Controlled oxidation of thiols to disulfides by diazenecarboxamides

Košmrlj, Janez; Kočevar, Marijan; Polanc, Slovenko

doi:10.1039/a808381i

Cited by 46 publications

(50 citation statements)

References 18 publications

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“…Under quasiphysiological conditions, selected diazenes interacted with natural thiols, particularly with GSH [14]. Further, in our previous study we have shown that the addition of diazenes may significantly reduce the intracellular GSH level [16,17].…”

Section: Discussionmentioning

confidence: 99%

“…Six new diazenecarboxamides (BR-25, UP-39, UP-11, JK-1024, RL-514 and RL-625) were synthesized from 1,4-disubstituted semicarbazides under mild reaction conditions using ceric ammonium nitrate as an oxidant [13,14]. The structures of these diazenes are given in figure 1.…”

Section: Drugsmentioning

confidence: 99%

“…However, they are unstable and therefore not suitable for experimental research and clinical application [12]. Recently we have synthesized new diazenecarboxamides (shortly diazenes) as selective oxidants for a mild transformation of various thiols to the corresponding disulfides [13,14]. Diazenes are stable in a solid state and solutions of different sol-vents or water, even during the extended period of time.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Effects of Diazenes on Tumor Cells in vitro

Moskatelo

Benjak²,

Laketa³

et al. 2002

Chemotherapy

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Background: We have shown previously that diazenecarboxamides (diazenes) were cytotoxic for several tumor cell lines. Their target seems to be the intracellular glutathione (GSH). To improve the solubility and biological activity of these drugs, new compounds have been synthesized. In the present study we examined the cytotoxic effect of six new diazenes: BR-25, UP-39, UP-11, JK-1024, RL-514 and RL-625. Methods: The cytotoxicity of diazenes was tested on nine human tumor cell lines: laryngeal carcinoma HEp2 cells, cervical carcinoma HeLa cells, mammary carcinoma MCF-7 cells, breast adenocarcinoma SK-BR-3 cells, and glioblastoma A1235 cells and their four drug-resistant cell lines. Cytotoxicity was determined using the colorimetric MTT assay. The intracellular GSH content (following the treatment with diazenes) was examined spectrophotometrically in human cervical carcinoma cells by the procedure developed by Tietze. Results: Results show that diazene UP-39 was mostly efficient, significantly reducing the cell survival of all nine cell lines examined, including four drug-resistant cell lines. Diazenes UP-11, RL-514 and BR-25 given in the highest concentrations decreased the survival of some examined cell lines, but to less than 50%. Diazenes RL-625 and JK-1024 had no influence on the cell survival. None of the examined diazenes significantly influenced the intracellular level of GSH. Conclusion: Our results suggest that diazene UP-39 may be a promising new drug for the treatment of tumors and encourage further research on this compound.

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Section: Discussionmentioning

confidence: 99%

Section: Drugsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Effects of Diazenes on Tumor Cells in vitro

Moskatelo

Benjak²,

Laketa³

et al. 2002

Chemotherapy

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“…10 A promising alternative to these so-called cocktails are hybrid molecules that are composed of two or more covalently bound drugs; the compounds that can possess combined pharmacological properties of the individual drugs 10,11 yet superior synergistic effects. 12,13 Over the past years, we have investigated redox-active 14 diazenecarboxamides as potential anti-cancer agents. 15 The results of the in vitro experiments suggested that they likely target tumour cell redox mechanism by oxidation of glutathione into glutathione disulphide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and X-ray Structural Analysis of the Ruthenium(III) Complex Na[trans-RuCl4(DMSO) (PyrDiaz)], the Diazene Derivative of Antitumor NAMI-Pyr

Vajs¹,

Pevec²,

Gazvoda³

et al. 2017

ACSi

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Novel tetrachloridoruthenium(III) complex Na[trans-RuCl 4 (DMSO)(PyrDiaz)] (3) with pyridine-tethered diazenedi-was synthesized by direct coupling of PyrDiaz with sodium trans-bis(dimethyl sulfoxide)tetrachloridoruthenate(III) (Na-[trans-Ru(DMSO) 2 Cl 4 ]). Compound 3 is the analogue of the antimetastatic Ru(III) complex NAMI-A and NAMI-Pyr. Single crystal X-ray diffraction analysis revealed that the compound 3 is a polymeric complex with the ruthenium and sodium centres.

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“…The synthesis and spectroscopic data of 1a, 1c, 1d, and 1i have already been published. 2,7 Other diazenes were obtained following the reaction conditions, depicted in Scheme 1, and were characterised as described in experimental section. Compounds which reduced the growth of any of the cell lines to less than 32% (negative numbers indicate cell kill), were passed on for evaluation in the full panel of 60 cell lines over a 5-log dose range.…”

Section: Introductionmentioning

confidence: 99%