New copper(II) thiohydantoin complexes: Synthesis, characterization, and assessment of their interaction with bovine serum albumin and DNA.
| Title: | New copper(II) thiohydantoin complexes: Synthesis, characterization, and assessment of their interaction with bovine serum albumin and DNA. |
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| Authors: | Tishchenko K; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Beloglazkina E; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Proskurnin M; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia. Electronic address: michael@analyt.chem.msu.ru.; Malinnikov V; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Guk D; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Muratova M; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Krasnovskaya O; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Udina A; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Skvortsov D; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Shafikov RR; Department of Bioengineering and Bioinformatics, Lomonosov Moscow State University, Leninskie Gory, Moscow 119234, Russia.; Ivanenkov Y; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia; Moscow Institute of Physics and Technology, 9 Institutskiy per., Dolgoprudny, Moscow Region 141701, Russian.; Aladinskiy V; Moscow Institute of Physics and Technology, 9 Institutskiy per., Dolgoprudny, Moscow Region 141701, Russian.; Sorokin I; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Gromov O; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Majouga A; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia.; Zyk N; Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russia. |
| Source: | Journal of inorganic biochemistry [J Inorg Biochem] 2017 Oct; Vol. 175, pp. 190-197. Date of Electronic Publication: 2017 Jul 21. |
| Publication Type: | Journal Article; Research Support, Non-U.S. Gov't |
| Language: | English |
| Journal Info: | Publisher: Elsevier Country of Publication: United States NLM ID: 7905788 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-3344 (Electronic) Linking ISSN: 01620134 NLM ISO Abbreviation: J Inorg Biochem Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: New York, Elsevier. |
| MeSH Terms: | Coordination Complexes/*chemical synthesis ; Coordination Complexes/*chemistry ; Copper/*chemistry ; DNA/*chemistry ; Serum Albumin, Bovine/*chemistry ; Thiohydantoins/*chemistry; Animals ; Cattle |
| Abstract: | New copper(II) complexes of 2-alkylthio-5-arylmethylene-4H-imidazolin-4-ones: (5Z)-2-(methylsulfanyl)-3-(prop-2-en-1-yl)-5-(pyridin-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one) (1a), (5Z,5'Z)-2,2'-(ethan-1,2-diyldisulfanyldiyl)bis(5-(2-pyridilmethylen)-3-allyl-3,5-dihydo-4Н-imidazole-4-one) (2a) and (5Z,5'Z)-3,3'-hexan-1,6-diylbis[5-(2-pyridilmethylen)-2-methylthiotetrahydro-4Н-imidazole-4-one)] (3a) were synthesized as possible anticancer drugs. Their structures were characterized by 1H NMR spectroscopy, elemental analysis, and X-ray crystallography. The composition of the complexes were found for 1a (Cu:L=1:1), 2a (Cu:L=2:1), and 3a (Cu:L=2:1). The chelation constants were found by competitive complexation with ethylenediamine tetraacetate: 1a (6.7±0.6)×1015M-1, 2a=(4.9±0.4)×1019M-2, and 3a (5.7±0.5)×1019M-2. Supramolecular binding with calf thymus DNA by competitive ethidium bromide quenching was made for complex 2a as the most promising anticancer model, the Stern-Volmer constants were found to be KSV=(8.0±0.4)×106M-1, Kq=(6.5±0.4)×105M-1. The binding of the complex 2a to BSA was made by the Scatchard method, the value of the constant is Kb=(1.9±0.2)×106M-1.; (Copyright © 2017 Elsevier Inc. All rights reserved.) |
| Contributed Indexing: | Keywords: 2-Alkylthio-5-arylmethylene-4H-imidazolin-4-one; BSA conjugation; Calf thymus DNA intercalation; Copper(II); Stability constant; Thiohydantoin |
| Substance Nomenclature: | 0 (Coordination Complexes); 0 (Thiohydantoins); 27432CM55Q (Serum Albumin, Bovine); 789U1901C5 (Copper); 9007-49-2 (DNA); 91080-16-9 (calf thymus DNA) |
| Entry Date(s): | Date Created: 20170731 Date Completed: 20180102 Latest Revision: 20180313 |
| Update Code: | 20260130 |
| DOI: | 10.1016/j.jinorgbio.2017.07.015 |
| PMID: | 28756175 |
| Database: | MEDLINE |
Journal Article; Research Support, Non-U.S. Gov't