Interconversion between S- and N-bound L-methionine adducts of Pt(dien)2+ (dien = diethylenetriamine) via dien ring-opened intermediates

Chen, Yu; Guo, Zijian; Murdoch, Piedad del Socorro; Zang, Erle; Sadler, Peter J.

doi:10.1039/a709282b

Cited by 30 publications

(19 citation statements)

References 19 publications

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“…These interactions have been associated with toxic side effects, detoxification, and resistance mechanisms, as well as with delivery of active species to the cell for ultimate binding to DNA. 23a , 29 − 31 …”

Section: Resultsmentioning

confidence: 99%

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

et al. 2014

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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 [RuCl3(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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Section: Resultsmentioning

confidence: 99%

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

et al. 2014

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“…19 Partial displacement of a dien ligand (from tridentate to bidentate) was previously observed in the presence of methionine, which has an amine nitrogen. 20 When the nitrogen-coordinated methionine complex had the pH lowered from 8 to 3, coordination of the sulfur displaced one of the dien nitrogens to form a long-lived intermediate. Also, the breaking of one Pt-N bond of en has been observed when chelation of a di-or tri-peptide occurs.…”

Section: Discussionmentioning

confidence: 99%

“…21 Likewise, the displacement of one nitrogen of dien was concurrent with the formation of a S,N chelate. 20 We have previously Furthermore, the reactions of N-AcMet and 5'-GMP with [Pt(dien)Cl] + have been widely studied and there is no partial displacement of dien by GMP in these reactions. Thus, the Et 2 dien ligand is unique among triamine ligands that have been previously studied in terms of the reactivity with N-AcMet.…”

Section: Discussionmentioning

confidence: 99%

Partial displacement of a triamine ligand from a platinum(II) complex after reaction with N-acetylmethionine

Williams

Gruner

Wright

et al. 2017

Inorganica Chimica Acta

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The compound [Pt(Et 2 dien)Cl]Cl, where Et 2 dien = N,N-diethyldiethylenetriamine, has been synthesized and reacted with N-acetylmethionine (N-AcMet) and guanosine 5'-monophosphate (5'-GMP). Reaction with 5'-GMP at pH 4 leads to formation of [Pt(Et 2 dien)(5'-GMP)] + , as expected. Reaction with N-AcMet occurs more rapidly than with 5'-GMP; when the reaction with N-AcMet occurs at low pH values (~2), one set of resonances is observed initially but a second set of resonances appears over several days as the initial set decreases. The initial set of resonances disappears slowly (several days) at pH 2 but disappears much faster (minutes to hours) if the pH is 4 or higher; the initial resonances do not reappear even if the pH is lowered. Reaction of the [Pt(Et 2 dien)Cl] + with a mixture of N-AcMet and 5'-GMP at pH 4 leads to formation of a unique set of NMR resonances that does not correspond to the resonances of either the 5'-GMP or the N-AcMet products; mass spectrometry identifies a new product corresponding to [Pt(Et 2 dien)(N-AcMet)(5'-GMP)], in which the Et 2 dien ligand is bidentate. Such a complex is also observed if 5'-GMP is added to a sample of [Pt(Et 2 dien)(N-AcMet)] + that has been kept at low pH, but it is not observed when N-AcMet is added to a sample of [Pt(Et 2 dien)(5'-GMP)] +. We propose that the additional set of resonances observed for [Pt(Et 2 dien)(N-AcMet)] + at low pH is due to a less stable conformation of the complex and the addition of 5'-GMP when this less stable conformation exists leads to displacement of one of the nitrogen atoms.

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“…(Barnhham et al, 1996) Several sulphur donor ligands are usually co-administered with platinum drugs to reduce the toxicity. (Chen et al, 1998;Berners-Price et al, 1996) It is widely accepted that, once formed, the Pt-nucleobase complexes are inert under mild conditions and in the absence of strong trans-labilising ligands. In contrast, the presence of strong nucleophiles, for instance sulphur-containing bio-molecules, could facilitate the dissociation of N-coordinated nucleobases from the Pt(II) complex.…”

Section: Interaction Of [Pt(terpy)cl] + Complex With Sulphur-and Nitrmentioning

confidence: 99%

“…It was noted that only in very acidic solutions (pH < 1) there is a possibility for protonation of the terminal amino groups of dien ligand, which leads to the opening of one chelate ring and the creation of S,N-chelat. (Chen et al, 1998) Reaction between [Pt(dien)Cl] + complexes and Lmethionine was studied in the presence of 5'-GMP, assuming the existence of competition of this two ligands. (Lampers & Reedijk, 1990;Soldatović & Bugarčić, 2005 INO, 5'-IMP and 5'-GMP can coordinate to metal ions via N1 and N7.…”

Section: Interaction Of [Pt(dien)cl] + Complex With Sulphur-and Nitromentioning

confidence: 99%

Interactions of the Platinum(II) Complexes with Nitrogen- and Sulfur-Bonding Bio-Molecules in Chronic Lymphocytic Leukemia

Bogojeski¹,

Petrović²,

Bugarčić³

2012

Chronic Lymphocytic Leukemia

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Interconversion between S- and N-bound L-methionine adducts of Pt(dien)2+ (dien = diethylenetriamine) via dien ring-opened intermediates

Cited by 30 publications

References 19 publications

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

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

Partial displacement of a triamine ligand from a platinum(II) complex after reaction with N-acetylmethionine

Interactions of the Platinum(II) Complexes with Nitrogen- and Sulfur-Bonding Bio-Molecules in Chronic Lymphocytic Leukemia

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