Palladium(II) complexes of quinolinylaminophosphonates: Synthesis, structural characterization, antitumor and antimicrobial activity

Juribašić, Marina; Molčanov, Krešimir; Kojić‐Prodić, Biserka; Bellotto, Lisa; Kralj, Marijeta; Zani, Franca; Tušek-Božić, Ljerka

doi:10.1016/j.jinorgbio.2011.03.011

Cited by 65 publications

(20 citation statements)

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“…In all the complexes the phosphoryl oxygen is not coordinated and is free to be involved in hydrogen bonding, which is the main feature of all structures of the quinolinylphosphonate complexes. Their structure, which was determined and described in our previous work by elemental, spectroscopic, and X-ray structural analysis [17], was supported by the present mass spectroscopic studies under positive ion electrospray ionization conditions.…”

Section: Resultssupporting

confidence: 78%

“…Investigations of the complex-forming behavior of three types of quinoline-based aminophosphonates towards palladium(II) ion, all containing three potential donor atoms, quinoline nitrogen, amino nitrogen, and phosphoryl oxygen, have shown that each type of these ligands forms complexes with different metal-ligand interactions ( Figure 1) [17]. Diethyl and dibutyl The bridging molecule is bonded to both palladium atoms, one through the quinoline and the other through the aminoquinoline nitrogen, whereas terminal ligand molecules are coordinated to one palladium via the quinoline nitrogen atom.…”

Section: Resultsmentioning

confidence: 99%

“…It was found that different types of investigated complexes, such as molecular dihalide adducts with trans and cis configuration, mononuclear and binuclear metallocyclic and ion-pair halide salt complexes, have shown good cell growth inhibitory effects. We recently reported the synthesis, structural characterization, and some biological properties of three types of dialkyl quinolinylaminophosphonates [15,16] and their palladium(II) complexes, mononuclear dihalide adducts either with cis-or trans-configuration, as well as dinuclear tetrahalide complexes [17]. In vitro biological evaluation of these compounds revealed no specific antimicrobial activity, whereas the majority of complexes demonstrated antiproliferative activity, which was especially pronounced in the case of dipalladium tetrahalide complexes of quinolinylaminobenzylphosphonates.…”

Section: Introductionmentioning

confidence: 99%

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Electrospray Ionization Mass Spectrometry of Palladium(II) Quinolinylaminophosphonate Complexes

Juribašić

Bellotto

Traldi

et al. 2011

J. Am. Soc. Mass Spectrom.

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The mass spectrometric behavior of palladium(II) halide complexes of three types of quinolinylaminophosphonates, diethyl and dibutyl esters of [α-anilino-(quinolin-2-yl)methyl] phosphonic (L1, L2), [α-anilino-(quinolin-3-yl) + is observed in the mass spectra of all the complexes, and its abundance as well as the fragmentation pathway depend on the type of the complex. In the cis complexes (1-4) the initial decomposition goes under two fragmentation routes: those in which the sodium molecular adduct sequentially loses halides HX/NaX and those in which this loss is in the competition with the loss of dialkyl phosphite. The predominant pathways for decomposition of trans dihalide (5-8) and tetrahalide (9-12) complexes include three competitive reactions; the loss of halides, dialkyl phosphites and the intact phosphonate ligand molecule and its fragments formed by ester dissociation or complete loss of the phosphonate ester moiety. A series of acetonitrile adducts and cluster ions derived from dimolecular clusters [2M + Na] + were also detected. The most important fragmentation patterns are rationalized and supported by the MS n studies.

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Section: Resultssupporting

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Electrospray Ionization Mass Spectrometry of Palladium(II) Quinolinylaminophosphonate Complexes

Juribašić

Bellotto

Traldi

et al. 2011

J. Am. Soc. Mass Spectrom.

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“…These compounds are widely used as broad-spectrum antiviral agents [6] and for treatment of bone diseases [7], while some complexes of platinum group metals exhibit remarkable antitumor activity [8][9][10][11]. a-Aminophosphonates act as isosteres of naturally occurring a-amino acids [3,12] and phosphates [12,13] and can be used as inhibitors of various enzymes and in metabolism regulation [1][2][3][4]13].…”

Section: Introductionmentioning

confidence: 99%

N–H···O=P hydrogen-bonded dimers as the main structural motif of aminophosphonate diesters

2011

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Crystal and molecular structures of three aminophosphonate diesters, diethyl and dibutyl [a-(quinolin-3-ylamino)-N-benzyl]phosphonates (1 and 2) and dibutyl [a-anilino-(quinolin-3-yl)methyl]phosphonate (3) were reported and comparatively discussed. Characteristic structural features for these compounds are strong N-HÁÁÁO=P hydrogen bonds that connect two organophosphorus molecules in cyclic centrosymmetric dimer. Phosphoryl oxygen forms additional interaction with a C-H donor from the nearby aromatic group. Dimer formation in solution was also confirmed using electrospray ionization mass spectrometry. Mass spectra of six structurally similar aminophosphonate derivatives, 1-3 along with diethyl [a-anilino-(quinolin-3-yl)methyl]phosphonate (4), diethyl and dibutyl [a-anilino-(quinolin-2-yl)methyl]phosphonates (5 and 6) were studied and dimolecular ions [2M ? Na] ? and [2M ? H] ? were observed.Keywords Aminophosphonate Á Hydrogen-bonded dimers Á X-ray structure analysis Á ESI mass spectrometry Electronic supplementary material The online version of this article (

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“…[11,12] Other key studies include the structural analysis of interaction behaviour in calixarene amino acid derivatives [13] and the structures of palladium(II) quinolinylaminophosphonate complexes. [14] Roughly two thirds of Biserka's CSD structures are organic, the remaining third containing at least one metal atom with an increasing fraction of polymeric coordination compounds since 2009.…”

Section: Biserka and The Csdmentioning

confidence: 99%

A Historical Perspective on Crystallography in Croatia and the Career of Biserka Kojić-Prodić from the Viewpoint of the CSD

et al. 2018

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There is a long history of chemical crystallography and use of the Cambridge Structural Database (CSD) in Croatia, which dates back to 1985 when the CSD first became accessible there thanks to the efforts of Biserka Kojić-Prodić as head of the National Affiliated Centre. On the occasion of Dr Kojić-Prodić's 80 th birthday we take the opportunity to look back at the history of crystallography in Croatia, and particularly in Biserka's career, from the point of view of the CSD. Biserka has been a prolific author and contributor of crystal structures over the years sharing over 400 structures and collaborating with over 270 different co-authors on a wide range of different types of structure.

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Palladium(II) complexes of quinolinylaminophosphonates: Synthesis, structural characterization, antitumor and antimicrobial activity

Cited by 65 publications

References 57 publications

Electrospray Ionization Mass Spectrometry of Palladium(II) Quinolinylaminophosphonate Complexes

Electrospray Ionization Mass Spectrometry of Palladium(II) Quinolinylaminophosphonate Complexes

N–H···O=P hydrogen-bonded dimers as the main structural motif of aminophosphonate diesters

A Historical Perspective on Crystallography in Croatia and the Career of Biserka Kojić-Prodić from the Viewpoint of the CSD

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