Photo-control of cancer cell growth by benzodiazo N-substituted pyrrole derivatives
| Autor: | Elisa Rivieccio, Marialuisa Menna, Concetta Imperatore, Annapina Russo, Carlo Altucci, Michela Varra, Luciano Mayol, Giulia Russo, Anna Ramunno, Mohammadhassan Valadan, Assunta Saide, Maria Scuotto |
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| Přispěvatelé: | Imperatore, Concetta, Scuotto, Maria, Valadan, Mohammadhassan, Rivieccio, Elisa, Saide, Assunta, Russo, Annapina, Altucci, Carlo, Menna, Marialuisa, Ramunno, Anna, Mayol, Luciano, Russo, Giulia, Varra, Michela |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Stereochemistry
General Chemical Engineering General Physics and Astronomy 02 engineering and technology 010402 general chemistry N Substituted pyrrole Diazocompounds Tubulin inhibitors 01 natural sciences chemistry.chemical_compound Microtubule Tubulin inhibitors N-Substituted pyrrole Diazocompounds Molecule Viability assay Pyrrole biology Diastereomer General Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences chemistry Cancer cell biology.protein 0210 nano-technology Cis–trans isomerism |
| Popis: | In order to expand the class of diazocompounds able to act as photo-activable microtubule inhibitors the potential of azo-heteroarenes has been explored. In this paper we focus on the synthesis, physical properties and biological effects of methyl rac-2-(2-((E)-(4-((R)-2,3-dihydroxypropoxy)phenyl) diazenyl)-1H-pyrrol-1-yl)-3-hydroxypropanoate (1a) and methyl rac-2-(2-((E)-(4-((S)-2,3-dihydroxypropoxy)phenyl) diazenyl)-1H-pyrrol-1-yl)-3-hydroxypropanoate (1b). Preliminary biological studies on the HCT-116 p53-/- cancer cell line have shown that the weak antiproliferative action of the trans isomers of these molecules, especially of 1a, is enhanced upon LED light irradiation at 435 nm. On A375 cells the molecules have not shown any effect on cell viability either in the dark or under irradiation. Moreover, the two diastereomeric components of 1a as pure stereomers have been synthesized and characterized for their chemical-physical properties. Interestingly, upon irradiation, 1a has shown an antiproliferative activity on the HCT-116 p53-/- cells greater than that of the pure stereomers, 1RR and 1RS. Tubulin polymerization assay has also demonstrated that 1a, 1RR and 1RS inhibit tubulin aggregation mostly after exposure of the samples to LED light irradiation. |
| Databáze: | OpenAIRE |
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