Antimestastatic Action of Triazene Derivatives

Giraldi, Tullio; Perissin, L.; Zorzet, Sonia; Rapozzi, Valentina

doi:10.1007/978-1-4615-3832-5_4

Cited by 7 publications

(2 citation statements)

References 37 publications

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“…Triazene [diazoamino group, R 1 −N1N2-N3(R 2 R 3 )] is the fundamental active group in a range of applications, from antitumor medicines , to molecular electronics . The triazene moiety is a good chromophore, with a deep color in solution and a low melting point.…”

Section: Nmr Spectra Of 1-aryl-33-dialkyltriazenesmentioning

confidence: 99%

Preparative Fluorous Mixture Synthesis of Diazonium-Functionalized Oligo(phenylene vinylene)s

Jian

Tour

2005

J. Org. Chem.

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[structure: see text] A series of building blocks for the synthesis of oligo(phenylene vinylene)s (OPVs) and hybrid oligomers were prepared, and alternating Heck coupling and Horner-Wadswoth-Emmons (HWE) reactions were used to couple the building blocks. Model studies were carried out to optimize the reaction strategies. The products were made to bear aryl diazonium functionalities that allow them to be used as surface grafting moieties in hybrid silicon/molecule assemblies. A library of OPV and hybrid oligomer tetramers was synthesized using fluorous mixture synthesis (FMS). The fluorous tags, which are secondary amines bearing different numbers of fluorine atoms, were synthesized and used as phase tags in mixture synthesis. The tags and substrates were anchored together by triazene linkages. The mixture synthesis was monitored by analytical HPLC on a fluorous column, and isolation of final OPV and hybrid oligomer tetramers was achieved by preparative HPLC. At the end of the FMS, after demixing, the tagged products were detagged by cleaving the triazene linkage and generating a series of aryl diazonium compounds. The fluorous tags could be recovered and reused. The NMR spectra of the 1-aryl-3,3-dialkyltriazenes are discussed.

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Section: Nmr Spectra Of 1-aryl-33-dialkyltriazenesmentioning

confidence: 99%

Preparative Fluorous Mixture Synthesis of Diazonium-Functionalized Oligo(phenylene vinylene)s

Jian

Tour

2005

J. Org. Chem.

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“…1), showed disassociation between the antimetastatic and antitumor effects in an experimental Lewis lung carcinoma 2 thus supporting the idea that these two properties might also be disassociated in other members of this series of compounds, similarly to what had been previously observed by Heyes for ethyl 5-(3,3dimethyl-1-triazenyl) -1H-2-methylimidazole-4-carboxylate 3 (23) and by Giraldi et al for the aryldimethyltriazenes. 4 In spite of these early observations it has been impossible to develop a triazene possessing primarily an antimetastatic effect, and the aryl-and heteroaryldimethyltriazenes remain a class of compounds showing mutagenic, 5 antitumor 6 and carcinogenic activities 7,8 to varying extents. The correlation of the mutagenic, antiproliferative and antimetastatic activities of the triazenes with some of their physico-chemical properties has received considerable attention 9 due to its relevance to the discovery of safer, more selective agents.…”

mentioning

confidence: 99%

Correlation of the antimetastatic properties of aryltriazenes with their electron impact ionization mass spectrometry

Tarzia

Diamantini

Tontini

et al. 1997

Rapid Commun. Mass Spectrom.

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Howard Watson describes how Hawkins\Brown's new Biochemistry Department for the University of Oxford represents an innovative new model for scientific research institutes. Spatially, its interior not only positively embraces and encourages social interaction and the fertilisation of ideas, but also brings art, architecture and science together under a single roof. Copyright © 2009 John Wiley & Sons, Ltd.

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Suppression of metastatic potential and up-regulation of gelatinases and uPA in LLC by protractedin vivo treatment with dacarbazine or razoxane

et al. 1997

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Treatment of mouse Lewis lung carcinoma with razoxane or dacarbazine was protracted for 10 transplant generations. While the capacity of the treated tumors to grow locally in immuno‐competent or in immuno‐depressed hosts was retained and not significantly modified, the metastatic phenotype was eliminated when the treated tumor cells were transplanted into immuno‐competent hosts. The reduction in metastatic potential was slightly less pronounced, in terms of both number and volume of metastases, when the treated tumor cells were transplanted into immuno‐depressed hosts. These properties were retained after 3 transplant generations without treatment. Northern blotting and zymography of primary‐tumor crude extracts revealed that treatment with either razoxane or dacarbazine for one generation approximately doubled the expression of MMP‐2 and MMP‐9, while lacking any effect on that of 1.0 and of 3.5 kb TIMP‐2. When the treatment was maintained for 10 generations, the expression of MMP‐2 and MMP‐9 for both drugs showed up‐regulation of approximately 10‐ and 2‐fold respectively. TIMP‐2 mRNA of 1.0 kb doubled its expression, while that of 3.5 kb registered just above the control. Dacarbazine doubled the expression of uPA after 10 generations, while razoxane boosted it approximately 3‐fold after either 1 or 10 generations. The permanent loss of metastatic phenotype induced in Lewis lung carcinoma by dacarbazine and razoxane is thus attributable to biological mechanisms independent of down‐regulation of expression and/or activation of the 2 gelatinases. Int. J. Cancer 72:1056–1061, 1997. © 1997 Wiley‐Liss, Inc.

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Antimestastatic Action of Triazene Derivatives

Cited by 7 publications

References 37 publications

Preparative Fluorous Mixture Synthesis of Diazonium-Functionalized Oligo(phenylene vinylene)s

Preparative Fluorous Mixture Synthesis of Diazonium-Functionalized Oligo(phenylene vinylene)s

Correlation of the antimetastatic properties of aryltriazenes with their electron impact ionization mass spectrometry

Suppression of metastatic potential and up-regulation of gelatinases and uPA in LLC by protractedin vivo treatment with dacarbazine or razoxane

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