Synthesis, characterization, and biological evaluation of new tetrazole-based platinum(II) and palladium(II) chlorido complexes - Potent cisplatin analogues and their trans isomers

Tatiyana V. Serebryanskaya, Tatiana Yung, Alexey A. Bogdanov, Andrei Shchebet, Steven Johnsen, Alexander S. Lyakhov, Ludmila S. Ivashkevich, Zhanna A. Ibrahimava, Tatiyana S. Garbuzenco, Tatiyana S. Kolesnikova, Natalya I. Melnova, Pavel N. Gaponik, Oleg A. Ivashkevich

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Two series of tetrazole-containing platinum(II) and palladium(II) chlorido complexes, trans-[ML2Cl2] (M = Pt, Pd) and cis-[PtL 2Cl2]·nH2O (n = 0, 1), where L is 1- or 2-substituted 5-aminotetrazole, have been synthesized and thoroughly characterized. Configuration of platinum(II) complexes obtained from the reaction of 5-aminotetrazoles with K2PtCl4 has been found to vary depending on the nature of tetrazole derivatives and reaction conditions. According to in vitro cytotoxic evaluation, only platinum complexes display noticeable antiproliferative effect, and their cytotoxicity depends strongly on their geometry and hydrophobicity of the carrier ligands. The most promising complexes are cis-[Pt(1-apt)2Cl2]·H 2O and cis-[Pt(2-abt)2Cl2]·H 2O, where 1-apt is 5-amino-1-phenyltetrazole and 2-abt is 5-amino-2-tert-butyltetrazole. In comparison with cisplatin, they show comparable cytotoxic potency against cisplatin-sensitive human cancer cell lines, cis-[Pt(2-abt)2Cl2]·H2O performing substantially higher activity against cisplatin-resistant cell lines. Cell cycle studies in H1299 cell line indicated that cis-[Pt(2-abt) 2Cl2]·H2O induced apoptosis launched from G2 accumulations. The DNA interaction with cis-[Pt(1-apt) 2Cl2]·H2O was followed by UV spectroscopy, circular dichroism, hydrodynamic and electrophoretic mobility studies. Both cis-[Pt(1-apt)2Cl2]·H2O and cis-[Pt(2-abt)2Cl2]·H2O complexes appeared to be significantly less toxic than cisplatin in mice, while only compound cis-[Pt(1-apt)2Cl2]·H2O displayed noticeable efficacy in vivo.

Original languageEnglish (US)
Pages (from-to)44-53
Number of pages10
JournalJournal of Inorganic Biochemistry
Volume120
DOIs
StatePublished - Mar 1 2013
Externally publishedYes

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Palladium
Platinum
Isomers
Cisplatin
Cells
Cell Line
Electrophoretic mobility
Poisons
Dichroism
Hydrodynamics
Cytotoxicity
Hydrophobicity
Circular Dichroism
Ultraviolet spectroscopy
Hydrophobic and Hydrophilic Interactions
Spectrum Analysis
Cell Cycle
Apoptosis
Ligands
Derivatives

Keywords

  • 5-Aminotetrazoles
  • Antitumor activity
  • Cisplatin analogues
  • DNA interaction
  • Palladium(II) complexes
  • Platinum(II) complexes

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

Cite this

Synthesis, characterization, and biological evaluation of new tetrazole-based platinum(II) and palladium(II) chlorido complexes - Potent cisplatin analogues and their trans isomers. / Serebryanskaya, Tatiyana V.; Yung, Tatiana; Bogdanov, Alexey A.; Shchebet, Andrei; Johnsen, Steven; Lyakhov, Alexander S.; Ivashkevich, Ludmila S.; Ibrahimava, Zhanna A.; Garbuzenco, Tatiyana S.; Kolesnikova, Tatiyana S.; Melnova, Natalya I.; Gaponik, Pavel N.; Ivashkevich, Oleg A.

In: Journal of Inorganic Biochemistry, Vol. 120, 01.03.2013, p. 44-53.

Research output: Contribution to journalArticle

Serebryanskaya, TV, Yung, T, Bogdanov, AA, Shchebet, A, Johnsen, S, Lyakhov, AS, Ivashkevich, LS, Ibrahimava, ZA, Garbuzenco, TS, Kolesnikova, TS, Melnova, NI, Gaponik, PN & Ivashkevich, OA 2013, 'Synthesis, characterization, and biological evaluation of new tetrazole-based platinum(II) and palladium(II) chlorido complexes - Potent cisplatin analogues and their trans isomers', Journal of Inorganic Biochemistry, vol. 120, pp. 44-53. https://doi.org/10.1016/j.jinorgbio.2012.12.001
Serebryanskaya, Tatiyana V. ; Yung, Tatiana ; Bogdanov, Alexey A. ; Shchebet, Andrei ; Johnsen, Steven ; Lyakhov, Alexander S. ; Ivashkevich, Ludmila S. ; Ibrahimava, Zhanna A. ; Garbuzenco, Tatiyana S. ; Kolesnikova, Tatiyana S. ; Melnova, Natalya I. ; Gaponik, Pavel N. ; Ivashkevich, Oleg A. / Synthesis, characterization, and biological evaluation of new tetrazole-based platinum(II) and palladium(II) chlorido complexes - Potent cisplatin analogues and their trans isomers. In: Journal of Inorganic Biochemistry. 2013 ; Vol. 120. pp. 44-53.
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AU - Serebryanskaya, Tatiyana V.

