Stereospecific ligands and their complexes. IV: Synthesis, characterization and cytotoxicity of novel platinum(IV) complexes with ethylenediamine-N,N′-di-S,S-2-propanoate and halogenido ligands: Crystal structure of s-cis-[Pt(S,S-eddp)Cl2]·4H2O and uns-cis-[Pt(S,S-eddp)Br2]

“…A small number of drugs used in medicine have ethylenediamine structure. The compounds previously analyzed by a group of researchers led by T. Sabo were actually ligands of Pt-complexated ethylenediamine and 1,3-propanediamine [9][10][11][12].…”

Section: Methods Developmentmentioning

confidence: 99%

Highly sensitive UHPLC—MS/MS method for quantification of ethylenediamine-N,N′-di-2-(3-cyclohexyl) propanoic acid derivatives in mouse serum

Tubić

Marković

Vladimirov

et al. 2017

Acta Chromatographica

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Summary. A series of new (S,S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl)propanoate esters has shown cytotoxic activity towards human leukemic cell lines. The aim of this study was to develop and validate a bioanalytical method for quantification of (S,S)-O, O-diethyl-ethylenediamine-N,N′-di-2-(3-cyclohexyl)propanoate dihydrochlorides (DE-EDCP) and its metabolite, substituted propanoic acid (EDCP), in mouse serum by ultra high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Structural analog, derivative of 1,3-propanediamine, was used as an internal standard (IS). Sample preparation employed protein precipitation by acetonitrile and subsequent centrifugation. Optimal UHPLC separation conditions were set to achieve simultaneous determination of both compounds in a short run time of 6 min. Additionally, the selected reaction monitoring (SRM) mode developed in this method allowed a highly sensitive, accurate, and precise identification of compounds of interest. The lower limit of quantitation (LOQ) was 1.3 ng mL −1 for DE-EDCP and 0.3 μg mL −1 for EDCP. The calibration curves were linear over the concentration range of 1.3-26.7 ng mL −1 and 0.3-6.7 μg mL −1 for DE-EDCP and EDCP, respectively. Precision (%CV) and accuracy (%RE) for DE-EDCP and EDCP ranged from 3.5% to 16.0% and from 1.8% to 14.4%, respectively.The validation process was performed in accordance with the regulatory guidance/guideline, and all of the obtained results met the established acceptance criteria. The newly developed and validated UHPLC-MS/MS method is rapid, sensitive, and selective, and it can be successfully applied to drug monitoring in nonclinical studies.

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“…However, when M = Pt(IV) all three isomers have been prepared and characterized in the case where edda-type = edda 4 and S,Seddp. 13,14 It was shown that s-cis geometry was favored in metal complexes with edda-type ligands forming five-membered chelate rings while uns-cis geometry was favored in complexes comprehending six-membered chelate rings. 4 The observed greater ring strain in the octahedral plane than out of the plane is accepted as a general reason for such distribution of geometrical isomers.…”

Section: Introductionmentioning

confidence: 99%

“…4,[15][16][17] The s-cis geometry was also proposed for the [M(edda)(H 2 O) 2 ] complex (M = Ni(II), Cu(II) and Co(III)). [14][15][16] While s-cis geometry of the pure [Cu(edda)(H 2 O) 2 ] complex is not yet crystallographically confirmed, the X-ray structure of the s-cis-[Ni(edda)(H 2 O) 2 ] complex was reported by several authors. 18,19 Furthermore, nickel(II) ion surrounded by bis N-hydroxymethyl-edda ligand (abbreviated as OHMeedda) also adopts s-cis geometry 19 while for the Ni-1,3-pdda complex (1,3-pdda stands for 1,3-propanediamine-N,N′-diacetate anion) the uns-cis geometry was found to be dominant one 20 by X-ray analysis.…”

Section: Introductionmentioning

confidence: 99%

Nickel(ii) in chelate N2O2 environment. DFT approach and in-depth molecular orbital and configurational analysis

et al. 2013

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The O-N-N-O-type tetradentate ligands H2S,S-eddp (H2S,S-eddp stands for S,S-ethylenediamine-N,N'-di-2-propionic acid) and H2edap (H2edap stands for ethylenediamine-N-acetic-N'-3-propionic acid) and the corresponding novel octahedral nickel(II) complexes have been prepared and characterized. N2O2 ligands coordinate to the nickel(II) ion via four donor atoms (two deprotonated carboxylate atoms and two amine nitrogens) affording octahedral geometry in the case of all investigated Ni(II) complexes. A six coordinate, octahedral geometry has been verified crystallographically for the s-cis-[Ni(S,S-eddp)(H2O)2] complex. Structural data correlating similarly chelated Ni(II) complexes have been used to carry out an extensive configuration analysis. Molecular mechanics and Density Functional Theory (DFT) have been used to model the most stable geometric isomer, yielding, at the same time, significant structural and spectroscopic (TDDFT) data. The results from density functional studies have been compared to X-ray data. Natural Bond Orbital (NBO) and Natural Energetic Decomposition Analysis (NEDA) have been done for the [Ni(edda-type)(H2O)(2-n)] and nH2O fragments. Molecular orbital analysis (MPA) is given as well. The infra-red and electronic absorption spectra of the complexes are discussed in comparison to the related complexes of known geometries.

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Stereospecific ligands and their complexes. IV: Synthesis, characterization and cytotoxicity of novel platinum(IV) complexes with ethylenediamine-N,N′-di-S,S-2-propanoate and halogenido ligands: Crystal structure of s-cis-[Pt(S,S-eddp)Cl2]·4H2O and uns-cis-[Pt(S,S-eddp)Br2]

Cited by 12 publications

References 33 publications

Platinum Complexes with Edda (Ethylenediamine -N, N - Diacetate) Ligands as Potential Anticancer Agents

Platinum Complexes with Edda (Ethylenediamine -N, N - Diacetate) Ligands as Potential Anticancer Agents

Highly sensitive UHPLC—MS/MS method for quantification of ethylenediamine-N,N′-di-2-(3-cyclohexyl) propanoic acid derivatives in mouse serum

Nickel(ii) in chelate N2O2 environment. DFT approach and in-depth molecular orbital and configurational analysis

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