Influence of hydrogen-bonding substituents on the cytotoxicity of RAPTA compounds

Claudine Scolaro, Tilmann J. Geldbach, Sébastien Rochat, Antoine Dorcier, Christian Gossens, Alberta Bergamo, Moreno Cocchietto, Ivano Tavernelli, Gianni Sava, Ursula Rothlisberger, Paul J. Dyson

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Abstract

A new series of organometallic ruthenium(II)-arene compounds of the type RuCl26-arene)(phosphine) (phosphine = 1,3,5-triaza-7-phosphaadamantane, PTA, and 3,7-diacetly-1,3,7-triaza-5- phosphabicyclo[3.3.1]nonane, DAPTA) with different potential hydrogen-bonding functionalities on the arene ligand have been prepared and studied for their antitumor activity. Cell viability studies using the TS/A mouse adenocarcinoma cancer cell line and the nontumorigenic HBL-100 human mammary cell line, combined with uptake determinations, are compared to the nonfunctionalized analogues, previously shown to be active on solid metastasizing tumors. The reactivity of the functionalized RAPTA compounds with a 14-mer oligonucleotide (established by mass spectrometry) has been rationalized by DFT calculations, which indicate that environmental factors are important.

Original languageEnglish
Pages (from-to)756-765
Number of pages10
JournalOrganometallics
Volume25
Issue number3
DOIs
Publication statusPublished - 30 Jan 2006

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phosphine
Cytotoxicity
cultured cells
phosphines
Hydrogen bonds
Cells
nonanes
oligonucleotides
Ruthenium compounds
hydrogen
viability
ruthenium
mice
mass spectroscopy
tumors
reactivity
cancer
Organometallics
analogs
Discrete Fourier transforms

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Scolaro, C., Geldbach, T. J., Rochat, S., Dorcier, A., Gossens, C., Bergamo, A., ... Dyson, P. J. (2006). Influence of hydrogen-bonding substituents on the cytotoxicity of RAPTA compounds. Organometallics, 25(3), 756-765. https://doi.org/10.1021/om0508841

Influence of hydrogen-bonding substituents on the cytotoxicity of RAPTA compounds. / Scolaro, Claudine; Geldbach, Tilmann J.; Rochat, Sébastien; Dorcier, Antoine; Gossens, Christian; Bergamo, Alberta; Cocchietto, Moreno; Tavernelli, Ivano; Sava, Gianni; Rothlisberger, Ursula; Dyson, Paul J.

In: Organometallics, Vol. 25, No. 3, 30.01.2006, p. 756-765.

Research output: Contribution to journalArticle

Scolaro, C, Geldbach, TJ, Rochat, S, Dorcier, A, Gossens, C, Bergamo, A, Cocchietto, M, Tavernelli, I, Sava, G, Rothlisberger, U & Dyson, PJ 2006, 'Influence of hydrogen-bonding substituents on the cytotoxicity of RAPTA compounds', Organometallics, vol. 25, no. 3, pp. 756-765. https://doi.org/10.1021/om0508841
Scolaro C, Geldbach TJ, Rochat S, Dorcier A, Gossens C, Bergamo A et al. Influence of hydrogen-bonding substituents on the cytotoxicity of RAPTA compounds. Organometallics. 2006 Jan 30;25(3):756-765. https://doi.org/10.1021/om0508841
Scolaro, Claudine ; Geldbach, Tilmann J. ; Rochat, Sébastien ; Dorcier, Antoine ; Gossens, Christian ; Bergamo, Alberta ; Cocchietto, Moreno ; Tavernelli, Ivano ; Sava, Gianni ; Rothlisberger, Ursula ; Dyson, Paul J. / Influence of hydrogen-bonding substituents on the cytotoxicity of RAPTA compounds. In: Organometallics. 2006 ; Vol. 25, No. 3. pp. 756-765.
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