AU - Yung, Tatiana

AU - Bogdanov, Alexey A.

AU - Shchebet, Andrei

AU - Johnsen, Steven

AU - Lyakhov, Alexander S.

AU - Ivashkevich, Ludmila S.

AU - Ibrahimava, Zhanna A.

AU - Garbuzenco, Tatiyana S.

AU - Kolesnikova, Tatiyana S.

AU - Melnova, Natalya I.

AU - Gaponik, Pavel N.

AU - Ivashkevich, Oleg A.

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N2 - Two series of tetrazole-containing platinum(II) and palladium(II) chlorido complexes, trans-[ML2Cl2] (M = Pt, Pd) and cis-[PtL 2Cl2]·nH2O (n = 0, 1), where L is 1- or 2-substituted 5-aminotetrazole, have been synthesized and thoroughly characterized. Configuration of platinum(II) complexes obtained from the reaction of 5-aminotetrazoles with K2PtCl4 has been found to vary depending on the nature of tetrazole derivatives and reaction conditions. According to in vitro cytotoxic evaluation, only platinum complexes display noticeable antiproliferative effect, and their cytotoxicity depends strongly on their geometry and hydrophobicity of the carrier ligands. The most promising complexes are cis-[Pt(1-apt)2Cl2]·H 2O and cis-[Pt(2-abt)2Cl2]·H 2O, where 1-apt is 5-amino-1-phenyltetrazole and 2-abt is 5-amino-2-tert-butyltetrazole. In comparison with cisplatin, they show comparable cytotoxic potency against cisplatin-sensitive human cancer cell lines, cis-[Pt(2-abt)2Cl2]·H2O performing substantially higher activity against cisplatin-resistant cell lines. Cell cycle studies in H1299 cell line indicated that cis-[Pt(2-abt) 2Cl2]·H2O induced apoptosis launched from G2 accumulations. The DNA interaction with cis-[Pt(1-apt) 2Cl2]·H2O was followed by UV spectroscopy, circular dichroism, hydrodynamic and electrophoretic mobility studies. Both cis-[Pt(1-apt)2Cl2]·H2O and cis-[Pt(2-abt)2Cl2]·H2O complexes appeared to be significantly less toxic than cisplatin in mice, while only compound cis-[Pt(1-apt)2Cl2]·H2O displayed noticeable efficacy in vivo.

AB - Two series of tetrazole-containing platinum(II) and palladium(II) chlorido complexes, trans-[ML2Cl2] (M = Pt, Pd) and cis-[PtL 2Cl2]·nH2O (n = 0, 1), where L is 1- or 2-substituted 5-aminotetrazole, have been synthesized and thoroughly characterized. Configuration of platinum(II) complexes obtained from the reaction of 5-aminotetrazoles with K2PtCl4 has been found to vary depending on the nature of tetrazole derivatives and reaction conditions. According to in vitro cytotoxic evaluation, only platinum complexes display noticeable antiproliferative effect, and their cytotoxicity depends strongly on their geometry and hydrophobicity of the carrier ligands. The most promising complexes are cis-[Pt(1-apt)2Cl2]·H 2O and cis-[Pt(2-abt)2Cl2]·H 2O, where 1-apt is 5-amino-1-phenyltetrazole and 2-abt is 5-amino-2-tert-butyltetrazole. In comparison with cisplatin, they show comparable cytotoxic potency against cisplatin-sensitive human cancer cell lines, cis-[Pt(2-abt)2Cl2]·H2O performing substantially higher activity against cisplatin-resistant cell lines. Cell cycle studies in H1299 cell line indicated that cis-[Pt(2-abt) 2Cl2]·H2O induced apoptosis launched from G2 accumulations. The DNA interaction with cis-[Pt(1-apt) 2Cl2]·H2O was followed by UV spectroscopy, circular dichroism, hydrodynamic and electrophoretic mobility studies. Both cis-[Pt(1-apt)2Cl2]·H2O and cis-[Pt(2-abt)2Cl2]·H2O complexes appeared to be significantly less toxic than cisplatin in mice, while only compound cis-[Pt(1-apt)2Cl2]·H2O displayed noticeable efficacy in vivo.

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