Ruthenium-nitrosyl complexes with glycine, L-alanine, L-valine, L-proline, D-proline, L-serine, L-threonine, and L-tyrosine

Synthesis, X-ray diffraction structures, spectroscopic and electrochemical properties, and antiproliferative activity

Anna Rathgeb, Andreas Böhm, Maria S. Novak, Anatolie Gavriluta, Orsolya Dömötör, Jean Bernard Tommasino, E. Enyedy, Sergiu Shova, Samuel Meier, Michael A. Jakupec, Dominique Luneau, Vladimir B. Arion

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The reactions of [Ru(NO)Cl5]2- with glycine (Gly), l-alanine (l-Ala), l-valine (l-Val), l-proline (l-Pro), d-proline (d-Pro), l-serine (l-Ser), l-threonine (l-Thr), and l-tyrosine (l-Tyr) in n-butanol or n-propanol afforded eight new complexes (1-8) of the general formula [RuCl 3(AA-H)(NO)]-, where AA = Gly, l-Ala, l-Val, l-Pro, d-Pro, l-Ser, l-Thr, and l-Tyr, respectively. The compounds were characterized by elemental analysis, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, UV-visible and ATR IR spectroscopy, cyclic voltammetry, and X-ray crystallography. X-ray crystallography studies have revealed that in all cases the same isomer type (from three theoretically possible) was isolated, namely mer(Cl),trans(NO,O)-[RuCl3(AA-H)(NO)], as was also recently reported for osmium analogues with Gly, l-Pro, and d-Pro (see Z. Anorg. Allg. Chem. 2013, 639, 1590-1597). Compounds 1, 4, 5, and 8 were investigated by ESI-MS with regard to their stability in aqueous solution and reactivity toward sodium ascorbate. In addition, cell culture experiments in three human cancer cell lines, namely, A549 (nonsmall cell lung carcinoma), CH1 (ovarian carcinoma), and SW480 (colon carcinoma), were performed, and the results are discussed in conjunction with the lipophilicity of compounds.

Original languageEnglish
Pages (from-to)2718-2729
Number of pages12
JournalInorganic Chemistry
Volume53
Issue number5
DOIs
Publication statusPublished - Mar 3 2014

Fingerprint

alanylglycine
Ruthenium
tyrosine
Valine
alanine
Threonine
glycine
Electrochemical properties
Proline
Glycine
Serine
ruthenium
Tyrosine
Electrospray ionization
cancer
X ray crystallography
X ray diffraction
Mass spectrometry
synthesis
Cells

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Ruthenium-nitrosyl complexes with glycine, L-alanine, L-valine, L-proline, D-proline, L-serine, L-threonine, and L-tyrosine : Synthesis, X-ray diffraction structures, spectroscopic and electrochemical properties, and antiproliferative activity. / Rathgeb, Anna; Böhm, Andreas; Novak, Maria S.; Gavriluta, Anatolie; Dömötör, Orsolya; Tommasino, Jean Bernard; Enyedy, E.; Shova, Sergiu; Meier, Samuel; Jakupec, Michael A.; Luneau, Dominique; Arion, Vladimir B.

In: Inorganic Chemistry, Vol. 53, No. 5, 03.03.2014, p. 2718-2729.

Research output: Contribution to journalArticle

Rathgeb, Anna ; Böhm, Andreas ; Novak, Maria S. ; Gavriluta, Anatolie ; Dömötör, Orsolya ; Tommasino, Jean Bernard ; Enyedy, E. ; Shova, Sergiu ; Meier, Samuel ; Jakupec, Michael A. ; Luneau, Dominique ; Arion, Vladimir B. / Ruthenium-nitrosyl complexes with glycine, L-alanine, L-valine, L-proline, D-proline, L-serine, L-threonine, and L-tyrosine : Synthesis, X-ray diffraction structures, spectroscopic and electrochemical properties, and antiproliferative activity. In: Inorganic Chemistry. 2014 ; Vol. 53, No. 5. pp. 2718-2729.
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T2 - Synthesis, X-ray diffraction structures, spectroscopic and electrochemical properties, and antiproliferative activity

AU - Rathgeb, Anna

AU - Böhm, Andreas

AU - Novak, Maria S.

AU - Gavriluta, Anatolie

AU - Dömötör, Orsolya

AU - Tommasino, Jean Bernard

AU - Enyedy, E.

AU - Shova, Sergiu

AU - Meier, Samuel

AU - Jakupec, Michael A.

AU - Luneau, Dominique

AU - Arion, Vladimir B.

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AB - The reactions of [Ru(NO)Cl5]2- with glycine (Gly), l-alanine (l-Ala), l-valine (l-Val), l-proline (l-Pro), d-proline (d-Pro), l-serine (l-Ser), l-threonine (l-Thr), and l-tyrosine (l-Tyr) in n-butanol or n-propanol afforded eight new complexes (1-8) of the general formula [RuCl 3(AA-H)(NO)]-, where AA = Gly, l-Ala, l-Val, l-Pro, d-Pro, l-Ser, l-Thr, and l-Tyr, respectively. The compounds were characterized by elemental analysis, electrospray ionization mass spectrometry (ESI-MS), 1H NMR, UV-visible and ATR IR spectroscopy, cyclic voltammetry, and X-ray crystallography. X-ray crystallography studies have revealed that in all cases the same isomer type (from three theoretically possible) was isolated, namely mer(Cl),trans(NO,O)-[RuCl3(AA-H)(NO)], as was also recently reported for osmium analogues with Gly, l-Pro, and d-Pro (see Z. Anorg. Allg. Chem. 2013, 639, 1590-1597). Compounds 1, 4, 5, and 8 were investigated by ESI-MS with regard to their stability in aqueous solution and reactivity toward sodium ascorbate. In addition, cell culture experiments in three human cancer cell lines, namely, A549 (nonsmall cell lung carcinoma), CH1 (ovarian carcinoma), and SW480 (colon carcinoma), were performed, and the results are discussed in conjunction with the lipophilicity of compounds.

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