133307-45-6Relevant articles and documents
Imidazo[1,2-a]quinoxalines derivatives grafted with amino acids: Synthesis and evaluation on A375 melanoma cells
Chouchou, Adrien,Patinote, Cindy,Cuq, Pierre,Bonnet, Pierre-Antoine,Deleuze-Masquéfa, Carine
, (2018)
Imiqualines (imidazoquinoxaline derivatives) are anticancer compounds with high cytotoxic activities on melanoma cell lines. The first generation of imiqualines, with two lead compounds (EAPB0203 and EAPB0503), shows remarkable in vitro (IC50 = 1 570 nM and IC50 = 200 nM, respectively, on the A375 melanoma cell line) and in vivo activity on melanoma xenografts. The second generation derivatives, EAPB02302 and EAPB02303, are more active, with IC50 = 60 nM and IC50 = 10 nM, respectively, on A375 melanoma cell line. The aim of this study was to optimize the bioavailability of imiqualine derivatives, without losing their intrinsic activity. For that, we achieved chemical modulation on the second generation of imiqualines by conjugating amino acids on position 4. A new series of twenty-five compounds was efficiently synthesized by using microwave assistance and tested for its activity on the A375 cell line. In the new series, compounds 11a, 9d and 11b show cytotoxic activities less than second generation compounds, but similar to that of the first generation ones (IC50 = 403 nM, IC50 = 128 nM and IC50 = 584 nM, respectively). The presence of an amino acid leads to significant enhancement of the water solubility for improved drugability.
Substantial Cellular Penetration of Fluorescent Imidazoquinoxalines
Patinote, Cindy,Cirnat, Natalina,Hadj-Kaddour, Kamel,Cuq, Pierre,Bonnet, Pierre-Antoine,Deleuze-Masquéfa, Carine
, p. 1499 - 1512 (2020/08/14)
Fluorescent tools have revolutionized our capability to visualize, probe, study, and understand the biological cellular properties, processes and dynamics, enabling researchers to improve their knowledge for example in cancer field. In this paper, we use the peculiar properties of our Imiqualines derivatives to study their cellular penetration and distribution in a human melanoma cell line A375 using confocal microscopy. Preliminary results on colocalization with the potent protein target c-Kit of our lead are also described.
Fluorescence Study of Imidazoquinoxalines
Patinote, Cindy,Hadj-Kaddour, Kamel,Damian, Marjorie,Deleuze-Masquéfa, Carine,Cuq, Pierre,Bonnet, Pierre-Antoine
, p. 1607 - 1611 (2017/09/13)
The fluorescence properties of eleven novel derivatives based on the imidazo[1,2-a]quinoxaline structures have been studied. The absorption and emission spectra of these compounds have been recorded in dimethylsulfoxide solution. The phenyl substituting group on position 1 gives them particular properties thanks to the diverse hydroxy or methoxy decorating moieties, especially when they are multiplied or mixed. The investigated fluorescence auto-quenching revealed that the decreasing fluorescence intensity correlated only with the chemical structures of the aromatic compounds.
