Anti-toxoplasma activity and DNA-binding of copper(II) and zinc(II) coordination compounds with 5-nitroimidazole-based ligands.

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  • Additional Information
    • Source:
      Publisher: Springer Country of Publication: Germany NLM ID: 9616326 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1432-1327 (Electronic) Linking ISSN: 09498257 NLM ISO Abbreviation: J Biol Inorg Chem Subsets: MEDLINE
    • Publication Information:
      Original Publication: Berlin : Springer, c1996-
    • Subject Terms:
      Coordination Complexes*/chemistry ; Toxoplasma*/metabolism ; Ornidazole* ; Nitroimidazoles*; Copper/chemistry ; Zinc/chemistry ; DNA/chemistry ; Ligands ; Crystallography, X-Ray
    • Abstract:
      Tetrahedral copper(II) and zinc(II) coordination compounds from 5-nitroimidazole derivatives, viz. 1-(2-chloroethyl)-2-methyl-5-nitroimidazole (cenz) and ornidazole 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (onz), were synthesized and spectroscopically characterized. Their molecular structures were determined by X-ray diffraction studies. The complexes [Cu(onz) 2 X 2 ], [Zn(onz) 2 X 2 ], [Cu(cenz) 2 X 2 ] and [Zn(cenz) 2 X 2 ] (X -  = Cl, Br), are stable in solution and exhibit positive LogD 7.4 values that are in the range for molecules capable of crossing the cell membrane via passive difussion. Their biological activity against Toxoplasma gondi was investigated, and IC 50 and lethal dose (LD 50 ) values were determined. The ornidazole copper(II) compounds showed very good antiparasitic activity in its tachyzoite morphology. The interaction of the coordination compounds with DNA was examined by circular dichroism, fluorescence (using intercalating ethidium bromide and minor groove binding Hoechst 33258) and UV-Vis spectroscopy. The copper(II) compounds interact with the minor groove of the biomolecule, whereas weaker electrostatic interactions take place with the zinc(II) compounds. The spectroscopic data achieved for the two series of complexes (namely with copper(II) and zinc(II) as metal center) agree with the respective DNA-damage features observed by gel electrophoresis.
      (© 2023. The Author(s).)
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    • Grant Information:
      IN206922 DGAPA-Universidad Nacional Autónoma de México; 5000-9035 PAPIT-FQ- Universidad Nacional Autónoma de México; PID2019-107006GB-C21 Spanish Ministerio de Ciencia e Innovación; PID2020-115537RB-I00 Spanish Ministerio de Ciencia e Innovación; RED2018-102471-T Spanish Ministerio de Ciencia e Innovación
    • Contributed Indexing:
      Keywords: Anti-toxoplasma activity; Coordination compounds; Copper(II) and zinc(II); DNA-damage; Nitroimidazole ligands
    • Accession Number:
      Y8U32AZ5O7 (4-nitroimidazole)
      789U1901C5 (Copper)
      0 (Coordination Complexes)
      24AG2WW15W (2-methyl-5-nitroimidazole)
      J41CSQ7QDS (Zinc)
      62XCK0G93T (Ornidazole)
      9007-49-2 (DNA)
      0 (Ligands)
      0 (Nitroimidazoles)
    • Publication Date:
      Date Created: 20231215 Date Completed: 20240410 Latest Revision: 20240613
    • Publication Date:
      20240613
    • Accession Number:
      PMC11001709
    • Accession Number:
      10.1007/s00775-023-02029-7
    • Accession Number:
      38099935