Study of dinuclear Rh(II) complexes of phenylalanine derivatives as potential anticancer agents by using X-ray fluorescence and X-ray absorption

Zs. Majer, Sz. Bősze, Ildikó Szabó, V. Mihucz, Anikó Gaál, Gábor Szilvágyi, Giancarlo Pepponi, Florian Meirer, Peter Wobrauschek, N. Szoboszlai, Dieter Ingerle, Christina Streli

Research output: Contribution to journalArticle

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Abstract

In vitro antitumor efficacy of several dinuclear bridgings and one chelate structure dirhodium(II) complex of N-protected phenylalanine derivatives were tested on HT-29 cells. The following synthesized and previously characterized complexes were applied in the present work: Rh2(OAc)4-n(O-Phe-Z)n (n=1-4, -O-Phe-Z=N-benzyloxycarbonyl-l-phenylalaninate), Rh2(OAc)4-n(O-Phe-Ac)n (n=1-4, -O-Phe-Ac=N-acetyl-l-phenylalaninate), Rh2(OAc)2(N-Me-D-Phe-O)2 corresponding to N-methyl-d-phenylalaninate as well as Rh2(OAc)4 (-OAc=acetate). Depending on the complex ligand type and its coordination number, the intracellular rhodium (Rh) content determined by total reflection X-ray fluorescence (TXRF) spectrometry in the HT-29 cells varied between 25 and 2500ng/106 cells. In vitro cytotoxicity and cytostatic evaluations of the compounds on HT-29 human cell culture were performed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium assay. Compared to Rh2(OAc)4, the Rh compounds containing one or two -O-Phe-Z moieties proved to be the most effective on the HT-29 cells. Moreover, synchrotron radiation TXRF-X-ray absorption near edge structure measurements suggested a change of the molecular symmetry of the dirhodium(II) center for the moderately in vitro cytotoxic, lipophilic l-phenylalanine derivative complexes, characterized also by low ligand exchange rate when they were studied on HT-29 cells.

Original languageEnglish
Pages (from-to)5157
Number of pages1
JournalMicrochemical Journal
Volume120
DOIs
Publication statusPublished - 2015

Fingerprint

Rhodium
X ray absorption
Phenylalanine
Antineoplastic Agents
Fluorescence
Derivatives
X rays
Rhodium compounds
Ligands
Cytostatic Agents
Cytotoxicity
Synchrotron radiation
Cell culture
Assays
Acetates
dirhodium tetraacetate
carbobenzoxyphenylalanine

Keywords

  • Amino acid ligand
  • Anticancer drug
  • Cellular
  • Dinuclear rhodium
  • Elemental uptake
  • TXRF-XANES

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

Cite this

Study of dinuclear Rh(II) complexes of phenylalanine derivatives as potential anticancer agents by using X-ray fluorescence and X-ray absorption. / Majer, Zs.; Bősze, Sz.; Szabó, Ildikó; Mihucz, V.; Gaál, Anikó; Szilvágyi, Gábor; Pepponi, Giancarlo; Meirer, Florian; Wobrauschek, Peter; Szoboszlai, N.; Ingerle, Dieter; Streli, Christina.

In: Microchemical Journal, Vol. 120, 2015, p. 5157.

Research output: Contribution to journalArticle

Majer, Zs. ; Bősze, Sz. ; Szabó, Ildikó ; Mihucz, V. ; Gaál, Anikó ; Szilvágyi, Gábor ; Pepponi, Giancarlo ; Meirer, Florian ; Wobrauschek, Peter ; Szoboszlai, N. ; Ingerle, Dieter ; Streli, Christina. / Study of dinuclear Rh(II) complexes of phenylalanine derivatives as potential anticancer agents by using X-ray fluorescence and X-ray absorption. In: Microchemical Journal. 2015 ; Vol. 120. pp. 5157.
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abstract = "In vitro antitumor efficacy of several dinuclear bridgings and one chelate structure dirhodium(II) complex of N-protected phenylalanine derivatives were tested on HT-29 cells. The following synthesized and previously characterized complexes were applied in the present work: Rh2(OAc)4-n(O-Phe-Z)n (n=1-4, -O-Phe-Z=N-benzyloxycarbonyl-l-phenylalaninate), Rh2(OAc)4-n(O-Phe-Ac)n (n=1-4, -O-Phe-Ac=N-acetyl-l-phenylalaninate), Rh2(OAc)2(N-Me-D-Phe-O)2 corresponding to N-methyl-d-phenylalaninate as well as Rh2(OAc)4 (-OAc=acetate). Depending on the complex ligand type and its coordination number, the intracellular rhodium (Rh) content determined by total reflection X-ray fluorescence (TXRF) spectrometry in the HT-29 cells varied between 25 and 2500ng/106 cells. In vitro cytotoxicity and cytostatic evaluations of the compounds on HT-29 human cell culture were performed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium assay. Compared to Rh2(OAc)4, the Rh compounds containing one or two -O-Phe-Z moieties proved to be the most effective on the HT-29 cells. Moreover, synchrotron radiation TXRF-X-ray absorption near edge structure measurements suggested a change of the molecular symmetry of the dirhodium(II) center for the moderately in vitro cytotoxic, lipophilic l-phenylalanine derivative complexes, characterized also by low ligand exchange rate when they were studied on HT-29 cells.",
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AU - Szabó, Ildikó

AU - Mihucz, V.

AU - Gaál, Anikó

AU - Szilvágyi, Gábor

AU - Pepponi, Giancarlo

AU - Meirer, Florian

AU - Wobrauschek, Peter

AU - Szoboszlai, N.

AU - Ingerle, Dieter

AU - Streli, Christina

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AB - In vitro antitumor efficacy of several dinuclear bridgings and one chelate structure dirhodium(II) complex of N-protected phenylalanine derivatives were tested on HT-29 cells. The following synthesized and previously characterized complexes were applied in the present work: Rh2(OAc)4-n(O-Phe-Z)n (n=1-4, -O-Phe-Z=N-benzyloxycarbonyl-l-phenylalaninate), Rh2(OAc)4-n(O-Phe-Ac)n (n=1-4, -O-Phe-Ac=N-acetyl-l-phenylalaninate), Rh2(OAc)2(N-Me-D-Phe-O)2 corresponding to N-methyl-d-phenylalaninate as well as Rh2(OAc)4 (-OAc=acetate). Depending on the complex ligand type and its coordination number, the intracellular rhodium (Rh) content determined by total reflection X-ray fluorescence (TXRF) spectrometry in the HT-29 cells varied between 25 and 2500ng/106 cells. In vitro cytotoxicity and cytostatic evaluations of the compounds on HT-29 human cell culture were performed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium assay. Compared to Rh2(OAc)4, the Rh compounds containing one or two -O-Phe-Z moieties proved to be the most effective on the HT-29 cells. Moreover, synchrotron radiation TXRF-X-ray absorption near edge structure measurements suggested a change of the molecular symmetry of the dirhodium(II) center for the moderately in vitro cytotoxic, lipophilic l-phenylalanine derivative complexes, characterized also by low ligand exchange rate when they were studied on HT-29 cells.

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