Electrochemistry of conjugated planar anticancer molecules: Irinotecan and Sunitinib
| Autor: | Anna Berlin, Gianni Zotti, Barbara Vercelli |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Anticancer molecule
Chemistry General Chemical Engineering Quinoline Imine 02 engineering and technology Electronic spectra Conjugated system Irinotecan 010402 general chemistry 021001 nanoscience & nanotechnology Electrochemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Sunitinib Moiety Molecule Organic chemistry 0210 nano-technology Acetonitrile Pyrrole |
| Zdroj: | Electrochimica acta 231 (2017): 336–343. doi:10.1016/j.electacta.2017.02.043 info:cnr-pdr/source/autori:Zotti G.; Berlin A.; Vercelli B./titolo:Electrochemistry of conjugated planar anticancer molecules: Irinotecan and Sunitinib/doi:10.1016%2Fj.electacta.2017.02.043/rivista:Electrochimica acta/anno:2017/pagina_da:336/pagina_a:343/intervallo_pagine:336–343/volume:231 |
| ISSN: | 0013-4686 |
| DOI: | 10.1016/j.electacta.2017.02.043 |
| Popis: | The evaluation of drug levels is important for personalized therapeutic approaches particularly in cancer care. To this end electrochemistry provides simplicity, low cost, high sensitivity and possibility of miniaturization. Here we report the electrochemistry and UV-visible spectroscopy of two extensively used planar conjugated anticancer molecules, Irinotecan (ITC) and Sunitinib (SUN), in aprotic medium and water. Comparison is made with model compounds without amine ends. The electronic spectra of ITC and SUN in dimethylsulfoxide show similar vibronic patterns (0.2 eV vibrational energy for both) with energy gaps of 3.1 and 2.5 eV respectively. Cyclic voltammetry in acetonitrile shows the same one-electron reduction peak (-1.9 V vs Ag/Ag+) and oxidation peaks at 1.45 and 0.65 V, both beyond the oxidation of the amine ends (0.45 V). In water the optical energy gaps are unchanged but the vibronic structure is almost lost and the oxidation processes are eased by 0.45 V for SUN and 1.10 V for ITC. The number of oxidatively exchanged electrons in water is two for ITC but four in two subsequent two-electron steps for SUN. The overall oxidation process for ITC likely involves the nucleophilic attack of a water molecule to the quinoline moiety. The first two-electron oxidation of SUN, involving the pyrrole moiety, leads possibly to the conjugated imine ring which is further oxidized to the N-oxide form. Lowering of the electron-transfer activation energy by water is assigned in part to release of molecular rigidity but in ITC the major role is assigned to a nucleophilic attack of water already in the activated state. |
| Databáze: | OpenAIRE |
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