Bouffier L., Gosse I., Demeunynck M., Mailley P.,
Bioelectrochemistry 2012, 88, 103-109.

We report here the electrochemical characterization of eight synthetic DNA intercalators based on the 4H-pyrido[4,3,2-kl]acridin-4-one structure. We found that the electrochemical behavior of these redox active drugs is strongly influenced by the nature of the solvent. A single two-electron reduction is observed in an aqueous phosphate buffer (PB) whereas two successive one-electron reductions are observed in aprotic solution (acetonitrile). The influence of the molecular structure on the potential values is addressed along with a comparison between the DNA binding constant (KDNA) and the cytotoxic activity against HT29 cells (IC50). For typical DNA intercalators, one could expect that toxicity will be roughly proportional to the DNA binding constant. Yet, a structure/activity comparison solely based on the DNA affinity was not conclusive. In contrast, a direct relationship was evidenced for the first time between the decimal logarithm of the in vitro bioactivity and the reduction potential of pyridoacridones recorded in PB at pH 7.0. Moreover, most of the bio/electrochemical relationships previously described for quinone-based drugs were reported with electrochemical characterization in aprotic solvents (typically acetonitrile, dimethylformamide or dimethylsulfoxide). But aqueous solution electrochemistry is definitely the most bio-relevant because the redox mechanism of quinone or iminoquinone reduction directly depends on the protic nature of the solvent.

 

