Synthesis and Study of 2-(Pyrrolesulfonylmethyl)-N-arylimines: A New Class of Inhibitors for Human Glutathione Transferase A1-1
| dc.contributor.author | Koutsoumpli, G. E. | en |
| dc.contributor.author | Dimaki, V. D. | en |
| dc.contributor.author | Thireou, T. N. | en |
| dc.contributor.author | Eliopoulos, E. E. | en |
| dc.contributor.author | Labrou, N. E. | en |
| dc.contributor.author | Varvounis, G. I. | en |
| dc.contributor.author | Conis, Y. D. | en |
| dc.date.accessioned | 2015-11-24T16:49:10Z | |
| dc.date.available | 2015-11-24T16:49:10Z | |
| dc.identifier.issn | 0022-2623 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/9438 | |
| dc.rights | Default Licence | - |
| dc.subject | hiv-1 reverse-transcriptase | en |
| dc.subject | pyrrolyl aryl sulfones | en |
| dc.subject | s-transferases | en |
| dc.subject | cisplatin resistance | en |
| dc.subject | drug-sensitivity | en |
| dc.subject | binding-site | en |
| dc.subject | cancer-cells | en |
| dc.subject | analogs | en |
| dc.subject | design | en |
| dc.subject | ligand | en |
| dc.title | Synthesis and Study of 2-(Pyrrolesulfonylmethyl)-N-arylimines: A New Class of Inhibitors for Human Glutathione Transferase A1-1 | en |
| heal.abstract | Overexpression of human GSTA1-1 in tumor cells is part of MDR mechanisms. We report on the synthesis of 11 pyrrole derivatives as hGSTA1-1 inhibitors starting from 1-methyl-2-[(2-nitrobenzylsulfanyl]-1H-pyrrole. Molecular modeling revealed two locations in the enzyme H binding site: the catalytic primary one accommodating shorter and longer derivatives and the secondary one, where shorter derivatives can occupy. Derivative 9, displaying the highest inhibition and bearing a p-nitroarylimino moiety, and derivative 4, lacking this moiety, were studied kinetically. Derivative 9 binds (K-i(9) = 71 +/- 4 mu M) at the primary site competitively vs CDNB. Derivative 4 binds (K-i(4) = 135 +/- 27 mu m) at the primary and secondary sites, allowing the binding of a second molecule (4 or CDNB) leading to formation of unreactive and reactive complexes, respectively. The arylmethylsulfonylpyrrole core structure is a new pharmacophore for hGSTA1-1, whereas its derivative 9 may serve as a lead structure. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | Doi 10.1021/Jm300385f | - |
| heal.identifier.secondary | <Go to ISI>://000307264100013 | - |
| heal.identifier.secondary | http://pubs.acs.org/doi/pdfplus/10.1021/jm300385f | - |
| heal.journalName | J Med Chem | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2012 | - |
| heal.publisher | American Chemical Society | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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