Metal complexes based on monosaccharide bicyclophosphites as new available chiral coordination systems

Nifantyev, E. E.; Koroteev, M. P.; Koroteev, Aleksander M.; Belsky, V. K.; Сташ, А. И.; Antipin, Mihkail Yu.; Лысенко, К. А.; Cao, Liping

doi:10.1016/s0022-328x(99)00245-4

Cited by 13 publications

(11 citation statements)

References 17 publications

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“…Another compound KP1558 (4c) ( Figure 3) and its analogues are prepared by replacing PTA with 3,5,6-bicyclophosphite--D-glucofuranoside ligands to obtain highly active compounds [39,40]. The lipophilicity of the complexes can be modulated by modifying the carbohydrate moiety to yield coordination compounds with high aqueous solubility ideally suited for intravenous administration or hydrophobic species that facilitate cellular uptake.…”

Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

“…The lipophilicity of the complexes can be modulated by modifying the carbohydrate moiety to yield coordination compounds with high aqueous solubility ideally suited for intravenous administration or hydrophobic species that facilitate cellular uptake. The hydrolytic behaviour, the affinity to proteins and model nucleobases, and the in vitro antineoplastic activity of the complexes were investigated against human SW480 (colon adenocarcinoma), CH1 (ovarian cancer), cisplatin-resistant A2780 (ovarian carcinoma), A549 (lung carcinoma), Me300 (melanoma), LNZ308 (glioblastoma), and HCEC (endothelial) cell lines [39,40]. In water, the phosphite ligand is hydrolyzed, and this process is activated by prior hydrolysis of the chlorido ligand at the ruthenium centre.…”

Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

“…The complex resulting from hydrolysis of the Ru-Cl bonds and P-O bonds of the ligand showed affinity towards albumin and transferrin, and it was also capable of binding to 9-ethylguanine (9EtG) with formation of 1 : 1 adducts. The complexes showed remarkably high activity in all tested cell lines, and cytotoxic activity of the compounds is believed to be enhanced by the alkyl moiety of the phosphite which makes the compound more lipophilic [39,40].…”

Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

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Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes

Motswainyana

Ajibade

2015

Advances in Chemistry

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Ruthenium compounds are highly regarded as potential drug candidates. The compounds offer the potential of reduced toxicity and can be tolerated in vivo. The various oxidation states, different mechanism of action, and the ligand substitution kinetics of ruthenium compounds give them advantages over platinum-based complexes, thereby making them suitable for use in biological applications. Several studies have focused attention on the interaction between active ruthenium complexes and their possible biological targets. In this paper, we review several ruthenium compounds which reportedly possess promising cytotoxic profiles: from the discovery of highly active compounds imidazolium [trans-tetrachloro(dmso)(imidazole)ruthenate(III)] (NAMI-A), indazolium [trans-tetrachlorobis(1H-indazole)ruthenate(III)](KP1019), and sodium trans-[tetrachloridobis(1H-indazole)ruthenate(III)] (NKP-1339) to the recent work based on both inorganic and organometallic ruthenium(II) compounds. Half-sandwich organometallic ruthenium complexes offer the opportunity of derivatization at the arene moiety, while the three remaining coordination sites on the metal centre can be functionalised with various coordination groups of various monoligands. It is clear from the review that these mononuclear ruthenium(II) compounds represent a strongly emerging field of research that will soon culminate into several ruthenium based antitumor agents.

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Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

Section: Organometallic Ruthenium(ii)mentioning

confidence: 99%

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Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes

Motswainyana

Ajibade

2015

Advances in Chemistry

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“…The spectrum of metal complex VI, ÄÄÄÄÄÄÄÄÄÄÄÄ recorded in standard conditions, contains four slightly broadened singlets. At the same time, the spectra of the free ligands and conformationally stable complexes always display well-defined J CP coupling constants [6]. In the case in hand, signal splitting is abolished by fast tetragonal pyramid3trigonal bipyramid izomerization.…”