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La Chimie au Service d’une Délivrance de l’Insuline en Boucle Fermée
mercredi 19 décembre 2012
Messager L., Ancla C., Lapeyre V., Ravaine V., Catargi B.Médecine Clinique Endocrinologie et Diabète 2012, 59, 38-45.  
Indirect Bipolar Electrodeposition
mardi 27 novembre 2012
Loget G., Roche J., Gianessi E., Bouffier L., Kuhn A.,J. Am. Chem.Soc. 2012, 134, 20033-20036. Based on the principles of bipolar electrochemistry, localized pH gradients are generated at the surface... Read More...
Light-Emitting Electrochemical Swimmers
lundi 8 octobre 2012
Sentic M., Loget G., Manojlovic D., Kuhn A., Sojic N.,Angew. Chem. Int. Ed. 2012, 51, 11284–11288. Swimmer in the dark: Propulsion of a conducting object is intrinsically coupled with light... Read More...
Controlled Orientation of Asymmetric Copper Deposits on Carbon Microobjects by Bipolar Electrochemistry
mercredi 19 septembre 2012
Fattah Z., Garrigue P., Lapeyre V., Kuhn A., Bouffier L.,J. Phys. Chem. C 2012, 116, 22021-22027. Asymmetric particles of various chemical compositions have attracted great attention because of their... Read More...
Quantification of Photoelectrogenerated Hydroxyl Radical on TiO2 by Surface Interrogation Scanning Electrochemical Microscopy
mardi 7 août 2012
Zigah D., Rodriguez-Lopez P., Bard A. J.,Phys. Chem. Chem. Phys. 2012, 14, 12764-12772. Asymmetric particles of various chemical compositions have attracted great attention because of their... Read More...
Development of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and p-Conjugated Groups
lundi 30 juillet 2012
Peyrard L., Dumartin M.-L., Chierici S., Pinet S., Jonusauskas G., Meyrand P., Gosse I.,J. Org. Chem. 2012, 77, 7023-7027. Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped... Read More...
Electrochemistry and Bioactivity Relationship of 6-Substituted-4H-Pyrido[4,3,2-kl]acridin-4-one Antitumor Drug Candidates
vendredi 27 juillet 2012
Bouffier L., Gosse I., Demeunynck M., Mailley P.,Bioelectrochemistry 2012, 88, 103-109. We report here the electrochemical characterization of eight synthetic DNA intercalators based on the...
True Bulk Synthesis of Janus Objects by Bipolar Electrochemistry
lundi 16 juillet 2012
Loget G., Roche J., Kuhn A.,Adv. Mater. 2012, 24, 5111-5116. Cover article Janus particles have different features/chemistry on two opposite sides (see figure). So far, they have been obtained mainly... Read More...
Direct Visualization of Symmetry Breaking during Janus Nanoparticle Formation
mardi 3 juillet 2012
Loget G., Lee T.-C., Taylor R. W., Mahajan S., Nicoletti O., Jones S. T., Coulston R. J., Lapeyre V., Garrigue P., Midgley P. A., Scherman O. A., Baumberg J. J., Kuhn A.,Small 2012, 8, 2698-2703. The... Read More...
Combined Macro/mesoporous Microelectrode Arrays (MEAs) for Low Noise Extracellular Recording of Neural Networks
mercredi 27 juin 2012
Heim M., Rousseau L., Reculusa S., Urbanova V., Mazzocco C., Joucla S., Bouffier L., Vytras K., Bartlett P., Kuhn A., Yvert B.Journal of Neurophysiology 2012, 15, 1793-1803. Microelectrode arrays... Read More...
Bulk Synthesis of Janus Objects and Asymmetric Patchy Particles
jeudi 10 mai 2012
Loget G., Kuhn A.,J. Mater. Chem. 2012, 22, 15457-15474. Feature article This review article highlights the most recent advances with respect to the preparation of Janus objects by bulk phase... Read More...
Bipolar Electrochemistry for Cargo-lifting in Fluid Channels
mercredi 15 février 2012
Loget G., Kuhn A.,Lab on a Chip 2012, 12, 1967-1971. Hot Paper, Cover Article We report for the first time the vertical propulsion of conducting beads in liquid filled capillaries by bipolar... Read More...
Origin and Control of Adhesion between Emulsion Drops Stabilised by Thermally-sensitive Soft Colloidal Particles
vendredi 20 janvier 2012
Destribats M., Lapeyre V., Sellier E., Leal Calderon F., Ravaine V., Schmitt V.,Langmuir 2012, 28, 3744-3755. We used soft microgels made of poly(N-isopropylacrylamide) (pNIPAM) of variable... Read More...
Site Selective Generation of Sol-gel Deposits in Layered Bi-metallic Macroporous Electrode Architectures
jeudi 19 janvier 2012
Lalo H., Bon Saint-Côme Y., Plano B., Etienne M., Walcarius E., Kuhn A.,Langmuir 2012, 28, 2323-2326. The elaboration of an original composite bimetallic macroporous electrode containing a... Read More...
The Fraction of Alpha-linolenic Acid present in the sn-2 position of Structured Triacylglycerols decreases in Lymph Chylomicrons and Plasma Triacylglycerols during the Course of Lipid Absorption in Rats
mercredi 30 novembre 2011
Couedelo L., Vaysse C., Vaique E., Guy A., Gosse I., Durand T., Pinet S., Cansell M., Combe N.Journal of Nutrition 2012, 142, 70-75. Little is known about the ability of α-linolenic acid (Ln) to... Read More...
Engineering of Complex Macroporous Materials through Controlled Electrodeposition in Colloidal Superstructures
mardi 29 novembre 2011
Heim M., Reculusa S., Ravaine S., Kuhn A.,Adv. Funct. Mater. 2012, 22, 538-545. Inside Cover Article Macroporous materials with a sophisticated architecture are obtained by electrochemical deposition... Read More...
Electrochemical Investigations of Dissolved and Surface Immobilised 2-Amino-1,4-Naphthoquinones in Aqueous Solutions
samedi 29 octobre 2011
Bouffier L., Lister K. E., Higgins S. J., Nichols R. J., Doneux T.,J. Electroanal. Chem. 2012, 664, 80-87. The electrochemistry of proton coupled electron transfer phenomena is an important... Read More...
Nanostructuration Strategies to Enhance Microelectrode Array (MEA) Performance for Neuronal Recording and Stimulation
mardi 18 octobre 2011
Heim M., Yvert B., Kuhn A.,J. Physiology - Paris 2012, 106, 137-145. Microelectrode arrays (MEAs) are widely used tools for recording and stimulating extracellular neuronal activity. Major... Read More...