Molybdenum complexes of the anticancer drug 6-mercaptopurine

Fischer, Berthold; Dubler, E.; Meienberger, Marc D.; Hegetschweiler, Kaspar

doi:10.1016/s0020-1693(98)00108-x

Cited by 15 publications

(8 citation statements)

References 23 publications

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“…However, in case of 6-MP complexes instead of an upfield, a downfield shift was observed in the >C=S resonance. This observation is consistent with the other reported studies [13,28]. Also in the 6-Mp complex, the C-5 and C-8 signals split into two resonances, showing that 6-Mp forms two geometrical isomers with palladium(II).…”

Section: Nmr Studiessupporting

confidence: 93%

“…6-Mercaptopurine and its riboside are anticancer metabolites and their complexes of Pd(II) and Pt(II) are known to exhibit antitumor activity [11][12][13]. In view of this importance, several complexes of thiones with Cu(I) [14][15][16][17], Ag(I) [18][19][20][21][22][23][24], Au(I) [25][26][27], Mo(II) [28], Pd(II) [29][30][31][32][33][34], Zn(II) [35][36][37][38][39], Cd(II) [39][40][41][42][43][44][45] and Hg(II) [46][47][48][49][50] have been widely studied. We have been interested in the spectral and structural chemistry of several metal ions with thiones in order to study their binding modes and to provide useful models for metalloproteins [16][17][18][19][20]26,…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, spectral characterization and antibacterial studies of palladium(II) complexes of heterocyclic thiones

et al. 2009

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Reactions of K2[PdCl4] with heterocyclic thiones in molar ratios of 1:2 and 1:4 in water-methanol medium yielded the palladium(II) complexes with the general formula of either [Pd(L)Cl2], [Pd(L)2]Cl2or [Pd(L)4]Cl2where L ═ Imidazolidine-2-thione (Imt), 2-Mercaptopyridine (Mpy), 2-Mercaptopyrimidine (Mpm), 6-Mercaptopurine (6-Mp) and Thionicotinamide (Tna). The complexes were characterized by elemental analysis and spectroscopic (IR,1H and13C NMR) methods. An upfield shift in the >C═S resonance of thiones in13C NMR and downfield shift in N–H or aromatic proton resonances in1H NMR are consistent with the sulfur coordination to palladium(II). The complexes were screened for antibacterial activity, and the results showed that the complexes exhibited moderate activities as compared to that of a standard drug.

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Section: Nmr Studiessupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Synthesis, spectral characterization and antibacterial studies of palladium(II) complexes of heterocyclic thiones

et al. 2009

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“…It is widely used as an effect medicine in treating a variety of diseases, such as rheumatologic disorder, lymphoblastic leukaemia, inflammatory bowel disease and prevention of rejection following organ transplantation [13–22]. The adsorption of 6MP on nanomaterials has received a lot of attentions because of the drug coordination to its chemotherapeutic activity [23–25]. Vivoni and co-workers [24] have experimentally reported the interaction between 6MP and a silver electrode using surface-enhanced Raman spectroscopy (SERS) and Urey-Bradley force field combined with semiempirical PM3 calculation.…”

Section: Introductionmentioning

confidence: 99%

“…The coordination of 6MP onto nanomaterials has been investigated, which can lead to slow releasing drugs of 6MP [26] and exploiting the reaction for heavy-metal determination [27]. Although there are many investigations about the coordination of 6MP to Ag nanoparticles forming AgNPs [10, 11, 23–27], they are only limited to investigate the experimental Raman spectroscopy and the scales and so on. What are the adsorption structures?…”

Section: Introductionmentioning

confidence: 99%

A new insight of structures, bonding and electronic properties for 6-mercaptopurine and Ag8 clusters configurations: a theoretical perspective

Ren

Chen

et al. 2019

BMC Chemistry

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Background Many reports have also shown that the silver nanoparticles can effectively increase the anticancer drug activity and intensely enhance the drug curative effect. The adsorption of 6MP on nanomaterials has received a lot of attentions because of the drug coordination to its chemotherapeutic activity. The geometrical structures, chemical bonds, molecular orbital properties as well as density of states for the configurations were analyzed to deeply understand the interactions between the 6MP and Ag 8 clusters for high effect anticancer drug production. Results In this work, the density functional theory B3LYP has been used to investigate the structures and properties of the configurations between 6-mercaptopurine (6MP) and Ag 8 clusters using 6-311++G** level as well as an effective pseudo potential LANL2DZ. The geometries of ten configurations were optimized with full freedom. The geometrical structures, chemical bonds, molecular orbital properties as well as density of states for partial configurations were analyzed based on the density functional calculations. Polarizable continuum solvent model (PCM) in self-consistent reaction field (SCRF) were used for the aqueous calculations. The influences of temperature and pressure on the stability of the predominant configurations in the gas phase were further considered using standard statistical thermodynamic methods from 50 to 500 K and at 1 bar or 100 bar. Conclusion The result shows that there are ten stable configurations in the gas phase and there is a strong chemical bond between a Ag and S atom in the most stable configuration. The analysis of density of states also shows that the Ag–S chemical bond in the most stable configuration has been formed. Moreover, the results show that the temperature and the pressure will significantly influence the stability of the configurations in the gas phase. Additionally, when the solvent effect was considered, we found that there are only seven stable configurations and the solvent have different effect on various configurations. Electronic supplementary material The online version of this article (10.1186/s13065-019-0573-z) contains supplementary material, which is available to authorized users.

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“…Molybdenum complexes of 6MP have been synthesized with the intent of deciphering the still obscure coordination behavior of molybdenum and oxopurines in the enzyme xanthine oxidase. 13 The inhibitory activity of 6-mercaptopurine riboside towards hepatocytic autophagy has also been established. 12 Along with its use as a therapeutic agent, 6MP has also been employed as a mediator in a number of electrochemical systems.…”

Section: Introductionmentioning

confidence: 99%

Normal-mode analysis of the Raman-active modes of the anti-tumor agent 6-mercaptopurine

Vivoni

Chen

Ejeh

et al. 2000

J. Raman Spectrosc.

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The Raman spectra of the antitumor agent 6‐mercaptopurine (6MP) in the solid and solution state were recorded in the 600–1700 cm−1 spectral region. The normal modes of 6MP were calculated using a Urey–Bradley empirical force field (UBFF) and with the PM3 semi‐empirical method. Prior to performing the normal‐mode calculations on 6MP, similar calculations were performed on methanethiol and thiophenol. The force constant parameters obtained from these calculations were then transferred to the 6MP calculations. The results of the normal‐mode calculations were compared with the observed spectra and an assignment of the vibrational modes is proposed. Based on changes in the wavenumbers of the Raman spectra between the solution and solid form 6MP and on normal‐mode calculations, it is proposed that in the solid form 6MP crystallizes in the tautomer form whereas in solution the molecule ionizes by losing the hydrogen at the N‐1 position. Copyright © 2000 John Wiley & Sons, Ltd.

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Molybdenum complexes of the anticancer drug 6-mercaptopurine

Cited by 15 publications

References 23 publications

Synthesis, spectral characterization and antibacterial studies of palladium(II) complexes of heterocyclic thiones

Synthesis, spectral characterization and antibacterial studies of palladium(II) complexes of heterocyclic thiones

A new insight of structures, bonding and electronic properties for 6-mercaptopurine and Ag8 clusters configurations: a theoretical perspective

Normal-mode analysis of the Raman-active modes of the anti-tumor agent 6-mercaptopurine

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