum(II) complexes

“…All the platinum compounds that have received approval for clinical use so far conform to this set of guidelines. In our previous studies, we investigated the platinum complexes involving different ammine/diamines as the carriers by using the same human tumor cell lines [14,27,28]. These carriers include 2NH 3 , N-cyclohexyl-1,3-propanediamine (NH 2 CH 2 CH 2 CH 2 NHR), 2-morpholinoethylamine (NH 2 CH 2 CH 2 NR 2 ) and histamine (NH 2 CH 2 CH 2 -CH 2 NR 2 ).…”

Platinum(II) oxalato complexes with adenine-based carrier ligands showing significant in vitro antitumor activity

“…The first one involves dachbased platinum(II) complexes containing various isomers and derivatives of 1,2-diaminocyclohexane (dach) as N-donor carrier ligands, while a leaving group differs from the oxalate dianion [5][6][7]. The second one comprises the platinum(II) oxalato complexes with bidentate oxalate dianion as a leaving group, and on the other hand, the carrier N-donor ligand differs from dach [8][9][10][11][12][13]. The prepared complexes 1-7 belong to the second group of the oxaliplatin derivatives.…”

Monocycloplatinated Solvento Complex Displays Turn-on Ratiometric Phosphorescence Responses to Histamine

“…Repeated attempts to grow single crystals of PtGR and PtHA were unsuccessful. The coordination geometry in PtHA was thus explored by performing quantum chemical calculations based on the crystal structure of an antitumor drug, cis -[Pt­(HA)­Cl 2 ] . Two possible coordination structures of PtHA were subjected to geometry optimization: one structure had an N,N-trans configuration of the quinolinyl nitrogen and the imidazolyl nitrogen, and the other had an N,N-cis configuration of the two nitrogens.…”

“…A pseudopotential (LANL2DZ) was applied to replace the inner core electrons of the Pt atom, leaving the outer core [(5s) 2 (5p) 6 ] electrons and the (5d) 8 valence electrons. On the basis of the crystal structure of an antitumor drug, cis -[Pt­(HA)­Cl 2 ], two possible coordination structures were used for the geometry optimization of PtHA: one structure had a trans configuration of the quinolinyl and imidazolyl nitrogens, and the other had a cis configuration of the two nitrogens. Frequency calculations were performed subsequently to assess the stability of the convergence.…”

“…A pseudopotential (LANL2DZ) was applied to replace the inner core electrons of the Pt atom, leaving the outer core [(5s) 2 (5p) 6 ] electrons and the (5d) 8 valence electrons. On the basis of the crystal structure of an antitumor drug, cis-[Pt(HA)Cl 2 ], 49 nitrogens, and the other had a cis configuration of the two nitrogens.…”