Literature DB >> 36015318

Antiproliferative Copper(II) Complexes Bearing Mixed Chelating Ligands: Structural Characterization, ROS Scavenging, In Silico Studies, and Anti-Melanoma Activity.

Rodica Olar1, Catalin Maxim1, Mihaela Badea1, Mihaela Bacalum2, Mina Raileanu2,3, Speranta Avram4, Nataša Čelan Korošin5, Teodora Burlanescu6, Arpad Mihai Rostas7.   

Abstract

Melanoma is a skin cancer characterized by rapid growth and spread for which current therapies produce both resistance and increased risk of infection. To develop new anti-melanoma biocompatible species, the series of complexes Cu(N-N)(bzac)(X)⋅nH2O (N-N: 1,10-phenanthroline/2,2'-bipyridine, Hbzac: 1-phenyl-1,3-butanedione, X: NO3/ClO4, and n = 0, 1) was studied. Single-crystal X-ray diffraction revealed a mononuclear structure for all complexes. The ability of the complexes to scavenge or trap reactive oxygen species such as O2⋅- and HO⋅ was proved by EPR spectroscopy experiments. All complexes inhibited B16 murine melanoma cells in a dose-dependent and nanomolar range, but the complexes with 1,10-phenanthroline were more active. Moreover, comparative activity on B16 and healthy BJ cells revealed a therapeutic index of 1.27-2.24. Bioinformatic methods were used to calculate the drug-likeness, pharmacokinetic, pharmacogenomic, and pharmacodynamic profiles of the compounds. The results showed that all compounds exhibit drug-likeness features, as well as promising absorption, distribution, metabolism, and excretion (ADME) properties, and no toxicity. The pharmacodynamics results showed that the neutral species appear to be good candidates for antitumor molecular targets (Tyrosyl-DNA phosphodiesterase 1, DNA-(apurinic or apyrimidinic site) lyase or Kruppel-like factor 5). Furthermore, the pharmacogenomic results showed a good affinity of the copper(II) complexes for the human cytochrome. These results recommend complexes bearing 1,10-phenanthroline as good candidates for developing drugs to melanoma alternative treatment.

Entities:  

Keywords:  ADME-Tox; Cu(II) complex; ROS; bioinformatics; cytotoxicity; melanoma cells; structure

Year:  2022        PMID: 36015318      PMCID: PMC9416163          DOI: 10.3390/pharmaceutics14081692

Source DB:  PubMed          Journal:  Pharmaceutics        ISSN: 1999-4923            Impact factor:   6.525


  41 in total

Review 1.  Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings.

Authors:  C A Lipinski; F Lombardo; B W Dominy; P J Feeney
Journal:  Adv Drug Deliv Rev       Date:  2001-03-01       Impact factor: 15.470

2.  Magnetic property, DFT calculation, and biological activity of bis[(μ(2)-chloro)chloro(1,10-phenanthroline)copper(II)] complex.

Authors:  Mohammad Mroueh; Costantine Daher; Essa Hariri; Sally Demirdjian; Samih Isber; Eun Sang Choi; Babak Mirtamizdoust; Hassan H Hammud
Journal:  Chem Biol Interact       Date:  2015-03-07       Impact factor: 5.192

Review 3.  A Perspective - can copper complexes be developed as a novel class of therapeutics?

Authors:  Mohamed Wehbe; Ada W Y Leung; Michael J Abrams; Chris Orvig; Marcel B Bally
Journal:  Dalton Trans       Date:  2017-08-22       Impact factor: 4.390

4.  Molecular properties that influence the oral bioavailability of drug candidates.

Authors:  Daniel F Veber; Stephen R Johnson; Hung-Yuan Cheng; Brian R Smith; Keith W Ward; Kenneth D Kopple
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

5.  The cytotoxicity of the anticancer drug elesclomol is due to oxidative stress indirectly mediated through its complex with Cu(II).

Authors:  Brian B Hasinoff; Arun A Yadav; Daywin Patel; Xing Wu
Journal:  J Inorg Biochem       Date:  2014-04-16       Impact factor: 4.155

6.  Identification of [CuCl(acac)(tmed)], a copper(II) complex with mixed ligands, as a modulator of Cu,Zn superoxide dismutase (Sod1p) activity in yeast.

Authors:  Ioana Dumitru; Cristian D Ene; Augustin M Ofiteru; Codruta Paraschivescu; Augustin M Madalan; Ion Baciu; Ileana C Farcasanu
Journal:  J Biol Inorg Chem       Date:  2012-06-20       Impact factor: 3.358

7.  Cardiotoxicity and antitumor activity of a copper(II)-doxorubicin chelate.

Authors:  E Monti; L Paracchini; F Piccinini; V Malatesta; F Morazzoni; R Supino
Journal:  Cancer Chemother Pharmacol       Date:  1990       Impact factor: 3.333

8.  Oxidative stress in malignant melanoma and non-melanoma skin cancer.

Authors:  C S Sander; F Hamm; P Elsner; J J Thiele
Journal:  Br J Dermatol       Date:  2003-05       Impact factor: 9.302

9.  Design and characterization of highly in vitro antitumor active ternary copper(II) complexes containing 2'-hydroxychalcone ligands.

Authors:  Radka Křikavová; Ján Vančo; Zdeněk Trávníček; Jakub Hutyra; Zdeněk Dvořák
Journal:  J Inorg Biochem       Date:  2016-07-09       Impact factor: 4.155

10.  Ternary copper(II) complex: NCI60 screening, toxicity studies, and evaluation of efficacy in xenograft models of nasopharyngeal carcinoma.

Authors:  Munirah Ahmad; Shazlan-Noor Suhaimi; Tai-Lin Chu; Norazlin Abdul Aziz; Noor-Kaslina Mohd Kornain; D S Samiulla; Kwok-Wai Lo; Chew-Hee Ng; Alan Soo-Beng Khoo
Journal:  PLoS One       Date:  2018-01-12       Impact factor: 3.240

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