Section: äääääääääääämentioning

confidence: 94%

“…These compounds are available, stable, and exhibit a tendency for coordination with transition metals [6,7].…”

mentioning

confidence: 99%

Rhodium(I) pentasubstituted cationic complexes on the basis of 1,2-O-Alkylidene-3,5,6-O-phosphinetriyl-α-D-glucofuranose

et al. 2004

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Reaction of 1,2-O-alkylidene-a-D-glucofuranose 3,5,6-phosphites with dicarbonylrhodium(I) acetylacetonate was studied. The structure of the reaction products is determined by the reagent ratio. At a 5 : 1 molar ratio, the step ligand-exchange process yields chiral complexes of the [RhL 5 ] + acac ! type. Dynamics of and anion exchange in these complexes are considered.Homoligand cationic complexes of rhodium(I) [RhL 5 ] + X ! have been scarcely explored. They have largely been synthesized on the basis of symmetrical acyclic trialkyl phosphites, as well as carcass phosphorinane3phosphorinane ligands, such as etriol phosphite, metriol phosphite, and adamantyl phosphite [1,2]. Described homoligand cationic rhodium(I) complexes are interesting from the chemical viewpoint. In the solid state they are stable and convenient to operate, and in solutions they undergo fluctuations due to the interconversion of the trigonal bipyramid and distorted tetragonal bipyramid forms [3,4]. It is very important that such complexes can be formed in situ during catalyst formation [5].Here we report on the first synthesis of optically active complexes [RhL 5 ] + X ! on the basis of acac .Rh(CO) 2 as complex-forming agent and unsymmetrical phospholane3phosphorinane systems, such as 1,2-O-isopropylidene-3,5,6-phosphabicyclo-a-Dglucofuranose (I), 1,2-O-cyclohexylidene-3,5,6-phos-ÄÄÄÄÄÄÄÄÄÄÄÄ phabicyclo-a-D-glucofuranose (II), and model 2,7,8-trioxa-1-phosphabicyclo[3,2,1]octane (III), as ligands. These compounds are available, stable, and exhibit a tendency for coordination with transition metals [6,7].Initiating these studies we expected that the ligandexchange reactions of acacRh(CO) 2 with compounds I and II would have certain specific features associated with the large size of the five carbohydratecontaining bicyclophosphite molecules coordinating to one rhodium atom. At the same time, the steric hindrance created by these ligands should not be too strong in view of the fact that the ligated part of the bicyclophosphites is a cone with small O3P3O bond angles. The sums of these angles in ligands I and II are as little as 293o and 295o, respectively [8].

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In Vitro Anticancer Activity and Biologically Relevant Metabolization of Organometallic Ruthenium Complexes with Carbohydrate‐Based Ligands

Berger

Hanif

Nazarov

et al. 2008

Chemistry A European J

117

100

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The synthesis and in vitro anticancer activity of dihalogenido(eta6-p-cymene)(3,5,6-bicyclophosphite-alpha-D-glucofuranoside)ruthenium(II) complexes are described. The compounds were characterized by NMR spectroscopy and ESI mass spectrometry, and the molecular structures of dichlorido-, dibromido- and diiodido(eta6-p-cymene)(3,5,6-bicyclophosphite-1,2-O-isopropylidene-alpha-D-glucofuranoside)ruthenium(II) were determined by X-ray diffraction analysis. The complexes were shown to undergo aquation of the first halido ligand in aqueous solution, followed by hydrolysis of a P--O bond of the phosphite ligand, and finally formation of dinuclear species. The hydrolysis mechanism was confirmed by DFT calculations. The aquation of the complexes was markedly suppressed in 100 mM NaCl solution, and notably only very slow hydrolysis of the P--O bond was observed. The complexes showed affinity towards albumin and transferrin and monoadduct formation with 9-ethylguanine. In vitro studies revealed that the 3,5,6-bicyclophosphite-1,2-O-cyclohexylidene-alpha-D-glucofuranoside complex is the most cytotoxic compound in human cancer cell lines (IC50 values from 30 to 300 microM depending on the cell line).

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Metal complexes based on monosaccharide bicyclophosphites as new available chiral coordination systems

Cited by 13 publications

References 17 publications

Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes

Anticancer Activities of Mononuclear Ruthenium(II) Coordination Complexes

Rhodium(I) pentasubstituted cationic complexes on the basis of 1,2-O-Alkylidene-3,5,6-O-phosphinetriyl-α-D-glucofuranose

In Vitro Anticancer Activity and Biologically Relevant Metabolization of Organometallic Ruthenium Complexes with Carbohydrate‐Based Ligands

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