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Water soluble palladium(ii) and platinum(ii) acyclic diaminocarbene complexes: solution behavior, DNA binding, and antiproliferative activity

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Abstract

Bis-ADC complexes cis-[Pd{C(NHC6H4NH2)N(H)R}2]Cl2 (R = Xyl 4a, Cy 4b, C6H4-4-F 4c) and cis-[Pt{C(NHC6H4NH2)N(H)R}2]Cl2 (R = Xyl 5a, Cy 5b, C6H4-4-F 5c) were synthesized via the metal-mediated coupling of two isocyanide ligands in cis-[MCl2(CNR)2] (M = Pd, Pt; R = Xyl, Cy, C6H4-4-F) and 1,2-diaminobenzene. New compounds 4c and 5a–c were characterized by HR ESI+-MS, IR, and 1H, 13C{1H} and 195Pt{1H} NMR spectroscopy; the structures of 4a and 5a were elucidated by single-crystal X-ray diffraction. The stability of the ADC complexes in aqueous media (5 mM NaCl) was monitored by UV absorption spectroscopy, HR ESI+ mass spectrometry, and 195Pt{1H} NMR spectroscopy (for 5a). Molar conductivity measurements in MeOH (ΛM = 167–173 Ω−1 mol−1 cm2) indicate that, in this solvent, the ADC complexes exist as dicationic species of [A][Q]2 type. The ADC complexes binding to CT DNA was investigated by means of spectroscopic and hydrodynamic techniques including UV absorption and circular dichroism spectroscopy, fluorescence spectroscopy, low-gradient viscometry, flow birefringence, and AFM imaging. As a result, complexes 4a and 5a were shown to bind double-stranded DNA predominantly via the formation of monofunctional adducts in the major groove of the macromolecule. Binding of the ADC complexes also provokes the formation of a large number of intermolecular DNA–DNA contacts in solution. The antiproliferative activity of all prepared ADC complexes 4a–c and 5a–c was evaluated in vitro against three human carcinoma cell lines (HT-29, MDA-MB-231, and MCF-7) and two non-tumorigenic cell lines (L929 and RC-124) and compared to that of cisplatin. Among the compounds studied, complexes 4a and 5a appeared to be the most active species with IC50 values in MCF-7 cells of about 10 μM.

Graphical abstract: Water soluble palladium(ii) and platinum(ii) acyclic diaminocarbene complexes: solution behavior, DNA binding, and antiproliferative activity

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Article information


Submitted
05 Jan 2020
Accepted
27 Feb 2020
First published
28 Feb 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Water soluble palladium(II) and platinum(II) acyclic diaminocarbene complexes: solution behavior, DNA binding, and antiproliferative activity

T. V. Serebryanskaya, M. A. Kinzhalov, V. Bakulev, G. Alekseev, A. Andreeva, P. V. Gushchin, A. V. Protas, A. S. Smirnov, T. L. Panikorovskii, P. Lippmann, I. Ott, C. M. Verbilo, A. V. Zuraev, A. S. Bunev, V. P. Boyarskiy and N. A. Kasyanenko, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ00060D

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